510:
487:
887:. A more recent, larger study, however, performed by the Cancers et Surrisque Associe aux Maladies inflamatoires intestinales En France (CESAME) indicated an overall rate of congenital malformations not significantly greater than the general population in France. The European Crohn's and Colitis Organisation (ECCO) concluded in a consensus paper in 2010 that while AZA and mercaptopurine have an FDA rating of D, new research in both animals and humans indicates that "thiopurines are safe and well tolerated during pregnancy."
848:, and inosine triphosphate pyrophosphatase (ITPA). People with specific allele variants will require dose adjustments, especially for those with homozygous variant genotypes. Large differences of TPMT and NUDT15 among ethnicities in terms of variant allele frequency should be taken into consideration in clinical practice. Caucasian people with a variant allele of the ITPA gene, experience higher rates of febrile neuropenia than people of other ethnic groups, due to differences in allelic frequencies among ethnicities.
40:
983:
Specifically, Mercaptopurine is a purine antimetabolite or purine antagonist as such inhibits DNA synthesis by inhibiting the production of the purine containing nucleotides, adenine and guanine thus halting DNA synthesis. Mercaptopurine also acts as an immunomodulator by inhibiting several pathways in nucleic acid biosynthesis preventing proliferation of cells involved in the determination and amplification of the immune response.
31:
4299:
929:
915:(often used to prevent gout) are at risk for mercaptopurine toxicity. The dose should be reduced or allopurinol should be discontinued. Several published studies have demonstrated that the use of allopurinol in combination with low dose 6-MP helps reduce 6-MP levels, which are toxic to liver tissue, whilst increasing the therapeutic levels of 6-MP for some inflammatory conditions.
875:) showed a seven-fold incidence of fetal abnormalities as well as a 20-fold increase in miscarriage. There were also anecdotal reports linking mercaptopurine with spontaneous abortion, leading to the US FDA rating both AZA and mercaptopurine as category D drugs. However, Davis et al. 1999 found mercaptopurine, compared to
786:
thiopurine nucleotides can help to optimize the efficacy and safety. Clinically, most hospitals resort to on-exchange LC-MS (liquid chromatography - mass spectrometry) but the newly developed approach of porous graphitic carbon based chromatography hyphenated with mass spectrometry appears superior
982:
Mercaptopurine is an antimetabolite antineoplastic, as such it interferes with normal metabolic processes within cells, typically by combining with enzymes, to disrupt DNA and RNA synthesis (cell-cycle S phase-specific) leading to death of rapidly proliferating cells, especially malignant ones.
1385:
Pecher D, Zelinkova Z, Lucenicova J, Peppelenbosch M, Dokupilova S, Mikusova V, et al. (November 2020). "Porous graphitic carbon based chromatography hyphenated with mass spectrometry: A new strategy for profiling thiopurine nucleotides in patients with inflammatory bowel diseases".
833:. Quarterly blood counts are necessary for people on mercaptopurine. People should stop taking the medication at least temporarily while considering alternate treatment if there is an unexplained, abnormally large drop in white blood cell count, or any other blood count.
894:
in animals and humans, though a study in 1990 found, "while the carcinogenic potential of 6-MP cannot be precluded, it can be only very weak or marginal." Another study in 1999 noted an increased risk of developing leukemia when taking large doses of 6-MP with other
1126:
can identify people with reduced TPMT activity, allowing for the adjustment of mercaptopurine dose or avoidance of the drug entirely. The FDA-approved drug label for mercaptopurine recommends testing for TPMT activity to identify people at risk for
1038:
Animal tumors that are resistant to mercaptopurine often have lost the ability to convert mercaptopurine to TIMP. However, it is clear that resistance to mercaptopurine may be acquired by other means as well, particularly in human
2038:
Nielsen OH, Vainer B, Rask-Madsen J. Review article: the treatment of inflammatory bowel disease with 6-mercaptopurine or azathioprine. Aliment
Pharmacol Ther. 2001 Nov;15(11):1699-708. doi: 10.1046/j.1365-2036.2001.01102.x. PMID
2003:
1759:
Coelho J, Beaugerie L, Colombel JF, Hébuterne X, Lerebours E, Lémann M, et al. (February 2011). "Pregnancy outcome in patients with inflammatory bowel disease treated with thiopurines: cohort from the CESAME Study".
1034:
Some mercaptopurine is converted to nucleotide derivatives of 6-thioguanine (6-TG) by the sequential actions of inosinate (IMP) dehydrogenase and xanthylate (XMP) aminase, converting TIMP to thioguanylic acid
1992:
1042:
It is not known exactly which of any one or more of the biochemical effects of mercaptopurine and its metabolites are directly or predominantly responsible for cell death.
2377:
4165:
1027:
pathway for purine ribonucleotide synthesis. Experiments indicate that radiolabeled mercaptopurine may be recovered from the DNA in the form of deoxythioguanosine.
1872:
Maekawa A, Nagaoka T, Onodera H, Matsushima Y, Todate A, Shibutani M, et al. (May 1990). "Two-year carcinogenicity study of 6-mercaptopurine in F344 rats".
4339:
2048:
Hansen, Barbara. "Purine and
Pyrimidine Metabolism." USMLE STEP 1 Biochemistry and Medical Genetics Lecture Notes. 2010 ed. N.p.: Kaplan, 2010. 288-90. Print.
146:
2187:
2577:
947:
1114:
polymorphisms that result in decreased or absent TPMT activity occur with a frequency of approximately 5%, meaning that about 0.25% of people are
782:. Treatment is discontinued in up to 30% of patients due these effects but therapeutic drug monitoring of the biologically active metabolites,
999:
2540:
1047:
70:
2475:
4225:
3277:
1023:
Both TIMP and MTIMP have been reported to inhibit glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the
590:
1947:
1930:
1192:
3106:
3086:
3071:
1050:(PRPP amidotransferase). Since this enzyme is the rate limiting factor for purine synthesis, this alters the synthesis and function of
1745:
856:
Mercaptopurine can lower the body's ability to fight off infection. Those taking it should get permission from a doctor to receive
754:
of taking mercaptopurine may include diarrhea, nausea, vomiting, loss of appetite, fatigue, stomach/abdominal pain, weakness, skin
1239:
2399:
2246:"Clinical Pharmacogenetics Implementation Consortium guidelines for thiopurine methyltransferase genotype and thiopurine dosing"
1363:
871:
This drug was formerly not recommended during pregnancy and early evidence indicated pregnant women on the drug (or the related
2373:
2293:
2172:
2107:
1978:
1915:
1858:
1803:
1612:
1549:
1486:
1439:"Inherited NUDT15 variant is a genetic determinant of mercaptopurine intolerance in children with acute lymphoblastic leukemia"
1160:
883:; every woman in the mercaptopurine arm of the study had fetal cardiac activity at follow-up (two weeks later) and was given a
3493:
4253:
2570:
2316:
719:
635:
121:
3860:
3012:
2968:
2846:
2509:
2555:
4329:
2771:
1819:"The second European evidence-based Consensus on the diagnosis and management of Crohn's disease: Special situations"
1272:
965:
610:
4270:
2563:
576:
4324:
3287:
264:
176:
102:
2188:"Pharmacogenomics in drug-metabolizing enzymes catalyzing anticancer drugs for personalized cancer chemotherapy"
3906:
2908:
2798:
1931:"Possible carcinogenic effect of 6-mercaptopurine on bone marrow stem cells: relation to thiopurine metabolism"
1071:
700:
335:
3828:
3811:
3686:
3450:
2828:
2225:
1288:
Sahasranaman S, Howard D, Roy S (August 2008). "Clinical pharmacology and pharmacogenetics of thiopurines".
