1109:
656:
633:
1815:
40:
1456:
1376:, the enzyme that breaks down azathioprine, thus increasing the toxicity of azathioprine. Low doses of allopurinol, though, have been shown to safely enhance the efficacy of azathioprine, especially in inflammatory bowel disease nonresponders. This may still lead to lower lymphocyte counts and higher rates of infection, therefore the combination requires careful monitoring.
31:
1608:
6929:
1038:, but if this is due to the drug or a predisposition related to Crohn's disease is unclear. Lower doses of azathioprine are used as a therapy in children with refractory or corticosteroid-dependent Crohn's disease, without causing many side effects. It may also be used to prevent flares in those with
1527:
varies greatly between individual patients, between 30 and 90%, because the drug is partly inactivated in the liver. Highest blood plasma concentrations, counting not only the drug itself, but also its metabolites, are reached after 1–2 hours, and the average plasma half-life is 26 to 80 minutes for
1157:
thiopurine nucleotides can help to optimize the efficacy and safety. Clinically, most hospitals resort to ion-exchange LC-MS (liquid chromotography – mass spectrometry) but the newly developed approach of porous graphitic carbon based chromatography hyphenated with mass spectrometry appears superior
1355:
Large single doses are generally well tolerated; a patient who took 7.5 g azathioprine (150 tablets) at once showed no relevant symptoms apart from vomiting, slightly decreased white blood cell count, and marginal changes in liver function parameters. Main symptoms of long-term overdosing are
1338:
is 50 to 250 times more common than in the general population, and between 60 and 90% of patients are affected 20 years after transplantation. The use of immunosuppressive medication including azathioprine in organ transplantation has been linked to increased rates of developing skin cancer.
3206:
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".
1277:, asserting that it is "known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans." Since August 2009, the U.S. FDA has required warnings to be placed on packaging with respect to increased risks of certain cancers.
1326:. Adolescents and young adult males were the majority of cases. They presented with a very aggressive disease course, and with one exception, died of the lymphoma. The FDA has required changes to the labeling to inform users and clinicians of the issue.
4835:
1244:
can identify patients with reduced TPMT activity, allowing for the adjustment of azathioprine dose or avoidance of the drug entirely. The FDA-approved drug label for azathioprine recommends testing for TPMT activity to identify patients at risk for
1871:
In April 1962, with regimens consisting of azathioprine and prednisone, the transplantation of kidneys to unrelated recipients (allotransplantation) was successful for the first time. For many years, this kind of dual therapy with azathioprine and
1080:
found that azathioprine reduced the number of relapses in the first year of treatment and disease progression in the first two to three years and did not find an increase in cancer, and noted the need for direct comparison of azathioprine and
1057:
It is used as an add-on therapy when steroid therapy is given by mouth for pemphigus and myasthenia gravis, as a "steroid-sparing" agent. Azathioprine is also used to maintain remission in people who have granulomatosis with polyangiitis.
1414:
Azathioprine can cause birth defects. A 2003 population-based study in
Denmark showed that the use of azathioprine and related mercaptopurine resulted in a seven-fold incidence of fetal abnormalities, as well as a 20-fold increase in
2454:
Remuzzi G, Lesti M, Gotti E, Ganeva M, Dimitrov BD, Ene-Iordache B, et al. (August 2004). "Mycophenolate mofetil versus azathioprine for prevention of acute rejection in renal transplantation (MYSS): a randomised trial".
2859:
Olszewska M, Kolacinska-Strasz Z, Sulej J, Labecka H, Cwikla J, Natorska U, et al. (2007). "Efficacy and safety of cyclophosphamide, azathioprine, and cyclosporine (ciclosporin) as adjuvant drugs in pemphigus vulgaris".
3162:
Weersma RK, Peters FT, Oostenbrug LE, van den Berg AP, van
Haastert M, Ploeg RJ, et al. (October 2004). "Increased incidence of azathioprine-induced pancreatitis in Crohn's disease compared with other diseases".
1152:
can also occur, especially in patients with Crohn's disease. Treatment is discontinued in up to 30% of patients due these effects but therapeutic drug monitoring of the biologically active metabolites,
1868:. When Calne asked Elion for related compounds to investigate, she suggested azathioprine, which was subsequently found out to be superior (as effective and less toxic to the bone marrow) by Calne.
1427:
in doses equivalent to human dosages, teratogenesis was observed. Transplant patients already on this drug should not discontinue on becoming pregnant. This contrasts with the later-developed drugs
278:
1181:(TPMT) is responsible for various activation and deactivation steps in azathioprine's mechanism of action. The first metabolic step that azathioprine undergoes in the body is the conversion to
2946:
Meggitt SJ, Gray JC, Reynolds NJ (March 2006). "Azathioprine dosed by thiopurine methyltransferase activity for moderate-to-severe atopic eczema: a double-blind, randomised controlled trial".
4062:
Chocair P, Duley J, Simmonds HA, Cameron JS, Ianhez L, Arap S, et al. (July 1993). "Low-dose allopurinol plus azathioprine/cyclosporin/prednisolone, a novel immunosuppressive regimen".
4950:
Thiersch JB (December 1962). "Effect of 6-(1'-methyl-4'-nitro-5'-imidazolyl)-mercaptopurine and 2-amino-6-(1'-methyl-4'-nitro-5'-imidazolyl)-mercaptopurine on the rat litter in utero".
