2430:
1486:
4304:
of
Gottingen was sponsored by a German pharmaceutical firm. In 1929, both terms announced the isolation of a pure crystal female sex hormone, estrone, in 1929, although Doisy and Allen did so two months earlier than Butenandt.27 By 1931, estrone was being commercially produced by Parke Davis in this country, and Schering-Kahlbaum in Germany. Interestingly, when Butenandt (who shared the Nobel Prize for chemistry in 1939) isolated estrone and analyzed its structure, he found that it was a steroid, the first hormone to be classed in this molecular family.
322:
227:
2472:
1722:
42:
1264:
33:
4673:
International
Conference on the Standardization of Sex Hormones, in London (1932), a standard preparation of estrone was established. The partial synthesis of estradiol and estrone from cholesterol and dehydroepiandrosterone was accomplished by Inhoffen and Howleg (Berlin 1940); the total synthesis was achieved by Anner and Miescher (Basel, 1948).
2683:
The risk of VTE is increased in those that use estrogens, those that currently have or have a history with VTE are at a greater risk of reoccurring VTE with the usage of estrogens. The use of estrogens within three weeks postpartum may increase the risk of developing a VTE. Risk of developing initial
4672:
The structure of the estrogenic hormones was stated by
Butenandt, Thayer, Marrian, and Hazlewood in 1930 and 1931 (see Butenandt 1980). Following the proposition of the Marrian group, the estrogenic hormones were given the trivial names of estradiol, estrone, and estriol. At the first meeting of the
4303:
When Allen and Doisy heard about the , they realized there was a rich and easily handled source of hormones in urine from which they could develop a potent extract. Allen and Doisy's research was sponsored by the committee, while that of their main rival, Adolt
Butenandt (b. 1903) of the University
2356:
of a steroid hormone refers to entry into the blood of the compound from all possible sources, including secretion from glands and conversion of prohormones into the steroid of interest. At steady state, the amount of hormone entering the blood from all sources will be equal to the rate at which it
584:
of estrone at the ERα and ERβ were 2.6% and 4.3% of those of estradiol, respectively. In accordance, the estrogenic activity of estrone has been reported to be approximately 4% of that of estradiol. In addition to its low estrogenic potency, estrone, unlike estradiol and estriol, is not accumulated
2700:
The use of estrogens may affect the ability to breastfeed and can change the composition of breastmilk. Estrogens have been used to suppress lactation which can result in a reduced total duration of lactation and reduced volume or inability to produce breastmilk. Composition of breastmilk produced
2674:
when there are changes in blood hormonal levels, including an increased level of estrone. Estrone, the major type of estrogen produced in post-menopausal women, was seen in greater concentrations from standard levels in those that were categorized as prefrail and in those that classified as frail.
4407:
Adolt
Friedrich Johann Butenandt was awarded the Nobel Prize in chemistry in 1939 "for his work on sex hormones"; In 1929 Butenandt isolated estrone in pure crystalline form. Both Butenandt and Edward Doisy isolated estrone simultaneously but independently in 1929. Butenandt took a big step
4369:
focused his research on the isolation of female sex hormones from hundreds of gallons of human pregnancy urine based on the discovery by
Ascheim and Zondeck in 1927 that the urine of pregnant women possessed estrogenic activity . In the summer of 1929, Doisy succeeded in the isolated of estrone
2625:
Estrone, as part of hormone replacement therapy (HRT), is frequently used to treat symptoms caused by estrogen deficiency in peri and post-menopausal women. This therapy aims to enhance overall health and relieve menopausal symptoms related to estrogen imbalance. Additionally, estrone and other
2357:
is being cleared (metabolic clearance rate) multiplied by blood concentration (production rate = metabolic clearance rate × concentration). If there is little contribution of prohormone metabolism to the circulating pool of steroid, then the production rate will approximate the secretion rate."
4638:
In 1926, Sir Alan S. Parkes and C.W Bellerby coined the basic word "estrin" to designate the hormone or hormones that induce estrus in animals, the time when female mammals are fertile and receptive to males. The terminology was extended to include the principal estrogens in humans, estrone,
2626:
estrogens are used to prevent osteoporosis in postmenopausal women who are at high risk of fractures and cannot tolerate alternative medications. Estrogens are absorbed efficiently by the body and subsequently inactivated in the liver, making them effective in HRT and osteoporosis prevention.
681:. In addition, estradiol levels were found to correlate with these effects, while estrone levels did not. These findings confirm that estrone has very low estrogenic activity, and also indicate that estrone does not diminish the estrogenic activity of estradiol. This contradicts some
1859:
3967:"American Association of Clinical Endocrinology Clinical Practice Guideline for the Diagnosis and Management of Nonalcoholic Fatty Liver Disease in Primary Care and Endocrinology Clinical Settings: Co-Sponsored by the American Association for the Study of Liver Diseases (AASLD)"
4472:
E. A. Doisy and A. Butenandt reported almost at the same time on the isolation of an estrogen-active substance in crystalline form from the urine of pregnant women. N. K. Adam suggested that this substance be named estrone because of the C-17-ketone group present
4370:(named by him theelin), simultaneously with but independent of Adolf Butenandt of the University of Gottingen in Germany. Doisy presented his results on the crystallization of estrone at the XIII International Physiological Congress in Boston in August 1929 .
2347:
of a steroid refers to the total secretion of the compound from a gland per unit time. Secretion rates have been assessed by sampling the venous effluent from a gland over time and subtracting out the arterial and peripheral venous hormone concentration. The
1852:
3287:
Selby P, McGarrigle HH, Peacock M (March 1989). "Comparison of the effects of oral and transdermal oestradiol administration on oestrogen metabolism, protein synthesis, gonadotrophin release, bone turnover and climacteric symptoms in postmenopausal women".
1845:
3338:
Powers MS, Schenkel L, Darley PE, Good WR, Balestra JC, Place VA (August 1985). "Pharmacokinetics and pharmacodynamics of transdermal dosage forms of 17 beta-estradiol: comparison with conventional oral estrogens used for hormone replacement".
4441:
Rational chemical studies of human sex hormones began in 1929 with Adolph
Butenandt's isolation of pure crystalline estrone, the follicular hormone, from the urine of pregnant women. Butenandt and Ruzicka shared the 1939 Nobel Prize in
2342:
of a steroid in the circulation is determined by the rate at which it is secreted from glands, the rate of metabolism of precursor or prehormones into the steroid, and the rate at which it is extracted by tissues and metabolized. The
2377:
When estrone is used too much or taken in large amounts, it can cause toxicity, leading to symptoms like nausea and vomiting. Estrone should be stored in its original package or container to maintain its quality and effectiveness.
1353:
The way estrone works is by entering the cells of certain tissues in the body and attaching to nuclear receptors. This interaction then influences how genes are expressed, leading to various physiological responses in the body.
718:
4408:
forward in the history of biochemistry when he isolated estrone from the urine of pregnant women. He named it "progynon" in his first publication, and then "folliculine", By 1932, he could determine its chemical structure,
3030:
The
Controversial Climacteric: The workshop moderators' reports presented at the Third International Congress on the Menopause, held in Ostend, Belgium, in June 1981, under the auspices of the International Menopause
3492:
De
Lignieres B, Basdevant A, Thomas G, Thalabard JC, Mercier-Bodard C, Conard J, et al. (March 1986). "Biological effects of estradiol-17 beta in postmenopausal women: oral versus percutaneous administration".
2662:. The use of estrogens hold a boxed warning with breast cancer for post-menopausal women as this can increase the risk of developing invasive breast cancer. Those with breast cancer become at a greater risk of
711:
2701:
was also seen to be different resulting in a reduced concentration of proteins in the milk. Babies of mothers that were taking estrogens while breastfeeding were seen to experience slower weight gain.
2416:
3101:
Escande A, Pillon A, Servant N, Cravedi JP, Larrea F, Muhn P, et al. (May 2006). "Evaluation of ligand selectivity using reporter cell lines stably expressing estrogen receptor alpha or beta".
4838:
704:
1374:, with the remainder (2.0 to 4.0%) circulating freely or unbound. It has about 24% of the relative binding affinity of estradiol for SHBG. As such, estrone is relatively poorly bound to SHBG.
5962:
5957:
5194:
3559:"Estriol and estrone interaction with the estrogen receptor. II. Estriol and estrone-induced inhibition of the cooperative binding of [3H]estradiol to the estrogen receptor"
4833:
4945:
2409:
3198:
Fishman J, Martucci CP (1980). "New
Concepts of Estrogenic Activity: The Role of Metabolites in the Expression of Hormone Action". In Pasetto N, Paoletti R, Ambrus JL (eds.).
657:
estradiol, clinical studies have shown that dosages of oral and transdermal estradiol achieving similar levels of estradiol possess equivalent and non-significantly different
7843:
5199:
2714:
Some common side effects seen with the usage of estrogens include: breast swelling, breast tenderness, vaginal itching, abnormal uterine bleeding, weight gain, hair loss,
144:
4818:
8249:
2402:
3379:
Fåhraeus L, Larsson-Cohn U (December 1982). "Oestrogens, gonadotrophins and SHBG during oral and cutaneous administration of oestradiol-17 beta to menopausal women".
8075:
7415:
4998:
5894:
4011:"Breast cancer, endometrial cancer, and cardiovascular events in participants who used vaginal estrogen in the Women's Health Initiative Observational Study"
2891:
The FDA has approved estrone based on its safety and effectiveness as per the rules outlined in sections 505 of the Federal Food, Drug, and Cosmetic Act.
4206:"Thrombotic risk during oral contraceptive use and pregnancy in women with factor V Leiden or prothrombin mutation: a rational approach to contraception"
3826:"Studies on phenolic steroids in human subjects. II. The metabolic fate and hepato-biliary-enteric circulation of C14-estrone and C14-estradiol in women"
514:. Relative to estradiol, both estrone and estriol have far weaker activity as estrogens. Estrone can be converted into estradiol, and serves mainly as a
3465:
Friel PN, Hinchcliffe C, Wright JV (March 2005). "Hormone replacement with estradiol: conventional oral doses result in excessive exposure to estrone".
1833:
It is one of the three primary types of estrogen and is produced in various parts of the body, including the placenta, ovaries, and peripheral tissues.
2650:
to be used at the lowest effective dose and for the shortest possible treatment period if used alone or with another hormone in the progestogen class.
7990:
5169:
7756:
5947:
3683:
7807:
7799:
3414:
Wright JV (December 2005). "Bio-identical steroid hormone replacement: selected observations from 23 years of clinical and laboratory practice".
3598:
Lundström E, Conner P, Naessén S, Löfgren L, Carlström K, Söderqvist G (2015). "Estrone - a partial estradiol antagonist in the normal breast".
7382:
2842:
group, was formally established in 1932 at the first meeting of the International Conference on the Standardization of Sex Hormones in London.
1465:
8142:
8137:
7635:
7630:
7625:
7495:
4095:"Plasma Aromatase Activity Index, Gonadotropins and Estrone Are Associated with Frailty Syndrome in Post-Menopausal Women with Breast Cancer"
8101:
8021:
7818:
7120:
6904:
361:
6607:
4334:
The first steroid hormone was isolated from the urine of pregnant women by Adolf Butenandt in 1929 (estrone; see Fig. 1) (Butenandt 1931).
7893:
7888:
7660:
7585:
1248:). = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours).
345:
InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1
7868:
7863:
7710:
7705:
6057:
5887:
4762:
4639:
estradiol, and estriol, in 1932 at the first meeting of the International Conference on the Standardization of Sex Hormones in London,
3948:
8203:
8036:
8031:
7715:
7550:
7505:
6854:
4503:
In 1929 the first estrogen, a steroid called "estrone," was isolated and purified by Doisy; he later won a Nobel Prize for this work.
3233:"International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators"
1236:
levels relative to baseline of ovariectomized rats after 24 to 72 hours of continuous administration via subcutaneous implant.
8254:
7873:
7781:
7776:
7766:
7680:
7605:
6617:
5124:
3793:
Radioactive Isotopes in Physiology Diagnostics and Therapy / Künstliche Radioaktive Isotope in Physiologie Diagnostik und Therapie
7720:
1593:
7396:
5445:
2826:
had been determined by Butenandt by 1932. Following the elucidation of its structure, estrone was additionally referred to as
8198:
5880:
4728:
4701:
4665:
4631:
4528:
4496:
4465:
4434:
4400:
4362:
4327:
4296:
3808:
3770:
3743:
3541:
3215:
3182:
3039:
3008:
581:
8193:
6689:
6167:
3901:
7927:
608:
1703:
1328:
621:
of estradiol, the ratio of estradiol levels to estrone levels is about 5 times higher on average than under normal
6152:
6147:
1458:
6200:
4988:
2951:
Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration".
336:
6216:
5400:
5119:
6771:
6337:
5144:
2352:
of a steroid is defined as the volume of blood that has been completely cleared of the hormone per unit time. The
440:
7351:
4145:"Different kinds of oral contraceptive pills in polycystic ovary syndrome: a systematic review and meta-analysis"
2734:
seen with the usage of estrogens include: increased risk of venous thromboembolism (VTE), stroke, breast cancer,
6411:
6379:
4804:
6602:
5751:
5385:
5094:
4755:
4093:
García-Sánchez J, Mafla-España MA, Tejedor-Cabrera C, Avellán-Castillo O, Torregrosa MD, Cauli O (March 2022).
3926:
3136:
Ruggiero RJ, Likis FE (2002). "Estrogen: physiology, pharmacology, and formulations for replacement therapy".
5696:
1451:
64:
5114:
5059:
8188:
6502:
1683:
1665:
1363:
777:
666:
279:
222:
7952:
6062:
6037:
5736:
5731:
5054:
8208:
6450:
5214:
1827:
1602:
577:
300:
5621:
4870:
6455:
5651:
5542:
5044:
4144:
1757:
1383:
654:
638:
534:
184:
5856:
5851:
5527:
5522:
5517:
5512:
4983:
4920:
4915:
4823:
7510:
7420:
6642:
4748:
4009:
Crandall CJ, Hovey KM, Andrews CA, Chlebowski RT, Stefanick ML, Lane DS, et al. (January 2018).
1203:
785:
744:
5631:
5626:
5616:
5611:
5532:
5154:
8071:
7833:
7746:
7371:
7064:
6597:
6592:
6492:
5691:
5562:
5224:
5184:
4993:
4968:
4865:
2870:
2783:
2751:
2484:: estrone (E1) has one, estradiol (E2) has two, estriol (E3) has three, and estetrol (E4) has four.
596:
515:
317:
5846:
5455:
4963:
4204:
van Vlijmen EF, Veeger NJ, Middeldorp S, Hamulyák K, Prins MH, Büller HR, Meijer K (August 2011).