695:, vomiting, and loss of appetite. Other serious side effects include an increased risk of future cancer and
3560:
3156:
1156:
837:
669:
505:
386:
4334:
3762:
466:
3152:
3122:
4289:
2942:
2123:"Pharmacogenetics of azathioprine in inflammatory bowel disease: a role for glutathione-S-transferase?"
1929:
Bo J, Schrøder H, Kristinsson J, Madsen B, Szumlanski C, Weinshilboum R, et al. (September 1999).
1817:
Van Assche G, Dignass A, Reinisch W, van der Woude CJ, Sturm A, De Vos M, et al. (February 2010).
1046:
6-MP ribonucleotide inhibits purine nucleotide synthesis and metabolism by inhibiting an enzyme called
864:. It is also recommended that, while on the drug, one should avoid those having recently received oral
731:
665:
455:
3047:
2025:
1106:
may have increased levels of TGN metabolites and an increased risk of severe bone marrow suppression (
4128:
4008:
3998:
1331:
2425:
Wang L, Pelleymounter L, Weinshilboum R, Johnson JA, Hebert JM, Altman RB, et al. (June 2010).
1565:"Impact of NUDT15 polymorphisms on thiopurines-induced myelotoxicity and thiopurines tolerance dose"
4180:
4113:
4083:
3701:
2951:
1094:
within the TPMT gene can lead to decreased or absent TPMT enzyme activity, and individuals who are
482:
2483:
4258:
3983:
3698:
3184:
3032:
2959:
2311:(in German) (8th ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 107, 936.
688:
132:
52:
4063:
4053:
3786:
3628:
2244:
Relling MV, Gardner EE, Sandborn WJ, Schmiegelow K, Pui CH, Yee SW, et al. (March 2011).
2121:
Stocco G, Pelin M, Franca R, De
Iudicibus S, Cuzzoni E, Favretto D, et al. (April 2014).
1500:
Moriyama T, Nishii R, Perez-Andreu V, Yang W, Klussmann FA, Zhao X, et al. (April 2016).
435:
3335:
2982:
2287:
2219:
2166:
2101:
1972:
1909:
1852:
1797:
1606:
1543:
1480:
1159:, and was clinically developed in collaboration with investigators at Memorial Hospital (now
1078:(TPMT) is responsible, in part, for the inactivation of 6-mercaptopurine. TPMT catalyzes the
770:, and painful or difficult urination. Other more serious side effects include black or tarry
766:, easy bruising or bleeding, pinpoint red spots on the skin, yellowing of eyes or skin, dark
751:
326:
2058:
Zaza G, Cheok M, Krynetskaia N, Thorn C, Stocco G, Hebert JM, et al. (September 2010).
1175:
could potentially be used as cancer drugs, and had become the director of
Memorial in 1948.
375:
3733:
3610:
3131:
1395:
395:
231:
1171:
programs for the US Army and had been involved in the work that led to the discovery that
8:
4018:
3918:
3897:
3618:
3440:
3272:
3003:
2899:
1164:
1148:
661:
281:
1717:
1399:
943:
509:
486:
290:
3076:
2585:
2451:
2426:
2270:
2245:
2149:
2122:
2084:
2059:
1960:
1897:
1785:
1698:
1589:
1564:
1526:
1501:
1463:
1438:
1419:
1313:
1152:
799:
758:, darkening of the skin, and hair loss. Serious adverse reactions include mouth sores,
739:
735:
718:
Mercaptopurine was approved for medical use in the United States in 1953. It is on the
677:
673:
1733:
1359:
1235:
80:
4200:
3774:
2608:
2544:
2505:
2456:
2355:
2312:
2275:
2207:
2154:
2089:
1952:
1889:
1840:
1777:
1737:
1690:
1685:
1668:
1649:
1594:
1531:
1468:
1423:
1411:
1305:
1268:
1144:
1103:
1091:
94:
1964:
1901:
1789:
1702:
1317:
4319:
4205:
3962:
3677:
3311:
3296:
3017:
2446:
2438:
2345:
2265:
2257:
2199:
2144:
2134:
2079:
2071:
1942:
1881:
1830:
1769:
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1680:
1639:
1584:
1576:
1521:
1513:
1458:
1450:
1403:
1339:
1297:
1172:
1168:
1132:
1107:
908:
884:
822:
818:
522:
315:
224:
201:
159:
2350:
2333:
4303:
3644:
3606:
3397:
2819:
2734:
2442:
2075:
1835:
1818:
1669:"Azathioprine, mercaptopurine and birth outcome: a population-based cohort study"
1437:
Yang JJ, Landier W, Yang W, Liu C, Hageman L, Cheng C, et al. (April 2015).
1020:
In addition, 6-methylthioinosinate (MTIMP) is formed by the methylation of TIMP.
219:
209:
2530:
4264:
3798:
3389:
2747:
2634:
2604:
2591:
2534:
2203:
1119:
1082:
of 6-mercaptopurine into the inactive metabolite 6-methylmercaptopurine – this
1010:
826:
712:
692:
39:
22:
1644:
1627:
1580:
1563:
Yin D, Xia X, Zhang J, Zhang S, Liao F, Zhang G, et al. (February 2017).
1407:
1301:
4313:
4138:
4098:
3468:
3341:
3222:
3165:
2923:
2872:
2139:
1948:
10.1002/(SICI)1097-0142(19990915)86:6<1080::AID-CNCR26>3.0.CO;2-5
1502:"NUDT15 polymorphisms alter thiopurine metabolism and hematopoietic toxicity"
1454:
1128:
1014:
1006:
880:
498:
1773:
4185:
4149:
4033:
4023:
3977:
3973:
3935:
3843:
3633:
3572:
3568:
3549:
3544:
3523:
3512:
3326:
3320:
3306:
3301:
3232:
3227:
3180:
3066:
2933:
2913:
2842:
2791:
2781:
2595:
2587:
2548:
2460:
2359:
2279:
2211:
2158:
2093:
1956:
1844:
1781:
1741:
1694:
1598:
1535:
1472:
1415:
1336:
World Health
Organization model list of essential medicines: 21st list 2019
1309:
1123:
1099:
991:
876:
872:
857:
811:
696:
681:
154:
2261:
1893:
1667:
Nørgård B, Pedersen L, Fonager K, Rasmussen SN, Sørensen HT (March 2003).
1653:
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4210:
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4190:
4175:
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4103:
4043:
4013:
3957:
3930:
3803:
3744:
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3539:
3501:
3483:
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3435:
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3364:
3354:
3205:
3190:
3170:
3056:
2987:
2973:
2928:
2861:
2856:
2833:
2808:
2776:
2719:
2682:
2659:
2644:
2639:
2624:
2332:
Payne K, Newman W, Fargher E, Tricker K, Bruce IN, Ollier WE (May 2007).