6989:
1274:
233:
1882:
has now replaced some of the azathioprine use due to a longer survival time, especially in heart-related transplantations. Moreover, despite being considerably more expensive,
1559:
and similar compounds in the intestinal wall, the liver, and on red blood cells, without the aid of enzymes. 6-MP is metabolized analogously to natural purines, giving thio
3603:
1257:(e.g., rs116855232, inducing R139C)) has been identified to be a causal factor for AZA-induced leukopenia through a genome wide association study (GWAS) in East Asians.
1539:, a substance that is not an active drug itself, but is activated in the body. This happens in several steps; at first, it is slowly and almost completely converted to
6736:
2416:
Nuyttens JJ, Harper J, Jenrette JM, Turrisi AT (January 2005). "Outcome of radiation therapy for renal transplant rejection refractory to chemical immunosuppression".
1626:
1763:. It is a pale yellow solid with a slightly bitter taste and a melting point of 238–245 °C. It is practically insoluble in water and only slightly soluble in
1311:
to which azathioprine may add additional risks. Those receiving azathioprine for rheumatoid arthritis may have a lower risk than those undergoing transplantation.
6949:
1492:
1116:
Nausea and vomiting are common adverse effects, especially at the beginning of a treatment. Such cases are met with taking azathioprine after meals or transient
916:
Azathioprine is used alone or in combination with other immunosuppressive therapy to prevent rejection following organ transplantation, and to treat an array of
5257:
3298:
2388:
1692:
127:
4107:"Allopurinol safely and effectively optimizes tioguanine metabolites in inflammatory bowel disease patients not responding to azathioprine and mercaptopurine"
5294:
752:
4246:"Low-dose azathioprine or mercaptopurine in combination with allopurinol can bypass many adverse drug reactions in patients with inflammatory bowel disease"
3424:
1015:
and corticosteroids may be combined or continued (if they were already in use) with azathioprine, but the combination with other DMARDs is not recommended.
3786:
3261:
1285:
1162:
5063:
Murray JE, Merrill JP, Harrison JH, Wilson RE, Dammin GJ (June 1963). "Prolonged survival of human-kidney homografts by immunosuppressive drug therapy".
5139:
Henry ML, Sommer BG, Ferguson RM (November 1985). "Beneficial effects of cyclosporine compared with azathioprine in cadaveric renal transplantation".
3764:
2585:
Biancone L, Tosti C, Fina D, Fantini M, De Nigris F, Geremia A, et al. (June 2003). "Review article: maintenance treatment of Crohn's disease".
6210:
1232:
polymorphisms that result in decreased or absent TPMT activity occur with a frequency of approximately 5%, meaning that about 0.25% of patients are
5174:
Modry DL, Oyer PE, Jamieson SW, Stinson EB, Baldwin JC, Reitz BA, et al. (May 1985). "Cyclosporine in heart and heart-lung transplantation".
4340:
3904:
4651:
Karran P, Attard N (January 2008). "Thiopurines in current medical practice: molecular mechanisms and contributions to therapy-related cancer".
1886:
is also increasingly being used in place of azathioprine in organ transplantation, as it is associated with less bone marrow suppression, fewer
1438:, the manufacturer advises not to breastfeed whilst taking azathioprine, but the "lactation risk category" reported by Thomas Hale in his book
6883:
4736:
4708:
4586:
4362:
3542:
3146:
2400:
1840:
Robert
Schwartz investigated the effect of 6-MP on the immune response in 1958 and discovered that it profoundly suppresses the formation of
905:
1061:
It can be very effective in eczema and atopic dermatitis, though it is not commonly used. The
British National Eczema Society lists it as a
6746:
6729:
3273:
1814:
1738:(programmed cell death). Increased apoptosis of mononuclear cells is seen in inflammatory bowel disease patients treated with azathioprine.
1012:
1004:
3802:
5203:"Clinical and cost-effectiveness of newer immunosuppressive regimens in renal transplantation: a systematic review and modelling study"
2220:
1680:; the former is the starting point for purine nucleotide biosynthesis, while the latter is one of the building blocks of DNA and RNA.
1132:. Hair loss is often seen in transplant patients receiving the drug, but rarely occurs under other indications. Because azathioprine
728:
6959:
6153:
5523:
2214:
1699:, one of the earlier steps in the synthesis of DNA and RNA. They achieve GPAT inhibition through a form of negative feedback called
1644:
772:
2104:
Singer O, McCune WJ (May 2017). "Update on maintenance therapy for granulomatosis with polyangiitis and microscopic polyangiitis".
5287:
1289:
1166:
823:
3735:
3483:"Clinical Pharmacogenetics Implementation Consortium guidelines for thiopurine methyltransferase genotype and thiopurine dosing"
1595:. Purines are needed to produce DNA and RNA. By inhibiting purine synthesis, less DNA and RNA are produced for the synthesis of
1280:
The risks involved seem to be related both to the duration and the dosage used. People who have previously been treated with an
6722:
6562:
4752:
3599:
2028:
1387:
1281:
1068:
It was widely used for the treatment of multiple sclerosis until the first half of the 1990s. Concerns about increased risk of
414:
263:
159:
1178:
870:
4156:"Effect of allopurinol on clinical outcomes in inflammatory bowel disease nonresponders to azathioprine or 6-mercaptopurine"
1876:
was the standard antirejection regimen, until cyclosporin was introduced into clinical practice (by Calne as well) in 1978.
908:. In 2018, it was the 358th most commonly prescribed medication in the United States, with more than 800,000 prescriptions.
3940:
3462:
1315:
1089:
2300:
Patel AA, Swerlick RA, McCall CO (September 2006). "Azathioprine in dermatology: the past, the present, and the future".
5359:
4923:
Elion GB, Callahan SW, Hitchings GH, Rundles RW (July 1960). "The metabolism of 2-amino-6-purine (B.W. 57-323) in man".