580:
of estrone for the human ERα and ERβ were 4.0% and 3.5% of those estradiol, respectively, and the
7359:
7269:
6894:
6884:
6819:
6347:
6117:
5440:
5285:
4657:
Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens
634:
572:
in mice, estradiol is about 10-fold more potent than estrone and about 100-fold more potent than
6157:
6132:
6072:
6067:
7327:
6879:
6359:
6284:
6279:
6232:
5746:
5656:
5592:
5537:
5380:
5174:
5089:
4978:
4875:
4828:
4795:
3733:
2866:
1293:
818:
658:
569:
565:
519:
6087:
4718:
4621:
4516:
4455:
4424:
4390:
4286:
3172:
2998:
8264:
7600:
7425:
7363:
6889:
6433:
6396:
6384:
6252:
5646:
5435:
5355:
4782:
4689:
4486:
3760:
3684:"Pharmacology of estrogens and progestogens: influence of different routes of administration"
3028:
2765:
884:
731:
604:
54:
6162:
6137:
6112:
6097:
6032:
5972:
5967:
5335:
5330:
5164:
5159:
4940:
4655:
4352:
4317:
1549:
1323:
from these tissues. In addition to aromatization of androstenedione, estrone is also formed
1126:
7020:
6677:
6416:
6322:
6264:
6042:
5821:
5681:
5229:
5189:
3423:
2611:
2605:
1867:
Production rates, secretion rates, clearance rates, and blood levels of major sex hormones
1222:
862:
840:
538:
288:
17:
6102:
5977:
5952:
5706:
5365:
5360:
5149:
5139:
204:
8:
8081:
7996:
7060:
6844:
6701:
6667:
6477:
6177:
5861:
5581:
5488:
5470:
5460:
5430:
5099:
5084:
5049:
4885:
4092:
2854:
2689:
2619:
1508:
1395:
1367:
1324:
1233:
766:
694:
674:
662:
618:
110:
6092:
3427:
321:
226:
164:
120:
8244:
8163:
7947:
7828:
7410:
7024:
6684:
6342:
6259:
6204:
6047:
6007:
5997:
5937:
5906:
5484:
5480:
5410:
5320:
5305:
5290:
5219:
4597:
4580:
4121:
4094:
4058:"The 2017 hormone therapy position statement of The North American Menopause Society".
4035:
4010:
3850:
3825:
3714:
3623:
3447:
3313:
3301:
3257:
3232:
2976:
2858:
2823:
2670:
when taking estrogens. Post-menopausal women with breast cancer can be seen to develop
2569:
1811:
1387:
1371:
1241:
994:
972:
950:
928:
617:
has confirmed the nature of estrone as a relatively inert precursor of estradiol. With
7751:
6027:
5726:
5721:
5395:
3575:
3558:
3149:
2782:, although Doisy and Allen isolated it two months before Butenandt. They isolated and
8239:
7761:
7535:
6984:
5992:
5987:
5914:
5903:
5450:
5370:
4955:
4895:
4724:
4697:
4661:
4627:
4602:
4561:
4524:
4492:
4461:
4430:
4396:
4358:
4323:
4292:
4257:
4227:
4180:
4126:
4075:
4040:
3988:
3855:
3804:
3766:
3739:
3706:
3664:
3615:
3580:
3537:
3510:
3474:
3439:
3396:
3356:
3352:
3305:
3262:
3211:
3178:
3153:
3118:
3078:
3035:
3004:
2968:
2874:
2846:
2819:
2643:
2525:
2387:
1753:
1730:
1611:
1473:
1415:
1297:
1207:
1016:
736:
645:
levels of estradiol, whereas estrone levels resemble the high levels seen during the
595:
is actually due to conversion into estradiol. As such, estrone is considered to be a
586:
554:
6142:
5774:
5769:
5711:
5280:
3718:
3627:
3451:
3317:
3073:
3056:
2980:
8259:
8234:
8229:
8011:
7480:
6445:
6192:
6077:
6017:
6012:
6002:
5982:
5942:
5636:
5552:
5425:
5420:
5415:
5375:
5340:
5325:
5315:
5310:
5300:
5295:
5204:
4973:
4890:
4880:
4592:
4553:
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4116:
4106:
4067:
4030:
4022:
3978:
3845:
3837:
3796:
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3654:
3607:
3570:
3502:
3431:
3388:
3348:
3297:
3252:
3244:
3203:
3145:
3110:
3068:
2960:
2671:
2639:
2635:
2577:
2559:
2543:
2516:
2481:
1777:
1556:
1542:
1532:
1518:
1423:
1419:
1399:
1312:
1170:
1148:
1104:
1082:
1060:
1038:
682:
653:. In spite of markedly elevated levels of estrone with oral estradiol but not with
642:
384:
6122:
5270:
3611:
7570:
7303:
7177:
6809:
6756:
6711:
6512:
5836:
5784:
5756:
5666:
5661:
5475:
5465:
5209:
5179:
5109:
5104:
5074:
4222:
4205:
4179:, Bethesda (MD): National Institute of Child Health and Human Development, 2006,
4071:
4026:
3880:
3800:
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2878:
2779:
2757:
2685:
2667:
2615:
2585:
2495:
2239:
2057:
2027:
1921:
1815:
1765:
1742:
1501:
1435:
1411:
1391:
1289:
1268:
691:
670:
646:
568:
estrogen than is estradiol, and as such, is a relatively weak estrogen. Given by
268:
7281:
7277:
7255:
3983:
3966:
3207:
8041:
7803:
7675:
7104:
6824:
6796:
6788:
6627:
6532:
6522:
6467:
6462:
6364:
6182:
6082:
5872:
5799:
5779:
5641:
5345:
5069:
5008:
4900:
4857:
4848:
4249:
4172:
4167:
4165:
3965:
Cusi K, Isaacs S, Barb D, Basu R, Caprio S, Garvey WT, et al. (May 2022).
2731:
2663:
2589:
2509:
2477:
1773:
1438:
of estrone is about 10 to 70 minutes and is similar to that of estradiol.
1316:
614:
511:
434:
4557:
4111:
3702:
3114:
2964:
1221:
rats after 72 hours with continuous administration of 1 μg/hour via
8223:
7655:
7490:
7465:
7245:
7163:
6996:
6974:
6829:
6706:
6438:
6289:
6247:
5567:
5064:
4565:
4544:
Campbell AD (1933). "Concerning Placental Hormones and Menstrual Disorders".
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2659:
2647:
2573:
1580:
1566:
1407:
1403:
1340:
622:
504:
422:
215:
16:
This article is about estrone as a hormone. For its use as a medication, see
4162:
3659:
3642:
3435:
2810:
in his second publication on the substance. Butenandt was later awarded the
7823:
7795:
7771:
7640:
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7475:
7470:
7460:
7263:
7229:
7219:
7215:
7150:
7144:
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6401:
6354:
6208:
6196:
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5789:
5741:
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5557:
5507:
5129:
5079:
4930:
4925:
4813:
4606:
4261:
4231:
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4130:
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3992:
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3619:
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3443:
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3157:
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2084:
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1281:
1225:
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3248:
2658:
Estrone is contraindicated for those that have or are suspected of having
1434:. Estrone can also be reversibly converted into estradiol by 17β-HSD. The
8168:
8096:
8061:
8056:
8016:
7986:
7972:
7962:
7957:
7786:
7730:
7725:
7620:
7615:
7595:
7545:
7520:
7515:
7440:
7430:
7347:
7343:
7339:
7331:
7321:
7317:
7285:
7273:
7259:
7251:
7191:
7124:
7068:
7040:
6874:
6849:
6721:
6622:
6497:
6421:
6391:
6242:
6222:
6172:
6126:
6022:
5826:
5716:
5601:
5499:
5390:
5027:
5003:
4790:
3530:"Proliferation of Breast Cells by Steroid Hormones and Their Metabolites"
2862:
2815:
2811:
2787:
2769:
2719:
2566:
2505:
1285:
1218:
906:
761:
690:
research suggesting that high concentrations of estrone might be able to
529:
In addition to its role as a natural hormone, estrone has been used as a
492:
472:
4694:
The Estrogen Elixir: A History of Hormone Replacement Therapy in America
41:
8111:
8091:
8066:
7913:
7858:
7813:
7791:
7700:
7695:
7665:
7650:
7645:
7610:
7500:
7455:
7435:
7313:
7307:
7211:
7199:
7159:
7140:
7116:
7100:
7010:
7006:
6980:
6966:
6919:
6914:
6909:
6899:
6869:
6839:
6834:
6814:
6751:
6672:
6652:
6637:
6632:
6577:
6527:
6428:
6369:
6302:
6297:
6274:
6212:
6187:
5831:
5275:
4771:
2850:
2776:
2646:(VTE), and those currently pregnant or breastfeeding. Estrogens hold a
2581:
1819:
1769:
1734:
1245:
630:
600:
530:
523:
476:
412:
195:
6612:
6107:
4740:
3841:
8106:
8086:
8026:
8006:
7848:
7685:
7560:
7555:
7540:
7525:
7485:
7367:
7335:
7293:
7241:
7237:
7233:
7223:
7203:
7187:
7136:
7112:
7108:
7096:
7088:
7084:
7044:
7032:
7016:
7002:
6992:
6988:
6944:
6804:
6778:
6766:
6741:
6731:
6716:
6696:
6647:
6547:
6542:
6517:
6507:
6472:
6332:
6307:
6269:
6227:
5816:
5764:
5255:
4910:
2795:
2739:
2443:
2174:
2000:
1803:
1761:
1738:
1494:
1477:
1320:
1304:
678:
650:
603:
of estradiol. In contrast to estradiol and estriol, estrone is not a
496:
480:
6052:
3491:
433:
Except where otherwise noted, data are given for materials in their
7977:
7967:
7670:
7530:
7450:
7445:
7378:
7195:
7132:
7128:
7092:
7080:
7052:
7048:
7036:
7028:
6958:
6746:
6736:
6582:
6567:
6552:
6487:
6482:
6327:
6237:
5250:
5239:
5036:
5013:
4905:
4203:
2715:
2459:
1745:
686:
507:
468:
243:
4969:
11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
1263:
143:
8132:
7878:
7690:
7590:
7580:
7575:
7355:
7299:
7289:
7181:
7056:
6864:
6859:
6761:
6726:
6657:
6557:
6374:
6312:
5265:
4774:
2773:
2760:
to be discovered. It was discovered in 1929 independently by the
2501:
2498:
2451:
1749:
1573:
1427:
1214:
591:
589:
into estradiol, most or all of the estrogenic potency of estrone
573:
550:
484:
464:
255:
2684:
VTE is also increased with familial history, genetic mutations:
2471:
1721:
1430:. Both of these transformations take place predominantly in the
8051:
8046:
7903:
7167:
7155:
6970:
6939:
6934:
6929:
6662:
6317:
2839:
2513:
2494:
Estrone, also known as estra-1,3,5(10)-trien-3-ol-17-one, is a
1674:
1650:
1641:
1626:
1620:
1336:
1301:
1211:
755:
726:
Selected biological properties of endogenous estrogens in rats
175:
7397:
4008:
1217:. Uterine weight = Percentage change in uterine wet weight of
561:
557:
8127:
8001:
7883:
7853:
7072:
6954:
6783:
3597:
2861:
of estrone. An alternative partial synthesis of estrone from
2791:
2563:
1823:
1807:
1431:
1332:
1308:
500:
155:
133:
85:)-7-Hydroxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1
305:
8147:
7928:
7838:
7207:
6962:
3527:
3100:
234:
3765:. Springer Science & Business Media. pp. 62, 64.
3528:
Kloosterboer HJ, Schoonen WG, Verheul HA (11 April 2008).
7982:
1271:, showing estrone on the lower right among the estrogens.
32:
4649:
4647:
4460:. Springer Science & Business Media. pp. 511–.
3337:
3177:. Springer Science & Business Media. pp. 548–.
4720:
The Hormones V1: Physiology, Chemistry and Applications
2992:
2990:
2881:
of estrone was achieved by Anner and Miescher in 1948.
6298:
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
4660:. Springer Science & Business Media. pp. 2–.
3634:
3464:
3286:
3027:
van Keep PA, Utian WH, Vermeulen A (6 December 2012).
3026:
2692:, and pregnancy-postpartum with the use of estrogens.
1822:
estrone in women, almost 90% is excreted in urine and
537:; for information on estrone as a medication, see the
4644:
4315:
3034:. Springer Science & Business Media. p. 92.
2814:
in 1939 for the isolation of estrone and his work on
4626:. Lippincott Williams & Wilkins. pp. 750–.
3495:
The Journal of Clinical Endocrinology and Metabolism
3378:
2987:
2392:
1441:
778:
4309:
3534:
Breast Cancer: Prognosis, Treatment, and Prevention
585:in estrogen target tissues. Because estrone can be
4623:Clinical Gynecologic Endocrinology and Infertility
4517:"Russel Earl Marker (1902–1995) - The Mexican Yam"
4247:
3964:
3823:
3643:"Diagram of the pathways of human steroidogenesis"
3640:
3230:
3191:
8250:Hormones of the hypothalamus-pituitary-gonad axis
4710:
4653:
4316:Nielsch U, Fuhrmann U, Jaroch S (30 March 2016).
4288:Science In The Bedroom: A History Of Sex Research
3791:Dorfman RI (1961). "Steroid Hormone Metabolism".
2996:
1199:
786:
745:
8221:
5902:
4984:11β-Hydroxyprogesterone (21-deoxycorticosterone)
4613:
4418:
4416:
4004:
4002:
3725:
2562:is 270.366 g/mol. It is a white, odorless,
267:
4395:. Chemical Heritage Foundation. pp. 255–.
4280:
4278:
4256:. Treasure Island (FL): StatPearls Publishing.
4243:
4241:
3929:. National Center for Biotechnology Information
3731:
3197:
3022:
3020:
2946:
2944:
2942:
2940:
2938:
2936:
2934:
2932:
2930:
2928:
2926:
2924:
487:. Estrone, as well as the other estrogens, are
119:
7402:Tooltip Selective estrogen receptor modulators
6757:Furostilbestrol (diethylstilbestrol difuroate)
6118:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
5286:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
4683:
4681:
4354:Estrogens, Estrogen Receptor and Breast Cancer
3786:
3784:
3782:
3521:
3374:
3372:
3370:
3333:
3331:
3329:
3327:
3282:
3280:
3278:
3276:
3096:
3094:
3092:
2922:
2920:
2918:
2916:
2914:
2912:
2910:
2908:
2906:
2904:
661:in terms of measures including suppression of
5948:3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
5888:
4756:
4716:
4413:
4384:
4382:
4380:
4378:
3999:
3752:
3556:
3341:American Journal of Obstetrics and Gynecology
3135:
2410:
1910:
1903:
1853:
1772:of estradiol that have one or more available
1459:
712:
6058:10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
4619:
4572:
4537:
4275:
4238:
3960:
3958:
3817:
3738:. Elsevier Health Sciences. pp. 2813–.
3591:
3458:
3407:
3017:
1331:(17β-HSD) in various tissues, including the
7933:Tooltip G protein-coupled estrogen receptor
6752:Fosfestrol (diethylstilbestrol diphosphate)
4678:
4654:Oettel M, Schillinger E (6 December 2012).