1083:
1079:
912:
861:
830:
771:
763:
88:
1344:
355:
4220:
4123:
4118:
4093:
4088:
4078:
4073:
4068:
4038:
4028:
3993:
3988:
3968:
3923:
3911:
3886:
3881:
3871:
3853:
3848:
3838:
3833:
3791:
3779:
3767:
3739:
3726:
3721:
3691:
3654:
3649:
3587:
3582:
3528:
3473:
3425:
3411:
3359:
3346:
3315:
3248:
3237:
3210:
3200:
3195:
3141:
3096:
3091:
2992:
2956:
2888:
2878:
2867:
2851:
2803:
2786:
2762:
2714:
2702:
2654:
1885:
1115:
1095:
1059:
891:
708:
552:
366:
1816:
1718:"Methotrexate compared with mercaptopurine for early induced abortion"
1384:
4235:
4215:
4170:
4160:
4154:
4058:
4003:
3952:
3876:
3866:
3821:
3808:
3749:
3711:
3639:
3577:
3518:
3507:
3463:
3420:
3379:
3373:
3369:
3331:
3258:
3253:
3243:
3215:
3175:
3136:
3111:
3101:
3061:
2707:
2697:
2692:
2687:
2649:
2427:"Very important pharmacogene summary: thiopurine S-methyltransferase"
1087:
896:
836:
Toxicity of mercaptopurine can be linked to genetic polymorphisms in
807:
803:
704:
301:
244:
74:
2424:
1517:
4144:
4108:
4048:
3816:
3754:
3534:
3430:
3402:
3081:
2918:
2334:"TPMT testing in rheumatology: any better than routine monitoring?"
1993:"PURINETHOL (mercaptopurine) tablet [Gate Pharmaceuticals]"
415:
346:
139:
116:
575:
3037:
2938:
2752:
2613:
2243:
1752:
995:
795:
30:
1758:
618:
InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
2677:
1871:
1666:
1267:(69 ed.). British Medical Association. 2015. p. 590.
987:
845:
775:
657:
446:
249:
1499:
1002:
and is itself converted to thio inosine monophosphate (TIMP).
2533:. In Pratt VM, McLeod HL, Rubinstein WS, et al. (eds.).
2120:
1086:
prevents mercaptopurine from further conversion into active,
978:
Official information from the package insert for purinethol:
865:
779:
767:
759:
566:
426:
1660:
911:, the enzyme that breaks down mercaptopurine. Those taking
471:
1928:
791:
755:
680:. For acute lymphocytic leukemia it is generally used with
406:
1118:
for these variants. However, an assay of TPMT activity in
2331:
2057:
1330:
1055:
1051:
2306:
1348:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
790:
Symptoms of allergic reaction to mercaptopurine include
1163:
in New York City). The collaboration was initiated by
720:
1143:
6-MP was discovered by Nobel Prize–winning scientists
1110:) when receiving mercaptopurine. In many ethnicities,
4287:
1715:
1362:. The American Society of Health-System Pharmacists.
1287:
1238:. The American Society of Health-System Pharmacists.
1810:
1709:
1005:TIMP inhibits several chemical reactions involving
938:
may be too technical for most readers to understand
334:
2502:The Emperor of All Maladies: A Biography of Cancer
1716:Davis AR, Miller L, Tamimi H, Gown A (June 1999).
1436:
1090:thioguanine nucleotide (TGN) metabolites. Certain
239:60 to 120 min., longer for its active metabolites
4311:
2214:. Archived from the original on 12 January 2013.
1922:
1874:Journal of Cancer Research and Clinical Oncology
1562:
314:
2374:"Label: Mercaptopurine – mercaptopurine tablet"
2239:
2237:
2235:
289:
787:with respect to patient care in this respect.
4340:World Health Organization essential medicines
2571:
2541:National Center for Biotechnology Information
1632:The Canadian Journal of Neurological Sciences
1135:being translated into routine clinical care.
1131:. Testing for TPMT activity is an example of
1048:phosphoribosyl pyrophosphate amidotransferase
2418:
2232:
2185:
2179:
2114:
2051:
1062:interconversion and glycoprotein synthesis.
707:may harm the baby. Mercaptopurine is in the
120:
1865:
1625:
703:are at higher risk of side effects. Use in
193:In general: ℞ (Prescription only)
2578:
2564:
2531:"Mercaptopurine Therapy and TPMT Genotype"
1673:Alimentary Pharmacology & Therapeutics
1230:
1228:
1226:
1224:
1222:
1220:
1218:
1216:
1214:
1009:(IMP), including the conversion of IMP to
508:
485:
374:
2499:
2450:
2349:
2300:
2269:
2148:
2138:
2083:
1946:
1834:
1684:
1643:
1588:
1525:
1462:
1343:
1290:European Journal of Clinical Pharmacology
966:Learn how and when to remove this message
950:, without removing the technical details.
394:
1265:British national formulary : BNF 69
986:Mercaptopurine (6-MP) competes with the
2307:Mutschler E, Schäfer-Korting M (2001).
1352:
1259:
1257:
1211:
918:
656:among others, is a medication used for
481:
354:
93:
4312:
2504:. New York: Scribner. pp. 91–92.
2495:
2493:
2473:
2250:Clinical Pharmacology and Therapeutics
1324:
1281:
1161:Memorial Sloan Kettering Cancer Center
819:suppress the production of blood cells
499:
185:
2559:
2002:. Gate Pharmaceuticals. August 2012.
1626:Esses SI, Morley TP (February 1983).
1366:from the original on 6 September 2015
1338:. Geneva: World Health Organization.
1242:from the original on 20 December 2016
948:make it understandable to non-experts
699:. Those with a genetic deficiency in
454:
434:
111:
79:
2528:
1254:
922:
902:
879:, was ineffective as a single-agent
158:
2847:ribonucleotide reductase inhibitors
2490:
2380:from the original on 6 October 2015
2006:from the original on 1 January 2014
1065:
1013:(XMP) and the conversion of IMP to
664:. Specifically it is used to treat
414:
305:
13:
3013:Ribonucleotide reductase inhibitor
2969:Ribonucleotide reductase inhibitor
2522:
2292:: CS1 maint: overridden setting (
2186:Fujita K, Sasaki Y (August 2007).
2171:: CS1 maint: overridden setting (
2106:: CS1 maint: overridden setting (
1977:: CS1 maint: overridden setting (
1914:: CS1 maint: overridden setting (
1857:: CS1 maint: overridden setting (
1802:: CS1 maint: overridden setting (
1748:from the original on 19 June 2006.
1611:: CS1 maint: overridden setting (
1548:: CS1 maint: overridden setting (
1485:: CS1 maint: overridden setting (
1017:(AMP) via adenylosuccinate (SAMP).
817:In some cases, mercaptopurine may
14:
4351:
2772:Dihydrofolate reductase inhibitor
2127:World Journal of Gastroenterology
1058:. Mercaptopurine interferes with
890:Mercaptopurine causes changes to
4297:
1823:Journal of Crohn's & Colitis
1686:10.1046/j.1365-2036.2003.01537.x
927:
539:
533:
38:
29:
2467:
2392:
2366:
2325:
2042:
2032:
2018:
1985:
1619:
1556:
745:
725:
623:Key:GLVAUDGFNGKCSF-UHFFFAOYSA-N
2909:Thymidylate synthase inhibitor
2799:Thymidylate synthase inhibitor
1493:
1430:
1378:
1185:
851:
701:thiopurine S-methyltransferase
545:
527:
1:
2829:Adenosine deaminase inhibitor
2670:Block microtubule disassembly
2431:Pharmacogenetics and Genomics
2064:Pharmacogenetics and Genomics
1734:10.1016/S0029-7844(98)00569-9
1178:
778:), bloody stools, and bloody
652:), sold under the brand name
2474:Bouton K (29 January 1989).
