38:
617:
594:
916:
29:
6692:
1155:, and profound gonadotoxicity. Other side effects may include easy bruising/bleeding, joint pain, mouth sores, slow-healing existing wounds, unusual decrease in the amount of urine or unusual tiredness or weakness. Potential side effects also include leukopenia, infection, bladder toxicity, and cancer.
1567:
Phosphoramide mustard, one of the principal toxic metabolites of cyclophosphamide, was synthesized and reported by
Friedman and Seligman in 1954 ...It was postulated that the presence of the phosphate bond to the nitrogen atom could inactivate the nitrogen mustard moiety, but the phosphate bond would
3709:
Gross R, Wulf G (1959). "Klinische und experimentelle
Erfahrungen mit zyk lischen und nichtzyklischen Phosphamidestern des N-Losl in der Chemotherapie von Tumoren" [Clinical and experimental experiences with metallic cyclical and non-cyclical Phosphamidestern the N-losl in the chemotherapy of
1517:
that does not give rise to the toxic metabolites phosphoramide mustard and acrolein. This is because carboxycyclophosphamide cannot undergo β-elimination (the carboxylate acts as an electron-donating group, nullifying the potential for transformation), preventing nitrogen mustard activation and
1350:(where the cumulative dose is typically less than 20 grams of cyclophosphamide) carries an AML risk of less than 1/2000, with some studies finding no increased risk compared to background. Other treatment regimens involving higher doses may carry risks of 1–2% or higher.
2986:
Radis CD, Kahl LE, Baker GL, Wasko MC, Cash JM, Gallatin A, Stolzer BL, Agarwal AK, Medsger TA, Kwoh CK (August 1995). "Effects of cyclophosphamide on the development of malignancy and on long-term survival of patients with rheumatoid arthritis. A 20-year followup study".
1405:. A small proportion of aldophosphamide freely diffuses into cells, where it is decomposed into two compounds, phosphoramide mustard and acrolein. The active metabolites of cyclophosphamide are highly protein bound and distributed to all tissues, are assumed to cross the
1216:(sodium 2-mercaptoethane sulfonate), a sulfhydryl donor which binds and detoxifies acrolein. Intermittent dosing of cyclophosphamide decreases cumulative drug dose, reduces bladder exposure to acrolein and has equal efficacy to daily treatment in the management of
903:. It is used to quickly control the disease. Due to its toxicity, it is replaced as soon as possible by less toxic drugs. Regular and frequent laboratory evaluations are required to monitor kidney function, avoid drug-induced bladder complications and screen for
1625:
Because of its impact on the immune system, it is used in animal studies. Rodents are injected intraperitoneally with either a single dose of 150 mg/kg or two doses (150 and 100 mg/kg) spread over two days. This can be used for applications such as:
1181:
when compounded by intravenous fluids administered to prevent drug-induced cystitis. While SIADH has been described primarily with higher doses of cyclophosphamide, it can also occur with the lower doses used in the management of inflammatory disorders.
1592:
Oncology). Brock and his team synthesised and screened more than 1,000 candidate oxazaphosphorine compounds. They converted the base nitrogen mustard into a nontoxic "transport form". This transport form was a prodrug, subsequently
1568:
be cleaved in gastric cancers and other tumors which had a high phosphamidase content. However, in studies carried out after the clinical efficacy of cyclophosphamide was demonstrated, phosphoramide mustard proved to be cytotoxic
1634:
may be concerned about potential human pathogenicity of an engineered microbe when conducting an MCAN review. Particularly for bacteria with potential consumer exposure they require testing of the microbe on immuno-compromised
1353:
Cyclophosphamide-induced AML, when it happens, typically presents some years after treatment, with incidence peaking around 3–9 years. After nine years, the risk falls to background. When AML occurs, it is often preceded by a
1419:
Cyclophosphamide metabolites are primarily excreted in the urine unchanged, and drug dosing should be appropriately adjusted in the setting of renal dysfunction. Drugs altering hepatic microsomal enzyme activity (e.g.,
1436:) may result in accelerated metabolism of cyclophosphamide into its active metabolites, increasing both pharmacologic and toxic effects of the drug; alternatively, drugs that inhibit hepatic microsomal enzymes (e.g.
3310:
Donelli MG, Bartosek I, Guaitani A, Martini A, Colombo T, Pacciarini MA, Modica R (April 1976). "Importance of pharmacokinetic studies on cyclophosphamide (NSC-26271) in understanding its cytotoxic effect".
2575:
Salido M, Macarron P, Hernández-García C, D'Cruz DP, Khamashta MA, Hughes GR (2003). "Water intoxication induced by low-dose cyclophosphamide in two patients with systemic lupus erythematosus".
2748:
Pryor BD, Bologna SG, Kahl LE (September 1996). "Risk factors for serious infection during treatment with cyclophosphamide and high-dose corticosteroids for systemic lupus erythematosus".
1601:
converted into the active, toxic form. The first clinical trials were published at the end of the 1950s. In 1959 it became the eighth cytotoxic anticancer agent to be approved by the
3461:
Kohn FR, Sladek NE (October 1985). "Aldehyde dehydrogenase activity as the basis for the relative insensitivity of murine pluripotent hematopoietic stem cells to oxazaphosphorines".
1275:
in males and females, the likelihood of which increases with cumulative drug dose and increasing patient age. Such infertility is usually temporary, but can be permanent. The use of
256:
5678:
2666:
Monach PA, Arnold LM, Merkel PA (January 2010). "Incidence and prevention of bladder toxicity from cyclophosphamide in the treatment of rheumatic diseases: a data-driven review".
6623:
3789:"Neutropenia induced in outbred mice by a simplified low-dose cyclophosphamide regimen: characterization and applicability to diverse experimental models of infectious diseases"
2783:
Suryaprasad A, Stone JH (July 2008). "When is it safe to stop
Pneumocystis jiroveci pneumonia prophylaxis? Insights from three cases complicating autoimmune diseases".
5899:
5889:
2322:
Singh G, Fries JF, Williams CA, Zatarain E, Spitz P, Bloch DA (February 1991). "Toxicity profiles of disease modifying antirheumatic drugs in rheumatoid arthritis".
5534:
3523:
Sistigu A, Viaud S, Chaput N, Bracci L, Proietti E, Zitvogel L (July 2011). "Immunomodulatory effects of cyclophosphamide and implementations for vaccine design".
3426:
Hall AG, Tilby MJ (September 1992). "Mechanisms of action of, and modes of resistance to, alkylating agents used in the treatment of haematological malignancies".
1174:
1551:
of recipient hosts (for donor T cells) has been used to enhance immunity in naïve hosts, and to enhance adoptive T cell immunotherapy regimens, as well as active
5714:
5904:
6752:
3406:
211:
5671:
1279:
in women of reproductive age before administration of intermittently dosed cyclophosphamide may diminish the risks of premature menopause and infertility.
5884:
3496:
Friedman OM, Wodinsky I, Myles A (April 1976). "Cyclophosphamide (NSC-26271)-related phosphoramide mustards- recent advances and historical perspective".
3839:"EPA: Notifications, FY 1998 to Present - Biotechnology Program under the Toxic Substances Control Act (TSCA) | New Chemicals Program | US EPA"
3226:
Giraud B, Hebert G, Deroussent A, Veal GJ, Vassal G, Paci A (August 2010). "Oxazaphosphorines: new therapeutic strategies for an old class of drugs".
6553:
3946:
1475:
The main effect of cyclophosphamide is due to its metabolite phosphoramide mustard. This metabolite is only formed in cells that have low levels of
5664:
2386:"Risk of serious infections with immunosuppressive drugs and glucocorticoids for lupus nephritis: a systematic review and network meta-analysis"
1335:(therapy-related AML, or "t-AML") is thought to occur either by cyclophosphamide-inducing mutations or selecting for a high-risk myeloid clone.
955:, and although concerns about toxicity restrict its use to patients with severe disease, it remains an important treatment for life-threatening
5754:
1655:
5924:
5729:
3381:
Vigouroux D, Voltaire L (1995). "" [Prolonged neuromuscular block induced by mivacurium in a patient treated with cyclophosphamide].
2042:"Comparative effectiveness of immunosuppressive drugs and corticosteroids for lupus nephritis: a systematic review and network meta-analysis"
1631:
135:
6573:
5594:
4646:
719:
6065:
5944:
5824:
4475:
4455:
4440:
3659:
3642:
1089:
D) except for life-threatening circumstances in the mother. Additional relative contraindications to the use of cyclophosphamide include
2299:
2282:
6548:
6245:
6185:
2470:
Malik SW, Myers JL, DeRemee RA, Specks U (December 1996). "Lung toxicity associated with cyclophosphamide use. Two distinct patterns".
3865:"Immunosuppressive effect of cyclophosphamide on white blood cells and lymphocyte subpopulations from peripheral blood of Balb/c mice"
6333:
5939:
5854:
5995:
3770:
3064:
1757:
1128:
1066:
1509:. ALDHs protect these actively proliferating tissues against toxic effects of phosphoramide mustard and acrolein by converting
1448:) result in slower conversion of cyclophosphamide into its metabolites and consequently reduced therapeutic and toxic effects.
1338:
This risk may be dependent on dose and other factors, including the condition, other agents or treatment modalities (including
4862:
3842:
1712:
5622:
3939:
1899:
1495:
888:
3338:
Koseoglu V, Chiang J, Chan KW (December 1999). "Acquired pseudocholinesterase deficiency after high-dose cyclophosphamide".
764:
2867:
Balow JE, Austin HA, Tsokos GC, Antonovych TT, Steinberg AD, Klippel JH (January 1987). "NIH conference. Lupus nephritis".
1543:
Enhanced grafting of adoptively transferred, tumor-reactive effector T cells by the creation of an immunologic space niche.
960:
5229:
3412:
1483:
N-7 positions (known as interstrand and intrastrand crosslinkages, respectively). This is irreversible and leads to cell
2091:
Gertz MA (December 2014). "Immunoglobulin light chain amyloidosis: 2014 update on diagnosis, prognosis, and treatment".
4381:
4337:
4215:
3924:
2703:"Controlled trial of pulse methylprednisolone versus two regimens of pulse cyclophosphamide in severe lupus nephritis"
6717:
4140:
739:
695:
5698:
5639:
3932:
980:
830:
6473:
4656:
2234:"Haploidentical bone marrow and stem cell transplantation: experience with post-transplantation cyclophosphamide"
1358:
phase, before developing into overt acute leukemia. Cyclophosphamide-induced leukemia will often involve complex
1113:
1054:
869:
379:
241:
2540:
Bressler RB, Huston DP (March 1985). "Water intoxication following moderate-dose intravenous cyclophosphamide".
2505:
Floyd JD, Nguyen DT, Lobins RL, Bashir Q, Doll DC, Perry MC (October 2005). "Cardiotoxicity of cancer therapy".
1065:
of the graft. The use of a high dose cyclophosphamide post-transplant in a half matched or haploidentical donor
6747:
6155:
5275:
4277:
4167:
1563:
As reported by O. M. Colvin in his study of the development of cyclophosphamide and its clinical applications,
1212:. Risks of hemorrhagic cystitis can be minimized with adequate fluid intake, avoidance of nighttime dosage and
3730:
5197:
5180:
5055:
4819:
4197:
1002:, cyclophosphamide is used for early phases of treatment and later substituted by other medications, such as
3905:
3566:
Friedman OM, Seligman AM (1954). "Preparation of N-Phosphorylated
Derivatives of Bis-β-chloroethylamine1a".
6737:
6665:
4929:
4525:
1602:
1548:
1328:
1308:
1109:
964:
612:
493:
3084:
2185:"HLA-haploidentical blood or marrow transplantation with high-dose, post-transplantation cyclophosphamide"
6200:
5894:
5687:
5131:
1663:
1304:
573:
4521:
4491:
6722:
6682:
4311:
5975:
5970:
4416:
6732:
5497:
5377:
5367:
3921:
Novel cyclic phosphoric acid ester amides, and the production thereof. (patent for cyclophosphamide).