1483:
1050:
Azathioprine is sometimes used in systemic lupus erythematosus, requiring a maintenance dose of 15 mg or higher of
968:
835:
815:
532:
178:
6979:
6964:
6900:
5468:
5280:
4354:
3731:
3723:
1564:
1514:
1391:
1270:
612:
5100:"Conversion from cyclosporine to azathioprine at three months reduces the incidence of chronic allograft nephropathy"
2679:"Increased risk of lymphoma among inflammatory bowel disease patients treated with azathioprine and 6-mercaptopurine"
6919:
5338:
4497:
Tallent MB, Simmons RL, Najarian JS (March 1970). "Birth defects in child of male recipient of kidney transplant".
4344:
1323:
1023:
Azathioprine has been used in the management of moderate to severe chronically active Crohn's disease, to maintain
957:
1833:
in 1957 (named BW 57-322) to produce 6-MP in a metabolically active, but masked form, and at first used as a
1419:. Birth defects in a child whose father was taking azathioprine have also been reported. Although no adequate and
6016:
2234:
1568:
1498:
3425:"Pharmacogenomics in drug-metabolizing enzymes catalyzing anticancer drugs for personalized cancer chemotherapy"
6969:
6396:
1826:
1795:
953:
1108:
1031:
Crohn's disease. The onset of action is slow, and it may require several months to achieve clinical response.
1767:
solvents such as chloroform, ethanol, and diethylether. It dissolves in alkaline aqueous solutions, where it
995:. The administration protocol starts either at the time of transplantation or within the following two days.
6888:
6391:
4019:
Sahasranaman S, Howard D, Roy S (August 2008). "Clinical pharmacology and pharmacogenetics of thiopurines".
1887:
1300:
1133:
858:
215:
3760:
651:
6790:
6196:
5622:
5303:
4541:
2052:"Inflammatory bowel disease and cancer: The role of inflammation, immunosuppression, and cancer treatment"
1982:
1861:
1719:
1560:
1508:
1190:
1027:(absence of disease activity) in corticosteroid-dependent patients, and to provide benefit in people with
972:
355:
2816:
Abu-Shakra M, Shoenfeld Y (2001). "Azathioprine therapy for patients with systemic lupus erythematosus".
1928:"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"
929:
6954:
6785:
6383:
3456:
1883:
5028:
Calne RY (February 1960). "The rejection of renal homografts. Inhibition in dogs by 6-mercaptopurine".
3374:"Pharmacogenetics of azathioprine in inflammatory bowel disease: a role for glutathione-S-transferase?"
601:
4830:
3900:
1224:
may have increased levels of TGN metabolites and an increased risk of severe bone marrow suppression (
449:
5272:
4985:
Schwartz R, Stack J, Dameshek W (October 1958). "Effect of 6-mercaptopurine on antibody production".
4889:
4833:, G. H. Hitchings; Yonkers & G. B. Elion, "Purine Derivatives", issued 1962-10-06
3975:
3816:
Gombar VK, Enslein K, Blake BW (May 1993). "Carcinogenicity of azathioprine: an S-AR investigation".
3216:
1927:
1853:
1718:
A portion of the nucleotides is additionally phosphorylated to the triphosphate forms. These bind to
1296:
1008:
949:
937:
921:
843:
819:
378:
4546:
3625:
Wang L, Pelleymounter L, Weinshilboum R, Johnson JA, Hebert JM, Altman RB, et al. (June 2010).
2338:
Evans WE (April 2004). "Pharmacogenetics of thiopurine S-methyltransferase and thiopurine therapy".
1072:
has led to a decreased use, yet it is still used in maintenance treatment for people who frequently
780:
InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
5604:
2728:"Safety of azathioprine and 6-mercaptopurine in pediatric patients with inflammatory bowel disease"
1860:, the British pioneer in transplantation, introduced 6-MP as an experimental immunosuppressant for
1696:
1322:– have been reported in patients treated with azathioprine. The majority occurred in patients with
1292:), although the methodology of past studies and the possible underlying mechanisms are questioned.
1212:
within the TPMT gene can lead to decreased or absent TPMT enzyme activity, and individuals who are
1062:
628:
435:
226:
6714:
6834:
6553:
5654:
5010:
4676:
4479:
4318:
4275:
4136:
4087:
4044:
3537:(in German) (8th ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 107, 936.
3240:
3188:
3014:
2971:
2928:
2885:
2841:
2659:
2610:
2480:
2363:
2129:
1779:
1715:) are most active in synthesizing purine, making new DNA, these cells are most strongly affected.
1700:
1304:
1149:
1039:
1024:
961:
917:
847:
831:
189:
6593:
6451:
3265:
1571:(TIMP) and several further intermediates. On a second path, the sulfur atom of 6-MP and TIMP is
827:
6603:
6289:
5730:
3962:
O'Donovan P, Perrett CM, Zhang X, Montaner B, Xu YZ, Harwood CA, et al. (September 2005).
3790:
1284:
may have an excessive risk of cancers if treated with azathioprine. Epidemiological studies by
6974:
6777:
6558:
6548:
5349:
5307:
5261:
5224:
5183:
5156:
5121:
5080:
5045:
5002:
4967:
4932:
4905:
4812:
4732:
4704:
4668:
4633:
4582:
4559:
4514:
4471:
4430:
4395:
4358:
4310:
4267:
4226:
4177:
4128:
4079:
4036:
4001:
3882:
3833:
3705:
3656:
3581:
3538:
3512:
3481:
Relling MV, Gardner EE, Sandborn WJ, Schmiegelow K, Pui CH, Yee SW, et al. (March 2011).