2443:10.1097/FPC.0b013e3283352860
2076:10.1097/FPC.0b013e328334338f
1836:10.1016/j.crohns.2009.09.009
1443:Journal of Clinical Oncology
812:inflammation of the pancreas
687:Common side effects include
670:acute promyelocytic leukemia
7:
2480:The New York Times Magazine
2351:10.1093/rheumatology/kel427
846:nudix hydrolase 15 (NUDT15)
57:Purinethol, Purixan, others
10:
4356:
2551:. Bookshelf ID: NBK100660.
2536:Medical Genetics Summaries
2204:10.2174/138920007781368890
1138:
732:acute lymphocytic leukemia
666:acute lymphocytic leukemia
517:Chemical and physical data
272:3,7-dihydropurine-6-thione
4248:
4129:Omacetaxine mepesuccinate
4009:Ciltacabtagene autoleucel
3999:Brexucabtagene autoleucel
3945:
3896:
3676:
3669:
3605:
3559:
3492:
3449:
3286:
3271:
3151:
3121:
3046:
3031:
3002:
2898:
2818:
2761:
2744:
2733:
2669:
2622:
2603:
2224:: CS1 maint: unfit URL (
1722:Obstetrics and Gynecology
1645:10.1017/s0317167100044486
1581:10.18632/oncotarget.14594
1408:10.1016/j.aca.2020.08.064
1332:World Health Organization
1302:10.1007/s00228-008-0478-6
1197:European Medicines Agency
842:-methyltransferase (TPMT)
631:
606:
586:
564:
551:
521:
516:
497:
465:
445:
425:
405:
385:
365:
345:
325:
300:
280:
260:
255:
243:
230:
218:
208:
200:
175:
170:
145:
131:
101:
87:
69:
61:
51:
46:
37:
28:
4330:IARC Group 3 carcinogens
4181:Talimogene laherparepvec
4114:Nadofaragene firadenovec
4084:Lisocabtagene maraleucel
3033:Topoisomerase inhibitors
2952:DNA polymerase inhibitor
2140:10.3748/wjg.v20.i13.3534
1455:10.1200/jco.2014.59.4671
3984:Axicabtagene ciloleucel
2588:chemotherapeutic agents
2192:Current Drug Metabolism
1774:10.1136/gut.2010.222893
715:family of medications.
689:bone marrow suppression
65:6-mercaptopurine (6-MP)
4325:Thiocarbonyl compounds
4166:Sitimagene ceradenovec
4064:Idecabtagene vicleucel
3629:Methyl aminolevulinate
1628:"Spinal arachnoiditis"
1388:Analytica Chimica Acta
684:. It is taken orally.
3640:Porphyrin derivatives
3336:Melphalan flufenamide
2983:Hypomethylating agent
2592:antineoplastic agents
2309:Arzneimittelwirkungen
2262:10.1038/clpt.2010.320
907:Allopurinol inhibits
829:. It may be toxic to
3969:Asparagine depleters
3898:Receptor antagonists
3812:+abiraterone acetate
2500:Mukherjee S (2010).
2400:"Purixan suspension"
2060:"Thiopurine pathway"
919:Mechanisms of action
730:It is used to treat
4019:Denileukin diftitox
3919:Retinoid X receptor
3619:Aminolevulinic acid
3441:Triethylenemelamine
3273:Crosslinking of DNA
3004:Deoxyribonucleotide
2943:+gimeracil/oteracil
1400:2020AcAC.1137...64P
1165:Cornelius P. Rhoads
1149:George H. Hitchings
1102:for these types of
662:autoimmune diseases
25:
4335:Purine antagonists
4275:Never to phase III
3077:Etirinotecan pegol
2486:on 7 October 2016.
1886:10.1007/BF01612898
1575:(8): 13575–13585.
1157:Tuckahoe, New York
1153:Burroughs Wellcome
1104:genetic variations
1092:genetic variations
1076:-methyltransferase
740:ulcerative colitis
678:ulcerative colitis
21:
4285:
4284:
4244:
4243:
4201:Tigilanol tiglate
3678:Enzyme inhibitors
3601:
3600:
3597:
3596:
3297:Nitrogen mustards
3267:
3266:
3027:
3026:
2729:
2728:
2318:978-3-8047-1763-3
1173:nitrogen mustards
1145:Gertrude B. Elion
976:
975:
968:
903:Drug interactions
823:white blood cells
752:adverse reactions
643:
642:
577:Interactive image
467:CompTox Dashboard
189:
114:
16:Chemical compound
4347:
4302:
4301:
4300:
4293:
4206:Tisagenlecleucel
3963:Arsenic trioxide
3674:
3673:
3607:Photosensitizers
3398:Alkyl sulfonates
3312:Cyclophosphamide
3284:
3283:
3223:Anthracenediones
3044:
3043:
3018:Hydroxycarbamide
2759:
2758:
2742:
2741:
2620:
2619:
2580:
2573:
2566:
2557:
2556:
2552:
2516:
2515:
2497:
2488:
2487:
2482:. Archived from
2476:"The Nobel Pair"
2471:
2465:
2464:
2454:
2422:
2416:
2415:
2413:
2411:
2396:
2390:
2389:
2387:
2385:
2370:
2364:
2363:
2353:
2329:
2323:
2322:
2304:
2298:
2297:
2291:
2283:
2273:
2241:
2230:
2229:
2223:
2215:
2183:
2177:
2176:
2170:
2162:
2152:
2142:
2118:
2112:
2111:
2105:
2097:
2087:
2055:
2049:
2046:
2040:
2036:
2030:
2029:
2022:
2016:
2015:
2013:
2011:
1997:
1989:
1983:
1982:
1976:
1968:
1950:
1926:
1920:
1919:
1913:
1905:
1869:
1863:
1862:
1856:
1848:
1838:
1814:
1808:
1807:
1801:
1793:
1756:
1750:
1749:
1713:
1707:
1706:
1688:
1664:
1658:
1657:
1647:
1623:
1617:
1616:
1610:
1602:
1592:
1560:
1554:
1553:
1547:
1539:
1529:
1497:
1491:
1490:
1484:
1476:
1466:
1434:
1428:
1427:
1382:
1376:
1375:
1373:
1371:
1360:"Mercaptopurine"
1356:
1350:
1349:
1347:
1328:
1322:
1321:
1285:
1279:
1278:
1261:
1252:
1251:
1249:
1247:
1236:"Mercaptopurine"
1232:
1209:
1208:
1206:
1204:
1193:"Xaluprine EPAR"
1189:
1169:chemical weapons
1133:pharmacogenetics
1108:myelosuppression
1066:Pharmacogenetics
971:
964:
960:
957:
951:
931:
930:
923:
909:xanthine oxidase
885:suction abortion
639:
638:
579:
559:
547:
541:
535:
529:
512:
501:
490:
489:
475:
473:
458:
438:
418:
398:
378:
358:
338:
318:
308:
307:
293:
235:
225:xanthine oxidase
187:
184:
162:
124:
113:
110:
97:
83:
42:
33:
26:
24:
20:
4355:
4354:
4350:
4349:
4348:
4346:
4345:
4344:
4310:
4309:
4308:
4298:
4296:
4288:
4286:
4281:
4280:
4265:Clinical trials
4240:
3946:Other/ungrouped
3941:
3892:
3665:
3645:Porfimer sodium
3593:
3555:
3488:
3445:
3275:
3263:
3147:
3117:
3035:
3023:
2998:
2894:
2814:
2750:
2748:antimetabolites
2746:
2745:DNA precursors/
2737:
2735:DNA replication
2725:
2665:
2635:Vinca alkaloids
2611:
2599:
2584:
2529:Dean L (2012).