1865:
1831:
1386:
1268:
1050:
562:
6458:
6005:
5844:
6727:
6583:
6498:
5549:
5482:
5452:
5070:
4320:
3105:
Huttunen KM, Raunio H, Rautio J (September 2011). "Prodrugs--from serendipity to rational design".
2701:
Boumpas DT, Austin HA, Vaughn EM, Klippel JH, Steinberg AD, Yarboro CH, Balow JE (September 1992).
1441:
1355:
1104:
D drug and causes birth defects. First trimester exposure to cyclophosphamide for the treatment of
589:
3593:
Colvin OM (August 1999). "An overview of cyclophosphamide development and clinical applications".
2623:
Emadi A, Jones RJ, Brodsky RA (November 2009). "Cyclophosphamide and cancer: golden anniversary".
2435:
Twohig KJ, Matthay RA (March 1990). "Pulmonary effects of cytotoxic agents other than bleomycin".
2349:
Lohrmann HP (1984). "The problem of permanent bone marrow damage after cytotoxic drug treatment".
5627:
5352:
5067:
4553:
4401:
4328:
1514:
1402:
1256:
1244:
1132:
904:
193:
125:
6145:
5774:
5432:
5422:
5155:
4997:
1659:
1456:
1398:
1332:
1248:
972:
814:
324:
3271:"Cyclophosphamide pharmacokinetics and dose requirements in patients with renal insufficiency"
1993:"Research and therapeutics-traditional and emerging therapies in systemic lupus erythematosus"
1684:
6712:
4704:
4351:
1452:
1327:
patients within the first decade after receiving cyclophosphamide, compared with one case of
1124:
542:
37:
5990:
5980:
6328:
6300:
6290:
5909:
5102:
4979:
4500:
1589:
1390:
1324:
1316:
1201:
1158:
Pulmonary injury appears rare, but can present with two clinical patterns: an early, acute
1140:
1070:
984:
976:
853:
502:
346:
5985:
1467:
agents can result in delayed bladder emptying and prolonged bladder exposure to acrolein.
482:
8:
6130:
6030:
5954:
5656:
5387:
5287:
5266:
4987:
4809:
4641:
4372:
4268:
1656:"cyclophosphamide – definition of cyclophosphamide in English from the Oxford dictionary"
1638:
Cyclophosphamide provides a positive control when studying immune-response of a new drug.
1236:
887:
Cyclophosphamide was approved for medical use in the United States in 1959. It is on the
408:
204:
200:
6324:
3761:
3731:"Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture"
3148:
Boddy AV, Yule SM (April 2000). "Metabolism and pharmacokinetics of oxazaphosphorines".
1753:
616:
593:
417:
145:
6603:
6358:
6159:
5690:
4445:
3954:
3815:
3788:
3548:
3363:
3251:
3173:
3130:
2927:
2849:
2730:
2648:
2600:
2412:
2385:
2258:
2249:
2233:
2209:
2184:
2165:
2116:
2068:
2041:
2017:
1992:
1968:
1943:
1808:
1783:
1343:
1163:
1101:
1086:
988:
956:
900:
865:
861:
826:
167:
3606:
3394:
3204:
2448:
6742:
6308:
6015:
5569:
5143:
3977:
3884:
3820:
3742:
3691:
3664:
3610:
3540:
3505:
3478:
3474:
3443:
3439:
3398:
3355:
3320:
3292:
3287:
3270:
3269:
Haubitz M, Bohnenstengel F, Brunkhorst R, Schwab M, Hofmann U, Busse D (April 2002).
3243:
3208:
3165:
3161:
3122:
3076:
3045:
3004:
2968:
2919:
2915:
2902:
Periti P, Mazzei T, Mini E (2002). "Clinical pharmacokinetics of depot leuprorelin".
2884:
2841:
2800:
2765:
2722:
2718:
2683:
2640:
2592:
2557:
2522:
2487:
2452:
2417:
2366:
2331:
2304:
2263:
2214:
2157:
2108:
2073:
2022:
1973:
1924:
1895:
1813:
1704:
1339:
1003:
952:
876:
family of medications. It is believed to work by interfering with the duplication of
790:
293:
280:
268:
159:
3367:
3177:
3134:
3040:
3023:
2931:
2820:"Frequency, risk factors and prophylaxis of infection in ANCA-associated vasculitis"
2652:
2604:
2120:
1537:
Elimination of T regulatory cells (CD4CD25 T cells) in naive and tumor-bearing hosts
1479:. Phosphoramide mustard forms DNA crosslinks both between and within DNA strands at
6593:
6313:
6195:
6010:
6000:
5914:
5574:
5331:
5046:
4665:
4386:
3876:
3838:
3810:
3800:
3654:
3602:
3575:
3552:
3532:
3470:
3435:
3390:
3347:
3282:
3235:
3200:
3157:
3114:
3035:
2996:
2963:
2958:
2946:
2911:
2876:
2831:
2792:
2757:
2734:
2714:
2675:
2632:
2584:
2549:
2514:
2479:
2444:
2407:
2397:
2358:
2294:
2253:
2245:
2204:
2196:
2169:
2147:
2100:
2063:
2053:
2012:
2004:
1963:
1959:
1955:
1942:
La Mantia L, Milanese C, Mascoli N, D'Amico R, Weinstock-Guttman B (January 2007).
1839:
1803:
1795:
1594:
1581:
1320:
1062:
873:
834:
798:
629:
306:
224:
55:
3787:
Zuluaga AF, Salazar BE, Rodriguez CA, Zapata AX, Agudelo M, Vesga O (March 2006).
3255:
2853:
2008:
1235:
arising secondary to cyclophosphamide usage can predispose people to a variety of
1112:
displays a pattern of anomalies labeled "cyclophosphamide embryopathy", including
6696:
6270:
6165:
6045:
5013:
4975:
4766:
4188:
4103:
3880:
3239:
3065:"Enzymatic basis of cyclophosphamide activation by hepatic microsomes of the rat"
2483:
2281:
Enns GM, Roeder E, Chan RT, Ali-Khan Catts Z, Cox VA, Golabi M (September 1999).
1689:
1526:
1510:
1464:
1460:
1437:
1382:
1217:
1194:
999:
968:
442:
334:
314:
20:
1916:
1799:
1342:), treatment length and intensity. For some regimens, it is rare. For instance,
1127:
from cyclophosphamide are related to the cumulative medication dose and include
130:
Lyophilized
Cytoxan, Endoxan, Cytoxan, Neosar, Procytox, Revimmune, Cycloblastin
6618:
6538:
6408:
6265:
6120:
6085:
5744:
5633:
5167:
4758:
4252:
4116:
4003:
3973:
3960:
2880:
2636:
2553:
2136:"The evolution of T-cell depletion in haploidentical stem-cell transplantation"
1374:
Oral cyclophosphamide is rapidly absorbed and then converted by mixed-function
1312:
1167:
1136:
1035:
971:
may respond to pulsed cyclophosphamide. Cyclophosphamide is also used to treat
806:
3917:
3628:
3536:
2588:
2402:
2058:
1397:, aldophosphamide. Most of the aldophosphamide is then oxidised by the enzyme
6706:
6558:
6433:
6318:
6280:
6175:
6140:
6075:
5874:
5834:
5734:
5507:
5467:
4837:
4710:
4591:
4534:
4292:
4241:
2947:"Hematologic malignant neoplasms after drug exposure in rheumatoid arthritis"
1614:
1530:
1347:
1031:
1027:
936:
818:
810:
706:
605:
3695:
3660:
10.1002/(SICI)1097-0142(19960801)78:3<542::AID-CNCR23>3.0.CO;2-Y
2518:
747:
InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
6643:
6613:
6588:
6543:
6488:
6483:
6468:
6463:
6453:
6448:
6373:
6275:
6255:
6240:
6235:
6230:
6215:
6110:
6100:
5929:
5869:
5804:
5799:
5794:
5789:
5769:
5759:
5554:
5518:
5402:
5392:
5346:
5342:
5304:
5212:
5002:
4941:
4937:
4918:
4913:
4892:
4881:
4695:
4689:
4675:
4670:
4601:
4596:
4549:
4435:
4302:
4282:
4211:
4160:
4150:
3964:
3956:
3888:
3824:
3805:
3614:
3544:
3359:
3351:
3296:
3247:
3169:
3126:
3049:
3000:
2972:
2923:
2845:
2804:
2761:
2687:
2644:
2596:
2526:
2421:
2308:
2300:
10.1002/(SICI)1096-8628(19990917)86:3<237::AID-AJMG8>3.0.CO;2-V
2267:
2218:
2161:
2112:
2077:
2026:
1977:
1928:
1917:"Goodpasture Syndrome (Anti-glomerular Basement Membrane Antibody Disease)"
1836:
World Health
Organization model list of essential medicines: 21st list 2019
1817:
1491:
1425:
1359:
1178:
1151:(hair loss) or thinning of hair, changes in color and texture of the hair,
1023:
1007:
932:
924:
786:
219:
3746:
3668:
3509:
3482:
3447:
3402:
3324:
3212:
3118:
3080:
3008:
2888:
2769:
2726:
2561:
2491:
2456:
2370:
2335:
1385:
system) in the liver to active metabolites. The main active metabolite is
6628:
6598:
6578:
6528:
6403:
6398:
6383:
6353:
6180:
6135:
6095:
6090:
6040:
6035:
6020:
5859:
5819:
5724:
5599:
5579:
5564:
5559:
5544:
5502:
5472:
5412:
5382:
5326:
5299:
5172:
5113:
5085:
5075:
5028:
4992:
4908:
4870:
4852:
4847:
4827:
4804:
4775:
4753:
4733:
4723:
4574:
4559:
4539:
4425:
4356:
4342:
4297:
4230:
4225:
4202:
4177:
4145:
4088:
4051:
4028:
4013:
4008:
3993:
1552:
1445:
1410:
1300:
1276:
1272:
1232:
1228:
1159:
1116:, ear and facial abnormalities, absence of digits and hypoplastic limbs.
1094:
1082:
1038:. It appears to be an alternative to the more traditional treatment with
1019:
857:
838:
153:
3763:
ISMP's List of Error-Prone
Abbreviations, Symbols, and Dose Designations
3579:
2574:
2283:"Apparent cyclophosphamide (cytoxan) embryopathy: a distinct phenotype?"
2200:
1844:
856:. Other severe side effects include an increased future risk of cancer,
462:
6608:
6568:
6513:
6503:
6443:
6428:
6413:
6393:
6368:
6363:
6343:
6338:
6295:
6285:
6250:
6225:
6205:
6170:
6149:
6105:
6080:
5864:
5829:
5814:
5809:
5778:
5739:
5719:
5589:
5492:
5487:
5462:
5457:
5447:
5442:
5437:
5407:
5397:
5362:
5357:
5337:
5292:
5280:
5255:
5250:
5240:
5222:
5217:
5207:
5202:
5160:
5148:
5136:
5108:
5095:
5090:
5060:
5023:
5018:
4956:
4951:
4897:
4842:
4794:
4780:
4728:
4715:
4684:
4617:
4606:
4579:
4569:
4564:
4510:
4465:
4460:
4361:
4325:
4257:
4247:
4236:
4220:
4172:
4155:
4131:
4083:
4071:
4023:
1613:
The abbreviation CP is common, although abbreviating drug names is not
1585:
1519:
1506:
1429:
1288:
1252:
1197:
995:
845:
671:
473:
2836:
2819:
2796:
2679:
2362:
2152:
2135:
2104:
1267:
Cyclophosphamide has been found to significantly increase the risk of
915:
6533:
6523:
6518:
6508:
6493:
6478:
6423:
6378:
6348:
6210:
6190:
6115:
6055:
6050:
5919:
5849:
5839:
5784:
5604:
5584:
5539:
5529:
5523:
5427:
5372:
5321:
5245:
5235:
5190:
5177:
5118:
5080:
5008:
4946:
4887:
4876:
4832:
4789:
4748:
4742:
4738:
4700:
4627:
4622:
4612:
4584:
4544:
4505:
4480:
4470:
4430:
4076:
4066:
4061:
4056:
4018:
1503:
1484:
1433:
1205:
1090:
1039:
849:
428:
359:
139:
3268:
3191:
Wiernik PH, Duncan JH (May 1971). "Cyclophosphamide in human milk".