3444:
3405:
3372:
Stocco G, Pelin M, Franca R, De
Iudicibus S, Cuzzoni E, Favretto D, et al. (April 2014).
3354:
3302:
3232:
3180:
3142:
3112:
3063:
3006:
2963:
2920:
2877:
2833:
2798:
2749:
2708:
2651:
2602:
2567:
2529:
2472:
2433:
2396:
2355:
2317:
2210:
2180:
2121:
2083:
1669:
1592:
1463:
1459:
1395:
1344:
1221:
1209:
1125:
992:
945:
941:
839:
302:
290:
109:
3676:"A common missense variant in NUDT15 confers susceptibility to thiopurine-induced leukopenia"
2204:
581:
6984:
6354:
6257:
5920:
5816:
5214:
5148:
5111:
5072:
5037:
4994:
4959:
4897:
4859:
4802:
4794:
4660:
4623:
4615:
4551:
4506:
4461:
4422:
4387:
4378:
Cleary BJ, Källén B (July 2009). "Early pregnancy azathioprine use and pregnancy outcomes".
4302:
4257:
4216:
4208:
4167:
4118:
4071:
4028:
3991:
3983:
3872:
3864:
3825:
3695:
3687:
3646:
3638:
3571:
3502:
3494:
3436:
3395:
3385:
3344:
3336:
3323:
Zaza G, Cheok M, Krynetskaia N, Thorn C, Stocco G, Hebert JM, et al. (September 2010).
3224:
3172:
3102:
3094:
3053:
3045:
2998:
2955:
2912:
2869:
2825:
2788:
2780:
2739:
2698:
2690:
2641:
2594:
2559:
2519:
2511:
2464:
2425:
2347:
2309:
2242:
2170:
2160:
2113:
2073:
2063:
1956:
1865:
1731:
1596:
1540:
1471:
1420:
1373:
1250:
1225:
1121:
668:
456:
371:
337:
57:
4703:(in German). Vol. 2 (25th ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag.
4532:
Polifka JE, Friedman JM (May 2002). "Teratogen update: azathioprine and 6-mercaptopurine".
541:
6933:
6800:
6653:
6538:
2989:
Casetta I, Iuliano G, Filippini G (February 2009). "Azathioprine for multiple sclerosis".
1912:
1907:
1685:
1657:
Azathioprine is converted within tissues to 6-MP, some of which is converted, in turn, to
1529:
1524:
1360:, and spontaneous bleeding, all of which are consequences of its bone-marrow suppression.
1082:
1077:
1007:(DMARD), azathioprine has been used for the management of the signs and symptoms of adult
988:
882:
521:
365:
345:
4105:
Sparrow MP, Hande SA, Friedman S, Lim WC, Reddy SI, Cao D, et al. (September 2005).
1684:
The nucleotides are incorporated into newly synthesized (but nonfunctional) DNA, halting
1343:(6-TG) in patients' DNA, which might trigger cancer when the patient is later exposed to
444:
4893:
4197:"Combination of thiopurines and allopurinol: adverse events and clinical benefit in IBD"
3979:
3220:
3141:(in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. pp. 4103–9.
1100:. A 2012 study showed that outcomes were worse with this combination than with placebo.
6894:
6543:
6411:
6059:
5893:
5872:
5868:
5864:
5492:
5329:
5098:
Bakker RC, Hollander AA, Mallat MJ, Bruijn JA, Paul LC, de Fijter JW (September 2003).
4628:
4603:
4221:
4196:
3996:
3963:
3877:
3852:
3700:
3675:
3651:
3626:
3507:
3482:
3400:
3373:
3349:
3324:
3107:
3082:
3058:
3033:
2916:
2793:
2768:
2703:
2678:
2524:
2499:
2175:
2148:
2078:
2051:
1873:
1830:
1477:
1435:
1295:
The various diseases requiring transplantation may in themselves increase the risks of
1237:
1182:
1097:
886:
655:
632:
39:
5041:
4807:
4782:
2959:
2769:"Azathioprine and 6-mercaptopurine for maintenance of remission in ulcerative colitis"
2744:
2727:
2468:
6943:
6844:
6821:
6767:
6693:
6623:
6533:
6440:
6226:
5926:
5848:
5800:
5780:
5638:
5554:
5405:
5371:
5201:
Woodroffe R, Yao GL, Meads C, Bayliss S, Ready A, Raftery J, et al. (May 2005).
5152:
5116:
5099:
4466:
4449:
4306:
4262:
4245:
4123:
4106:
4075:
3829:
3244:
3176:
3018:
2873:
2646:
2629:
2351:
1849:
1807:
1712:
1677:
1673:
1658:
1576:
1380:
1340:
1246:
890:
739:
644:
315:
151:
4756:
4680:
4483:
4091:
4048:
3192:
2932:
2889:
2845:
2663:
2614:
2550:
Sandborn WJ (1998). "Azathioprine: state of the art in inflammatory bowel disease".
2484:
2367:
2262:
2133:
2024:
1672:
and thioguanylic acid, respectively. These nucleotides masquerade, respectively, as
137:
6856:
6750:
6703:
6663:
6648:
6643:
6359:
6309:
6304:
6284:
6164:
6159:
6022:
6007:
5955:
5931:
5878:
5755:
5745:
5564:
5481:
5476:
5434:
5387:
5311:
5014:
4322:
4279:
4140:
3049:
2975:
2903:
Richman DP, Agius MA (December 2003). "Treatment of autoimmune myasthenia gravis".
2784:
2598:
1834:
1661:
by the addition of an amino group. Both 6-MP and 6-thioguanine are conjugated with
1347:. Patients taking azathioprine were found to be abnormally sensitive to UVA light.