2525:
2523:Further reading
2520:
2519:
2512:
2498:
2491:
2472:
2468:
2423:
2419:
2409:
2407:
2398:
2397:
2393:
2383:
2381:
2372:
2371:
2367:
2330:
2326:
2319:
2305:
2301:
2285:
2284:
2242:
2233:
2217:
2216:
2184:
2180:
2164:
2163:
2133:(13): 3534–41.
2119:
2115:
2099:
2098:
2056:
2052:
2047:
2043:
2037:
2033:
2024:
2023:
2019:
2009:
2007:
1995:
1991:
1990:
1986:
1970:
1969:
1927:
1923:
1907:
1906:
1870:
1866:
1850:
1849:
1815:
1811:
1795:
1794:
1757:
1753:
1714:
1710:
1665:
1661:
1624:
1620:
1604:
1603:
1561:
1557:
1541:
1540:
1518:10.1038/ng.3508
1506:Nature Genetics
1498:
1494:
1478:
1477:
1449:(11): 1235–42.
1435:
1431:
1394:(1137): 64–73.
1383:
1379:
1369:
1367:
1358:
1357:
1353:
1329:
1325:
1286:
1282:
1275:
1263:
1262:
1255:
1245:
1243:
1234:
1233:
1212:
1202:
1200:
1199:. 30 April 2009
1191:
1190:
1186:
1181:
1141:
1120:red blood cells
1068:
998:for the enzyme
972:
961:
955:
952:
944:help improve it
941:
932:
928:
921:
905:
854:
827:red blood cells
748:
736:Crohn's disease
728:
674:Crohn's disease
634:
632:
627:
624:
619:
614:
613:
602:
599:
594:
593:
582:
557:
544:
538:
532:
493:
469:
461:
441:
421:
401:
381:
361:
341:
321:
304:
296:
276:
273:
268:
267:
233:
210:Bioavailability
202:Pharmacokinetic
196:
166:
134:
127:
17:
12:
11:
5:
4353:
4343:
4342:
4337:
4332:
4327:
4322:
4307:
4306:
4283:
4282:
4279:
4278:
4277:
4276:
4273:
4262:
4256:
4250:
4249:
4246:
4245:
4242:
4241:
4239:
4238:
4233:
4228:
4223:
4218:
4213:
4208:
4203:
4198:
4193:
4188:
4183:
4178:
4173:
4168:
4163:
4158:
4152:
4141:
4136:
4131:
4126:
4121:
4116:
4111:
4106:
4101:
4096:
4091:
4086:
4081:
4076:
4071:
4066:
4061:
4056:
4051:
4046:
4041:
4036:
4031:
4026:
4021:
4016:
4011:
4006:
4001:
3996:
3991:
3986:
3981:
3965:
3960:
3955:
3949:
3947:
3943:
3942:
3940:
3939:
3927:
3915:
3902:
3900:
3894:
3893:
3891:
3890:
3884:
3879:
3874:
3869:
3857:
3851:
3846:
3841:
3836:
3825:
3819:
3814:
3806:
3799:PARP inhibitor
3795:
3783:
3771:
3759:
3758:
3757:
3752:
3747:
3742:
3730:
3724:
3719:
3714:
3709:
3695:
3682:
3680:
3671:
3667:
3666:
3664:
3663:
3657:
3652:
3647:
3636:
3631:
3626:
3621:
3615:
3613:
3603:
3602:
3599:
3598:
3595:
3594:
3592:
3591:
3585:
3580:
3575:
3565:
3563:
3557:
3556:
3554:
3553:
3547:
3542:
3531:
3526:
3521:
3516:
3504:
3498:
3496:
3490:
3489:
3487:
3486:
3481:
3476:
3471:
3466:
3461:
3455:
3453:
3451:Platinum-based
3447:
3446:
3444:
3443:
3438:
3433:
3428:
3416:
3415:
3409:
3393:
3392:
3387:
3382:
3377:
3367:
3362:
3350:
3349:
3344:
3339:
3329:
3324:
3318:
3309:
3304:
3292:
3290:
3281:
3269:
3268:
3265:
3264:
3262:
3261:
3256:
3251:
3246:
3241:
3235:
3230:
3219:
3213:
3208:
3203:
3198:
3193:
3188:
3178:
3173:
3166:Anthracyclines
3161:
3159:
3149:
3148:
3146:
3145:
3139:
3127:
3125:
3119:
3118:
3116:
3115:
3109:
3104:
3099:
3094:
3089:
3084:
3079:
3074:
3069:
3064:
3052:
3050:
3041:
3029:
3028:
3025:
3024:
3022:
3021:
3008:
3006:
3000:
2999:
2997:
2996:
2990:
2978:
2977:
2964:
2963:
2947:
2946:
2936:
2931:
2926:
2921:
2916:
2904:
2902:
2896:
2895:
2893:
2892:
2886:
2884:Mercaptopurine
2875:
2870:
2865:
2859:
2854:
2838:
2837:
2824:
2822:
2816:
2815:
2813:
2812:
2806:
2795:
2789:
2784:
2779:
2767:
2765:
2756:
2739:
2731:
2730:
2727:
2726:
2724:
2723:
2711:
2705:
2700:
2695:
2690:
2685:
2673:
2671:
2667:
2666:
2664:
2663:
2657:
2652:
2647:
2642:
2630:
2628:
2617:
2601:
2600:
2586:Intracellular
2583:
2582:
2575:
2568:
2560:
2554:
2553:
2524:
2521:
2518:
2517:
2511:978-1439170915
2510:
2489:
2466:
2417:
2406:. 9 April 2019
2391:
2365:
2324:
2317:
2299:
2231:
2178:
2113:
2050:
2041:
2031:
2026:"Chemotherapy"
2017:
1984:
1921:
1864:
1809:
1768:(2): 198–203.