2702:
1494:
toxicity as ALDHs are present in relatively large concentrations in
6438:
6418:
6388:
6260:
6220:
6070:
6060:
5934:
5513:
5477:
5417:
5185:
5123:
4903:
4799:
4771:
4450:
4287:
3864:
3759:
1941:
1894:(11th ed.). Philadelphia: Elsevier. 2020. pp. 1007–1091.
1406:
1394:
1296:
1292:
1190:
1152:
1148:
1144:
940:
928:
802:
794:
522:
453:
28:
1170:
is a major problem with people treated with higher dose regimens.
1042:
in people who are ill-suited for autologous stem cell transplant.
694:
6648:
6633:
6563:
6025:
5749:
4406:
4307:
4121:
3982:
1480:
1421:
1416:
It is specifically in the oxazaphosphorine group of medications.
1375:
1259:, but some advocate its use when receiving high-dose medication.
1240:
1209:
822:
16:
Medication used as chemotherapy and to suppress the immune system
2231:
1331:
in 119 rheumatoid arthritis patients with no history. Secondary
1061:
against the person receiving them. GVHD can often be avoided by
4046:
1598:
1540:
Induction of T cell growth factors, such as type I IFNs, and/or
1378:
1105:
1058:
553:
364:
3309:
844:
Most people develop side effects. Common side effects include
3786:
3028:
Hematology. American
Society of Hematology. Education Program
3024:"Etiology and management of therapy-related myeloid leukemia"
1499:
1213:
685:
533:
339:
2280:
2232:
Robinson TM, O'Donnell PV, Fuchs EJ, Luznik L (April 2016).
578:
3863:
Huyan XH, Lin YP, Gao T, Chen RY, Fan YM (September 2011).
3753:
2866:
1866:"Cyclophosphamide: Martindale: The Complete Drug Reference"
1476:
513:
112:
100:
91:
73:
64:
5686:
3225:
2700:
2472:
American
Journal of Respiratory and Critical Care Medicine
2321:
82:
3069:
The
Journal of Pharmacology and Experimental Therapeutics
1830:
881:
877:
399:-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide
5699:
3522:
2040:
Singh JA, Hossain A, Kotb A, Wells GA (September 2016).
1848:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
1572:(footnote omitted), but to have a low therapeutic index
1175:
syndrome of inappropriate antidiuretic hormone secretion
2504:
2469:
2384:
Singh JA, Hossain A, Kotb A, Wells G (September 2016).
889:
World Health Organization's List of Essential Medicines
1597:
into cancer cells. Once in the cells, the prodrug was
6680:
3495:
2944:
2817:
2383:
2039:
1756:. The American Society of Health-System Pharmacists.
1173:
High-dose intravenous cyclophosphamide can cause the
94:
88:
85:
79:
67:
61:
58:
3104:
109:
103:
70:
2985:
1555:strategies, inducing objective antitumor immunity.
97:
76:
3337:
3228:Expert Opinion on Drug Metabolism & Toxicology
2945:Bernatsky S, Clarke AE, Suissa S (February 2008).
2665:
1081:Like other alkylating agents, cyclophosphamide is
837:, among other conditions. It is taken by mouth or
3643:"The history of the oxazaphosphorine cytostatics"
3383:Annales Françaises d'Anesthésie et de Réanimation
3380:
2622:
6704:
3690:]. Asta-Forschung und Therapie (in German).
3565:
2901:
2782:
2747:
1204:, which is associated with microscopic or gross
441:
3862:
2818:Kronbichler A, Jayne DR, Mayer G (March 2015).
2811:
2618:
2616:
2614:
1923:. Treasure Island, USA: StatPearls Publishing.
1490:Cyclophosphamide has relatively little typical
963:(DMARDs) have been ineffective. For example,
923:The main use of cyclophosphamide is with other
416:
2539:
2133:
1914:
1588:were developed by Norbert Brock and ASTA (now
994:Because of its potential side effects such as
899:Cyclophosphamide is used to treat cancers and
6753:World Health Organization essential medicines
5672:
3940:
3219:
3190:
2434:
3141:
2611:
1990:
1863:
1045:
5955:
3489:
3454:
3056:
1948:The Cochrane Database of Systematic Reviews
1018:Cyclophosphamide, used in combination with
785:among other names, is a medication used as
298:In general: ℞ (Prescription only)
6006:Allopregnanedione (5α-dihydroprogesterone)
5679:
5665:
3947:
3933:
3460:
2824:European Journal of Clinical Investigation
1748:
1746:
1744:
1742:
1740:
1738:
1736:
1734:
1732:
1730:
615:
592:
481:
3814:
3804:
3760:Institute for Safe Medication Practices,
3708:
3658:
3425:
3286:
3147:
3039:
2962:
2835:
2411:
2401:
2298:
2257:
2208:
2151:
2067:
2057:
2016:
1967:
1944:"Cyclophosphamide for multiple sclerosis"
1843:
1807:
1777:
1775:
1069:reduces GVHD, even after using a reduced
1057:because of the immune reactions of donor
501:
5704:Tooltip Constitutive androstane receptor
3681:
3568:Journal of the American Chemical Society
3062:
2348:
1291:and may increase the risk of developing
1129:chemotherapy-induced nausea and vomiting
914:
825:. As an immune suppressor it is used in
1784:"Updates in ANCA-associated vasculitis"
1781:
1727:
1362:, which carries a worse prognosis than
1085:and contraindicated in pregnant women (
1067:hematopoietic stem cell transplantation
588:
461:
158:
6705:
6459:Pregnanedione (5β-dihydroprogesterone)
5845:Pregnanedione (5β-dihydroprogesterone)
3592:
3021:
1824:
1772:
1608:
1470:
1463:. Tricyclic antidepressants and other
1307:of the bladder or other malignancies.
953:decreases the immune system's response
946:
793:. As chemotherapy it is used to treat
606:
274:
5660:
3928:
3728:
3640:
2182:
2090:
1838:. Geneva: World Health Organization.
1455:activity and may result in prolonged
961:disease-modifying antirheumatic drugs
561:
541:
287:
144:
3912:. U.S. National Library of Medicine.
2287:American Journal of Medical Genetics
1864:Brayfield, A, ed. (9 January 2017).
1859:
1857:
1855:
1525:Cyclophosphamide induces beneficial
1459:when administered concurrently with
1076:
223:
4216:ribonucleotide reductase inhibitors
2134:Or-Geva N, Reisner Y (March 2016).
1991:Davis LS, Reimold AM (April 2017).
1760:from the original on 2 January 2017
1185:
521:
432:
13:
4382:Ribonucleotide reductase inhibitor
4338:Ribonucleotide reductase inhibitor
2250:10.1053/j.seminhematol.2016.01.005
1872:. London, UK: Pharmaceutical Press
1715:from the original on 25 April 2015
664:
14:
6764:
4141:Dihydrofolate reductase inhibitor
3898:
3607:10.2174/1381612805666230110214512
2625:Nature Reviews. Clinical Oncology
1892:Brenner & Rector's The Kidney
1852:
1580:Cyclophosphamide and the related
1013:
250:
178:
6690:
3869:International Immunopharmacology
3776:from the original on 2011-10-27.
3688:Chemotherapy of malignant tumors
3288:10.1046/j.1523-1755.2002.00279.x
3162:10.2165/00003088-200038040-00001
3063:Cohen JL, Jao JY (August 1970).
2916:10.2165/00003088-200241070-00003
1788:European Journal of Rheumatology
1533:. Suggested mechanisms include:
1451:Cyclophosphamide reduces plasma
1247:. No published guidelines cover
1177:(SIADH) and a potentially fatal
981:granulomatosis with polyangiitis
831:granulomatosis with polyangiitis
652:
646:
640:
54:
36:
27:
3856:
3845:from the original on 2015-06-21
3831:
3780:
3722:
3702:
3675:
3634:
3621:
3586:
3559:
3516:
3419:
3374:
3331:
3303:
3262:
3184:
3098:
3041:10.1182/asheducation-2007.1.453
3015:
2979:
2938:
2895:
2860:
2776:
2741:
2694:
2659:
2568:
2533:
2498:
2463:
2428:
2377:
2342:
2315:
2274:
2225:
2176:
2127:
2084:
2033:
1984:
1935:
1915:DeVrieze BW, Hurley JA (2019).
1409:and are known to be present in
1369:
1147:, darkening of the skin/nails,
1119:
1055:allogeneic stem cell transplant
894:
752:Key:CMSMOCZEIVJLDB-UHFFFAOYSA-N
6011:Allopregnanolone (brexanolone)
4278:Thymidylate synthase inhibitor
4168:Thymidylate synthase inhibitor
3684:Chemotherapie maligner Tumoren
2964:10.1001/archinternmed.2007.107
2140:British Journal of Haematology
2093:American Journal of Hematology
1960:10.1002/14651858.CD002819.pub2
1908:
1884:
1697:
1690:Merriam-Webster.com Dictionary
1677:
1648:
1262:
1053:(GVHD) is a major barrier for
1030:has documented efficacy as an
848:, loss of appetite, vomiting,
658:
634:
263:
1:
6666:Receptor/signaling modulators
6624:Tropanyl 3,5-dimethulbenzoate
6474:Pregnenolone 16α-carbonitrile
4198:Adenosine deaminase inhibitor
4039:Block microtubule disassembly
3595:Current Pharmaceutical Design
3395:10.1016/S0750-7658(05)80493-9
3205:10.1016/s0140-6736(71)92474-3
2951:Archives of Internal Medicine
2542:Archives of Internal Medicine
2449:10.1016/S0272-5231(21)00670-5
1642:
868:. Cyclophosphamide is in the
3881:10.1016/j.intimp.2011.04.011
3475:10.1016/0006-2952(85)90719-1
3440:10.1016/0268-960X(92)90028-O
3240:10.1517/17425255.2010.487861
2719:10.1016/0140-6736(92)92292-n
2507:Journal of Clinical Oncology
2484:10.1164/ajrccm.154.6.8970380
1782:Pagnoux C (September 2016).
1329:chronic lymphocytic leukemia
1309:Myeloproliferative neoplasms
1251:prophylaxis for people with
1223:
965:systemic lupus erythematosus
7:
6201:Dodecylbenzenesulfonic acid
5960:Tooltip Pregnane X receptor
5688:Xenobiotic-sensing receptor
3525:Seminars in Immunopathology
3340:Bone Marrow Transplantation
2869:Annals of Internal Medicine
2324:The Journal of Rheumatology
2189:Bone Marrow Transplantation
2009:10.1093/rheumatology/kew417
1800:10.5152/eurjrheum.2015.0043
1620:
1305:transitional cell carcinoma
1282:
1162:and a chronic, progressive
927:agents in the treatment of
846:low white blood cell counts
10:
6769:
2881:10.7326/0003-4819-106-1-79
2637:10.1038/nrclinonc.2009.146
2554:10.1001/archinte.145.3.548
1584:–derived alkylating agent
1558:
919:A Cyclophosphamide IV drip
791:suppress the immune system
624:Chemical and physical data
6657:
5953:
5697:
5617:
5498:Omacetaxine mepesuccinate
5378:Ciltacabtagene autoleucel
5368:Brexucabtagene autoleucel
5314:
5265:
5045:
5038:
4974:
4928:
4861:
4818:
4655:
4640:
4520:
4490:
4415:
4400:
4371:
4267:
4187:
4130:
4113:
4102:
4038:
3991:
3972:
3537:10.1007/s00281-011-0245-0
3150:Clinical Pharmacokinetics
2904:Clinical Pharmacokinetics
2589:10.1191/0961203303lu421cr
2437:Clinics in Chest Medicine
2403:10.1186/s12916-016-0673-8
2059:10.1186/s13643-016-0328-z
1832:World Health Organization
1709:National Cancer Institute
1442:tricyclic antidepressants
1387:4-hydroxycyclophosphamide
1051:Graft-versus-host disease
1046:Graft-versus-host disease
910:
854:bleeding from the bladder
760:
735:
715:
705:
683:
670:
628:
623:
604:
572:
552:
532:
512:
492:
472:
452:
427:
407:
375:
370:
358:
345:
333:
323:
313:
305:
240:
235:
210:
192:
166:
152:
134:
124:
49:
44:
35:
26:
6718:IARC Group 1 carcinogens
6584:Testosterone isocaproate
6499:Reverse triiodothyronine
5550:Talimogene laherparepvec
5483:Nadofaragene firadenovec
5453:Lisocabtagene maraleucel
4402:Topoisomerase inhibitors
4321:DNA polymerase inhibitor
3729:Brock N (January 1989).