1241:
1217:
1085:, conflicting conclusions regarding cancer, and the potential for long-term risks.
246:
241:
4293:
Oliveira A, Sanches M, Selores M (October 2011). "Azathioprine-induced pellagra".
3576:
3559:
4450:"Azathioprine, mercaptopurine and birth outcome: a population-based cohort study"
4212:
3642:
3340:
2429:
2117:
481:
6839:
6830:
6825:
6805:
6698:
6638:
6628:
6618:
6518:
6508:
6498:
6493:
6458:
6369:
6364:
6339:
6329:
6319:
6294:
6279:
6274:
6232:
6202:
6188:
6183:
6169:
6112:
6070:
6065:
6051:
6046:
6032:
6012:
5965:
5941:
5899:
5883:
5854:
5838:
5806:
5790:
5785:
5760:
5710:
5700:
5695:
5690:
5679:
5669:
5574:
5486:
5444:
5429:
5423:
5419:
5366:
5247:
5076:
3926:
3288:
1879:
1803:
1799:
1791:
1787:
1752:
1666:
1556:
1416:
1369:
1357:
1335:
1201:
1197:
1145:
1117:
851:
145:
5251:
4426:
4413:
Tagatz GE, Simmons RL (January 1975). "Pregnancy after renal transplantation".
4244:
Ansari A, Patel N, Sanderson J, O'Donohue J, Duley JA, Florin TH (March 2010).
3674:
Yang SK, Hong M, Baek J, Choi H, Zhao W, Jung Y, et al. (September 2014).
3440:
3292:
2829:
2563:
2313:
1288:
have provided "sufficient" evidence of azathioprine carcinogenicity in humans (
6863:
6851:
6688:
6683:
6668:
6608:
6598:
6583:
6578:
6573:
6523:
6513:
6503:
6468:
6446:
6432:
6344:
6334:
6324:
6314:
6299:
6242:
6237:
6216:
6131:
6126:
6084:
6078:
5979:
5936:
5832:
5822:
5775:
5765:
5740:
5735:
5725:
5720:
5715:
5705:
5664:
5649:
5644:
5628:
5569:
5549:
5498:
5458:
5439:
5381:
4998:
4172:
4155:
4032:
3931:
3228:
2515:
1841:
1764:
1748:
1428:
1308:
1266:
1233:
1213:
1069:
1051:
933:
704:
512:
4510:
3390:
3002:
2068:
1528:
azathioprine and 3–5 hours for drug plus metabolites. 20 to 30% are bound to
22:
6795:
6759:
6678:
6673:
6658:
6633:
6588:
6568:
6528:
6463:
6427:
6349:
6145:
6098:
6027:
5993:
5960:
5770:
5750:
5659:
5559:
5399:
4901:
4619:
3987:
3868:
2694:
1857:
1768:
1760:
1756:
1735:
1548:
1455:
1205:
1141:
984:
956:, and others. It is also an important therapy and steroid-sparing agent for
925:
878:
393:
131:
5265:
5228:
5125:
5084:
5049:
5006:
4971:
4936:
4816:
4672:
4637:
4563:
4475:
4399:
4314:
4271:
4230:
4181:
4132:
4040:
4005:
3886:
3709:
3660:
3585:
3516:
3448:
3409:
3358:
3306:
3236:
3184:
3116:
3067:
3010:
2967:
2924:
2881:
2837:
2802:
2712:
2655:
2606:
2533:
2476:
2437:
2359:
2321:
2239:
World Health
Organization model list of essential medicines: 21st list 2019
2184:
2125:
2087:
1856:
of transplanted tissues and organs, and
Schwartz's researches on 6-MP, Sir
5187:
5160:
4963:
4909:
4518:
4448:
Nørgård B, Pedersen L, Fonager K, Rasmussen SN, Sørensen HT (March 2003).
4083:
3837:
3498:
3098:
2753:
2571:
30:
6613:
6488:
6177:
5685:
5595:
5531:
5453:
4434:
3936:
3558:
Payne K, Newman W, Fargher E, Tricker K, Bruce IN, Ollier WE (May 2007).
2677:
Kandiel A, Fraser AG, Korelitz BI, Brensinger C, Lewis JD (August 2005).
2498:
Suarez-Almazor ME, Spooner C, Belseck E (2000). Suarez-Almazor ME (ed.).
1580:
1403:
1383:
1319:
1035:
866:
862:
492:
222:
173:
4863:
4850:
Blicke FF, Godt HC (1954). "Diuretics. I. 3-Substituted
Paraxanthines".
2247:
501:
6106:
4555:
4391:
3083:"Prednisone, azathioprine, and N-acetylcysteine for pulmonary fibrosis"
2165:
1845:
1536:
1193:
1137:
1073:
1028:
846:. It is listed by the International Agency for Research on Cancer as a
467:
6421:
6252:
4798:
4350:
4154:
Sparrow MP, Hande SA, Friedman S, Cao D, Hanauer SB (February 2007).
3727:
3627:"Very important pharmacogene summary: thiopurine S-methyltransferase"
2767:
Timmer A, Patton PH, Chande N, McDonald JW, MacDonald JK (May 2016).
1727:
1708:
1704:
1662:
1572:
1552:
1424:
1254:
1129:
874:
592:
453:
398:
5219:
5202:
4664:
3964:"Azathioprine and UVA light generate mutagenic oxidative DNA damage"
3691:
4579:
Medications and
Mothers' Milk: A Manual of Lactational Pharmacology
3560:"TPMT testing in rheumatology: any better than routine monitoring?"