4581:"Estrogenic Hormones: Their Clinical Usage"
4508:
4457:Clinical Endocrinology: Theory and Practice
4346:
4344:
4342:
3896:
3894:
3779:
3735:Endocrinology – E-Book: Adult and Pediatric
3550:
3485:
3367:
3324:
3273:
3224:
3174:Clinical Endocrinology: Theory and Practice
3129:
3089:
3048:
2997:Hornstein T, Schwerin JL (1 January 2012).
2901:
2622:, but it is now mostly no longer marketed.
1229:
767:
6895:Triphenylmethylethylene (triphenylpropene)
6219:, many others; via estrogenic metabolites)
6143:17α-Epiestriol (16α-hydroxy-17α-estradiol)
5895:
5881:
5281:17α-Epiestriol (16α-hydroxy-17α-estradiol)
4763:
4749:
4375:
3875:
3873:
3871:
3869:
3824:Sandberg AA, Slaunwhite WR (August 1957).
3416:Annals of the New York Academy of Sciences
3057:"Bioidentical hormones for maturing women"
2614:estrogen for medical use, for instance in
2417:
2403:
1860:
1846:
1466:
1452:
719:
705:
320:
225:
203:
5915:
4596:
4478:
4422:
4221:
4120:
4110:
4034:
3982:
3955:
3849:
3758:
3658:
3574:
3256:
3138:Journal of Midwifery & Women's Health
3072:
3054:
2678:
1196:
737:
522:of estradiol. It is both a precursor and
287:
4717:Pincus G, Thimann KV (2 December 2012).
4578:
4543:
4339:
4284:
3891:
3231:Prossnitz ER, Arterburn JB (July 2015).
2584:at high temperatures, with the products
2424:Structures of major endogenous estrogens
1830:causes a delay in excretion of estrone.
1818:. Following an intravenous injection of
1262:
549:Estrone is an estrogen, specifically an
4770:
4687:
4521:A Biographical History of Endocrinology
4514:
4453:
4392:Nobel Laureates in Chemistry, 1901–1992
4177:Drugs and Lactation Database (LactMed®)
3949:"Drugs@FDA: FDA Approved Drug Products"
3866:
3790:
3732:Jameson JL, De Groot LJ (18 May 2010).
3170:
316:
8222:
5065:Adrenosterone (11-ketoandrostenedione)
4429:. Infobase Publishing. pp. 127–.
4388:
3413:
2822:of estrone was known by 1931, and its
2457:
2441:
1768:) occurs in the case of estradiol and
1710:
1701:
1696:
1681:
1672:
1648:
1639:
1609:
1600:
1578:
1571:
1554:
1547:
1530:
1523:
1362:Estrone is bound approximately 16% to
544:
503:, though they can also be formed from
216:
5876:
5276:16β-Epiestriol (16β-hydroxyestradiol)
4744:
4620:Fritz MA, Speroff L (28 March 2012).
4484:
3830:The Journal of Clinical Investigation
2576:of 254.5 °C (490 °F) and a
2449:
2436:
1663:
1618:
1591:
1564:
1540:
1516:
1506:
1499:
641:dosages of estradiol results in low,
637:of estradiol. Oral administration of
582:relative transactivational capacities
348:Key: DNXHEGUUPJUMQT-CBZIJGRNSA-N
183:
163:
58:3-Hydroxyestra-1,3,5(10)-trien-17-one
4350:
3902:"Material Safety Data Sheet Estrone"
3887:. U.S. National Library of Medicine.
3681:
2950:
2629:
2523:was derived from the chemical terms
1492:
783:Tooltip Sex hormone-binding globulin
5446:Estradiol 3-glucuronide 17β-sulfate
3941:
3563:The Journal of Biological Chemistry
3003:. Cengage Learning. pp. 369–.
2806:and subsequently referred to it as
2752:Estrone (medication) § History
2642:, history of some cancers, stroke,
2508:at the C1, C3, and C5 positions, a
1307:. This reaction occurs in both the
609:G protein-coupled estrogen receptor
258:
242:
13:
4248:Delgado BJ, Lopez-Ojeda W (2023).
3557:Sasson S, Notides AC (July 1983).
3302:10.1111/j.1365-2265.1989.tb02232.x
14:
8276:
7294:taleranol (teranol, β-zearalanol)
6209:metandienone (methandrostenolone)
4989:18-Hydroxy-11-deoxycorticosterone
4839:11β,17α,21-Trihydroxypregnenolone
3641:Häggström M, Richfield D (2014).
2725:
2610:Estrone has been available as an
1288:. The principal pathway involves
791:Tooltip relative binding affinity
750:Tooltip relative binding affinity
8204:Progesterone receptor modulators
7958:Afimoxifene (4-hydroxytamoxifen)
6840:Prinaberel (ERB-041, WAY-202041)
4319:New Approaches to Drug Discovery
4173:"Contraceptives, Oral, Combined"
3795:. Springer. pp. 1223–1241.
3759:Buchsbaum HJ (6 December 2012).
2798:women. Doisy and Allen named it
2695:
2653:
2470:
2428:
1752:) in humans. In addition to the
1720:
1484:
1329:17β-hydroxysteroid dehydrogenase
396:
40:
31:
8255:Hormones of the pregnant female
7901:Coregulator-binding modulators:
6168:17β-Methyl-17α-dihydroequilenin
5195:Dihydrotestosterone glucuronide
4585:California and Western Medicine
4515:Loriaux DL (23 February 2016).
4447:
4197:
4137:
4086:
4051:
3919:
3675:
3536:. CRC Press. pp. 343–366.
3200:The Menopause and Postmenopause
3074:10.1016/j.maturitas.2009.08.002
2704:
2634:The use of estrone has several
1898:Reference range (serum levels)
1357:
1275:
1258:
1195:Values are mean ± SD or range.
611:(affinity >10,000 nM).
437:(at 25 °C , 100 kPa).
6732:Erteberel (SERBA-1, LY-500307)
4866:3α,5α-Tetrahydrocorticosterone
4291:. Basic Books. pp. 128–.
3164:
2599:
2519:at the C17 position. The name
1319:, and estrone is subsequently
576:. According to one study, the
402:
390:
1:
8189:Receptor/signaling modulators
6153:17α-Ethynyl-3β-androstanediol
6148:17α-Ethynyl-3α-androstanediol
5145:3α-Androstanediol glucuronide
4579:Fluhmann CF (November 1938).
4454:Labhart A (6 December 2012).
4389:Laylin JK (30 October 1993).
3612:10.3109/09513590.2015.1062866
3576:10.1016/S0021-9258(20)82036-5
3171:Labhart A (6 December 2012).
3150:10.1016/s1526-9523(02)00233-7
2894:
2532:(estra-1,3,5(10)-triene) and
1377:
1327:from estradiol by the enzyme
1296:, with androstenedione being
369:O=C43(CC2c1ccc(O)cc1CC23CC4)C
8199:Androgen receptor modulators
6503:Lynestrenol phenylpropionate
4834:17α,21-Dihydroxypregnenolone
4223:10.1182/blood-2011-03-345678
4072:10.1097/GME.0000000000000921
4027:10.1097/GME.0000000000000956
3801:10.1007/978-3-642-49761-2_39
3353:10.1016/0002-9378(85)90569-1
3202:. Springer. pp. 43–52.
3055:Chervenak J (October 2009).
2381:
1797:
1364:sex hormone-binding globulin
667:follicle-stimulating hormone
479:estrogens, the others being
89:-cyclopentaphenanthren-1-one
7:
8194:Estrogens and antiestrogens
7844:Oxabicycloheptene sulfonate
7531:Etacstil (GW-5638, DPC-974)
6707:Doisynoestrol (fenocycline)
6451:Ethinylestradiol 3-benzoate
5963:3β,5α-Dihydrolevonorgestrel
5958:3α,5α-Dihydrolevonorgestrel
5215:Etiocholanolone glucuronide
5200:Dihydrotestosterone sulfate
4723:. Elsevier. pp. 360–.
4696:. JHU Press. pp. 21–.
4688:Watkins ES (6 March 2007).
4546:Annals of Internal Medicine
4491:. MSU Press. pp. 54–.
4426:Chemistry: Decade by Decade
4423:Greenberg A (14 May 2014).
4357:. IOS Press. pp. 4–5.
4285:Bullough VL (19 May 1995).
3984:10.1016/j.eprac.2022.03.010
3600:Gynecological Endocrinology
3467:Alternative Medicine Review
3208:10.1007/978-94-011-7230-1_5
2857:in 1936, and was the first
2802:, while Butenandt named it
2638:, some examples including:
1828:Enterohepatic recirculation
772:Tooltip Luteinizing hormone
578:relative binding affinities
475:. It is one of three major
417:270.366 g/mol
10:
8281:
7911:Noncompetitive inhibitors:
7536:Ethamoxytriphetol (MER-25)
6697:Dimestrol (dianisylhexene)
6456:Ethinylestradiol sulfonate
5115:16α-Hydroxyandrostenedione
5060:11β-Hydroxyandrostenedione
5045:11-Ketodihydrotestosterone
4485:Rooke T (1 January 2012).
3532:. In Pasqualini JR (ed.).
2838:, on the basis of its C17
2749:
2745:
2603:
2512:at the C3 position, and a
2385:
2053:
1267:Comprehensive overview of
697:the actions of estradiol.
535:menopausal hormone therapy
15:
8181:
8156:
8120:
7953:7β-Hydroxyepiandrosterone
7940:
7926:
7739:
7511:Desmethylchlorotrianisene
7392:
6690:Diethylstilbestrol esters
6643:Bisdehydrodoisynolic acid
6063:11β-Chloromethylestradiol
6038:7β-Hydroxyepiandrosterone
5927:
5920:Tooltip Estrogen receptor
5913:
5808:
5737:7β-Hydroxyepiandrosterone
5732:7α-Hydroxyepiandrosterone
5580:
5498:
5238:
5055:7β-Hydroxyepiandrosterone
5035:
5026:
4954:
4856:
4847:
4781:
4558:10.7326/0003-4819-7-3-330
4322:. Springer. pp. 7–.
4216:(8): 2055–61, quiz 2375.
4112:10.3390/curroncol29030144
4066:(7): 728–753. July 2017.
3703:10.1080/13697130500148875
3115:10.1016/j.bcp.2006.02.002
2965:10.1080/13697130500148875
2709:
2328:
2283:
2238:
2173:
2110:
1917:
1897:
1892:
1887:
1882:
1877:
1874:
1871:
1836:
1826:within 4 to 5 days.
1754:metabolic transformations
1204:Relative binding affinity
1191:
742:Tooltip Estrogen receptor
431:
377:
357:
332:
103:
95:
63:
53:
48:
39:
30:
8017:Fulvestrant (ICI-182780)
7834:Methylpiperidinopyrazole
7787:Fulvestrant (ICI-182780)
7270:Resorcylic acid lactones
6493:Hydroxyestrone diacetate
6429:Etamestrol (eptamestrol)
5622:5α-Dihydrocorticosterone
5563:Pregnanediol glucuronide
5225:Testosterone glucuronide
5185:Androsterone glucuronide
5125:16α-Hydroxy-DHEA sulfate
4994:18-Hydroxycorticosterone
4946:3α,5α-Tetrahydrocortisol
4871:5α-Dihydrocorticosterone
4523:. Wiley. pp. 345–.
3103:Biochemical Pharmacology
2869:(DHEA) was developed by
2350:metabolic clearance rate
1223:subcutaneously implanted
7328:Synthetic xenoestrogens
6885:Triphenylchloroethylene
6820:Methestrol dipropionate
6348:Polyestradiol phosphate
5857:11β-Hydroxyprogesterone
5852:11α-Hydroxyprogesterone
5528:20β-Dihydroprogesterone
5523:20α-Dihydroprogesterone
5518:17α-Hydroxyprogesterone
5513:16α-Hydroxyprogesterone
5441:Estradiol 3-glucuronide
4921:17α-Hydroxyprogesterone
4916:17α-Hydroxypregnenolone
4824:17α-Hydroxypregnenolone
4819:11β-Hydroxypregnenolone
4488:The Quest for Cortisone
3647:WikiJournal of Medicine
3436:10.1196/annals.1356.039
3237:Pharmacological Reviews
2877:in 1939 or 1940, and a
7421:4'-Hydroxynorendoxifen
7416:2-Phenylbenzothiophene
7290:zeranol (α-zearalanol)
6993:phlorizin (phloridzin)
6880:Triphenylbromoethylene
6779:ICI-85966 (Stilbostat)
6360:Estramustine phosphate
6233:Bolandiol dipropionate
5657:11-Deoxycorticosterone
5632:5β-Dihydroprogesterone
5627:5α-Dihydroprogesterone
5617:3β-Dihydroprogesterone
5612:3α-Dihydroprogesterone
5538:11-Deoxycorticosterone
5533:5α-Dihydroprogesterone
5175:Androstenediol sulfate
5155:5β-Dihydrotestosterone
4999:18-Hydroxyprogesterone
4979:11-Deoxycorticosterone
4876:11-Deoxycorticosterone
4829:21-Hydroxypregnenolone
3393:10.1530/acta.0.1010592
3290:Clinical Endocrinology
2867:dehydroepiandrosterone
2756:Estrone was the first
2679:Venous Thromboembolism
2644:venous thromboembolism
1756:shown in the diagram,
1272:
669:levels, inhibition of
639:menopausal replacement
570:subcutaneous injection
520:metabolic intermediate
7601:Miproxifene phosphate
7426:27-Hydroxycholesterol
6890:Triphenyliodoethylene
6434:Ethinylandrostenediol
6397:Estrogenic substances
6385:Polyestriol phosphate
6253:Cloxestradiol acetate
5847:7α-Hydroxycholesterol
5827:Calcidiol/Calcifediol
5456:Estradiol 17β-sulfate
5436:Estradiol glucuronide
5356:27-Hydroxycholesterol
4964:5α-Dihydroaldosterone
4809:-Dihydroxycholesterol
3660:10.15347/wjm/2014.005
3507:10.1210/jcem-62-3-536
3249:10.1124/pr.114.009712
2871:Hans Herloff Inhoffen
1311:and in certain other
1266:
471:, and a minor female
65:Systematic IUPAC name
6915:WAY-204688 (SIM-688)
6727:ERB-196 (WAY-202196)
6678:Dienestrol diacetate
6417:Estrone methyl ether
6323:Esterified estrogens
6265:Conjugated estrogens
6158:17β-Dihydroequilenin
6133:17α-Dihydroequilenin
6073:15α-Hydroxyestradiol
6068:11β-Methoxyestradiol
6043:8,9-Dehydroestradiol
5822:7-Dehydrocholesterol
5682:Pregnenolone sulfate
5230:Testosterone sulfate
5190:Androsterone sulfate
3381:Acta Endocrinologica
2853:was accomplished by
2606:Estrone (medication)
2580:of 1.23. Estrone is
1348:Mechanism of Action:
1300:into estrone by the
539:estrone (medication)
18:Estrone (medication)
8082:Propylpyrazoletriol
7997:Diarylpropionitrile
6845:Propylpyrazoletriol
6702:Dimethylstilbestrol
6668:Diarylpropionitrile
6478:Etynodiol diacetate
6178:Abiraterone acetate
6088:16α-Fluoroestradiol
5862:Cholesterol sulfate
5597:-Hydroxycholesterol
5489:estradiol palmitate
5471:Estriol glucuronide
5461:Estrone glucuronide
5431:Estradiol disulfate
5100:Dihydrotestosterone
5085:Dehydroandrosterone
5050:11-Ketotestosterone
4886:11-Ketoprogesterone
4800:-Hydroxycholesterol
3428:2005NYASA1057..506W
2855:Russell Earl Marker
2690:prothrombin-G20210A
2620:menopausal symptoms
2496:naturally occurring
1868:
1812:estrogen conjugates
1509:Estrone glucuronide
1396:estrone glucuronide
1388:estrogen conjugates
1234:Luteinizing hormone
727:
675:menopausal symptoms
663:luteinizing hormone
619:oral administration
564:. It is a far less
545:Biological activity
27:
8164:Diethylstilbestrol
7948:2-Methoxyestradiol
7879:TAS-108 (SR-16234)
7829:Methylepitiostanol
7767:EM-800 (SCH-57050)
7691:TAS-108 (SR-16234)
7411:2-Phenylbenzofuran
7025:8-prenylnaringenin
6685:Diethylstilbestrol
6343:Lipoidal estradiol
6318:ERA-63 (ORG-37663)
6260:Conjugated estriol
6205:methyltestosterone
6163:17β-Dihydroequilin
6138:17α-Dihydroequilin
6113:16β-Hydroxyestrone
6098:16α-Hydroxyestrone
6048:8,9-Dehydroestrone
6033:7α-Methylestradiol
6008:4-Methoxyestradiol
5998:4-Hydroxyestradiol
5973:3β-Hydroxytibolone
5968:3α-Hydroxytibolone
5938:2-Hydroxyestradiol
5485:estradiol stearate
5481:Lipoidal estradiol
5411:2-Methoxyestradiol
5336:16β-Hydroxyestrone
5331:16α-Hydroxyestrone
5321:4-Methoxyestradiol
5306:4-Hydroxyestradiol
5291:2-Hydroxyestradiol
5220:Epietiocholanolone
5165:3β-Etiocholanediol
5160:3α-Etiocholanediol
4956:Mineralocorticoids
4941:5α-Dihydrocortisol
3971:Endocrine Practice
3927:"Estrone -PubChem"
2859:chemical synthesis
2824:chemical structure
2231:<37–140 pmol/L
2191:<37–360 pmol/L
2019:<37–210 pmol/L
1841:
1784:See template page.