3498:Cancer Treatment Reports
3463:Biochemical Pharmacology
3313:Cancer Treatment Reports
2989:Arthritis and Rheumatism
2785:Arthritis and Rheumatism
2750:Arthritis and Rheumatism
2668:Arthritis and Rheumatism
1356:myelodysplastic syndrome
1253:rheumatological diseases
1245:opportunistic infections
205:by injection into a vein
5976:17α-Hydroxyprogesterone
5971:17α-Hydroxypregnenolone
5353:Axicabtagene ciloleucel
3957:chemotherapeutic agents
3910:Drug Information Portal
3793:BMC Infectious Diseases
3641:Brock N (August 1996).
3107:Pharmacological Reviews
2519:10.1200/JCO.2005.08.789
1547:Thus, cyclophosphamide
1515:carboxycyclophosphamide
1403:carboxycyclophosphamide
1323:, occurred in 5 of 119
1257:immunosuppressive drugs
1133:bone marrow suppression
943:and some solid tumors.
727:O=P1(OCCCN1)N(CCCl)CCCl
5535:Sitimagene ceradenovec
5433:Idecabtagene vicleucel
4998:Methyl aminolevulinate
3806:10.1186/1471-2334-6-55
3352:10.1038/sj.bmt.1702097
3001:10.1002/art.1780380815
2762:10.1002/art.1780390906
2238:Seminars in Hematology
2183:Fuchs EJ (June 2015).
2003:(suppl_1): i100–i113.
1660:OxfordDictionaries.com
1578:
1496:bone marrow stem cells
1457:neuromuscular blockade
1399:aldehyde dehydrogenase
1333:acute myeloid leukemia
1125:Adverse drug reactions
1100:Cyclophosphamide is a
973:minimal change disease
920:
815:small cell lung cancer
711:2 °C (36 °F)
6748:Chloroethyl compounds
5715:6,7-Dimethylesculetin
5009:Porphyrin derivatives
4705:Melphalan flufenamide
4352:Hypomethylating agent
3961:antineoplastic agents
3918:U.S. patent 3,018,302
3629:U.S. patent 3,018,302
3119:10.1124/pr.110.003459
1705:"NCI Drug Dictionary"
1565:
1097:or bladder toxicity.
918:
839:injection into a vein
6302:Hypericum perforatum
6291:Hetacillin potassium
5338:Asparagine depleters
5267:Receptor antagonists
5181:+abiraterone acetate
3275:Kidney International
1595:actively transported
1529:effects in adaptive
1453:pseudocholinesterase
1325:rheumatoid arthritis
1317:non-Hodgkin lymphoma
1287:Cyclophosphamide is
1202:hemorrhagic cystitis
1141:hemorrhagic cystitis
1093:, active infection,
1071:conditioning regimen
985:Goodpasture syndrome
977:rheumatoid arthritis
905:bone marrow toxicity
880:and the creation of
6738:Phosphorodiamidates
6131:Cyproterone acetate
6031:Amlodipine besylate
5388:Denileukin diftitox
5288:Retinoid X receptor
4988:Aminolevulinic acid
4810:Triethylenemelamine
4642:Crosslinking of DNA
4373:Deoxyribonucleotide
4312:+gimeracil/oteracil
3682:Wilmanns H (1958).
3580:10.1021/ja01632a006
2201:10.1038/bmt.2015.92
1711:. 2 February 2011.
1609:Society and culture
1471:Mechanism of action
1269:premature menopause
1032:off-label treatment
957:autoimmune diseases
947:Autoimmune diseases
901:autoimmune diseases
283:(Prescription only)
259:(Prescription only)
23:
6604:Thonzonium bromide
6359:Methylprednisolone
6160:prasterone sulfate
5644:Never to phase III
4446:Etirinotecan pegol
3906:"Cyclophosphamide"
3022:Larson RA (2007).
2478:(6 Pt 1): 1851–6.
2195:(Suppl 2): S31–6.
2046:Systematic Reviews
1754:"Cyclophosphamide"
1693:. Merriam-Webster.
1685:"cyclophosphamide"
1666:on August 25, 2012
1389:, which exists in
1271:in females and of
1114:growth restriction
1102:pregnancy category
1087:pregnancy category
989:multiple sclerosis
921:
866:pulmonary fibrosis
862:allergic reactions
827:nephrotic syndrome
319:>75% (by mouth)
19:
6723:Nitrogen mustards
6675:
6674:
6309:Indinavir sulfate
6016:Alpha-Lipoic acid
5991:Δ-Androstenedione
5981:Δ-Androstenedione
5654:
5653:
5613:
5612:
5570:Tigilanol tiglate
5047:Enzyme inhibitors
4970:
4969:
4966:
4965:
4666:Nitrogen mustards
4636:
4635:
4396:
4395:
4098:
4097:
2837:10.1111/eci.12410
2797:10.1002/art.23822
2680:10.1002/art.25061
2363:10.1159/000225819
2153:10.1111/bjh.13868
2105:10.1002/ajh.23828
1901:978-0-323-53265-5
1870:MedicinesComplete
1208:and occasionally
1077:Contraindications
1004:mycophenolic acid
951:Cyclophosphamide
781:), also known as
772:
771:
696:Interactive image
574:CompTox Dashboard
291:
278:
266:
254:
182:
6760:
6733:Oxazaphosphinans
6695:
6694:
6693:
6686:
6594:Thiamylal sodium
6329:γ-linolenic acid
6325:α-Linolenic acid
6323:Linolenic acid:
6314:Lasalocid sodium
6304:(St John's wort)
6196:Docusate calcium
6126:Cyclophosphamide
6001:Allopregnanediol
5986:Δ-Androstenediol
5961:
5957:
5915:Ethinylestradiol
5765:Cyclophosphamide
5705:
5701:
5681:
5674:
5667:
5658:
5657:
5575:Tisagenlecleucel
5332:Arsenic trioxide
5043:
5042:
4976:Photosensitizers
4767:Alkyl sulfonates
4681:Cyclophosphamide
4653:
4652:
4592:Anthracenediones
4413:
4412:
4387:Hydroxycarbamide
4128:
4127:
4111:
4110:
3989:
3988:
3949:
3942:
3935:
3926:
3925:
3920:
3913:
3893:
3892:
3860:
3854:
3853:
3851:
3850:
3835:
3829:
3828:
3818:
3808:
3784:
3778:
3777:
3775:
3768:
3757:
3751:
3750:
3726:
3720:
3719:
3712:Strahlentherapie
3706:
3700:
3699:
3679:
3673:
3672:
3662:
3638:
3632:
3631:
3625:
3619:
3618:
3590:
3584:
3583:
3563:
3557:
3556:
3520:
3514:
3513:
3493:
3487:
3486:
3458:
3452:
3451:
3423:
3417:
3416:
3411:
3378:
3372:
3371:
3335:
3329:
3328:
3307:
3301:
3300:
3290:
3266:
3260:
3259:
3223:
3217:
3216:
3188:
3182:
3181:
3145:
3139:
3138:
3102:
3096:
3095:
3093:
3092:
3083:. Archived from
3060:
3054:
3053:
3043:
3019:
3013:
3012:
2983:
2977:
2976:
2966:
2942:
2936:
2935:
2899:
2893:
2892:
2864:
2858:
2857:
2839:
2815:
2809:
2808:
2780:
2774:
2773:
2745:
2739:
2738:
2698:
2692:
2691:
2663:
2657:
2656:
2620:
2609:
2608:
2572:
2566:
2565:
2537:
2531:
2530:
2502:
2496:
2495:
2467:
2461:
2460:
2432:
2426:
2425:
2415:
2405:
2381:
2375:
2374:
2346:
2340:
2339:
2319:
2313:
2312:
2302:
2278:
2272:
2271:
2261:
2229:
2223:
2222:
2212:
2180:
2174:
2173:
2155:
2131:
2125:
2124:
2088:
2082:
2081:
2071:
2061:
2037:
2031:
2030:
2020:
1988:
1982:
1981:
1971:
1939:
1933:
1932:
1912:
1906:
1905:
1888:
1882:
1881:
1879:
1877:
1861:
1850:
1849:
1847:
1828:
1822:
1821:
1811:
1779:
1770:
1769:
1767:
1765:
1750:
1725:
1724:
1722:
1720:
1701:
1695:
1694:
1681:
1675:
1674:
1672:
1671:
1662:. Archived from
1652:
1582:nitrogen mustard
1527:immunomodulatory
1321:multiple myeloma
1200:and can lead to
1193:is toxic to the
1186:Bladder bleeding
1063:T-cell depletion
931:, some forms of
874:nitrogen mustard
870:alkylating agent
835:organ transplant
833:, and following
799:multiple myeloma
775:Cyclophosphamide
768:
767:
698:
678:
666:
660:
654:
648:
642:
636:
619:
608:
597:
596:
582:
580:
565:
545:
525:
505:
485:
465:
445:
435:
434:
420:
350:
289:
286:
276:
273:
265:
262:
252:
249:
227:
180:
177:
162:
148:
119:
118:
115:
114:
111:
106:
105:
102:
99:
96:
93:
90:
87:
84:
81:
78:
75:
72:
69:
66:
63:
60:
40:
31:
24:
22:
21:Cyclophosphamide
18:
6768:
6767:
6763:
6762:
6761:
6759:
6758:
6757:
6728:Organochlorides
6703:
6702:
6701:
6691:
6689:
6681:
6678:
6676:
6671:
6653:
6554:Suberoylanilide
6271:Fluorometholone
6166:Dibunate sodium
6046:Aurothioglucose
5959:
5949:
5885:3,17β-Estradiol
5703:
5693:
5685:
5655:
5650:
5649:
5634:Clinical trials
5609:
5315:Other/ungrouped
5310:
5261:
5034:
5014:Porfimer sodium
4962:
4924:
4857:
4814:
4644:
4632:
4516:
4486:
4404:
4392:
4367:
4263:
4183:
4119:
4117:antimetabolites
4115:
4114:DNA precursors/
4106:
4104:DNA replication
4094:
4034:
4004:Vinca alkaloids
3980:
3968:
3953:
3916:
3904:
3901:
3896:
3861:
3857:
3848:
3846:
3837:
3836:
3832:
3785:
3781:
3773:
3766:
3758:
3754:
3735:Cancer Research
3727:
3723:
3707:
3703:
3680:
3676:
3639:
3635:
3627:
3626:
3622:
3591:
3587:
3564:
3560:
3521:
3517:
3494:
3490:
3469:(19): 3465–71.
3459:
3455:
3424:
3420:
3409:
3379:
3375:
3336:
3332:
3308:
3304:
3281:(4): 1495–501.
3267:
3263:
3224:
3220:
3189:
3185:
3146:
3142:
3103:
3099:
3090:
3088:
3061:
3057:
3020:
3016:
2984:
2980:
2943:
2939:
2900:
2896:
2865:
2861:
2816:
2812:
2781:
2777:
2746:
2742:
2713:(8822): 741–5.
2699:
2695:
2664:
2660:
2621:
2612:
2573:
2569:
2538:
2534:
2513:(30): 7685–96.