3493:(3). Clinical Pharmacogenetics Implementation Consortium: 387–391.
2630:"Review article: treatment of perianal fistulizing Crohn's disease"
2149:"Current and emerging treatment options in the management of lupus"
1703:. Because actively replicating cells (such as cancer cells and the
1200:
of 6-MP into the inactive metabolite 6-methylmercaptopurine – this
561:
6120:
5973:
1783:
1544:
1249:. Indeed, testing for TPMT activity is one of the few examples of
873:. Other serious risk factors include an increased risk of certain
727:
718:
572:
4731:(in German). Stuttgart: Deutscher Apotheker Verlag. p. 340.
4380:
Birth
Defects Research. Part A, Clinical and Molecular Teratology
6092:
6040:
6001:
5987:
5541:
5415:
4987:
Proceedings of the Society for Experimental Biology and Medicine
3081:
Raghu G, Anstrom KJ, King TE, Lasky JA, Martinez FJ (May 2012).
1723:
865:. Bone-marrow suppression is especially common in people with a
552:
324:
296:
6718:
5276:
1431:
and mycophenolate, which are contraindicated during pregnancy.
1034:
Azathioprine treatment is associated with an increased risk of
309:
168:
5949:
1935:
1601:
983:
Azathioprine is used to prevent rejections of kidney or liver
898:
894:
93:
5250:. In Pratt VM, McLeod HL, Rubinstein WS, et al. (eds.).
3291:. In Pratt VM, McLeod HL, Rubinstein WS, et al. (eds.).
1852:
and Gertrude Elion in discovering the immunological basis of
1253:
being translated into routine clinical care. Missense SNP in
1774:
Azathioprine is synthesized from 5-chloro-1-methyl-4-nitro-1
881:
may result in harm to the baby. Azathioprine belongs to the
617:
75:
3791:"Azathioprine – 5. Summary of Data Reported and Evaluation"
272:
200:
81:
78:
69:
5176:
Canadian Journal of Surgery. Journal Canadien de Chirurgie
4880:
Elion GB (April 1989). "The purine path to chemotherapy".
1236:
for these variants. However, an assay of TPMT activity in
960:(such as Crohn's disease and ulcerative colitis) and for
63:
2251:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
987:, usually in conjunction with other therapies including
285:
1622:
906:
World Health Organization's List of Essential Medicines
797:
4694:
4692:
4690:
1442:
lists azathioprine as "L3", termed "moderately safe".
6917:
4727:
Steinhilber D, Schubert-Zsilavecz M, Roth HJ (2005).
2391:(January 2012). "Azathioprine, Azathioprine Sodium".
2027:. The American Society of Health-System Pharmacists.
1065:
for severe to moderate cases of these skin diseases.
96:
84:
66:
60:
2552:
Scandinavian Journal of Gastroenterology. Supplement
2206:
Autoimmune Bullous Diseases: Approach and Management
1523:
Azathioprine is absorbed from the gut to about 88%.
1228:) when receiving azathioprine. In many ethnicities,
1092:
was azathioprine in combination with prednisone and
90:
87:
6814:
6776:
6758:
6481:
6409:
6382:
6267:
5910:
5612:
5603:
5594:
5587:
5540:
5522:
5513:
5467:
5398:
5328:
5319:
1617:
may be too technical for most readers to understand
1204:prevents 6-MP from further conversion into active,
1196:. The TPMT enzyme is responsible, in part, for the
738:
716:
703:
667:
662:
643:
611:
591:
571:
551:
531:
511:
491:
466:
434:
405:
392:
377:
370:Activated non-enzymatically, deactivated mainly by
364:
354:
344:
336:
262:
257:
232:
214:
188:
158:
144:
126:
118:
108:
72:
51:
46:
3787:International Agency for Research on Cancer (IARC)
3262:International Agency for Research on Cancer (IARC)
3032:Casetta I, Iuliano G, Filippini G (October 2007).
2991:Journal of Neurology, Neurosurgery, and Psychiatry
1575:. The end products of azathioprine metabolism are
1208:thioguanine nucleotide (TGN) metabolites. Certain
904:Azathioprine was first made in 1957. It is on the
4755:. Small Molecule Pathway Database. Archived from
2395:. American Society of Health-System Pharmacists.
1112:Two generic azathioprine oral tablets, 50 mg each
975:from human donors, and for rheumatoid arthritis.
3761:"FDA: Cancer Warnings Required for TNF Blockers"
3728:"Report On Carcinogens – Twelfth Edition – 2011"
3132:
3130:
3128:
3126:
2500:"Azathioprine for treating rheumatoid arthritis"
480:
3476:
3474:
3472:
3318:
3316:
2333:
2331:
1120:administration. Side effects that are probably
443:
4776:
4774:
4722:
4720:
2302:Journal of the American Academy of Dermatology
2050:Axelrad JE, Lichtiger S, Yajnik V (May 2016).
1794:, which is then cyclized and chlorinated with
1493:hypoxanthine-guanine phosphoribosyltransferase
1390:muscle relaxants, but increases the effect of
1158:with respect to patient care in this respect.
6990:World Health Organization essential medicines
6730:
5288:
5258:National Center for Biotechnology Information
3901:"Imuran (azathioprine) Tablets and Injection"
3299:National Center for Biotechnology Information
2389:American Society of Health-System Pharmacists
1782:. The synthesis of the former starts with an
1693:phosphoribosyl pyrophosphate amidotransferase
1394:muscle relaxants. It can also interfere with
8:
4604:"Pharmacogenetics in the rheumatic diseases"
3853:"Risks and benefits of azathioprine therapy"
3528:
3526:
3256:
3254:
1890:, and a lower incidence of acute rejection.