1731:metabolic pathways
1550:16α-Hydroxyestrone
1474:Metabolic pathways
1416:catechol estrogens
1406:, and can also be
1366:(SHBG) and 80% to
1273:
1208:estrogen receptors
1127:16α-Hydroxyestrone
995:4-Methoxyestradiol
973:4-Hydroxyestradiol
951:2-Methoxyestradiol
929:2-Hydroxyestradiol
700:
555:estrogen receptors
533:, for instance in
441:Infobox references
25:
8217:
8216:
8209:List of estrogens
8177:
8176:
7922:
7921:
7762:Cytestrol acetate
6985:isoliquiritigenin
6927:Unknown/unsorted:
6613:β-LGND2 (GTx-878)
6193:Anabolic steroids
6103:16α-Iodoestradiol
5993:4-Fluoroestradiol
5988:4-Androstenedione
5978:3β-Androstanediol
5953:3α-Androstanediol
5904:Estrogen receptor
5870:
5869:
5707:3α-Androstanediol
5576:
5575:
5451:Estradiol sulfate
5371:4-Androstenedione
5366:3β-Androstanediol
5361:3α-Androstanediol
5150:3β-Androstanediol
5140:3α-Androstanediol
5022:
5021:
4896:21-Deoxycortisone
4730:978-0-323-14206-9
4703:978-0-8018-8602-7
4667:978-3-642-58616-3
4633:978-1-4511-4847-3
4530:978-1-119-20247-9
4498:978-1-60917-326-5
4467:978-3-642-96158-8
4436:978-1-4381-0978-7
4402:978-0-8412-2690-6
4364:978-0-9673355-4-4
4329:978-3-319-28914-4
4298:978-0-465-07259-0
3842:10.1172/JCI103524
3810:978-3-642-49477-2
3772:978-1-4612-5525-3
3745:978-1-4557-1126-0
3697:(Suppl 1): 3–63.
3569:(13): 8118–8122.
3543:978-1-4200-5873-4
3217:978-94-011-7232-5
3184:978-3-642-96158-8
3109:(10): 1459–1469.
3041:978-94-011-7253-0
3010:978-1-285-40102-7
2959:(Suppl 1): 3–63.
2847:partial synthesis
2828:ketohydroxyestrin
2820:molecular formula
2636:contraindications
2630:Contraindications
2491:
2490:
2388:List of estrogens
2368:
2367:
2331:Notes and sources
2289:Follicular phase
2276:1100–7300 pmol/L
2244:Follicular phase
2179:Follicular phase
2114:Follicular phase
1791:
1790:
1400:sulfotransferases
1256:
1255:
1017:4-Fluoroestradiol
625:circumstances in
615:Clinical research
449:Chemical compound
447:
446:
301:CompTox Dashboard
145:Interactive image
8272:
8076:2,2',5'-PCB-4-OH
8012:Ethinylestradiol
7938:
7937:
7934:
7930:
7671:Rimostil (P-081)
7481:Chlorotrianisene
7403:
7399:
7178:Metalloestrogens
6957:-related (e.g.,
6772:Hexestrol esters
6446:Ethinylestradiol
6338:Estradiol esters
6093:16α-Hydroxy-DHEA
6078:16-Ketoestradiol
6018:5-Androstenediol
6013:4-Methoxyestrone
6003:4-Hydroxyestrone
5983:4-Androstenediol
5943:2-Hydroxyestrone
5925:
5924:
5921:
5917:
5897:
5890:
5883:
5874:
5873:
5637:Allopregnanolone
5553:Allopregnanediol
5426:4-Methoxyestriol
5421:2-Methoxyestriol
5416:2-Methoxyestrone
5401:16α-Hydroxy-DHEA
5376:5-Androstenediol
5341:16-Ketoestradiol
5326:4-Methoxyestrone
5316:4-Hydroxyestrone
5311:4-Hydroxyestriol
5301:2-Hydroxyestrone
5296:2-Hydroxyestriol
5205:Etiocholanedione
5170:Androstanetriols
5120:16α-Hydroxy-DHEA
5033:
5032:
4974:11-Deoxycortisol
4891:21-Deoxycortisol
4881:11-Deoxycortisol
4854:
4853:
4765:
4758:
4751:
4742:
4741:
4735:
4734:
4714:
4708:
4707:
4685:
4676:
4675:
4651:
4642:
4641:
4617:
4611:
4610:
4600:
4576:
4570:
4569:
4541:
4535:
4534:
4512:
4506:
4505:
4482:
4476:
4475:
4451:
4445:
4444:
4420:
4411:
4410:
4386:
4373:
4372:
4351:Parl FF (2000).
4348:
4337:
4336:
4313:
4307:
4306:
4282:
4273:
4272:
4270:
4268:
4245:
4236:
4235:
4225:
4201:
4195:
4194:
4193:
4191:
4169:
4160:
4159:
4157:
4155:
4149:academic.oup.com
4141:
4135:
4134:
4124:
4114:
4105:(3): 1744–1760.
4099:Current Oncology
4090:
4084:
4083:
4055:
4049:
4048:
4038:
4006:
3997:
3996:
3986:
3962:
3953:
3952:
3945:
3939:
3938:
3936:
3934:
3923:
3917:
3916:
3914:
3912:
3907:. ScienceLab.com
3906:
3898:
3889:
3888:
3877:
3864:
3863:
3853:
3836:(8): 1266–1278.
3821:
3815:
3814:
3788:
3777:
3776:
3756:
3750:
3749:
3729:
3723:
3722:
3688:
3679:
3673:
3672:
3662:
3638:
3632:
3631:
3595:
3589:
3588:
3578:
3554:
3548:
3547:
3525:
3519:
3518:
3489:
3483:
3482:
3462:
3456:
3455:
3411:
3405:
3404:
3376:
3365:
3364:
3347:(8): 1099–1106.
3335:
3322:
3321:
3284:
3271:
3270:
3260:
3228:
3222:
3221:
3195:
3189:
3188:
3168:
3162:
3161:
3133:
3127:
3126:
3098:
3087:
3086:
3076:
3052:
3046:
3045:
3024:
3015:
3014:
3000:Biology of Women
2994:
2985:
2984:
2948:
2849:of estrone from
2832:oxohydroxyestrin
2818:in general. The
2672:frailty syndrome
2640:hypersensitivity
2578:specific gravity
2560:molecular weight
2544:chemical formula
2474:
2473:
2463:
2455:
2447:
2439:
2432:
2431:
2419:
2412:
2405:
2393:
2362:
2256:700–3600 pmol/L
2211:699–1250 pmol/L
2076:3.1–12.2 nmol/L
2046:600–2500 pmol/L
1967:6.9–34.7 nmol/L
1912:
1905:
1885:production rate
1869:
1862:
1855:
1848:
1840:
1748:(e.g., estrone,
1733:involved in the
1724:
1723:
1713:
1708:
1706:
1699:
1688:
1686:
1679:
1677:
1670:
1668:
1655:
1653:
1646:
1644:
1631:
1629:
1623:
1616:
1614:
1607:
1605:
1598:
1596:
1583:
1576:
1569:
1559:
1557:4-Methoxyestrone
1552:
1545:
1543:2-Methoxyestrone
1535:
1533:4-Hydroxyestrone
1528:
1521:
1519:2-Hydroxyestrone
1511:
1504:
1497:
1488:
1487:
1468:
1461:
1454:
1442:
1424:4-hydroxyestrone
1420:2-hydroxyestrone
1231:
1201:
1198:
1171:2-Methoxyestriol
1149:2-Hydroxyestriol
1105:4-Methoxyestrone
1083:4-Hydroxyestrone
1061:2-Methoxyestrone
1039:2-Hydroxyestrone
792:
788:
784:
780:
773:
769:
751:
747:
743:
739:
728:
721:
714:
707:
699:
673:, and relief of
643:follicular phase
499:mainly from the
459:), also spelled
404:
398:
392:
385:Chemical formula
325:
324:
309:
307:
291:
271:
260:
246:
229:
218:
207:
187:
167:
147:
123:
44:
35:
28:
24:
8280:
8279:
8275:
8274:
8273:
8271:
8270:
8269:
8220:
8219:
8218:
8213:
8173:
8152:
8116:
7932:
7918:
7752:7β-Hydroxy-DHEA
7735:
7571:Levormeloxifene
7401:
7394:
7388:
7304:deoxymiroestrol
7172:-hinokiresinol)
6810:Methallenestril
6712:Doisynolic acid
6513:Methylestradiol
6028:7α-Hydroxy-DHEA
5919:
5909:
5901:
5871:
5866:
5837:Cholecalciferol
5804:
5785:Androstadienone
5757:Etiocholanolone
5727:7β-Hydroxy-DHEA
5722:7α-Hydroxy-DHEA
5667:Isopregnanolone
5662:Epipregnanolone
5572:
5494:
5476:Estriol sulfate
5466:Estrone sulfate
5396:7α-Hydroxy-DHEA
5234:
5210:Etiocholanolone
5180:Androstenetriol
5110:Epitestosterone
5105:Epiandrosterone
5075:Androstenedione
5018:
4950:
4858:Glucocorticoids
4849:Corticosteroids
4843:
4777:
4769:
4739:
4738:
4731:
4715:
4711:
4704:
4686:
4679:
4668:
4652:
4645:
4634:
4618:
4614:
4577:
4573:
4542:
4538:
4531:
4513:
4509:
4499:
4483:
4479:
4468:
4452:
4448:
4437:
4421:
4414:
4403:
4387:
4376:
4365:
4349:
4340:
4330:
4314:
4310:
4299:
4283:
4276:
4266:
4264:
4246:
4239:
4202:
4198:
4189:
4187:
4171:
4170:
4163:
4153:
4151:
4143:
4142:
4138:
4091:
4087:
4057:
4056:
4052:
4007:
4000:
3963:
3956:
3947:
3946:
3942:
3932:
3930:
3925:
3924:
3920:
3910:
3908:
3904:
3900:
3899:
3892:
3879:
3878:
3867:
3822:
3818:
3811:
3789:
3780:
3773:
3757:
3753:
3746:
3730:
3726:
3686:
3682:Kuhl H (2005).