2503:
2499:
2468:
2464:
2433:
2429:
2382:
2378:
2347:
2343:
2320:
2316:
2279:
2275:
2230:
2226:
2181:
2177:
2132:
2128:
2099:(12): 1132–40.
2089:
2085:
2038:
2034:
1989:
1985:
1954:(1): CD002819.
1940:
1936:
1913:
1909:
1902:
1890:
1889:
1885:
1875:
1873:
1862:
1853:
1829:
1825:
1780:
1773:
1763:
1761:
1752:
1751:
1728:
1718:
1716:
1703:
1702:
1698:
1683:
1682:
1678:
1669:
1667:
1654:
1653:
1649:
1645:
1623:
1611:
1561:
1549:preconditioning
1511:aldophosphamide
1473:
1465:anticholinergic
1461:succinylcholine
1438:corticosteroids
1401:(ALDH) to make
1383:cytochrome P450
1372:
1285:
1265:
1226:
1218:lupus nephritis
1188:
1122:
1079:
1048:
1016:
1000:ovarian failure
969:lupus nephritis
949:
913:
897:
763:
761:
756:
753:
748:
743:
742:
731:
728:
723:
722:
701:
676:
663:
657:
651:
645:
639:
600:
576:
568:
548:
528:
508:
488:
468:
448:
431:
423:
403:
400:
383:
382:
348:
325:Protein binding
315:Bioavailability
307:Pharmacokinetic
301:
231:
195:
188:
169:
108:
57:
53:
17:
12:
11:
5:
6766:
6756:
6755:
6750:
6745:
6740:
6735:
6730:
6725:
6720:
6715:
6700:
6699:
6673:
6672:
6670:
6669:
6662:
6658:
6655:
6654:
6652:
6651:
6646:
6637:
6636:
6631:
6626:
6621:
6619:Troleandomycin
6616:
6611:
6606:
6601:
6596:
6591:
6586:
6581:
6576:
6571:
6566:
6561:
6556:
6551:
6546:
6541:
6539:Spironolactone
6536:
6531:
6526:
6521:
6516:
6511:
6506:
6501:
6496:
6491:
6486:
6481:
6476:
6471:
6466:
6461:
6456:
6451:
6446:
6441:
6436:
6431:
6426:
6421:
6416:
6411:
6409:Norelgestromin
6406:
6401:
6396:
6391:
6386:
6381:
6376:
6371:
6366:
6361:
6356:
6351:
6346:
6341:
6336:
6331:
6321:
6316:
6311:
6306:
6298:
6293:
6288:
6283:
6278:
6273:
6268:
6266:Flucloxacillin
6263:
6258:
6253:
6248:
6243:
6238:
6233:
6228:
6223:
6218:
6213:
6208:
6203:
6198:
6193:
6188:
6183:
6178:
6173:
6168:
6163:
6153:
6143:
6138:
6133:
6128:
6123:
6121:Corticosterone
6118:
6113:
6108:
6103:
6098:
6093:
6088:
6086:Chlorpromazine
6083:
6078:
6073:
6068:
6063:
6058:
6053:
6048:
6043:
6038:
6033:
6028:
6023:
6018:
6013:
6008:
6003:
5998:
5993:
5988:
5983:
5978:
5973:
5964:
5962:
5951:
5950:
5948:
5947:
5942:
5937:
5932:
5927:
5922:
5917:
5912:
5907:
5905:17-Androstanol
5902:
5900:3β-Androstanol
5897:
5895:3α-Androstenol
5892:
5890:3α-Androstanol
5887:
5878:
5877:
5872:
5867:
5862:
5857:
5852:
5847:
5842:
5837:
5832:
5827:
5822:
5817:
5812:
5807:
5802:
5797:
5792:
5787:
5782:
5772:
5767:
5762:
5757:
5752:
5747:
5745:Chlorpromazine
5742:
5737:
5732:
5727:
5722:
5717:
5708:
5706:
5695:
5694:
5684:
5683:
5676:
5669:
5661:
5652:
5651:
5648:
5647:
5646:
5645:
5642:
5631:
5625:
5619:
5618:
5615:
5614:
5611:
5610:
5608:
5607:
5602:
5597:
5592:
5587:
5582:
5577:
5572:
5567:
5562:
5557:
5552:
5547:
5542:
5537:
5532:
5527:
5521:
5510:
5505:
5500:
5495:
5490:
5485:
5480:
5475:
5470:
5465:
5460:
5455:
5450:
5445:
5440:
5435:
5430:
5425:
5420:
5415:
5410:
5405:
5400:
5395:
5390:
5385:
5380:
5375:
5370:
5365:
5360:
5355:
5350:
5334:
5329:
5324:
5318:
5316:
5312:
5311:
5309:
5308:
5296:
5284:
5271:
5269:
5263:
5262:
5260:
5259:
5253:
5248:
5243:
5238:
5226:
5220:
5215:
5210:
5205:
5194:
5188:
5183:
5175:
5168:PARP inhibitor
5164:
5152:
5140:
5128:
5127:
5126:
5121:
5116:
5111:
5099:
5093:
5088:
5083:
5078:
5064:
5051:
5049:
5040:
5036:
5035:
5033:
5032:
5026:
5021:
5016:
5005:
5000:
4995:
4990:
4984:
4982:
4972:
4971:
4968:
4967:
4964:
4963:
4961:
4960:
4954:
4949:
4944:
4934:
4932:
4926:
4925:
4923:
4922:
4916:
4911:
4900:
4895:
4890:
4885:
4873:
4867:
4865:
4859:
4858:
4856:
4855:
4850:
4845:
4840:
4835:
4830:
4824:
4822:
4820:Platinum-based
4816:
4815:
4813:
4812:
4807:
4802:
4797:
4785:
4784:
4778:
4762:
4761:
4756:
4751:
4746:
4736:
4731:
4719:
4718:
4713:
4708:
4698:
4693:
4687:
4678:
4673:
4661:
4659:
4650:
4638:
4637:
4634:
4633:
4631:
4630:
4625:
4620:
4615:
4610:
4604:
4599:
4588:
4582:
4577:
4572:
4567:
4562:
4557:
4547:
4542:
4535:Anthracyclines
4530:
4528:
4518:
4517:
4515:
4514:
4508:
4496:
4494:
4488:
4487:
4485:
4484:
4478:
4473:
4468:
4463:
4458:
4453:
4448:
4443:
4438:
4433:
4421:
4419:
4410:
4398:
4397:
4394:
4393:
4391:
4390:
4377:
4375:
4369:
4368:
4366:
4365:
4359:
4347:
4346:
4333:
4332:
4316:
4315:
4305:
4300:
4295:
4290:
4285:
4273:
4271:
4265:
4264:
4262:
4261:
4255:
4253:Mercaptopurine
4244:
4239:
4234:
4228:
4223:
4207:
4206:
4193:
4191:
4185:
4184:
4182:
4181:
4175:
4164:
4158:
4153:
4148:
4136:
4134:
4125:
4108:
4100:
4099:
4096:
4095:
4093:
4092:
4080:
4074:
4069:
4064:
4059:
4054:
4042:
4040:
4036:
4035:
4033:
4032:
4026:
4021:
4016:
4011:
3999:
3997:
3986:
3970:
3969:
3955:Intracellular
3952:
3951:
3944:
3937:
3929:
3923:
3922:
3914:
3900:
3899:External links
3897:
3895:
3894:
3855:
3830:
3779:
3752:
3721:
3701:
3674:
3633:
3620:
3585:
3558:
3515:
3488:
3453:
3418:
3373:
3346:(12): 1367–8.
3330:
3319:(4): 395–401.
3302:
3261:
3234:(8): 919–938.
3218:
3183:
3156:(4): 291–304.
3140:
3097:
3055:
3014:
2978:
2937:
2910:(7): 485–504.
2894:
2859:
2810:
2775:
2756:(9): 1475–82.
2740:
2693:
2658:
2631:(11): 638–47.
2610:
2567:
2532:
2497:
2462:
2427:
2376:
2341:
2314:
2273:
2224:
2175:
2126:
2083:
2032:
1983:
1934:
1907:
1900:
1883:
1851:
1823:
1794:(3): 122–133.
1771:
1726:
1696:
1676:
1646:
1644:
1641:
1640:
1639:
1636:
1622:
1619:
1610:
1607:
1560:
1557:
1545:
1544:
1541:
1538:
1472:
1469:
1371:
1368:
1313:acute leukemia
1284:
1281:
1264:
1261:
1225:
1222:
1187:
1184:
1168:Cardiotoxicity
1121:
1118:
1078:
1075:
1047:
1044:
1036:AL amyloidosis
1015:
1014:AL amyloidosis
1012:
948:
945:
912:
909:
896:
893:
807:ovarian cancer
770:
769:
758:
757:
755:
754:
751:
749:
746:
738:
737:
736:
733:
732:
730:
729:
726:
718:
717:
716:
713:
712:
709:
703:
702:
700:
699:
691:
689:
681:
680:
674:
668:
667:
661:
655:
649:
643:
637:
632:
626:
625:
621:
620:
610:
602:
601:
599:
598:
585:
583:
570:
569:
567:
566:
558:
556:
550:
549:
547:
546:
538:
536:
530:
529:
527:
526:
518:
516:
510:
509:
507:
506:
498:
496:
490:
489:
487:
486:
478:
476:
470:
469:
467:
466:
458:
456:
450:
449:
447:
446:
438:
436:
425:
424:
422:
421:
413:
411:
405:
404:
402:
401:
386:
378:
377:
376:
373:
372:
368:
367:
362:
356:
355:
352:
343:
342:
337:
331:
330:
327:
321:
320:
317:
311:
310:
303:
302:
300:
299:
296:
284:
271:
260:
246:
244:
238:
237:
233:
232:
230:
229:
216:
214:
208:
207:
198:
196:administration
190:
189:
187:
186:
184:
174:
172:
164:
163:
156:
150:
149:
142:
132:
131:
128:
122:
121:
51:
47:
46:
42:
41:
33:
32:
15:
9:
6:
4:
3:
2:
6765:
6754:
6751:
6749:
6746:
6744:
6741:
6739:
6736:
6734:
6731:
6729:
6726:
6724:
6721:
6719:
6716:
6714:
6711:
6710:
6708:
6698:
6688:
6687:
6684:
6679:
6668:
6667:
6663:
6660:
6659:
6656:
6650:
6647:
6645:
6642:
6639:
6638:
6635:
6632:
6630:
6627:
6625:
6622:
6620:
6617:
6615:
6612:
6610:
6607:
6605:
6602:
6600:
6597:
6595:
6592:
6590:
6587:
6585:
6582:
6580:
6577:
6575:
6572:
6570:
6567:
6565:
6562:
6560:
6559:Sulfisoxazole
6557:
6555:
6552:
6550:
6547:
6545:
6542:
6540:
6537:
6535:
6532:
6530:
6527:
6525:
6522:
6520:
6517:
6515:
6512:
6510:
6507:
6505:
6502:
6500:
6497:
6495:
6492:
6490:
6487:
6485:
6482:
6480:
6477:
6475:
6472:
6470:
6467:
6465:
6462:
6460:
6457:
6455:
6452:
6450:
6447:
6445:
6442:
6440:
6437:
6435:
6434:Phenobarbital
6432:
6430:
6427:
6425:
6422:
6420:
6417:
6415:
6412:
6410:
6407:
6405:
6402:
6400:
6397:
6395:
6392:
6390:
6387:
6385:
6382:
6380:
6377:
6375:
6372:
6370:
6367:
6365:
6362:
6360:
6357:
6355:
6352:
6350:
6347:
6345:
6342:
6340:
6337:
6335:
6332:
6330:
6326:
6322:
6320:
6319:Levothyroxine
6317:
6315:
6312:
6310:
6307:
6305:
6303:
6299:
6297:
6294:
6292:
6289:
6287:
6284:
6282:
6281:Guggulsterone
6279:
6277:
6274:
6272:
6269:
6267:
6264:
6262:
6259:
6257:
6254:
6252:
6249:
6247:
6244:
6242:
6239:
6237:
6234:
6232:
6229:
6227:
6224:
6222:
6219:
6217:
6214:
6212:
6209:
6207:
6204:
6202:
6199:
6197:
6194:
6192:
6189:
6187:
6184:
6182:
6179:
6177:
6176:Dicloxacillin
6174:
6172:
6169:
6167:
6164:
6161:
6157:
6154:
6151:
6147:
6144:
6142:
6141:Dexamethasone
6139:
6137:
6134:
6132:
6129:
6127:
6124:
6122:
6119:
6117:
6114:
6112:
6109:
6107:
6104:
6102:
6099:
6097:
6094:
6092:
6089:
6087:
6084:
6082:
6079:
6077:
6076:Cephaloridine
6074:
6072:
6069:
6067:
6064:
6062:
6059:
6057:
6054:
6052:
6049:
6047:
6044:
6042:
6039:
6037:
6034:
6032:
6029:
6027:
6024:
6022:
6019:
6017:
6014:
6012:
6009:
6007:
6004:
6002:
5999:
5997:
5994:
5992:
5989:
5987:
5984:
5982:
5979:
5977:
5974:
5972:
5969:
5966:
5965:
5963:
5958:
5952:
5946:
5943:
5941:
5938:
5936:
5933:
5931:
5928:
5926:
5923:
5921:
5918:
5916:
5913:
5911:
5908:
5906:
5903:
5901:
5898:
5896:
5893:
5891:
5888:
5886:
5883:
5880:
5879:
5876:
5875:Valproic acid
5873:
5871:
5868:
5866:
5863:
5861:
5858:
5856:
5853:
5851:
5848:
5846:
5843:
5841:
5838:
5836:
5835:Phenobarbital
5833:
5831:
5828:
5826:
5823:
5821:
5818:
5816:
5813:
5811:
5808:
5806:
5803:
5801:
5798:
5796:
5793:
5791:
5788:
5786:
5783:
5780:
5776:
5773:
5771:
5768:
5766:
5763:
5761:
5758:
5756:
5753:
5751:
5748:
5746:
5743:
5741:
5738:
5736:
5735:Carbamazepine
5733:
5731:
5728:
5726:
5723:
5721:
5718:
5716:
5713:
5710:
5709:
5707:
5702:
5696:
5692:
5689:
5682:
5677:
5675:
5670:
5668:
5663:
5662:
5659:
5643:
5641:
5638:
5637:
5635:
5632:
5629:
5626:
5624:
5621:
5620:
5616:
5606:
5603:
5601:
5598:
5596:
5593:
5591:
5588:
5586:
5583:
5581:
5578:
5576:
5573:
5571:
5568:
5566:
5563:
5561:
5558:
5556:
5553:
5551:
5548:
5546:
5543:
5541:
5538:
5536:
5533:
5531:
5528:
5525:
5522:
5520:
5516:
5515:
5511:
5509:
5508:Tabelecleucel
5506:
5504:
5501:
5499:
5496:
5494:
5491:
5489:
5486:
5484:
5481:
5479:
5476:
5474:
5471:
5469:
5468:Lurbinectedin
5466:
5464:
5461:
5459:
5456:
5454:
5451:
5449:
5446:
5444:
5441:
5439:
5436:
5434:
5431:
5429:
5426:
5424:
5421:
5419:
5416:
5414:
5411:
5409:
5406:
5404:
5401:
5399:
5396:
5394:
5391:
5389:
5386:
5384:
5381:
5379:
5376:
5374:
5371:
5369:
5366:
5364:
5361:
5359:
5356:
5354:
5351:
5348:
5344:
5340:
5339:
5335:
5333:
5330:
5328:
5325:
5323:
5320:
5319:
5317:
5313:
5306:
5302:
5301:
5297:
5294:
5290:
5289:
5285:
5282:
5278:
5277:
5273:
5272:
5270:
5268:
5264:
5257:
5254:
5252:
5249:
5247:
5244:
5242:
5239:
5237:
5233:
5231:
5227:
5224:
5221:
5219:
5216:
5214:
5211:
5209:
5206:
5204:
5200:
5199:
5195:
5192:
5189:
5187:
5184:
5182:
5179:
5176:
5174:
5170:
5169:
5165:
5162:
5158:
5157:
5153:
5150:
5146:
5145:
5141:
5138:
5134:
5133:
5129:
5125:
5122:
5120:
5117:
5115:
5112:
5110:
5107:
5106:
5105:
5104:
5100:
5097:
5094:
5092:
5089:
5087:
5084:
5082:
5079:
5077:
5073:
5072:
5069:
5065:
5062:
5058:
5057:
5053:
5052:
5050:
5048:
5044:
5041:
5037:
5030:
5027:
5025:
5022:
5020:
5017:
5015:
5011:
5010:
5006:
5004:
5001:
4999:
4996:
4994:
4991:
4989:
4986:
4985:
4983:
4981:
4977:
4973:
4958:
4955:
4953:
4950:
4948:
4945:
4943:
4939:
4936:
4935:
4933:
4931:
4930:Intercalation
4927:
4920:
4917:
4915:
4912:
4910:
4906:
4905:
4901:
4899:
4896:
4894:
4891:
4889:
4886:
4883:
4879:
4878:
4874:
4872:
4869:
4868:
4866:
4864:
4860:
4854:
4851:
4849:
4846:
4844:
4841:
4839:
4838:Dicycloplatin
4836:
4834:
4831:
4829:
4826:
4825:
4823:
4821:
4817:
4811:
4808:
4806:
4803:
4801:
4798:
4796:
4793:
4791:
4787:
4786:
4782:
4779:
4777:
4773:
4770:
4768:
4764:
4763:
4760:
4757:
4755:
4752:
4750:
4747:
4744:
4740:
4737:
4735:
4732:
4730:
4727:
4725:
4721:
4720:
4717:
4714:
4712:
4711:Prednimustine
4709:
4706:
4702:
4699:
4697:
4694:
4691:
4688:
4686:
4682:
4679:
4677:
4674:
4672:
4669:
4667:
4663:
4662:
4660:
4658:
4654:
4651:
4648:
4643:
4639:
4629:
4626:
4624:
4621:
4619:
4616:
4614:
4611:
4608:
4605:
4603:
4600:
4598:
4594:
4593:
4589:
4586:
4583:
4581:
4578:
4576:
4573:
4571:
4568:
4566:
4563:
4561:
4558:
4555:
4551:
4548:
4546:
4543:
4541:
4537:
4536:
4532:
4531:
4529:
4527:
4526:Intercalation
4523:
4519:
4512:
4509:
4507:
4503:
4502:
4498:
4497:
4495:
4493:
4489:
4482:
4479:
4477:
4474:
4472:
4469:
4467:
4464:
4462:
4459:
4457:
4454:
4452:
4449:
4447:
4444:
4442:
4439:
4437:
4434:
4432:
4428:
4427:
4423:
4422:
4420:
4418:
4414:
4411:
4408:
4403:
4399:
4388:
4384:
4383:
4379:
4378:
4376:
4374:
4370:
4363:
4360:
4358:
4354:
4353:
4349:
4348:
4344:
4340:
4339:
4335:
4334:
4330:
4329:+daunorubicin
4327:
4323:
4322:
4318:
4317:
4313:
4309:
4306:
4304:
4301:
4299:
4296:
4294:
4293:Doxifluridine
4291:
4289:
4286:
4284:
4280:
4279:
4275:
4274:
4272:
4270:
4266:
4259:
4256:
4254:
4250:
4249:
4245:
4243:
4242:Rabacfosadine
4240:
4238:
4235:
4232:
4229:
4227:
4224:
4222:
4218:
4217:
4213:
4209:
4208:
4204:
4200:
4199:
4195:
4194:
4192:
4190:
4186:
4179:
4176:
4174:
4170:
4169:
4165:
4162:
4159:
4157:
4154:
4152:
4149:
4147:
4143:
4142:
4138:
4137:
4135:
4133:
4129:
4126:
4123:
4118:
4112:
4109:
4105:
4101:
4090:
4086:
4085:
4081:
4078:
4075:
4073:
4070:
4068:
4065:
4063:
4060:
4058:
4055:
4053:
4049:
4048:
4044:
4043:
4041:
4037:
4030:
4027:
4025:
4022:
4020:
4017:
4015:
4012:
4010:
4006:
4005:
4001:
4000:
3998:
3995:
3990:
3987:
3984:
3979:
3975:
3971:
3966:
3962:
3958:
3950:
3945:
3943:
3938:
3936:
3931:
3930:
3927:
3919:
3915:
3911:
3907:
3903:
3902:
3890:
3886:
3882:
3878:
3875:(9): 1293–7.
3874:
3870:
3866:
3859:
3844:
3840:
3834:
3826:
3822:
3817:
3812:
3807:
3802:
3798:
3794:
3790:
3783:
3772:
3765:
3764:
3756:
3748:
3744:
3740:
3736:
3732:
3725:
3717:
3714:(in German).
3713:
3710:tumors].
3705:
3697:
3693:
3689:
3685:
3678:
3670:
3666:
3661:
3656:
3652:
3648:
3644:
3637:
3630:
3624:
3616:
3612:
3608:
3604:
3601:(8): 555–60.
3600:
3596:
3589:
3581:
3577:
3573:
3569:
3562:
3554:
3550:
3546:
3542:
3538:
3534:
3531:(4): 369–83.
3530:
3526:
3519:
3511:
3507:
3504:(4): 337–46.
3503:
3499:
3492:
3484:
3480:
3476:
3472:
3468:
3464:
3457:
3449:
3445:
3441:
3437:
3434:(3): 163–73.
3433:
3429:
3428:Blood Reviews
3422:
3414:
3408:
3404:
3400:
3396:
3392:
3389:(6): 508–10.
3388:
3385:(in French).
3384:
3377:
3369:
3365:
3361:
3357:
3353:
3349:
3345:
3341:
3334:
3326:
3322:
3318:
3314:
3306:
3298:
3294:
3289:
3284:
3280:
3276:
3272:
3265:
3257:
3253:
3249:
3245:
3241:
3237:
3233:
3229:
3222:
3214:
3210:
3206:
3202:
3199:(7705): 912.
3198:
3194:
3187:
3179:
3175:
3171:
3167:
3163:
3159:
3155:
3151:
3144:
3136:
3132:
3128:
3124:
3120:
3116:
3113:(3): 750–71.
3112:
3108:
3101:
3087:on 2021-08-28
3086:
3082:
3078:
3075:(2): 206–10.
3074:
3070:
3066:
3059:
3051:
3047:
3042:
3037:
3033:
3029:
3025:
3018:
3010:
3006:
3002:
2998:
2995:(8): 1120–7.
2994:
2990:
2982:
2974:
2970:
2965:
2960:
2957:(4): 378–81.
2956:
2952:
2948:
2941:
2933:
2929:
2925:
2921:
2917:
2913:
2909:
2905:
2898:
2890:
2886:
2882:
2878:
2874:
2870:
2863:
2855:
2851:
2847:
2843:
2838:
2833:
2830:(3): 346–68.
2829:
2825:
2821:
2814:
2806:
2802:
2798:
2794:
2791:(7): 1034–9.
2790:
2786:
2779:
2771:
2767:
2763:
2759:
2755:
2751:
2744:
2736:
2732:
2728:
2724:
2720:
2716:
2712:
2708:
2704:
2697:
2689:
2685:
2681:
2677:
2673:
2669:
2662:
2654:
2650:
2646:
2642:
2638:
2634:
2630:
2626:
2619:
2617:
2615:
2606:
2602:
2598:
2594:
2590:
2586:
2582:
2578:
2571:
2563:
2559:
2555:
2551:
2547:
2543:
2536:
2528:
2524:
2520:
2516:
2512:
2508:
2501:
2493:
2489:
2485:
2481:
2477:
2473:
2466:
2458:
2454:
2450:
2446:
2442:
2438:
2431:
2423:
2419:
2414:
2409:
2404:
2399:
2395:
2391:
2387:
2380:
2372:
2368:
2364:
2360:
2356:
2352:
2345:
2337:
2333:
2330:(2): 188–94.