1751:
1708:
1659:
1618:
1555:
1492:
1429:
1377:
1351:
1323:
1280:
1273:
1253:
1210:
1183:
1182:
1180:
1177:
1167:, who had run
1140:
1137:
1067:
1064:
1044:
1043:
1040:
1036:
1032:
1031:
1030:
1029:
1028:
1018:
1011:xanthylic acid
984:
974:
973:
935:
933:
926:
920:
917:
904:
901:
853:
850:
747:
744:
727:
724:
713:antimetabolite
693:liver toxicity
646:Mercaptopurine
641:
640:
629:
628:
626:
625:
622:
620:
617:
609:
608:
607:
604:
603:
601:
600:
597:
589:
588:
587:
584:
583:
581:
580:
572:
570:
562:
561:
555:
549:
548:
542:
536:
530:
525:
519:
518:
514:
513:
503:
495:
494:
492:
491:
478:
476:
463:
462:
460:
459:
451:
449:
443:
442:
440:
439:
431:
429:
423:
422:
420:
419:
411:
409:
403:
402:
400:
399:
391:
389:
383:
382:
380:
379:
371:
369:
363:
362:
360:
359:
351:
349:
343:
342:
340:
339:
331:
329:
323:
322:
320:
319:
311:
309:
298:
297:
295:
294:
286:
284:
278:
277:
275:
274:
271:
263:
262:
261:
258:
257:
253:
252:
247:
241:
240:
237:
228:
227:
222:
216:
215:
212:
206:
205:
198:
197:
195:
194:
191:
181:
179:
173:
172:
168:
167:
165:
164:
151:
149:
143:
142:
137:
135:administration
129:
128:
126:
125:
122:Mercaptopurine
107:
105:
99:
98:
91:
85:
84:
77:
67:
66:
63:
59:
58:
55:
49:
48:
44:
43:
35:
34:
23:Mercaptopurine
15:
9:
6:
4:
3:
2:
4352:
4341:
4338:
4336:
4333:
4331:
4328:
4326:
4323:
4321:
4318:
4317:
4315:
4305:
4295:
4294:
4291:
4274:
4272:
4269:
4268:
4266:
4263:
4260:
4257:
4255:
4252:
4251:
4247:
4237:
4234:
4232:
4229:
4227:
4224:
4222:
4219:
4217:
4214:
4212:
4209:
4207:
4204:
4202:
4199:
4197:
4194:
4192:
4189:
4187:
4184:
4182:
4179:
4177:
4174:
4172:
4169:
4167:
4164:
4162:
4159:
4156:
4153:
4151:
4147:
4146:
4142:
4140:
4139:Tabelecleucel
4137:
4135:
4132:
4130:
4127:
4125:
4122:
4120:
4117:
4115:
4112:
4110:
4107:
4105:
4102:
4100:
4099:Lurbinectedin
4097:
4095:
4092:
4090:
4087:
4085:
4082:
4080:
4077:
4075:
4072:
4070:
4067:
4065:
4062:
4060:
4057:
4055:
4052:
4050:
4047:
4045:
4042:
4040:
4037:
4035:
4032:
4030:
4027:
4025:
4022:
4020:
4017:
4015:
4012:
4010:
4007:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3982:
3979:
3975:
3971:
3970:
3966:
3964:
3961:
3959:
3956:
3954:
3951:
3950:
3948:
3944:
3937:
3933:
3932:
3928:
3925:
3921:
3920:
3916:
3913:
3909:
3908:
3904:
3903:
3901:
3899:
3895:
3888:
3885:
3883:
3880:
3878:
3875:
3873:
3870:
3868:
3864:
3862:
3858:
3855:
3852:
3850:
3847:
3845:
3842:
3840:
3837:
3835:
3831:
3830:
3826:
3823:
3820:
3818:
3815:
3813:
3810:
3807:
3805:
3801:
3800:
3796:
3793:
3789:
3788:
3784:
3781:
3777:
3776:
3772:
3769:
3765:
3764:
3760:
3756:
3753:
3751:
3748:
3746:
3743:
3741:
3738:
3737:
3736:
3735:
3731:
3728:
3725:
3723:
3720:
3718:
3715:
3713:
3710:
3708:
3704:
3703:
3700:
3696:
3693:
3689:
3688:
3684:
3683:
3681:
3679:
3675:
3672:
3668:
3661:
3658:
3656:
3653:
3651:
3648:
3646:
3642:
3641:
3637:
3635:
3632:
3630:
3627:
3625:
3622:
3620:
3617:
3616:
3614:
3612:
3608:
3604:
3589:
3586:
3584:
3581:
3579:
3576:
3574:
3570:
3567:
3566:
3564:
3562:
3561:Intercalation
3558:
3551:
3548:
3546:
3543:
3541:
3537:
3536:
3532:
3530:
3527:
3525:
3522:
3520:
3517:
3514:
3510:
3509:
3505:
3503:
3500:
3499:
3497:
3495:
3491:
3485:
3482:
3480:
3477:
3475:
3472:
3470:
3469:Dicycloplatin
3467:
3465:
3462:
3460:
3457:
3456:
3454:
3452:
3448:
3442:
3439:
3437:
3434:
3432:
3429:
3427:
3424:
3422:
3418:
3417:
3413:
3410:
3408:
3404:
3401:
3399:
3395:
3394:
3391:
3388:
3386:
3383:
3381:
3378:
3375:
3371:
3368:
3366:
3363:
3361:
3358:
3356:
3352:
3351:
3348:
3345:
3343:
3342:Prednimustine
3340:
3337:
3333:
3330:
3328:
3325:
3322:
3319:
3317:
3313:
3310:
3308:
3305:
3303:
3300:
3298:
3294:
3293:
3291:
3289:
3285:
3282:
3279:
3274:
3270:
3260:
3257:
3255:
3252:
3250:
3247:
3245:
3242:
3239:
3236:
3234:
3231:
3229:
3225:
3224:
3220:
3217:
3214:
3212:
3209:
3207:
3204:
3202:
3199:
3197:
3194:
3192:
3189:
3186:
3182:
3179:
3177:
3174:
3172:
3168:
3167:
3163:
3162:
3160:
3158:
3157:Intercalation
3154:
3150:
3143:
3140:
3138:
3134:
3133:
3129:
3128:
3126:
3124:
3120:
3113:
3110:
3108:
3105:
3103:
3100:
3098:
3095:
3093:
3090:
3088:
3085:
3083:
3080:
3078:
3075:
3073:
3070:
3068:
3065:
3063:
3059:
3058:
3054:
3053:
3051:
3049:
3045:
3042:
3039:
3034:
3030:
3019:
3015:
3014:
3010:
3009:
3007:
3005:
3001:
2994:
2991:
2989:
2985:
2984:
2980:
2979:
2975:
2971:
2970:
2966:
2965:
2961:
2960:+daunorubicin
2958:
2954:
2953:
2949:
2948:
2944:
2940:
2937:
2935:
2932:
2930:
2927:
2925:
2924:Doxifluridine
2922:
2920:
2917:
2915:
2911:
2910:
2906:
2905:
2903:
2901:
2897:
2890:
2887:
2885:
2881:
2880:
2876:
2874:
2873:Rabacfosadine
2871:
2869:
2866:
2863:
2860:
2858:
2855:
2853:
2849:
2848:
2844:
2840:
2839:
2835:
2831:
2830:
2826:
2825:
2823:
2821:
2817:
2810:
2807:
2805:
2801:
2800:
2796:
2793:
2790:
2788:
2785:
2783:
2780:
2778:
2774:
2773:
2769:
2768:
2766:
2764:
2760:
2757:
2754:
2749:
2743:
2740:
2736:
2732:
2721:
2717:
2716:
2712:
2709:
2706:
2704:
2701:
2699:
2696:
2694:
2691:
2689:
2686:
2684:
2680:
2679:
2675:
2674:
2672:
2668:
2661:
2658:
2656:
2653:
2651:
2648:
2646:
2643:
2641:
2637:
2636:
2632:
2631:
2629:
2626:
2621:
2618:
2615:
2610:
2606:
2602:
2597:
2593:
2589:
2581:
2576:
2574:
2569:
2567:
2562:
2561:
2558:
2550:
2546:
2542:
2538:
2537:
2532:
2527:
2526:
2513:
2507:
2503:
2496:
2494:
2485:
2481:
2477:
2470:
2462:
2458:
2453:
2448:
2444:
2440:
2436:
2432:
2428:
2421:
2405:
2401:
2395:
2379:
2375:
2369:
2361:
2357:
2352:
2347:
2343:
2339:
2335:
2328:
2320:
2314:
2310:
2303:
2295:
2289:
2281:
2277:
2272:
2267:
2263:
2259:
2256:(3): 387–91.