3680:
3676:
3639:
3635:
3596:
3592:
3555:
3551:
3544:
3526:
3522:
3490:
3486:
3463:
3459:
3412:
3408:
3377:
3368:
3336:
3325:
3285:
3274:
3229:
3225:
3218:
3196:
3192:
3185:
3169:
3165:
3134:
3130:
3099:
3090:
3053:
3049:
3042:
3025:
3018:
3011:
2995:
2988:
2949:
2902:
2897:
2887:
2879:total synthesis
2834:, and the name
2780:Adolf Butenandt
2758:steroid hormone
2754:
2748:
2732:adverse effects
2728:
2712:
2707:
2698:
2686:factor V Leiden
2681:
2668:bone metastases
2656:
2632:
2616:hormone therapy
2608:
2602:
2595:
2586:carbon monoxide
2557:
2553:
2549:
2546:of estrone is C
2492:
2487:
2486:
2485:
2475:
2467:
2466:
2465:
2464:
2458:
2456:
2450:
2448:
2442:
2440:
2437:
2433:
2429:
2425:
2423:
2390:
2384:
2373:
2364:
2363:
2354:production rate
2334:
2332:
2279:400–2600 pg/mL
2259:250–1300 pg/mL
2240:Estrone sulfate
2146:310–660 pmol/L
2126:110–400 pmol/L
2103:0.7–2.8 nmol/L
2091:
2064:
2058:Androstenedione
2034:
2028:Estrone sulfate
2007:
1980:
1970:200–1000 ng/dL
1955:
1940:2.8–7.3 nmol/L
1928:
1922:Androstenedione
1895:clearance rate
1894:
1890:secretion rate
1889:
1884:
1879:
1866:
1839:
1816:estrone sulfate
1810:in the form of
1800:
1794:
1792:
1787:
1786:
1785:
1766:glucuronidation
1725:
1717:
1716:
1715:
1714:
1711:
1709:
1704:
1702:
1700:
1697:
1694:
1691:
1689:
1684:
1682:
1680:
1675:
1673:
1671:
1666:
1664:
1661:
1658:
1656:
1651:
1649:
1647:
1642:
1640:
1637:
1634:
1632:
1627:
1625:
1621:
1619:
1617:
1612:
1610:
1608:
1603:
1601:
1599:
1594:
1592:
1589:
1586:
1584:
1579:
1577:
1572:
1570:
1565:
1562:
1560:
1555:
1553:
1548:
1546:
1541:
1538:
1536:
1531:
1529:
1524:
1522:
1517:
1514:
1512:
1507:
1505:
1502:Estrone sulfate
1500:
1498:
1493:
1489:
1485:
1481:
1472:
1436:blood half-life
1412:cytochrome P450
1392:estrone sulfate
1380:
1360:
1349:
1315:, particularly
1290:androstenedione
1278:
1269:steroidogenesis
1261:
790:
782:
771:
749:
741:
725:
671:bone resorption
647:first trimester
629:women and with
547:
450:
443:
438:
407:
401:
395:
387:
373:
370:
365:
364:
353:
350:
349:
346:
340:
339:
328:
310:
303:
294:
274:
261:
249:
210:
190:
170:
150:
137:
126:
113:
99:
91:
90:
59:
21:
12:
11:
5:
8278:
8268:
8267:
8262:
8257:
8252:
8247:
8242:
8237:
8232:
8215:
8214:
8212:
8211:
8206:
8201:
8196:
8191:
8186:
8182:
8179:
8178:
8175:
8174:
8172:
8171:
8166:
8160:
8158:
8154:
8153:
8151:
8150:
8145:
8140:
8135:
8130:
8124:
8122:
8118:
8117:
8115:
8114:
8109:
8104:
8099:
8094:
8089:
8084:
8079:
8069:
8064:
8059:
8054:
8049:
8044:
8042:Hydroxytyrosol
8039:
8034:
8029:
8024:
8019:
8014:
8009:
8004:
7999:
7994:
7980:
7975:
7970:
7965:
7960:
7955:
7950:
7944:
7942:
7935:
7924:
7923:
7920:
7919:
7917:
7916:
7907:
7906:
7897:
7896:
7891:
7886:
7881:
7876:
7871:
7866:
7861:
7856:
7851:
7846:
7841:
7836:
7831:
7826:
7821:
7816:
7811:
7789:
7784:
7779:
7774:
7769:
7764:
7759:
7757:Chloroindazole
7754:
7749:
7743:
7741:
7737:
7736:
7734:
7733:
7728:
7723:
7718:
7713:
7708:
7703:
7698:
7693:
7688:
7683:
7678:
7676:Spironolactone
7673:
7668:
7663:
7658:
7653:
7648:
7643:
7638:
7633:
7628:
7623:
7618:
7613:
7608:
7603:
7598:
7593:
7588:
7583:
7578:
7573:
7568:
7563:
7558:
7553:
7548:
7543:
7538:
7533:
7528:
7523:
7518:
7513:
7508:
7503:
7498:
7493:
7488:
7483:
7478:
7473:
7468:
7463:
7458:
7453:
7448:
7443:
7438:
7433:
7428:
7423:
7418:
7413:
7407:
7405:
7390:
7389:
7387:
7386:
7377:Others (e.g.,
7375:
7325:
7311:
7297:
7267:
7249:
7227:
7185:
7175:
7153:
7148:
7105:liquiritigenin
7014:
7000:
6978:
6952:Xenoestrogens:
6948:
6947:
6942:
6937:
6932:
6923:
6922:
6917:
6912:
6907:
6902:
6897:
6892:
6887:
6882:
6877:
6872:
6867:
6862:
6857:
6852:
6847:
6842:
6837:
6832:
6827:
6825:Paroxypropione
6822:
6817:
6812:
6807:
6802:
6794:
6786:
6781:
6776:
6775:
6774:
6764:
6759:
6754:
6749:
6744:
6739:
6737:Estrobin (DBE)
6734:
6729:
6724:
6719:
6714:
6709:
6704:
6699:
6694:
6693:
6692:
6682:
6681:
6680:
6670:
6665:
6660:
6655:
6650:
6645:
6640:
6635:
6630:
6628:Allenolic acid
6625:
6620:
6615:
6610:
6605:
6600:
6595:
6586:
6585:
6580:
6575:
6570:
6565:
6560:
6555:
6550:
6545:
6540:
6535:
6533:Norethisterone
6530:
6525:
6523:Mytatrienediol
6520:
6515:
6510:
6505:
6500:
6495:
6490:
6485:
6480:
6475:
6470:
6468:Ethylestradiol
6465:
6463:Ethinylestriol
6460:
6459:
6458:
6453:
6443:
6442:
6441:
6431:
6426:
6425:
6424:
6419:
6414:
6412:Estrone esters
6404:
6399:
6394:
6389:
6388:
6387:
6382:
6380:Estriol esters
6372:
6367:
6365:Estrapronicate
6362:
6357:
6352:
6351:
6350:
6345:
6340:
6330:
6325:
6320:
6315:
6310:
6305:
6300:
6295:
6287:
6282:
6277:
6272:
6267:
6262:
6257:
6256:
6255:
6245:
6240:
6235:
6230:
6225:
6220:
6190:
6185:
6183:Alestramustine
6180:
6175:
6170:
6165:
6160:
6155:
6150:
6145:
6140:
6135:
6130:
6120:
6115:
6110:
6105:
6100:
6095:
6090:
6085:
6083:16-Ketoestrone
6080:
6075:
6070:
6065:
6060:
6055:
6050:
6045:
6040:
6035:
6030:
6025:
6020:
6015:
6010:
6005:
6000:
5995:
5990:
5985:
5980:
5975:
5970:
5965:
5960:
5955:
5950:
5945:
5940:
5931:
5929:
5922:
5911:
5910:
5900:
5899:
5892:
5885:
5877:
5868:
5867:
5865:
5864:
5859:
5854:
5849:
5840:
5839:
5834:
5829:
5824:
5812:
5810:
5806:
5805:
5803:
5802:
5800:Estratetraenol
5797:
5792:
5787:
5782:
5780:Androstadienol
5777:
5775:3β-Androstenol
5772:
5770:3α-Androstenol
5760:
5759:
5754:
5749:
5744:
5739:
5734:
5729:
5724:
5719:
5714:
5712:3α-Androstenol
5709:
5700:
5699:
5694:
5689:
5684:
5679:
5674:
5669:
5664:
5659:
5654:
5649:
5644:
5642:Corticosterone
5639:
5634:
5629:
5624:
5619:
5614:
5605:
5604:
5599:
5586:
5584:
5578:
5577:
5574:
5573:
5571:
5570:
5565:
5560:
5555:
5546:
5545:
5540:
5535:
5530:
5525:
5520:
5515:
5510:
5504:
5502:
5496:
5495:
5493:
5492:
5478:
5473:
5468:
5463:
5458:
5453:
5448:
5443:
5438:
5433:
5428:
5423:
5418:
5413:
5404:
5403:
5398:
5393:
5388:
5383:
5378:
5373:
5368:
5363:
5358:
5349:
5348:
5346:16-Ketoestrone
5343:
5338:
5333:
5328:
5323:
5318:
5313:
5308:
5303:
5298:
5293:
5288:
5283:
5278:
5273:
5268:
5263:
5258:
5253:
5244:
5242:
5236:
5235:
5233:
5232:
5227:
5222:
5217:
5212:
5207:
5202:
5197:
5192:
5187:
5182:
5177:
5172:
5167:
5162:
5157:
5152:
5147:
5142:
5133:
5132:
5127:
5122:
5117:
5112:
5107:
5102:
5097:
5092:
5087:
5082:
5077:
5072:
5070:Androstenediol
5067:
5062:
5057:
5052:
5047:
5041:
5039:
5030:
5024:
5023:
5020:
5019:
5017:
5016:
5011:
5009:Corticosterone
5006:
5001:
4996:
4991:
4986:
4981:
4976:
4971:
4966:
4960:
4958:
4952:
4951:
4949:
4948:
4943:
4934:
4933:
4928:
4923:
4918:
4913:
4908:
4903:
4901:Corticosterone
4898:
4893:
4888:
4883:
4878:
4873:
4868:
4862:
4860:
4851:
4845:
4844:
4842:
4841:
4836:
4831:
4826:
4821:
4816:
4811:
4802:
4793:
4787:
4785:
4779:
4778:
4768:
4767:
4760:
4753:
4745:
4737:
4736:
4729:
4709:
4702:
4677:
4666:
4643:
4632:
4612:
4591:(5): 362–366.
4571:
4536:
4529:
4507:
4497:
4477:
4466:
4446:
4435:
4412:
4401:
4374:
4363:
4338:
4328:
4308:
4297:
4274:
4237:
4196:
4161:
4136:
4085:
4050:
3998:
3977:(5): 528–562.
3954:
3940:
3918:
3890:
3865:
3816:
3809:
3778:
3771:
3751:
3744:
3724:
3674:
3633:
3606:(9): 747–749.
3590:
3549:
3542:
3520:
3501:(3): 536–541.
3484:
3457:
3422:(1): 506–524.
3406:
3387:(4): 592–596.
3366:
3323:
3296:(3): 241–249.
3272:
3243:(3): 505–540.
3223:
3216:
3190:
3183:
3163:
3144:(3): 130–138.
3128:
3088:
3047:
3040:
3016:
3009:
2986:
2899:
2898:
2896:
2893:
2885:
2875:Walter Hohlweg
2790:form from the
2747:
2744:
2727:
2726:Adverse effect
2724:
2711:
2708:
2706:
2703:
2697:
2694:
2680:
2677:
2655:
2652:
2631:
2628:
2604:Main article:
2601:
2598:
2593:
2590:carbon dioxide
2555:
2551:
2547:
2510:hydroxyl group
2489:
2488:
2469:
2468:
2435:
2434:
2427:
2426:
2422:
2421:
2414:
2407:
2399:
2398:
2397:
2396:
2391:
2383:
2380:
2371:
2366:
2365:
2345:secretion rate
2333:
2330:
2329:
2326:
2325:
2322:
2319:
2316:
2313:
2310:
2306:
2305:
2304:0.1–0.9 ng/mL
2302:
2299:
2296:
2293:
2290:
2287:
2281:
2280:
2277:
2274:
2271:
2270:Insignificant
2268:
2265:
2261:
2260:
2257:
2254:
2251:
2250:Insignificant
2248:
2245:
2242:
2236:
2235:
2232:
2229:
2226:
2225:Insignificant
2223:
2220:
2219:Postmenopause
2216:
2215:
2214:190–341 pg/mL
2212:
2209:
2206:
2203:
2200:
2196:
2195:
2192:
2189:
2186:
2183:
2180:
2177:
2171:
2170:
2167:
2166:22–230 pmol/L
2164:
2161:
2160:Insignificant
2158:
2155:
2154:Postmenopause
2151:
2150:
2147:
2144:
2141:
2138:
2135:
2131:
2130:
2127:
2124:
2121:
2118:
2115:
2112:
2108:
2107:
2104:
2101:
2098:
2095:
2092:
2089:
2087:
2081:
2080:
2077:
2074:
2071:
2068:
2065:
2062:
2060:
2055:
2051:
2050:
2049:200–900 pg/mL
2047:
2044:
2041:
2040:Insignificant
2038:
2035:
2032:
2030:
2024:
2023:
2020:
2017:
2014:
2011:
2008:
2005:
2003:
1997:
1996:
1993:
1992:37–250 pmol/L
1990:
1987:
1984:
1981:
1978:
1976:
1972:
1971:
1968:
1965:
1962:
1959:
1956:
1953:
1951:
1945:
1944:
1941:
1938:
1935:
1932:
1929:
1926:
1924:
1919:
1915:
1914:
1907:
1900:
1899:
1896:
1891:
1886:
1881:
1876:
1873:
1865:
1864:
1857:
1850:
1842:
1838:
1835:
1799:
1796:
1789:
1788:
1719:
1718:
1491:
1490:
1483:
1482:
1471:
1470:
1463:
1456:
1448:
1447:
1446:
1445:
1440:
1404:glucuronidases
1379:
1376:
1359:
1356:
1347:
1317:adipose tissue
1282:biosynthesized
1277:
1274:
1260:
1257:
1254:
1253:
1252:See template.
1219:ovariectomized
1189:
1188:
1185:
1182:
1179:
1176:
1173:
1167:
1166:
1163:
1160:
1157:
1154:
1151:
1145:
1144:
1141:
1138:
1135:
1132:
1129:
1123:
1122:
1119:
1116:
1113:
1110:
1107:
1101:
1100:
1097:
1094:
1091:
1088:
1085:
1079:
1078:
1075:
1072:
1069:
1066:
1063:
1057:
1056:
1053:
1050:
1047:
1044:
1041:
1035:
1034:
1031:
1028:
1025:
1022:
1019:
1013:
1012:
1009:
1006:
1003:
1000:
997:
991:
990:
987:
984:
981:
978:
975:
969:
968:
965:
962:
959:
956:
953:
947:
946:
943:
940:
937:
934:
931:
925:
924:
921:
918:
915:
912:
909:
903:
902:
899:
896:
893:
890:
887:
881:
880:
877:
874:
871:
868:
865:
859:
858:
855:
852:
849:
846:
843:
837:
836:
833:
830:
827:
824:
821:
819:Estradiol (E2)
815:
814:
811:
808:
805:
802:
799:
795:
794:
775:
764:
759:
756:Uterine weight
753:
734:
724:
723:
716:
709:
701:
546:
543:
526:of estradiol.