1275:U.S. Department of Health and Human Services
967:In the United States, it is approved by the
177:
21:
3451:. Archived from the original on 2013-01-12.
3038:The Cochrane Database of Systematic Reviews
2773:The Cochrane Database of Systematic Reviews
2504:The Cochrane Database of Systematic Reviews
1583:purines, which are excreted via the urine.
1286:International Agency for Research on Cancer
1163:International Agency for Research on Cancer
6737:
6723:
6715:
5609:
5600:
5591:
5519:
5325:
5295:
5281:
5273:
4454:Alimentary Pharmacology & Therapeutics
4250:Alimentary Pharmacology & Therapeutics
4111:Alimentary Pharmacology & Therapeutics
3165:Alimentary Pharmacology & Therapeutics
2634:Alimentary Pharmacology & Therapeutics
2587:Alimentary Pharmacology & Therapeutics
2099:
2097:
2019:
2017:
2015:
2013:
2011:
2009:
2007:
2005:
2003:
1730:, thus sending activated T cells and
1423:have taken place in humans, when given to
1379:Azathioprine decreases the effects of the
1054:in those who experience recurrent flares.
654:
631:
520:
5218:
5115:
4806:
4627:
4545:
4465:
4261:
4220:
4171:
4122:
4021:European Journal of Clinical Pharmacology
3995:
3876:
3699:
3650:
3575:
3506:
3399:
3389:
3348:
3106:
3057:
2792:
2743:
2702:
2645:
2523:
2246:
2198:
2196:
2194:
2174:
2164:
2077:
2067:
1691:The nucleotides act to inhibit glutamine-
1645:Learn how and when to remove this message
1629:, without removing the technical details.
1269:in the 12th Report on Carcinogens by the
540:
5248:"Azathioprine Therapy and TPMT Genotype"
4875:
4873:
4852:Journal of the American Chemical Society
4160:Clinical Gastroenterology and Hepatology
3289:"Azathioprine Therapy and TPMT Genotype"
2862:American Journal of Clinical Dermatology
2295:
2293:
2291:
2289:
2287:
2285:
2283:
1504:MeTIMP: methyl-thioinosine monophosphate
1454:
1339:Azathioprine causes the accumulation of
1107:
6924:
4781:Maltzman JS, Koretzky GA (April 2003).
4699:Dinnendahl, V, Fricke, U, eds. (2011).
4341:Pharmaceutical Society of Great Britain
3533:Mutschler E, Schäfer-Korting M (2001).
2449:
2447:
1899:
1695:(GPAT), one of the enzymes involved in
1124:reactions include dizziness, diarrhea,
777:
757:
744:238 to 245 °C (460 to 473 °F)
627:
500:
419:
150:
4334:
4332:
4195:Govani SM, Higgins PD (October 2010).
3851:McGovern DP, Jewell DP (August 2005).
3487:Clinical Pharmacology and Therapeutics
3454:
2545:
2543:
2383:
2381:
2379:
2377:
2263:"Azathioprine - Drug Usage Statistics"
1665:, and then phosphorylated to form the
1532:while circulating in the bloodstream.
991:, other immunosuppressants, and local
645:
20:
6950:Disease-modifying antirheumatic drugs
4952:Journal of Reproduction and Fertility
4787:The Journal of Clinical Investigation
4783:"Azathioprine: old drug, new actions"
3943:from the original on October 14, 2012
3600:"Label: Imuran - azathioprine tablet"
3034:"Azathioprine for multiple sclerosis"
2241:. Geneva: World Health Organization.
1627:make it understandable to non-experts
1402:), resulting in at least one case to
1186:
600:
580:
136:
7:
4346:British National Formulary, Issue 45
3606:from the original on 20 October 2014
1987:Union Register of medicinal products
1844:when given to rabbits together with
1726:, blocking synthesis of the protein
1013:Nonsteroidal anti-inflammatory drugs
1005:disease-modifying antirheumatic drug
889:family of medications. It works via
245:
5065:The New England Journal of Medicine
3087:The New England Journal of Medicine
2031:from the original on 20 August 2016
1778:-imidazole and 6-mercaptopurine in
560:
471:
3927:"Skin cancer alert for organ drug"
3907:from the original on March 2, 2012
3423:Fujita K, Sasaki Y (August 2007).
2917:10.1212/01.wnl.0000098887.24618.a0
1599:, thus causing immunosuppression.
1265:Azathioprine is listed as a human
818:. It is used for the treatment of
14:
3767:from the original on July 3, 2012
3741:from the original on 16 July 2012
3378:World Journal of Gastroenterology
2056:World Journal of Gastroenterology
1848:. Following the work done by Sir
1579:(38%) and various methylated and
1148:is recommended during treatment.
388:3–5 hours (drug plus metabolites)
6927:
5117:10.1046/j.1523-1755.2003.00175.x
4608:Annals of the Rheumatic Diseases
4467:10.1046/j.1365-2036.2003.01537.x
4307:10.1111/j.1346-8138.2010.01189.x
4263:10.1111/j.1365-2036.2009.04221.x
4201:Journal of Crohn's & Colitis
4124:10.1111/j.1365-2036.2005.02583.x
3805:from the original on 2006-09-06.
3276:from the original on 2006-06-04.
3177:10.1111/j.1365-2036.2004.02197.x
2874:10.2165/00128071-200708020-00004
2647:10.1111/j.1365-2036.2004.02060.x
2352:10.1097/00007691-200404000-00018
2223:from the original on 2016-12-21.