2255:
2251:
2247:
2240:
2238:
2236:
2227:
2221:
2213:
2209:
2205:
2201:
2198:(6): 554–62.
2197:
2193:
2189:
2182:
2174:
2168:
2160:
2156:
2151:
2146:
2141:
2136:
2132:
2128:
2124:
2117:
2109:
2103:
2095:
2091:
2086:
2081:
2077:
2073:
2069:
2065:
2061:
2054:
2045:
2035:
2027:
2021:
2005:
2001:
1994:
1988:
1980:
1974:
1966:
1962:
1958:
1954:
1949:
1944:
1941:(6): 1080–6.
1940:
1936:
1932:
1925:
1917:
1911:
1903:
1899:
1895:
1891:
1887:
1883:
1880:(3): 245–50.
1879:
1875:
1868:
1860:
1854:
1846:
1842:
1837:
1832:
1829:(1): 63–101.
1828:
1824:
1820:
1813:
1805:
1799:
1791:
1787:
1783:
1779:
1775:
1771:
1767:
1763:
1755:
1747:
1743:
1739:
1735:
1731:
1727:
1723:
1719:
1712:
1704:
1700:
1696:
1692:
1687:
1682:
1679:(6): 827–34.
1678:
1674:
1670:
1663:
1655:
1651:
1646:
1641:
1637:
1633:
1629:
1622:
1614:
1608:
1600:
1596:
1591:
1586:
1582:
1578:
1574:
1570:
1566:
1559:
1551:
1545:
1537:
1533:
1528:
1523:
1519:
1515:
1512:(4): 367–73.
1511:
1507:
1503:
1496:
1488:
1482:
1474:
1470:
1465:
1460:
1456:
1452:
1448:
1444:
1440:
1433:
1425:
1421:
1417:
1413:
1409:
1405:
1401:
1397:
1393:
1389:
1381:
1365:
1361:
1355:
1346:
1341:
1337:
1333:
1327:
1319:
1315:
1311:
1307:
1303:
1299:
1296:(8): 753–67.
1295:
1291:
1284:
1276:
1274:9780857111562
1270:
1266:
1260:
1258:
1241:
1237:
1231:
1229:
1227:
1225:
1223:
1221:
1219:
1217:
1215:
1198:
1194:
1188:
1184:
1176:
1174:
1170:
1166:
1162:
1158:
1154:
1150:
1146:
1136:
1134:
1130:
1129:myelotoxicity
1125:
1121:
1117:
1113:
1109:
1105:
1101:
1097:
1093:
1089:
1085:
1081:
1077:
1075:
1063:
1061:
1057:
1053:
1049:
1041:
1037:
1033:
1026:
1022:
1021:
1019:
1016:
1015:adenylic acid
1012:
1008:
1007:inosinic acid
1004:
1003:
1001:
997:
993:
989:
985:
981:
980:
979:
970:
967:
959:
956:December 2014
949:
945:
939:
936:This section
934:
925:
924:
916:
914:
910:
900:
898:
893:
888:
886:
882:
881:abortifacient
878:
874:
869:
867:
863:
859:
858:immunizations
849:
847:
843:
841:
834:
832:
828:
824:
820:
815:
813:
809:
805:
801:
797:
793:
788:
785:
781:
777:
773:
769:
765:
761:
757:
753:
743:
741:
737:
733:
723:
721:
716:
714:
710:
706:
702:
698:
694:
690:
685:
683:
679:
675:
671:
667:
663:
659:
655:
651:
647:
637:
630:
621:
616:
615:
612:
605:
598:S=c1ncc2ncc12
596:
595:
592:
585:
578:
574:
573:
571:
568:
563:
556:
554:
550:
526:
524:
520:
515:
511:
507:
504:
502:
500:ECHA InfoCard
496:
488:
484:
483:DTXSID0020810
480:
479:
477:
468:
464:
457:
453:
452:
450:
448:
444:
437:
433:
432:
430:
428:
424:
417:
413:
412:
410:
408:
404:
397:
393:
392:
390:
388:
384:
377:
373:
372:
370:
368:
364:
357:
353:
352:
350:
348:
344:
337:
333:
332:
330:
328:
324:
317:
313:
312:
310:
303:
299:
292:
288:
287:
285:
283:
279:
270:
269:
266:
259:
254:
251:
248:
246:
242:
238:
236:
229:
226:
223:
221:
217:
213:
211:
207:
203:
199:
192:
190: Rx-only
183:
182:
180:
178:
174:
169:
161:
156:
153:
152:
150:
148:
144:
141:
138:
136:
130:
123:
118:
109:
108:
106:
104:
100:
96:
92:
90:
86:
82:
78:
76:
72:
68:
64:
60:
56:
54:
50:
47:Clinical data
45:
41:
36:
32:
27:
19:
4186:Tazemetostat
4150:Alitretinoin
4143:
4054:Estramustine
4034:Elsamitrucin
4024:Eflornithine
3978:Pegaspargase
3974:Asparaginase
3967:
3936:Testolactone
3929:
3917:
3905:
3859:
3844:Panobinostat
3827:
3797:
3785:
3773:
3761:
3732:
3697:
3685:
3638:
3634:Padeliporfin
3573:Dactinomycin
3569:Streptomyces
3550:Temozolomide
3545:Mitozolomide
3533:
3524:Mitobronitol
3513:Procarbazine
3506:
3494:Nonclassical
3419:
3396:
3390:Streptozocin
3355:Nitrosoureas
3353:
3327:Chlorambucil
3321:Trofosfamide
3307:Chlormethine
3302:Bendamustine
3295:
3233:Mitoxantrone
3228:Losoxantrone
3221:
3181:Daunorubicin
3164:
3130:
3067:Camptothecin
3055:
3011:
2981:
2967:
2950:
2934:Fluorouracil
2914:Capecitabine
2907:
2883:
2877:
2841:
2827:
2797:
2792:Pralatrexate
2782:Methotrexate
2770:
2713:
2676:
2633:
2535:
2501:
2484:the original
2479:
2469:
2437:(6): 401–5.
2434:
2430:
2420:
2408:. Retrieved
2403:
2394:
2382:. Retrieved
2368:
2344:(5): 727–9.
2341:
2338:Rheumatology
2337:
2327:
2308:
2302:
2288:cite journal
2253:
2249:
2220:cite journal
2195:
2191:
2181:
2167:cite journal
2130:
2126:
2116:
2102:cite journal
2070:(9): 573–4.
2067:
2063:
2053:
2044:
2034:
2020:
2008:. Retrieved
1999:
1987:
1973:cite journal
1938:
1934:
1924:
1910:cite journal
1877:
1873:
1867:
1853:cite journal
1826:
1822:
1812:
1798:cite journal
1765:
1761:
1754:
1728:(6): 904–9.