512:adipose tissue
448:
445:
444:
439:
435:standard state
432:
429:
428:
425:
419:
418:
415:
409:
408:
405:
399:
393:
388:
383:
380:
379:
375:
374:
372:
371:
368:
360:
359:
358:
355:
354:
352:
351:
347:
344:
343:
335:
334:
333:
330:
329:
327:
326:
313:
311:
299:
296:
295:
293:
292:
284:
282:
276:
275:
273:
272:
264:
262:
254:
251:
250:
248:
247:
239:
237:
231:
230:
220:
212:
211:
209:
208:
200:
198:
192:
191:
189:
188:
180:
178:
172:
171:
169:
168:
160:
158:
152:
151:
149:
148:
140:
138:
131:
128:
127:
125:
124:
116:
114:
109:
106:
105:
101:
100:
97:
93:
92:
68:
67:
61:
60:
57:
51:
50:
46:
45:
37:
36:
9:
6:
4:
3:
2:
8277:
8266:
8263:
8261:
8258:
8256:
8253:
8251:
8248:
8246:
8243:
8241:
8238:
8236:
8233:
8231:
8228:
8227:
8225:
8210:
8207:
8205:
8202:
8200:
8197:
8195:
8192:
8190:
8187:
8184:
8183:
8180:
8170:
8167:
8165:
8162:
8161:
8159:
8155:
8149:
8146:
8144:
8141:
8139:
8136:
8134:
8131:
8129:
8126:
8125:
8123:
8119:
8113:
8110:
8108:
8105:
8103:
8100:
8098:
8095:
8093:
8090:
8088:
8085:
8083:
8080:
8077:
8073:
8070:
8068:
8065:
8063:
8060:
8058:
8055:
8053:
8050:
8048:
8045:
8043:
8040:
8038:
8035:
8033:
8030:
8028:
8025:
8023:
8020:
8018:
8015:
8013:
8010:
8008:
8005:
8003:
8000:
7998:
7995:
7992:
7988:
7984:
7981:
7979:
7976:
7974:
7971:
7969:
7966:
7964:
7961:
7959:
7956:
7954:
7951:
7949:
7946:
7945:
7943:
7939:
7936:
7931:
7925:
7915:
7912:
7909:
7908:
7905:
7902:
7899:
7898:
7895:
7892:
7890:
7887:
7885:
7882:
7880:
7877:
7875:
7872:
7870:
7867:
7865:
7862:
7860:
7857:
7855:
7852:
7850:
7847:
7845:
7842:
7840:
7837:
7835:
7832:
7830:
7827:
7825:
7822:
7820:
7817:
7815:
7812:
7809:
7805:
7801:
7797:
7793:
7790:
7788:
7785:
7783:
7780:
7778:
7775:
7773:
7770:
7768:
7765:
7763:
7760:
7758:
7755:
7753:
7750:
7748:
7745:
7744:
7742:
7738:
7732:
7729:
7727:
7724:
7722:
7719:
7717:
7714:
7712:
7709:
7707:
7704:
7702:
7699:
7697:
7694:
7692:
7689:
7687:
7684:
7682:
7679:
7677:
7674:
7672:
7669:
7667:
7664:
7662:
7659:
7657:
7656:Pipendoxifene
7654:
7652:
7649:
7647:
7644:
7642:
7639:
7637:
7634:
7632:
7629:
7627:
7624:
7622:
7619:
7617:
7614:
7612:
7609:
7607:
7604:
7602:
7599:
7597:
7594:
7592:
7589:
7587:
7584:
7582:
7579:
7577:
7574:
7572:
7569:
7567:
7564:
7562:
7559:
7557:
7554:
7552:
7549:
7547:
7544:
7542:
7539:
7537:
7534:
7532:
7529:
7527:
7524:
7522:
7519:
7517:
7514:
7512:
7509:
7507:
7504:
7502:
7499:
7497:
7494:
7492:
7491:Clomifenoxide
7489:
7487:
7484:
7482:
7479:
7477:
7474:
7472:
7469:
7467:
7466:Brilanestrant
7464:
7462:
7459:
7457:
7454:
7452:
7449:
7447:
7444:
7442:
7439:
7437:
7434:
7432:
7429:
7427:
7424:
7422:
7419:
7417:
7414:
7412:
7409:
7408:
7406:
7400:
7391:
7384:
7380:
7376:
7373:
7369:
7365:
7361:
7357:
7353:
7349:
7345:
7341:
7337:
7333:
7329:
7326:
7323:
7319:
7315:
7312:
7309:
7305:
7302:-like (e.g.,
7301:
7298:
7295:
7291:
7287:
7283:
7279:
7275:
7271:
7268:
7265:
7261:
7257:
7253:
7250:
7247:
7246:guggulsterone
7243:
7239:
7235:
7231:
7230:Phytosteroids
7228:
7225:
7221:
7217:
7213:
7209:
7205:
7201:
7197:
7193:
7189:
7186:
7183:
7179:
7176:
7173:
7171:
7165:
7164:enterolactone
7161:
7157:
7154:
7152:
7149:
7146:
7142:
7138:
7134:
7130:
7126:
7122:
7118:
7114:
7110:
7106:
7102:
7098:
7094:
7090:
7086:
7082:
7078:
7074:
7070:
7066:
7062:
7058:
7054:
7050:
7046:
7042:
7038:
7034:
7030:
7026:
7022:
7018:
7015:
7012:
7008:
7004:
7001:
6998:
6997:wedelolactone
6994:
6990:
6986:
6982:
6979:
6976:
6975:photoanethole
6972:
6968:
6964:
6960:
6956:
6953:
6950:
6949:
6946:
6943:
6941:
6938:
6936:
6933:
6931:
6928:
6925:
6924:
6921:
6918:
6916:
6913:
6911:
6908:
6906:
6903:
6901:
6898:
6896:
6893:
6891:
6888:
6886:
6883:
6881:
6878:
6876:
6873:
6871:
6868:
6866:
6863:
6861:
6858:
6856:
6853:
6851:
6848:
6846:
6843:
6841:
6838:
6836:
6833:
6831:
6830:Pentafluranol
6828:
6826:
6823:
6821:
6818:
6816:
6813:
6811:
6808:
6806:
6803:
6801:
6799:
6795:
6793:
6791:
6787:
6785:
6782:
6780:
6777:
6773:
6770:
6769:
6768:
6765:
6763:
6760:
6758:
6755:
6753:
6750:
6748:
6745:
6743:
6740:
6738:
6735:
6733:
6730:
6728:
6725:
6723:
6720:
6718:
6715:
6713:
6710:
6708:
6705:
6703:
6700:
6698:
6695:
6691:
6688:
6687:
6686:
6683:
6679:
6676:
6675:
6674:
6671:
6669:
6666:
6664:
6661:
6659:
6656:
6654:
6651:
6649:
6646:
6644:
6641:
6639:
6636:
6634:
6631:
6629:
6626:
6624:
6621:
6619:
6616:
6614:
6611:
6609:
6606:
6604:
6601:
6599:
6596:
6594:
6591:
6590:Nonsteroidal:
6588:
6587:
6584:
6581:
6579:
6576:
6574:
6571:
6569:
6566:
6564:
6561:
6559:
6556:
6554:
6551:
6549:
6546:
6544:
6541:
6539:
6536:
6534:
6531:
6529:
6526:
6524:
6521:
6519:
6516:
6514:
6511:
6509:
6506:
6504:
6501:
6499:
6496:
6494:
6491:
6489:
6486:
6484:
6481:
6479:
6476:
6474:
6471:
6469:
6466:
6464:
6461:
6457:
6454:
6452:
6449:
6448:
6447:
6444:
6440:
6439:Ethandrostate
6437:
6436:
6435:
6432:
6430:
6427:
6423:
6420:
6418:
6415:
6413:
6410:
6409:
6408:
6405:
6403:
6400:
6398:
6395:
6393:
6390:
6386:
6383:
6381:
6378:
6377:
6376:
6373:
6371:
6368:
6366:
6363:
6361:
6358:
6356:
6353:
6349:
6346:
6344:
6341:
6339:
6336:
6335:
6334:
6331:
6329:
6326:
6324:
6321:
6319:
6316:
6314:
6311:
6309:
6306:
6304:
6301:
6299:
6296:
6294:
6292:
6288:
6286:
6283:
6281:
6278:
6276:
6273:
6271:
6268:
6266:
6263:
6261:
6258:
6254:
6251:
6250:
6249:
6248:Cloxestradiol
6246:
6244:
6241:
6239:
6236:
6234:
6231:
6229:
6226:
6224:
6221:
6218:
6214:
6210:
6206:
6202:
6198:
6194:
6191:
6189:
6186:
6184:
6181:
6179:
6176:
6174:
6171:
6169:
6166:
6164:
6161:
6159:
6156:
6154:
6151:
6149:
6146:
6144:
6141:
6139:
6136:
6134:
6131:
6128:
6124:
6123:17α-Estradiol
6121:
6119:
6116:
6114:
6111:
6109:
6106:
6104:
6101:
6099:
6096:
6094:
6091:
6089:
6086:
6084:
6081:
6079:
6076:
6074:
6071:
6069:
6066:
6064:
6061:
6059:
6056:
6054:
6051:
6049:
6046:
6044:
6041:
6039:
6036:
6034:
6031:
6029:
6026:
6024:
6021:
6019:
6016:
6014:
6011:
6009:
6006:
6004:
6001:
5999:
5996:
5994:
5991:
5989:
5986:
5984:
5981:
5979:
5976:
5974:
5971:
5969:
5966:
5964:
5961:
5959:
5956:
5954:
5951:
5949:
5946:
5944:
5941:
5939:
5936:
5933:
5932:
5930:
5926:
5923:
5918:
5912:
5908:
5905:
5898:
5893:
5891:
5886:
5884:
5879:
5878:
5875:
5863:
5860:
5858:
5855:
5853:
5850:
5848:
5845:
5842:
5841:
5838:
5835:
5833:
5830:
5828:
5825:
5823:
5820:
5818:
5814:
5813:
5811:
5807:
5801:
5798:
5796:
5793:
5791:
5788:
5786:
5783:
5781:
5778:
5776:
5773:
5771:
5768:
5766:
5762:
5761:
5758:
5755:
5753:
5750:
5748:
5745:
5743:
5740:
5738:
5735:
5733:
5730:
5728:
5725:
5723:
5720:
5718:
5715:
5713:
5710:
5708:
5705:
5702:
5701:
5698:
5695:
5693:
5690:
5688:
5685:
5683:
5680:
5678:
5675:
5673:
5670:
5668:
5665:
5663:
5660:
5658:
5655:
5653:
5650:
5648:
5645:
5643:
5640:
5638:
5635:
5633:
5630:
5628:
5625:
5623:
5620:
5618:
5615:
5613:
5610:
5607:
5606:
5603:
5600:
5598:
5596:
5591:
5588:
5587:
5585:
5583:
5582:Neurosteroids
5579:
5569:
5568:Pregnanetriol
5566:
5564:
5561:
5559:
5556:
5554:
5551:
5548:
5547:
5544:
5541:
5539:
5536:
5534:
5531:
5529:
5526:
5524:
5521:
5519:
5516:
5514:
5511:
5509:
5506:
5505:
5503:
5501:
5497:
5490:
5486:
5482:
5479:
5477:
5474:
5472:
5469:
5467:
5464:
5462:
5459:
5457:
5454:
5452:
5449:
5447:
5444:
5442:
5439:
5437:
5434:
5432:
5429:
5427:
5424:
5422:
5419:
5417:
5414:
5412:
5409:
5406:
5405:
5402:
5399:
5397:
5394:
5392:
5389:
5387:
5384:
5382:
5379:
5377:
5374:
5372:
5369:
5367:
5364:
5362:
5359:
5357:
5354:
5351:
5350:
5347:
5344:
5342:
5339:
5337:
5334:
5332:
5329:
5327:
5324:
5322:
5319:
5317:
5314:
5312:
5309:
5307:
5304:
5302:
5299:
5297:
5294:
5292:
5289:
5287:
5284:
5282:
5279:
5277:
5274:
5272:
5271:17α-Estradiol
5269:
5267:
5264:
5262:
5259:
5257:
5254:
5252:
5249:
5246:
5245:
5243:
5241:
5237:
5231:
5228:
5226:
5223:
5221:
5218:
5216:
5213:
5211:
5208:
5206:
5203:
5201:
5198:
5196:
5193:
5191:
5188:
5186:
5183:
5181:
5178:
5176:
5173:
5171:
5168:
5166:
5163:
5161:
5158:
5156:
5153:
5151:
5148:
5146:
5143:
5141:
5138:
5135:
5134:
5131:
5128:
5126:
5123:
5121:
5118:
5116:
5113:
5111:
5108:
5106:
5103:
5101:
5098:
5096:
5093:
5091:
5088:
5086:
5083:
5081:
5078:
5076:
5073:
5071:
5068:
5066:
5063:
5061:
5058:
5056:
5053:
5051:
5048:
5046:
5043:
5042:
5040:
5038:
5034:
5031:
5029:
5025:
5015:
5012:
5010:
5007:
5005:
5002:
5000:
4997:
4995:
4992:
4990:
4987:
4985:
4982:
4980:
4977:
4975:
4972:
4970:
4967:
4965:
4962:
4961:
4959:
4957:
4953:
4947:
4944:
4942:
4939:
4936:
4935:
4932:
4929:
4927:
4924:
4922:
4919:
4917:
4914:
4912:
4909:
4907:
4904:
4902:
4899:
4897:
4894:
4892:
4889:
4887:
4884:
4882:
4879:
4877:
4874:
4872:
4869:
4867:
4864:
4863:
4861:
4859:
4855:
4852:
4850:
4846:
4840:
4837:
4835:
4832:
4830:
4827:
4825:
4822:
4820:
4817:
4815:
4812:
4810:
4808:
4803:
4801:
4799:
4794:
4792:
4789:
4788:
4786:
4784:
4780:
4776:
4773:
4766:
4761:
4759:
4754:
4752:
4747:
4746:
4743:
4732:
4726:
4722:
4721:
4713:
4705:
4699:
4695:
4691:
4684:
4682:
4674:
4669:
4663:
4659:
4658:
4650:
4648:
4640:
4635:
4629:
4625:
4624:
4616:
4608:
4604:
4599:
4594:
4590:
4586:
4582:
4575:
4567:
4563:
4559:
4555:
4551:
4547:
4540:
4532:
4526:
4522:
4518:
4511:
4504:
4500:
4494:
4490:
4489:
4481:
4474:
4469:
4463:
4459:
4458:
4450:
4443:
4438:
4432:
4428:
4427:
4419:
4417:
4409:
4404:
4398:
4394:
4393:
4385:
4383:
4381:
4379:
4371:
4366:
4360:
4356:
4355:
4347:
4345:
4343:
4335:
4331:
4325:
4321:
4320:
4312:
4305:
4300:
4294:
4290:
4289:
4281:
4279:
4263:
4259:
4255:
4251:
4244:
4242:
4233:
4229:
4224:
4219:
4215:
4211:
4207:
4200:
4186:
4182:
4178:
4174:
4168:
4166:
4150:
4146:
4140:
4132:
4128:
4123:
4118:
4113:
4108:
4104:
4100:
4096:
4089:
4081:
4077:
4073:
4069:
4065:
4061:
4054:
4046:
4042:
4037:
4032:
4028:
4024:
4020:
4016:
4012:
4005:
4003:
3994:
3990:
3985:
3980:
3976:
3972:
3968:
3961:
3959:
3950:
3944:
3928:
3922:
3903:
3897:
3895:
3886:
3882:
3876:
3874:
3872:
3870:
3861:
3857:
3852:
3847:
3843:
3839:
3835:
3831:
3827:
3820:
3812:
3806:
3802:
3798:
3794:
3787:
3785:
3783:
3774:
3768:
3764:
3763:
3762:The Menopause
3755:
3747:
3741:
3737:
3736:
3728:
3720:
3716:
3712:
3708:
3704:
3700:
3696:
3692:
3685:
3678:
3670:
3666:
3661:
3656:
3652:
3648:
3644:
3637:
3629:
3625:
3621:
3617:
3613:
3609:
3605:
3601:
3594:
3586:
3582:
3577:
3572:
3568:
3564:
3560:
3553:
3545:
3539:
3535:
3531:
3524:
3516:
3512:
3508:
3504:
3500:
3496:
3488:
3480:
3476:
3472:
3468:
3461:
3453:
3449:
3445:
3441:
3437:
3433:
3429:
3425:
3421:
3417:
3410:
3402:
3398:
3394:
3390:
3386:
3382:
3375:
3373:
3371:
3362:
3358:
3354:
3350:
3346:
3342:
3334:
3332:
3330:
3328:
3319:
3315:
3311:
3307:
3303:
3299:
3295:
3291:
3283:
3281:
3279:
3277:
3268:
3264:
3259:
3254:
3250:
3246:
3242:
3238:
3234:
3227:
3219:
3213:
3209:
3205:
3201:
3194:
3186:
3180:
3176:
3175:
3167:
3159:
3155:
3151:
3147:
3143:
3139:
3132:
3124:
3120:
3116:
3112:
3108:
3104:
3097:
3095:
3093:
3084:
3080:
3075:
3070:
3066:
3062:
3058:
3051:
3043:
3037:
3033:
3032:
3023:
3021:
3012:
3006:
3002:
3001:
2993:
2991:
2982:
2978:
2974:
2970:
2966:
2962:
2958:
2954:
2947:
2945:
2943:
2941:
2939:
2937:
2935:
2933:
2931:
2929:
2927:
2925:
2923:
2921:
2919:
2917:
2915:
2913:
2911:
2909:
2907:
2905:
2900:
2892:
2889:
2888:
2882:
2880:
2876:
2872:
2868:
2864:
2860:
2856:
2852:
2848:
2843:
2841:
2837:
2833:
2829:
2825:
2821:
2817:
2813:
2809:
2805:
2801:
2797:
2793:
2789:
2785:
2781:
2778:
2775:
2771:
2767:
2763:
2759:
2753:
2743:
2741:
2737:
2733:
2723:
2721:
2717:
2702:
2696:Breastfeeding
2693:
2691:
2687:
2676:
2673:
2669:
2665:
2664:hypercalcemia
2661:
2660:breast cancer
2654:Breast Cancer
2651:
2649:
2648:boxed warning
2645:
2641:
2637:
2627:
2623:
2621:
2617:
2613:
2607:
2597:
2591:
2587:
2583:
2579:
2575:
2574:melting point
2571:
2568:
2565:
2561:
2545:
2540:
2538:
2537:
2531:
2530:
2528:
2522:
2518:
2515:
2511:
2507:
2503:
2500:
2497:
2483:
2479:
2461:
2453:
2445:
2420:
2415:
2413:
2408:
2406:
2401:
2400:
2395:
2394:
2389:
2379:
2375:
2374:
2361:See template.