2329:
2325:
2318:
2310:
2306:
2301:
2296:
2293:(3): 237–41.
2292:
2288:
2284:
2277:
2269:
2265:
2260:
2255:
2251:
2247:
2243:
2239:
2235:
2228:
2220:
2216:
2211:
2206:
2202:
2198:
2194:
2190:
2186:
2179:
2171:
2167:
2163:
2159:
2154:
2149:
2146:(5): 667–84.
2145:
2141:
2137:
2130:
2122:
2118:
2114:
2110:
2106:
2102:
2098:
2094:
2087:
2079:
2075:
2070:
2065:
2060:
2055:
2051:
2047:
2043:
2036:
2028:
2024:
2019:
2014:
2010:
2006:
2002:
1998:
1994:
1987:
1979:
1975:
1970:
1965:
1961:
1957:
1953:
1949:
1945:
1938:
1930:
1926:
1922:
1918:
1911:
1903:
1897:
1893:
1887:
1871:
1867:
1860:
1858:
1856:
1846:
1841:
1837:
1833:
1827:
1819:
1815:
1810:
1805:
1801:
1797:
1793:
1789:
1785:
1778:
1776:
1759:
1755:
1749:
1747:
1745:
1743:
1741:
1739:
1737:
1735:
1733:
1731:
1714:
1710:
1706:
1700:
1692:
1691:
1686:
1680:
1665:
1661:
1657:
1651:
1647:
1637:
1633:
1629:
1628:
1627:
1618:
1617:in medicine.
1616:
1615:best practice
1606:
1604:
1600:
1599:enzymatically
1596:
1591:
1587:
1583:
1577:
1575:
1571:
1564:
1556:
1554:
1550:
1542:
1539:
1536:
1535:
1534:
1532:
1531:immunotherapy
1528:
1523:
1521:
1516:
1512:
1508:
1505:
1501:
1497:
1493:
1488:
1486:
1482:
1478:
1468:
1466:
1462:
1458:
1454:
1449:
1447:
1443:
1439:
1435:
1431:
1427:
1423:
1417:
1414:
1412:
1408:
1404:
1400:
1396:
1392:
1388:
1384:
1380:
1377:
1367:
1365:
1361:
1357:
1351:
1349:
1348:breast cancer
1345:
1341:
1336:
1334:
1330:
1326:
1322:
1318:
1314:
1310:
1306:
1302:
1298:
1294:
1290:
1280:
1278:
1274:
1270:
1260:
1258:
1254:
1250:
1246:
1242:
1238:
1234:
1230:
1221:
1219:
1215:
1211:
1207:
1203:
1199:
1196:
1192:
1183:
1180:
1176:
1171:
1169:
1165:
1161:
1156:
1154:
1150:
1146:
1142:
1138:
1134:
1130:
1126:
1117:
1115:
1111:
1107:
1103:
1098:
1096:
1092:
1088:
1084:
1074:
1072:
1068:
1064:
1060:
1056:
1052:
1043:
1041:
1037:
1033:
1029:
1028:dexamethasone
1025:
1021:
1011:
1009:
1005:
1001:
997:
992:
990:
986:
982:
978:
974:
970:
966:
962:
958:
954:
944:
942:
938:
937:neuroblastoma
934:
930:
926:
917:
908:
906:
902:
892:
890:
885:
883:
879:
875:
871:
867:
863:
859:
855:
851:
847:
842:
840:
836:
832:
828:
824:
820:
819:neuroblastoma
816:
812:
811:breast cancer
808:
804:
800:
796:
792:
788:
784:
783:cytophosphane
780:
776:
766:
759:
750:
745:
744:
741:
734:
725:
724:
721:
714:
710:
708:
707:Melting point
704:
697:
693:
692:
690:
687:
682:
675:
673:
669:
633:
631:
627:
622:
618:
614:
611:
609:
607:ECHA InfoCard
603:
595:
591:
590:DTXSID5020364
587:
586:
584:
575:
571:
564:
560:
559:
557:
555:
551:
544:
540:
539:
537:
535:
531:
524:
520:
519:
517:
515:
511:
504:
500:
499:
497:
495:
491:
484:
480:
479:
477:
475:
471:
464:
460:
459:
457:
455:
451:
444:
440:
439:
437:
430:
426:
419:
415:
414:
412:
410:
406:
398:
394:
390:
385:
384:
381:
374:
369:
366:
363:
361:
357:
353:
351:
344:
341:
338:
336:
332:
328:
326:
322:
318:
316:
312:
308:
304:
297:
295:
285:
282:
272:
270:
261:
258:
248:
247:
245:
243:
239:
234:
226:
221:
218:
217:
215:
213:
209:
206:
202:
199:
197:
191:
185:
176:
175:
173:
171:
165:
161:
157:
155:
151:
147:
143:
141:
137:
133:
129:
127:
123:
117:
52:
50:Pronunciation
48:
45:Clinical data
43:
39:
34:
30:
25:
6713:Hepatotoxins
6677:
6664:
6644:Ketoconazole
6641:Antagonists:
6640:
6614:Troglitazone
6589:Tetracycline
6544:Spiroxatrine
6489:Quingestrone
6484:Progesterone
6469:Pregnenolone
6464:Pregnanolone
6454:Pregnanediol
6449:Prednisolone
6374:Mifepristone
6301:
6276:Griseofulvin
6256:Fenbendazole
6241:Famprofazone
6236:Erythromycin
6231:Epothilone B
6216:Eburnamonine
6125:
6111:Clotrimazole
6101:Clofenvinfos
6036:Antimycotics
5967:
5930:Okadaic acid
5882:Antagonists:
5881:
5870:Troglitazone
5805:Mifepristone
5800:Methoxychlor
5795:Griseofulvin
5790:Ellagic acid
5770:Cypermethrin
5764:
5760:Clotrimazole
5711:
5555:Tazemetostat
5519:Alitretinoin
5512:
5423:Estramustine
5403:Elsamitrucin
5393:Eflornithine
5347:Pegaspargase
5343:Asparaginase
5336:
5305:Testolactone
5298:
5286:
5274:
5228:
5213:Panobinostat
5196:
5166:
5154:
5142:
5130:
5101:
5066:
5054:
5007:
5003:Padeliporfin
4942:Dactinomycin
4938:Streptomyces
4919:Temozolomide
4914:Mitozolomide
4902:
4893:Mitobronitol
4882:Procarbazine
4875:
4863:Nonclassical
4788:
4765:
4759:Streptozocin
4724:Nitrosoureas
4722:
4696:Chlorambucil
4690:Trofosfamide
4680:
4676:Chlormethine
4671:Bendamustine
4664:
4602:Mitoxantrone
4597:Losoxantrone
4590:
4550:Daunorubicin
4533:
4499:
4436:Camptothecin
4424:
4380:
4350:
4336:
4319:
4303:Fluorouracil
4283:Capecitabine
4276:
4246:
4210:
4196:
4166:
4161:Pralatrexate
4151:Methotrexate
4139:
4082:
4045:
4002:
3909:
3872:
3868:
3858:
3847:. Retrieved
3833:
3796:
3792:
3782:
3762:
3755:
3738:
3734:
3724:
3715:
3711:
3704:
3687:
3683:
3677:
3653:(3): 542–7.
3650:
3646:
3636:
3623:
3598:
3594:
3588:
3574:(3): 655–8.
3571:
3567:
3561:
3528:
3524:
3518:
3501:
3497:
3491:
3466:
3462:
3456:
3431:
3427:
3421:
3386:
3382:
3376:
3343:
3339:
3333:
3316:
3312:
3305:
3278:
3274:
3264:
3231:
3227:
3221:
3196:
3192:
3186:
3153:
3149:
3143:
3110:
3106:
3100:
3089:. Retrieved
3085:the original
3072:
3068:
3058:
3031:
3027:
3017:
2992:
2988:
2981:
2954:
2950:
2940:
2907:
2903:
2897:
2875:(1): 79–94.
2872:
2868:
2862:
2827:
2823:
2813:
2788:
2784:
2778:
2753:
2749:
2743:
2710:
2706:
2696:
2671:
2667:
2661:
2628:
2624:
2583:(8): 636–9.
2580:
2576:
2570:
2548:(3): 548–9.
2545:
2541:
2535:
2510:
2506:
2500:
2475:
2471:
2465:
2443:(1): 31–54.
2440:
2436:
2430:
2393:
2390:BMC Medicine
2389:
2379:
2357:(3): 180–4.
2354:
2350:
2344:
2327:
2323:
2317:
2290:
2286:
2276:
2241:
2237:
2227:
2192:
2188:
2178:
2143:
2139:
2129:
2096:
2092:
2086:
2049:
2045:
2035:
2000:
1997:Rheumatology
1996:
1986:
1951:
1947:
1937:
1920:
1910:
1891:
1886:
1874:. Retrieved
1869:
1845:10665/325771
1835:
1826:
1791:
1787:
1762:. Retrieved
1717:. Retrieved
1708:
1699:
1688:
1679:
1668:. Retrieved
1664:the original
1650:
1624:
1612:
1579:
1573:
1569:
1566:
1562:
1546:
1524:
1492:chemotherapy
1489:
1474:
1450:
1426:barbiturates
1418:
1415:
1373:
1370:Pharmacology
1363:
1360:cytogenetics
1352:
1340:radiotherapy
1337:
1311:, including
1289:carcinogenic
1286:
1266:
1227:
1189:
1179:hyponatremia
1172:
1157:
1137:stomach ache
1123:
1120:Side effects
1099:
1080:
1049:
1024:lenalidomide
1017:
1008:azathioprine
993:
967:with severe
950:
933:brain cancer
925:chemotherapy
922:
898:
895:Medical uses
886:
843:
787:chemotherapy
782:
778:
774:
773:
762:
396:
392:
388:
347:Elimination
242:Legal status
236:Legal status
6629:Zafirlukast
6599:Thiothixene
6579:Terconazole
6529:Simvastatin
6404:Nisoldipine
6399:Nilvadipine
6384:Nicardipine
6354:Metacycline
6181:Dimercaprol
6136:Demecolcine
6096:Clindamycin
6091:Ciglitazone
6041:Artemisinin
6021:Ambrisentan
5925:Nigramide J
5860:Telmisartan
5820:Nicardipine
5730:Benfuracarb
5725:Artemisinin
5630:from market
5600:Vorasidenib
5580:Trabectedin
5565:Tiazofurine
5560:Tebentafusp
5545:Tagraxofusp
5503:Plitidepsin
5473:Mitoguazone
5413:Epacadostat
5383:Demecolcine
5327:Aflibercept
5300:Sex steroid
5173:Fuzuloparib
5114:Carfilzomib
5086:Palbociclib
5076:Abemaciclib
5029:Verteporfin
4993:Efaproxiral
4909:Dacarbazine
4871:Altretamine
4853:Satraplatin
4848:Oxaliplatin
4828:Carboplatin
4805:Triaziquone
4776:Mannosulfan
4754:Ranimustine
4734:Fotemustine
4575:Pirarubicin
4560:Doxorubicin
4554:+cytarabine
4540:Aclarubicin
4501:Podophyllum
4426:Camptotheca
4357:Azacitidine
4343:Gemcitabine
4298:Floxuridine
4231:Fludarabine
4226:Clofarabine
4212:Halogenated
4203:Pentostatin
4178:Raltitrexed
4146:Aminopterin
4089:Ixabepilone
4084:Epothilones
4052:Cabazitaxel
4029:Vinorelbine
4014:Vincristine
4009:Vinblastine
3994:microtubule
2674:(1): 9–21.
2244:(2): 90–7.