1725:
1721:
1711:
1676:
1672:
1662:
1635:
1631:
1621:
1607:cite journal
1572:
1568:
1558:
1544:cite journal
1509:
1505:
1495:
1481:cite journal
1446:
1442:
1432:
1391:
1387:
1380:
1368:. Retrieved
1354:
1345:10665/325771
1335:
1326:
1293:
1289:
1283:
1264:
1244:. Retrieved
1201:. Retrieved
1196:
1187:
1142:
1124:genetic test
1111:
1100:heterozygous
1073:
1069:
1045:
1024:
992:hypoxanthine
990:derivatives
977:
962:
953:
937:
906:
889:
877:methotrexate
873:azathioprine
870:
862:vaccinations
855:
839:
835:
816:
789:
783:
750:Some of the
749:
746:Side effects
729:
726:Medical uses
717:
697:pancreatitis
686:
682:methotrexate
653:
649:
645:
644:
633:
232:Elimination
177:Legal status
171:Legal status
103:License data
18:
4261:from market
4231:Vorasidenib
4211:Trabectedin
4196:Tiazofurine
4191:Tebentafusp
4176:Tagraxofusp
4134:Plitidepsin
4104:Mitoguazone
4044:Epacadostat
4014:Demecolcine
3958:Aflibercept
3931:Sex steroid
3804:Fuzuloparib
3745:Carfilzomib
3717:Palbociclib
3707:Abemaciclib
3660:Verteporfin
3624:Efaproxiral
3540:Dacarbazine
3502:Altretamine
3484:Satraplatin
3479:Oxaliplatin
3459:Carboplatin
3436:Triaziquone
3407:Mannosulfan
3385:Ranimustine
3365:Fotemustine
3206:Pirarubicin
3191:Doxorubicin
3185:+cytarabine
3171:Aclarubicin
3132:Podophyllum
3057:Camptotheca
2988:Azacitidine
2974:Gemcitabine
2929:Floxuridine
2862:Fludarabine
2857:Clofarabine
2843:Halogenated
2834:Pentostatin
2809:Raltitrexed
2777:Aminopterin
2720:Ixabepilone
2715:Epothilones
2683:Cabazitaxel
2660:Vinorelbine
2645:Vincristine
2640:Vinblastine
2625:microtubule
2010:31 December
1638:(1): 2–10.
1084:methylation
1080:methylation
1072:thiopurine
1070:The enzyme
913:allopurinol
892:chromosomes
852:Precautions
838:thiopurine
831:bone marrow
764:sore throat
560: g·mol
506:100.000.035
436:CHEBI:50667
256:Identifiers
89:MedlinePlus
62:Other names
53:Trade names
4314:Categories
4226:Verdinexor
4221:Venetoclax
4124:Oblimersen
4119:Navitoclax
4094:Lucanthone
4089:Lonidamine
4079:Lifileucel
4074:Ivosidenib
4069:Imetelstat
4039:Enasidenib
4029:Elesclomol
3994:Bexarotene
3989:Belzutifan
3924:Bexarotene
3912:Atrasentan
3887:Umbralisib
3882:Idelalisib
3872:Copanlisib
3854:Vorinostat
3849:Romidepsin
3839:Entinostat
3834:Belinostat
3792:Masoprocol
3780:Tiazofurin
3768:Anagrelide
3740:Bortezomib
3727:Seliciclib
3722:Ribociclib
3702:inhibitors
3692:Tipifarnib
3655:Temoporfin
3650:Talaporfin
3588:Plicamycin
3583:Mitomycins
3529:Pipobroman
3508:Hydrazines
3474:Nedaplatin
3426:Carboquone
3421:Aziridines
3412:Treosulfan
3360:Carmustine
3347:Uramustine
3316:Ifosfamide
3288:Alkylating
3249:Bisantrene
3238:Pixantrone
3211:Valrubicin
3201:Idarubicin
3196:Epirubicin
3142:Teniposide
3097:Lurtotecan
3092:Irinotecan
2993:Decitabine
2957:Cytarabine
2900:Pyrimidine
2889:Tioguanine
2879:Thiopurine
2868:Nelarabine
2852:Cladribine
2804:Pemetrexed
2787:Pemetrexed
2763:Folic acid
2703:Paclitaxel
2655:Vinflunine
1569:Oncotarget
1246:8 December
1179:References
1122:or a TPMT
1116:homozygous
1096:homozygous
1060:nucleotide
1039:leukemias.
806:, trouble
709:thiopurine
654:Purinethol
565:3D model (
553:Molar mass
456:ChEMBL1425
396:PKK6MUZ20G
367:ChemSpider
327:IUPHAR/BPS
282:CAS Number
265:IUPAC name
220:Metabolism
4271:Phase III
4259:Withdrawn
4236:Vosaroxin
4216:Veliparib
4171:Sotorasib
4161:Selinexor
4155:Tretinoin
4145:Retinoids
4059:Glasdegib
4004:Celecoxib
3953:Adagrasib
3877:Duvelisib
3867:Alpelisib
3822:Rucaparib
3809:Niraparib
3750:Oprozomib
3712:Alvocidib
3578:Bleomycin
3535:Triazenes
3519:Etoglucid
3464:Cisplatin
3380:Nimustine
3374:Semustine
3370:Lomustine
3332:Melphalan
3259:Menogaril
3254:Crisnatol
3244:Amsacrine
3216:Zorubicin
3176:Amrubicin
3137:Etoposide
3112:Topotecan
3107:Silatecan
3102:Rubitecan
3087:Gimatecan
3072:Cositecan
3062:Belotecan
2738:inhibitor
2708:Tesetaxel
2698:Ortataxel
2693:Larotaxel
2688:Docetaxel
2650:Vindesine
2039:11683683.
1424:225287631
1370:28 August
1088:cytotoxic
897:cytotoxic
868:vaccine.
808:breathing
804:dizziness
705:pregnancy
245:Excretion
234:half-life
133:Routes of
81:Monograph
75:Drugs.com
4304:Medicine
4109:Mitotane
4049:Eribulin
3817:Olaparib
3755:Ixazomib
3431:Thiotepa
3403:Busulfan
3082:Exatecan
2919:Carmofur
2627:assembly
2590: /
2549:28520348
2543:(NCBI).
2461:20154640
2404:DailyMed
2384:11 March
2378:Archived
2360:17255139
2280:21270794
2212:17691917
2159:24707136
2094:19952870
2004:Archived
2000:DailyMed
1965:45441636
1957:10491537
1902:21675626
1845:21122490
1790:25614617
1782:21115547
1746:Archived
1742:10362152
1703:25314258
1695:12641505
1599:28088792
1536:26878724
1473:25624441
1416:33153610
1364:Archived
1334:(2019).
1318:27475772
1310:18506437
1240:Archived
800:swelling
636:(verify)
347:DrugBank
214:5 to 37%
147:ATC code
140:By mouth
117:DailyMed
4320:Purines
3038:S phase
2939:Tegafur
2753:S phase
2678:Taxanes
2614:M phase
2452:3086840
2410:9 April
2271:3098761
2150:3974520
2085:3098750
1894:2370249
1654:6404543
1590:5355121
1527:5029084
1464:4375304
1396:Bibcode
1203:25 June
1139:History
1035:(TGMP).
1025:de novo
996:guanine
942:Please
899:drugs.
821:, both
796:itching
672:(APL),
668:(ALL),
523:Formula
356:DB01033
302:PubChem
291:50-44-2
163:)
157: (
155:L01BB02
119::
95:a682653
4290:Portal
4254:WHO-EM
3863:(Pi3K)
2820:Purine
2623:Block
2547:
2508:
2459:
2449:
2358:
2315:
2278:
2268:
2210:
2157:
2147:
2092:
2082:
1963:
1955:
1935:Cancer
1900:
1892:
1843:
1788:
1780:
1740:
1701:
1693:
1652:
1597:
1587:
1534:
1524:
1471:
1461:
1422:
1414:
1316:
1308:
1271:
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