2360:
2355:
2351:
2346:
2341:
2340:concentration
2337:
2327:
2323:
2321:19–45 nmol/L
2320:
2317:
2314:
2311:
2309:Luteal phase
2308:
2307:
2303:
2301:0.3–3 nmol/L
2300:
2297:
2294:
2291:
2288:
2286:
2282:
2278:
2275:
2272:
2269:
2266:
2264:Luteal phase
2263:
2262:
2258:
2255:
2252:
2249:
2246:
2243:
2241:
2237:
2233:
2230:
2227:
2224:
2221:
2218:
2217:
2213:
2210:
2207:
2204:
2201:
2199:Luteal phase
2198:
2197:
2193:
2190:
2187:
2184:
2181:
2178:
2176:
2172:
2168:
2165:
2162:
2159:
2156:
2153:
2152:
2149:80–180 pg/mL
2148:
2145:
2142:
2139:
2136:
2134:Luteal phase
2133:
2132:
2129:30–110 pg/mL
2128:
2125:
2122:
2119:
2116:
2113:
2109:
2105:
2102:
2099:
2096:
2093:
2088:
2086:
2083:
2082:
2079:89–350 ng/dL
2078:
2075:
2072:
2069:
2066:
2061:
2059:
2056:
2052:
2048:
2045:
2042:
2039:
2036:
2031:
2029:
2026:
2025:
2021:
2018:
2015:
2012:
2009:
2004:
2002:
1999:
1998:
1994:
1991:
1988:
1985:
1982:
1977:
1974:
1973:
1969:
1966:
1963:
1960:
1957:
1952:
1950:
1947:
1946:
1943:80–210 ng/dL
1942:
1939:
1936:
1933:
1930:
1925:
1923:
1920:
1916:
1908:
1902:
1901:
1870:
1863:
1858:
1856:
1851:
1849:
1844:
1843:
1834:
1831:
1829:
1825:
1821:
1817:
1813:
1809:
1805:
1795:
1783:
1779:
1775:
1771:
1767:
1763:
1759:
1755:
1751:
1747:
1744:
1740:
1736:
1732:
1728:
1707:
1695:
1692:
1687:
1678:
1669:
1662:
1659:
1654:
1645:
1638:
1635:
1630:
1624:
1615:
1606:
1597:
1590:
1587:
1582:
1581:16-Epiestriol
1575:
1568:
1567:17-Epiestriol
1563:
1558:
1551:
1544:
1539:
1534:
1527:
1520:
1515:
1510:
1503:
1496:
1479:
1475:
1469:
1464:
1462:
1457:
1455:
1450:
1449:
1444:
1443:
1439:
1437:
1433:
1429:
1425:
1421:
1417:
1414:enzymes into
1413:
1409:
1405:
1401:
1397:
1393:
1389:
1385:
1375:
1373:
1369:
1365:
1355:
1351:
1350:
1344:
1342:
1341:mammary gland
1338:
1334:
1330:
1326:
1322:
1318:
1314:
1310:
1306:
1303:
1299:
1295:
1291:
1287:
1283:
1270:
1265:
1251:
1247:
1243:
1239:
1235:
1227:
1226:osmotic pumps
1224:
1220:
1216:
1213:
1209:
1205:
1194:
1190:
1186:
1183:
1180:
1177:
1174:
1172:
1169:
1168:
1164:
1161:
1158:
1155:
1152:
1150:
1147:
1146:
1142:
1139:
1136:
1133:
1130:
1128:
1125:
1124:
1120:
1117:
1114:
1111:
1108:
1106:
1103:
1102:
1098:
1095:
1092:
1089:
1086:
1084:
1081:
1080:
1076:
1073:
1070:
1067:
1064:
1062:
1059:
1058:
1054:
1051:
1048:
1045:
1042:
1040:
1037:
1036:
1032:
1029:
1026:
1023:
1020:
1018:
1015:
1014:
1010:
1007:
1004:
1001:
998:
996:
993:
992:
988:
985:
982:
979:
976:
974:
971:
970:
966:
963:
960:
957:
954:
952:
949:
948:
944:
941:
938:
935:
932:
930:
927:
926:
922:
919:
916:
913:
910:
908:
907:17α-Estradiol
905:
904:
900:
897:
894:
891:
888:
886:
885:Estetrol (E4)
883:
882:
878:
875:
872:
869:
866:
864:
861:
860:
856:
853:
850:
847:
844:
842:
839:
838:
834:
831:
828:
825:
822:
820:
817:
816:
812:
809:
806:
803:
800:
797:
796:
789:
781:
776:
770:
765:
763:
760:
757:
754:
748:
740:
735:
733:
730:
729:
722:
717:
715:
710:
708:
703:
702:
698:
696:
693:
689:
688:
684:
680:
676:
672:
668:
664:
660:
656:
652:
648:
644:
640:
636:
632:
628:
627:premenopausal
624:
623:physiological
620:
616:
612:
610:
606:
602:
598:
594:
593:
588:
583:
579:
575:
571:
567:
563:
559:
556:
552:
542:
540:
536:
532:
527:
525:
521:
517:
513:
509:
506:
502:
498:
494:
490:
486:
482:
478:
474:
470:
466:
462:
458:
454:
442:
436:
430:
426:
424:
423:Melting point
421:
420:
416:
414:
411:
410:
389:
386:
382:
381:
376:
367:
366:
363:
356:
342:
341:
338:
331:
323:
319:
318:DTXSID4022367
315:
314:
312:
302:
298:
297:
290:
286:
285:
283:
281:
278:
277:
270:
266:
265:
263:
257:
253:
252:
245:
241:
240:
238:
236:
233:
232:
228:
224:
221:
219:
217:ECHA InfoCard
214:
213:
206:
202:
201:
199:
197:
194:
193:
186:
182:
181:
179:
177:
174:
173:
166:
162:
161:
159:
157:
154:
153:
146:
142:
141:
139:
135:
130:
129:
122:
118:
117:
115:
112:
108:
107:
102:
94:
88:
84:
80:
76:
72:
66:
62:
56:
52:
47:
43:
38:
34:
29:
23:
19:
8265:Sex hormones
7910:
7900:
7824:Mepitiostane
7772:Epitiostanol
7641:Ormeloxifene
7566:Lasofoxifene
7476:Camizestrant
7471:Broparestrol
7461:Bazedoxifene
7383:rotundifuran
7332:alkylphenols
7282:β-zearalenol
7278:α-zearalenol
7264:stigmasterol
7256:β-sitosterol
7252:Phytosterols
7220:triclocarban
7216:methoxychlor
7169:
7151:Lavender oil
7145:tectorigenin
7077:formononetin
6951:
6926:
6797:
6789:
6589:
6573:Quinestradol
6563:Promestriene
6538:Noretynodrel
6406:
6402:Estromustine
6355:Estramustine
6290:
6197:testosterone
5934:
5843:
5815:
5795:Androsterone
5790:Androstenone
5763:
5752:DHEA sulfate
5742:Androsterone
5704:Androstanes:
5703:
5687:Progesterone
5677:Pregnenolone
5672:Pregnanolone
5608:
5594:
5590:Cholestanes:
5589:
5558:Pregnanediol
5550:Metabolites:
5549:
5508:Progesterone
5500:Progestogens
5408:Metabolites:
5407:
5386:DHEA sulfate
5352:
5260:
5247:
5137:Metabolites:
5136:
5130:Testosterone
5095:DHEA sulfate
5080:Androsterone
5028:Sex steroids
4938:Metabolites:
4937:
4931:Progesterone
4926:Pregnenolone
4814:Pregnenolone
4806:
4797:
4719:
4712:
4693:
4690:"Beginnings"
4671:
4656:
4637:
4622:
4615:
4588:
4584:
4574:
4549:
4545:
4539:
4520:
4510:
4502:
4487:
4480:
4471:
4456:
4449:
4440:
4425:
4406:
4391:
4368:
4353:
4333:
4318:
4311:
4302:
4287:
4265:. Retrieved
4253:
4213:
4209:
4199:
4188:, retrieved
4176:
4152:. Retrieved
4148:
4139:
4102:
4098:
4088:
4063:
4059:
4053:
4021:(1): 11–20.
4018:
4014:
3974:
3970:
3943:
3931:. Retrieved
3921:
3909:. Retrieved
3884:
3833:
3829:
3819:
3792:
3761:
3754:
3734:
3727:
3694:
3690:
3677:
3650:
3646:
3636:
3603:
3599:
3593:
3566:
3562:
3552:
3533:
3523:
3498:
3494:
3487:
3473:(1): 36–41.
3470:
3466:
3460:
3419:
3415:
3409:
3384:
3380:
3344:
3340:
3293:
3289:
3240:
3236:
3226:
3199:
3193:
3173:
3166:
3141:
3137:
3131:
3106:
3102:
3067:(2): 86–89.
3064:
3060:
3050:
3029:
2999:
2956:
2952:
2890:
2884:
2883:
2844:
2835:
2831:
2827:
2816:sex hormones
2807:
2803:
2799:
2766:Edward Doisy
2755:
2736:hypertension
2729:
2713:
2705:Side effects
2699:
2682:
2657:
2633:
2624:
2609:
2541:
2535:
2533:
2526:
2524:
2520:
2506:double bonds
2493:
2438:Estrone (E1)
2376:
2370:
2369:
2358:
2353:
2349:
2344:
2339:
2335:
2285:Progesterone
2234:10–38 pg/mL
2194:10–98 pg/mL
2106:20–81 ng/dL
2085:Testosterone
2022:10–57 pg/mL
1995:10–70 pg/mL
1949:Testosterone
1878:Reproductive
1875:Sex hormone
1832:
1801:
1793:
1781:
1727:Description:
1726:
1712:unidentified
1698:unidentified
1693:
1690:
1660:
1657:
1636:
1633:
1588:
1585:
1561:
1537:
1525:
1513:
1408:hydroxylated
1381:
1361:
1358:Distribution
1352:
1346:
1345:
1294:intermediate
1279:
1276:Biosynthesis
1259:Biochemistry
1249:
1237:
1192:
863:Estriol (E3)
841:Estrone (E1)
685:
613:
590:
548:
528:
460:
456:
452:
451:
104:Identifiers
98:Oestrone; E1
96:Other names
86:
82:
78:
74:
70:
22:
8169:Zearalenone
8121:Antagonists
8097:Resveratrol
8062:Nonylphenol
8057:Niacinamide
7973:Bisphenol A
7963:Aldosterone
7792:Glyceollins
7740:Antagonists
7731:Zuclomifene
7726:Zindoxifene
7636:NNC 45-1506
7631:NNC 45-0781
7626:NNC 45-0320
7621:NNC 45-0095
7616:Nitromifene
7596:Miproxifene
7546:Fispemifene
7521:Enclomifene
7516:Droloxifene
7496:CN-55945-27
7441:Afimoxifene
7431:Acefluranol
7322:rhaponticin
7318:resveratrol
7314:Stilbenoids
7286:zearalenone
7274:zearalanone
7260:campesterol
7192:alternariol
7125:pinocembrin
7069:epicatechin
7041:biochanin A
6981:Chalconoids
6875:Terfluranol
6850:Quadrosilan
6722:Elacestrant
6623:Allenestrol
6498:Lynestrenol
6422:Estropipate
6392:Estrofurate
6243:Clomestrone
6223:Atrimustine
6173:Abiraterone
6127:alfatradiol
5717:7-Keto-DHEA
5602:Cholesterol
5391:7-Keto-DHEA
5004:Aldosterone
4791:Cholesterol
3933:6 September
3911:21 February
3691:Climacteric
2953:Climacteric
2863:cholesterol
2812:Nobel Prize
2788:crystalline
2786:estrone in
2770:Edgar Allen
2764:scientists
2720:anaphylaxis
2600:Medical use
2582:combustible
2567:crystalline
2324:6–14 ng/mL
2318:2100 L/day
2298:2100 L/day
2295:1.7 mg/day
2267:180 μg/day
2247:100 μg/day
2208:1200 L/day
2205:240 μg/day
2202:250 μg/day
2188:1200 L/day
2169:6–60 pg/mL
2163:1610 L/day
2143:2200 L/day
2140:150 μg/day
2137:260 μg/day
2123:2200 L/day
2117:110 μg/day
2094:190 μg/day
2073:2000 L/day
2070:2.8 mg/day
2067:3.2 mg/day
2016:1600 L/day
1989:2050 L/day
1986:110 μg/day
1983:150 μg/day
1961:6.2 mg/day
1958:6.5 mg/day
1937:2200 L/day
1934:1.6 mg/day
1931:2.8 mg/day
1802:Estrone is
1770:metabolites
1758:conjugation
1382:Estrone is
1372:circulation
1298:transformed
1286:cholesterol
1280:Estrone is
1244:(i.e., not
1175:0.01 ± 0.00
1109:0.13 ± 0.04
1065:0.01 ± 0.00
955:0.05 ± 0.04
762:Uterotrophy
679:hot flashes
655:transdermal
633:(non-oral)
587:transformed
493:cholesterol
489:synthesized
473:sex hormone
378:Properties
223:100.000.150
165:CHEBI:17263
8224:Categories
8112:Tectoridin
8092:Raloxifene
8067:Oleuropein
7914:Trilostane
7859:Prochloraz
7819:MDL-101906
7814:ICI-164384
7701:Trioxifene
7696:Toremifene
7666:Raloxifene
7651:Panomifene
7646:Ospemifene
7611:Nafoxidine
7501:Cyclofenil
7456:Arzoxifene
7436:Acolbifene
7368:phthalates
7336:bisphenols
7308:miroestrol
7212:methiocarb
7200:endosulfan
7188:Pesticides
7160:enterodiol
7141:tectoridin
7121:penduletin
7117:naringenin
7101:kaempferol
7017:Flavonoids
7011:psoralidin
7007:coumestrol
7003:Coumestans
6967:dianethole
6920:WAY-214156
6910:WAY-200070
6905:WAY-169916
6900:WAY-166818
6870:SKF-82,958
6835:Phenestrol
6815:Methestrol
6800:-Hexestrol
6792:-Butestrol
6673:Dienestrol
6653:Carbestrol
6638:Bifluranol
6633:Benzestrol
6578:Quinestrol
6528:Nilestriol
6370:Estrazinol
6303:Epimestrol
6293:-Estradiol
6275:Cyclotriol
6213:nandrolone
6188:Almestrone
6023:7-Oxo-DHEA
5935:Steroidal:
5907:modulators
5832:Calcitriol
5765:Pheromones
5609:Pregnanes:
4783:Precursors
4772:Endogenous
4552:(3): 330.