1719:20 December
1553:vaccination
1518:subsequent
1446:allopurinol
1411:breast milk
1391:equilibrium
1344:CMF-therapy
1301:skin cancer
1277:leuprorelin
1273:infertility
1263:Infertility
1233:lymphopenia
1229:Neutropenia
1160:pneumonitis
1095:neutropenia
1083:teratogenic
1020:thalidomide
858:infertility
679: g·mol
613:100.000.015
371:Identifiers
154:MedlinePlus
126:Trade names
6707:Categories
6609:Tianeptine
6574:Tenylidone
6569:Tacrolimus
6514:Rimexolone
6504:Rifampicin
6444:Plicamycin
6429:Paclitaxel
6414:Omeprazole
6394:Nifedipine
6369:Mevastatin
6364:Metyrapone
6344:Lovastatin
6339:Loratadine
6296:Hyperforin
6286:Haloprogin
6251:Felodipine
6226:Enzacamene
6206:Dronabinol
6171:Diclazuril
6150:prasterone
6106:Chloroxine
6081:Cephradine
6051:Bile acids
5865:Tolnaftate
5830:Permethrin
5815:Nevirapine
5810:Nefazodone
5779:prasterone
5740:Carvedilol
5720:Amiodarone
5691:modulators
5595:Verdinexor
5590:Venetoclax
5493:Oblimersen
5488:Navitoclax
5463:Lucanthone
5458:Lonidamine
5448:Lifileucel
5443:Ivosidenib
5438:Imetelstat
5408:Enasidenib
5398:Elesclomol
5363:Bexarotene
5358:Belzutifan
5293:Bexarotene
5281:Atrasentan
5256:Umbralisib
5251:Idelalisib
5241:Copanlisib
5223:Vorinostat
5218:Romidepsin
5208:Entinostat
5203:Belinostat
5161:Masoprocol
5149:Tiazofurin
5137:Anagrelide
5109:Bortezomib
5096:Seliciclib
5091:Ribociclib
5071:inhibitors
5061:Tipifarnib
5024:Temoporfin
5019:Talaporfin
4957:Plicamycin
4952:Mitomycins
4898:Pipobroman
4877:Hydrazines
4843:Nedaplatin
4795:Carboquone
4790:Aziridines
4781:Treosulfan
4729:Carmustine
4716:Uramustine
4685:Ifosfamide
4657:Alkylating
4618:Bisantrene
4607:Pixantrone
4580:Valrubicin
4570:Idarubicin
4565:Epirubicin
4511:Teniposide
4466:Lurtotecan
4461:Irinotecan
4362:Decitabine
4326:Cytarabine
4269:Pyrimidine
4258:Tioguanine
4248:Thiopurine
4237:Nelarabine
4221:Cladribine
4173:Pemetrexed
4156:Pemetrexed
4132:Folic acid
4072:Paclitaxel
4024:Vinflunine
3849:2015-07-01
3741:(1): 1–7.
3091:2014-05-02
2826:(Review).
2396:(1): 137.
2052:(1): 155.
1921:StatPearls
1764:8 December
1670:2016-01-20
1643:References
1586:ifosfamide
1520:alkylation
1507:epithelium
1504:intestinal
1430:rifampicin
1255:receiving
1198:epithelium
996:amenorrhea
684:3D model (
672:Molar mass
543:CHEBI:4027
503:6UXW23996M
474:ChemSpider
409:CAS Number
380:IUPAC name
354:3–12 hours
335:Metabolism
6534:Sirolimus
6524:Ritonavir
6519:Riodipine
6509:Rifaximin
6494:Reserpine
6479:Proadifen
6424:Oxatomide
6379:Nafcillin
6349:Meclizine
6211:Droxidopa
6191:Docetaxel
6116:Colforsin
6066:Bumecaine
6056:Bithionol
5968:Agonists:
5945:T-0901317
5920:Meclizine
5850:Reserpine
5840:Phenytoin
5825:Octicizer
5785:Efavirenz
5712:Agonists:
5640:Phase III
5628:Withdrawn
5605:Vosaroxin
5585:Veliparib
5540:Sotorasib
5530:Selinexor
5524:Tretinoin
5514:Retinoids
5428:Glasdegib
5373:Celecoxib
5322:Adagrasib
5246:Duvelisib
5236:Alpelisib
5191:Rucaparib
5178:Niraparib
5119:Oprozomib
5081:Alvocidib
4947:Bleomycin
4904:Triazenes
4888:Etoglucid
4833:Cisplatin
4749:Nimustine
4743:Semustine
4739:Lomustine
4701:Melphalan
4628:Menogaril
4623:Crisnatol
4613:Amsacrine
4585:Zorubicin
4545:Amrubicin
4506:Etoposide
4481:Topotecan
4476:Silatecan
4471:Rubitecan
4456:Gimatecan
4441:Cositecan
4431:Belotecan
4107:inhibitor
4077:Tesetaxel
4067:Ortataxel
4062:Larotaxel
4057:Docetaxel
4019:Vindesine
3799:(1): 55.
3034:: 453–9.
1876:12 August
1485:apoptosis
1434:phenytoin
1393:with its
1293:lymphomas
1237:bacterial
1224:Infection
1206:hematuria
1091:lactation
1040:melphalan
975:, severe
929:lymphomas
850:hair loss
360:Excretion
349:half-life
194:Routes of
168:Pregnancy
146:Monograph
140:Drugs.com
6743:Prodrugs
6697:Medicine
6661:See also
6549:SR-12813
6439:Piperine
6419:Orlistat
6389:Nicotine
6261:Fentanyl
6246:Febantel
6221:Ecopipam
6186:Dinaline
6071:Cafestol
6061:Bosentan
5935:PK-11195
5478:Mitotane
5418:Eribulin
5186:Olaparib
5124:Ixazomib
4800:Thiotepa
4772:Busulfan
4451:Exatecan
4288:Carmofur
3996:assembly
3959: /
3889:21530682
3843:Archived
3825:16545113
3771:archived
3718:: 361–7.
3696:73296245
3615:10469891
3545:21611872
3368:22946564
3360:10627651
3297:11918757
3248:20446865
3178:39787288
3170:10803453
3135:25381232
3127:21737530
3050:18024664
2973:18299492
2932:10873321
2924:12083977
2846:25627555
2805:18576286
2688:20039416
2653:18219134
2645:19786984
2605:26125211
2597:12945725
2527:16234530
2422:27623861
2351:Oncology
2309:10482872
2268:27000732
2219:26039204
2162:26684279
2121:85480421
2113:25407896
2078:27619512
2027:28375452
1978:17253481
1929:29083697
1834:(2019).
1818:27733943
1758:Archived
1713:Archived
1621:Research
1570:in vitro
1407:placenta
1395:tautomer
1297:leukemia
1191:Acrolein
1164:fibrosis
1153:lethargy
1149:alopecia
1145:diarrhea
941:leukemia
803:leukemia
795:lymphoma
765:(verify)
563:ChEMBL88
454:DrugBank
212:ATC code
201:By mouth
170:category
6649:Sesamin
6634:Zeranol
6564:Suramin
6334:LOE-908
6026:AMI-193
5940:S-07662
5855:TCPOBOP
5750:Chrysin
4407:S phase
4308:Tegafur
4122:S phase
4047:Taxanes
3983:M phase
3816:1434751
3747:2491747
3669:8697402
3553:3360104
3510:1277209
3483:2996550
3448:1422285
3413:2947795
3403:8745976
3325:1277213
3213:4102054
3081:4393764
3009:7639809
2889:3789582
2770:8814058
2735:8800101
2727:1356175
2562:3977522
2492:8970380
2457:1691069
2413:5022202
2371:6374556
2336:1673721
2259:4806368
2210:4634886
2170:1093277
2069:5020478
2018:5850311
1969:8078225
1809:5058451
1574:in vivo
1559:History
1481:guanine
1422:alcohol
1379:enzymes
1376:oxidase
1364:de novo
1210:dysuria
1195:bladder
823:sarcoma
789:and to
630:Formula
463:DB00531
429:PubChem
418:50-18-0
329:>60%
267::
228:)
222: (
220:L01AA01
183: D
160:a682080
6683:Portal
6156:DHEA-S
5996:AA-861
5623:WHO-EM
5232:(Pi3K)
4189:Purine
3992:Block
3887:
3823:
3813:
3745:
3694:
3667:
3647:Cancer
3613:
3551:
3543:
3508:
3481:
3446:
3410:
3401:
3366:
3358:
3323:
3295:
3256:695545
3254:
3246:
3211:
3193:Lancet
3176:
3168:
3133:
3125:
3079:
3048:
3007:
2971:
2930:
2922:
2887:
2854:870510
2852:
2844:
2803:
2768:
2733:
2725:
2707:Lancet
2686:
2651:
2643:
2603:
2595:
2560:
2525:
2490:
2455:
2420:
2410:
2369:
2334:
2307:
2266:
2256:
2217:
2207:
2168:
2160:
2119:
2111:
2076:
2066:
2025:
2015:
1976:
1966:
1927:
1898:
1816:
1806:
1590:Baxter
1283:Cancer
1241:fungal
1106:cancer
1059:T cell
959:where
911:Cancer
864:, and
852:, and
821:, and
720:SMILES
677:261.08
554:ChEMBL
523:D07760
365:Kidney
294:℞-only
292:
279:
269:℞-only
255:
120:
5755:CITCO
5144:IMPDI
5039:Other
3774:(PDF)
3767:(PDF)
3686:[
3549:S2CID
3407:INIST
3364:S2CID
3252:S2CID
3174:S2CID
3131:S2CID
2928:S2CID
2850:S2CID
2731:S2CID
2649:S2CID
2601:S2CID
2577:Lupus
2166:S2CID
2117:S2CID
1635:rats.
1500:liver
1444:, or
1432:, or
1366:AML.
1214:mesna
1110:lupus
740:InChI
686:JSmol
534:ChEBI
340:Liver
6327:and
6146:DHEA
5910:AITC
5775:DHEA
5230:PIKI
5198:HDAC
4647:CCNS
3885:PMID
3821:PMID
3743:PMID
3692:OCLC
3665:PMID
3611:PMID
3541:PMID
3506:PMID
3479:PMID
3444:PMID
3399:PMID
3356:PMID
3321:PMID
3293:PMID
3244:PMID
3209:PMID
3166:PMID
3123:PMID
3077:PMID
3046:PMID
3032:2007
3005:PMID
2969:PMID
2920:PMID
2885:PMID
2842:PMID
2801:PMID
2766:PMID
2723:PMID
2684:PMID
2641:PMID
2593:PMID
2558:PMID
2523:PMID
2488:PMID
2453:PMID
2418:PMID
2367:PMID
2332:PMID
2305:PMID
2264:PMID
2215:PMID
2158:PMID
2109:PMID
2074:PMID
2023:PMID
1974:PMID
1952:2007
1925:PMID
1896:ISBN
1878:2017
1814:PMID
1766:2016
1721:2016
1630:The
1502:and
1477:ALDH
1346:for
1319:and
1243:and
1026:and
987:and
872:and
514:KEGG
494:UNII
483:2804
443:2907
309:data
136:AHFS
5956:PXR
5700:CAR
5276:ERA
5132:PhI
5103:PrI
5068:CDK
4980:PDT
3978:MIs
3974:SPs
3965:L01
3877:doi
3811:PMC
3801:doi
3655:doi
3603:doi
3576:doi
3533:doi
3471:doi
3436:doi
3391:doi
3348:doi
3283:doi
3236:doi
3201:doi
3158:doi
3115:doi
3073:174
3036:doi
2997:doi
2959:doi
2955:168
2912:doi
2877:doi
2873:106
2832:doi
2793:doi
2758:doi
2715:doi
2711:340
2676:doi
2633:doi
2585:doi
2550:doi
2546:145
2515:doi
2480:doi
2476:154
2445:doi
2408:PMC
2398:doi
2359:doi
2295:doi
2254:PMC
2246:doi
2205:PMC
2197:doi
2148:doi
2144:172
2101:doi
2064:PMC
2054:doi
2013:PMC
2005:doi
1964:PMC
1956:doi
1840:hdl
1804:PMC
1796:doi
1632:EPA
1603:FDA
1513:to
1249:PCP
1231:or
1108:or
1034:of
1022:or
1006:or
998:or
882:RNA
878:DNA
579:EPA
433:CID
281:POM
225:WHO
6709::
5636::
5156:LI
5056:FI
4522:II
4492:II
4314:))
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