4442:chemistry.
4254:StatPearls
4250:"Estrogen"
3881:"Estrogen"
2895:References
2865:by way of
2851:ergosterol
2808:folliculin
2777:biochemist
2750:See also:
2386:See also:
2315:24 mg/day
2312:25 mg/day
2273:146 L/day
2253:146 L/day
2228:910 L/day
2185:80 μg/day
2182:90 μg/day
2157:40 μg/day
2120:80 μg/day
2100:500 L/day
2097:60 μg/day
2043:167 L/day
2037:80 μg/day
2013:50 μg/day
2010:60 μg/day
1964:950 L/day
1741:and other
1735:metabolism
1384:conjugated
1378:Metabolism
1325:reversibly
1246:endogenous
1238:Footnotes:
774:levels (%)
695:antagonize
631:parenteral
601:prohormone
531:medication
524:metabolite
477:endogenous
413:Molar mass
289:2DI9HA706A
196:ChemSpider
185:ChEMBL1405
132:3D model (
111:CAS Number
55:IUPAC name
8245:Estrogens
8107:Tamoxifen
8087:Quercetin
8027:Genistein
8007:Estradiol
7991:o',p'-DDE
7894:ZK-191703
7889:ZK-164015
7849:Phenytoin
7747:(R,R)-THC
7686:Tamoxifen
7661:Promensil
7586:LY-117018
7561:Idoxifene
7556:ICI-55548
7541:Femarelle
7526:Endoxifen
7486:Clomifene
7242:diosgenin
7238:digitalis
7234:digitoxin
7224:triclosan
7204:fenarimol
7137:quercetin
7113:myricetin
7109:mirificin
7097:glycitein
7089:genistein
7085:glabridin
7045:calycosin
7033:baicalein
6989:phloretin
6945:ZK-283197
6805:Mestilbol
6767:Hexestrol
6742:Fenestrel
6717:Efavirenz
6648:Butestrol
6603:2,8-DHHHC
6598:(S,S)-THC
6593:(R,R)-THC
6548:Pentolame
6543:Orestrate
6518:Moxestrol
6508:Mestranol
6473:Etynodiol
6333:Estradiol
6308:Equilenin
6270:Cyclodiol
6228:Bolandiol
5817:Vitamin D
5256:Estradiol
5248:Estranes:
5240:Estrogens
5037:Androgens
4911:Cortisone
4566:0003-4819
4060:Menopause
4015:Menopause
3669:2002-4436
3061:Maturitas
2740:vaginitis
2588:(CO) and
2572:, with a
2476:Note the
2444:Estradiol
2382:Chemistry
2372:Toxicity:
2292:2 mg/day
2222:6 μg/day
2175:Estradiol
2001:Estradiol
1893:Metabolic
1798:Excretion
1762:sulfation
1746:estrogens
1739:estradiol
1495:Estradiol
1480:in humans
1478:estradiol
1305:aromatase
1242:Synthetic
1232:levels =
1153:0.9 ± 0.3
1131:2.8 ± 1.0
1043:1.9 ± 0.8
999:1.3 ± 0.2
911:4.2 ± 0.8
889:0.5 ± 0.2
692:partially
683:cell-free
651:pregnancy
597:precursor
541:article.
516:precursor
508:androgens
481:estradiol
467:, a weak
8240:Estranes
8185:See also
7987:p,p'-DDT
7978:Daidzein
7968:Atrazine
7941:Agonists
7869:RU-58668
7864:RU-39411
7711:U-11555A
7706:TZE-5323
7451:Anordrin
7446:Anordiol
7379:agnuside
7356:parabens
7196:dieldrin
7168:nyasol (
7133:puerarin
7129:prunetin
7093:genistin
7081:glabrene
7053:daidzein
7049:catechin
7037:baicalin
7029:apigenin
6959:anethole
6747:FERb 033
6583:Tibolone
6568:RU-16117
6553:Prodiame
6488:Hippulin
6483:Hexolame
6328:Estetrol
6238:Butolame
5928:Agonists
5543:5α-DHDOC
5251:Estetrol
5014:Cortisol
4906:Cortisol
4775:steroids
4607:18744783
4262:30855848
4232:21659542
4185:30000354
4131:35323344
4080:28650869
4045:28816933
3993:35569886
3860:13463090
3719:24616324
3711:16112947
3628:13617050
3620:26190536
3479:15771561
3452:38877163
3444:16399916
3318:26077537
3267:26023144
3158:12071379
3123:16554039
3083:19766414
2981:24616324
2973:16112947
2886:Approval
2804:progynon
2796:pregnant
2784:purified
2772:and the
2762:American
2716:jaundice
2612:injected
2558:and its
2478:hydroxyl
2460:Estetrol
2359:Sources:
2111:Estrone
1975:Estrone
1814:such as
1804:excreted
1782:Sources:
1774:hydroxyl
1426:or into
1418:such as
1390:such as
1321:secreted
1250:Sources:
1181:Inactive
1143:<0.5
1134:552 ± 42
1071:Inactive
1049:Inactive
1021:180 ± 43
961:Inactive
895:Inactive
870:468 ± 30
848:490 ± 22
826:506 ± 20
732:Estrogen
687:in-vitro
677:such as
497:secreted
469:estrogen
461:oestrone
26:Estrone
8260:Ketones
8235:Phenols
8230:Sterols
8157:Unknown
8133:Estriol
8037:GPER-L2
8032:GPER-L1
7716:U-11634
7591:Menerba
7581:LN-2299
7576:LN-1643
7551:GW-7604
7506:D-15413
7338:(e.g.,
7330:(e.g.,
7316:(e.g.,
7300:Steroid
7272:(e.g.,
7254:(e.g.,
7232:(e.g.,
7190:(e.g.,
7182:cadmium
7180:(e.g.,
7158:(e.g.,
7156:Lignans
7057:daidzin
7021:7,8-DHF
7019:(incl.
7005:(e.g.,
6983:(e.g.,
6865:SERBA-2
6860:SC-4289
6855:SC-3296
6762:GTx-758
6658:D-15414
6608:β-LGND1
6558:Prolame
6407:Estrone
6375:Estriol
6313:Equilin
6195:(e.g.,
6108:16α-LE2
5844:Others:
5483:(e.g.,
5353:Others:
5266:Estriol
5261:Estrone
4598:1659459
4473:(1933).
4267:31 July
4190:31 July
4154:31 July
4122:8947022
4036:5734988
3885:PubChem
3851:1072719
3585:6863280
3515:3080464
3424:Bibcode
3401:6818806
3361:2992279
3310:2512035
3258:4485017
3031:Society
2836:estrone
2800:theelin
2746:History
2521:estrone
2502:steroid
2499:estrane
2452:Estriol
1888:Gonadal
1820:labeled
1760:(e.g.,
1750:estriol
1743:natural
1705:17β-HSD
1595:17β-HSD
1574:Estriol
1526:Estrone
1428:estriol
1370:in the
1368:albumin
1313:tissues
1215:cytosol
1212:uterine
1210:of rat
1068:103 ± 7
1052:110–142
1046:130 ± 9
977:45 ± 12
936:285 ± 8
798:Control
659:potency
607:of the
592:in vivo
574:estriol
553:of the
551:agonist
505:adrenal
485:estriol
465:steroid
463:, is a
453:Estrone
256:PubChem
121:53-16-7
8052:Niacin
8047:Kepone
7904:ERX-11
7874:SS1020
7782:ERB-88
7777:ERA-90
7681:SS1010
7606:MRL-37
6971:dianol
6940:ERB-79
6935:ERA-45
6930:ERB-26
6663:DCW234
6618:AC-186
6285:DHEA-S
6217:esters
6201:esters
6053:8β-VE2
5809:Others
4805:20α,22
4727:
4700:
4664:
4630:
4605:
4595:
4564:
4527:
4495:
4464:
4433:
4399:
4361:
4326:
4295:
4260:
4230:
4183:
4129:
4119:
4078:
4043:
4033:
3991:
3858:
3848:
3807:
3769:
3742:
3717:
3709:
3667:
3626:
3618:
3583:
3540:
3513:
3477:
3450:
3442:
3399:
3359:
3316:
3308:
3265:
3255:
3214:
3181:
3156:
3121:
3081:
3038:
3007:
2979:
2971:
2840:ketone
2774:German
2738:, and
2718:, and
2710:Common
2570:powder
2514:ketone
2482:groups
2480:(–OH)
2336:Notes:
2054:Women
1913:units
1906:units
1880:phase
1837:Levels
1778:groups
1776:(–OH)
1676:CYP450
1652:CYP450
1643:CYP450
1628:UGT1A9
1622:UGT1A3
1339:, and
1337:uterus
1309:gonads
1302:enzyme
1292:as an
1193:Notes:
1087:11 ± 4
1074:95–100
933:24 ± 7
867:10 ± 4
845:11 ± 8
635:routes
605:ligand
566:potent
501:gonads
427:254.5
362:SMILES
244:D00067
176:ChEMBL
49:Names
8128:CCL18
8002:Equol
7884:ZB716
7854:PHTPP
7721:Y-134
7398:SERMs
7393:Mixed
7073:equol
6955:Anise
6784:M2613
5697:THDOC
5652:DHDOC
4210:Blood
3905:(PDF)
3715:S2CID
3687:(PDF)
3653:(1).
3624:S2CID
3448:S2CID
3314:S2CID
2977:S2CID
2792:urine
2730:Some
2564:solid
2517:group
2504:with
2338:"The
1883:Blood
1824:feces
1808:urine
1432:liver
1386:into
1333:liver
1284:from
1118:65–92
1096:21–50
942:31–61
832:12–19
491:from
337:InChI
156:ChEBI
134:JSmol
8148:MIBE
8143:G-36
8138:G-15
8072:PCBs
7929:GPER
7839:MIBE
7372:PCBs
7364:PHBA
7360:PBBs
7208:HPTE
7065:EGCG
6963:anol
6798:meso
6790:meso
6280:DHEA
6215:and
6199:and
5747:DHEA
5381:DHEA
5090:DHEA
4725:ISBN
4698:ISBN
4662:ISBN
4628:ISBN
4603:PMID
4562:ISSN
4525:ISBN
4493:ISBN
4462:ISBN
4431:ISBN
4397:ISBN
4359:ISBN
4324:ISBN
4293:ISBN
4269:2023
4258:PMID
4228:PMID
4192:2023
4181:PMID
4156:2023
4127:PMID
4076:PMID
4041:PMID
3989:PMID
3935:2009
3913:2013
3856:PMID
3805:ISBN
3767:ISBN
3740:ISBN
3707:PMID
3665:ISSN
3616:PMID
3581:PMID
3538:ISBN
3511:PMID
3475:PMID
3440:PMID
3420:1057
3397:PMID
3357:PMID
3306:PMID
3263:PMID
3212:ISBN
3179:ISBN
3154:PMID
3119:PMID
3079:PMID
3036:ISBN
3005:ISBN
2969:PMID
2873:and
2768:and
2688:and
2666:and
2618:for
2542:The
2527:estr
2462:(E4)
2454:(E3)
2446:(E2)
1918:Men
1909:Non-
1872:Sex
1764:and
1729:The
1685:COMT
1667:COMT
1422:and
1402:and
1394:and
1140:7–24
1077:120
967:130
876:8–18
835:100
793:(%)
779:SHBG
665:and
560:and
495:and
483:and
280:UNII
269:5870
235:KEGG
205:5660
81:,11a
8102:STX
8022:G-1
7983:DDT
7804:III
7352:DDT
7350:),
7348:BPS
7344:BPF
7340:BPA
7240:),
7170:cis
7061:ECG
6291:ent
5692:THB
5647:DHC
4593:PMC
4554:doi
4218:doi
4214:118
4117:PMC
4107:doi
4068:doi
4031:PMC
4023:doi
3979:doi
3846:PMC
3838:doi
3797:doi
3699:doi
3655:doi
3608:doi
3571:doi
3567:258
3503:doi
3432:doi
3389:doi
3385:101
3349:doi
3345:152
3298:doi
3253:PMC
3245:doi
3204:doi
3146:doi
3111:doi
3069:doi
2961:doi
2830:or
2794:of
2596:).
2592:(CO
2536:one
2534:ket
1806:in
1737:of
1613:STS
1604:EST
1476:of
1410:by
1398:by
1206:to
1200:RBA
1156:302
1137:+++
1121:12
1112:338
1099:35
1090:351
1027:+++
1002:260
958:101
945:28
873:+++
857:20
851:+++
829:+++
823:100
810:100
804:100
787:RBA
758:(%)
752:(%)
746:RBA
649:of
599:or
562:ERβ
558:ERα
518:or
510:in
306:EPA
259:CID
77:,9b
73:,3b
69:(3a
8226::
7989:,
7808:IV
7806:,
7802:,
7800:II
7798:,
7381:,
7370:,
7366:,
7362:,
7358:,
7354:,
7346:,
7342:,
7334:,
7320:,
7306:,
7292:,
7288:,
7284:,
7280:,
7276:,
7262:,
7258:,
7244:,
7222:,
7218:,
7214:,
7210:,
7206:,
7202:,
7198:,
7194:,
7166:,
7162:,
7143:,
7139:,
7135:,
7131:,
7127:,
7123:,
7119:,
7115:,
7111:,
7107:,
7103:,
7099:,
7095:,
7091:,
7087:,
7083:,
7079:,
7075:,
7071:,
7067:,
7063:,
7059:,
7055:,
7051:,
7047:,
7043:,
7039:,
7035:,
7031:,
7027:,
7023:,
7009:,
6995:,
6991:,
6987:,
6973:,
6969:,
6965:,
6961:,
6211:,
6207:,
6203:,
5916:ER
5593:24
5487:,
4796:22
4692:.
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4670:.
4646:^
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3251:.
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3140:.
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1911:SI
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1228:.
1202:=
1197:ER
1187:4
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1093:++
1055:8
1033:?
1011:9
1005:++
989:?
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879:3
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768:LH
738:ER
457:E1
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2006:–
1979:–
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