1825:Azathioprine was synthesized by
1813:
1606:
1368:Other purine analogues, such as
928:, systemic lupus erythematosus,
824:granulomatosis with polyangiitis
685:
679:
56:
38:
29:
2106:Current Opinion in Rheumatology
785:Key:LMEKQMALGUDUQG-UHFFFAOYSA-N
114:Azasan, Imuran, Jayempi, others
4602:Cronstein BN (November 2004).
3050:10.1002/14651858.CD003982.pub2
2785:10.1002/14651858.CD000478.pub4
2599:10.1046/j.1365-2036.17.s2.20.x
1913:Merriam-Webster.com Dictionary
1356:infections of unclear origin,
1179:thiopurine S-methyltransferase
871:thiopurine S-methyltransferase
760:Cn1cnc(N(=O)=O)c1Sc2ncnc3ncc23
697:
691:
673:
1:
5042:10.1016/S0140-6736(60)90343-3
3631:Pharmacogenetics and Genomics
3329:Pharmacogenetics and Genomics
2960:10.1016/S0140-6736(06)68340-2
2745:10.1016/S0016-5085(98)70251-3
2726:Kirschner BS (October 1998).
2469:10.1016/S0140-6736(04)16808-6
1983:"Jayempi Product information"
1488:6-MMP: 6-methylmercaptopurine
1440:Medications and Mothers' Milk
1406:and fatal medullary aplasia.
1316:hepatosplenic T-cell lymphoma
1090:idiopathic pulmonary fibrosis
5360:dihydroorotate dehydrogenase
5207:Health Technology Assessment
5153:10.1016/0002-9610(85)90431-3
4213:10.1016/j.crohns.2010.02.009
4076:10.1016/0140-6736(93)91287-V
3830:10.1016/0165-7992(93)90083-8
3643:10.1097/FPC.0b013e3283352860
3341:10.1097/FPC.0b013e328334338f
2997:(2): 131–2, discussion 132.
2628:Rutgeerts P (October 2004).
2430:10.1016/j.radonc.2004.08.011
2118:10.1097/BOR.0000000000000382
1484:thiopurine methyltransferase
1144:; regular monitoring of the
969:Food and Drug Administration
857:Common side effects include
836:systemic lupus erythematosus
816:immunosuppressive medication
810:, sold under the brand name
386:26–80 minutes (azathioprine)
16:Immunosuppressive medication
5339:purine synthesis inhibitors
5141:American Journal of Surgery
5077:10.1056/NEJM196306132682401
4925:Cancer Chemotherapy Reports
4415:Annals of Internal Medicine
4355:British Medical Association
3795:Summaries & Evaluations
3732:National Toxicology Program
3724:National Toxicology Program
3577:10.1093/rheumatology/kel427
3270:Summaries & Evaluations
2340:Therapeutic Drug Monitoring
2147:Jordan N, D'Cruz D (2016).
1565:deoxyguanosine triphosphate
1515:deoxyguanosine triphosphate
1410:Pregnancy and breastfeeding
1271:National Toxicology Program
1140:and be more susceptible to
7006:
5268:. Bookshelf ID: NBK100661.
5253:Medical Genetics Summaries
4427:10.7326/0003-4819-82-1-113
4295:The Journal of Dermatology
3441:10.2174/138920007781368890
3309:. Bookshelf ID: NBK100661.
3294:Medical Genetics Summaries
2830:10.1191/096120301676669495
2564:10.1080/003655298750027290
2393:AHFS Drug Information 2012
2314:10.1016/j.jaad.2005.07.059
1434:Traditionally, as for all
1324:inflammatory bowel disease
1169:(carcinogenic to humans).
1134:suppresses the bone marrow
1088:A widely used therapy for
1019:Inflammatory bowel disease
958:inflammatory bowel disease
850:. It is taken by mouth or
663:Chemical and physical data
6878:
5524:IL-1 receptor antagonists
4999:10.3181/00379727-99-24281
4173:10.1016/j.cgh.2006.11.020
4033:10.1007/s00228-008-0478-6
3461:: CS1 maint: unfit URL (
3229:10.1016/j.aca.2020.08.064
2516:10.1002/14651858.CD001461
2418:Radiotherapy and Oncology
2235:World Health Organization
2153:ImmunoTargets and Therapy
1961:European Medicines Agency
1569:thioinosine monophosphate
1499:thioinosine monophosphate
893:to disrupt the making of
869:deficiency of the enzyme
793:
768:
748:
410:
37:
28:
6960:IARC Group 1 carcinogens
6397:Anti-lymphocyte globulin
4511:10.1001/jama.211.11.1854
3391:10.3748/wjg.v20.i13.3534
3003:10.1136/jnnp.2008.144972
2209:. Springer. p. 83.
2069:10.3748/wjg.v22.i20.4794
1888:opportunistic infections
1827:George Herbert Hitchings
1796:phosphorus pentachloride
1555:–). This is mediated by
1462:for azathioprine (AZA).
1334:In transplant patients,
1305:hepatobiliary carcinomas
1301:squamous cell carcinomas
954:restrictive lung disease
848:group 1 human carcinogen
6392:Anti-thymocyte globulin
5304:Immunosuppressive drugs
4902:10.1126/science.2649979
4620:10.1136/ard.2004.028217
4339:Mehta DK, et al. (
3988:10.1126/science.1114233
3869:10.1136/gut.2004.053231
3763:. FDA. August 4, 2009.
3429:Current Drug Metabolism
2695:10.1136/gut.2004.049460
1421:well-controlled studies
1136:, patients can develop
859:bone-marrow suppression
6791:Sodium aurothiosulfate
6197:Interleukin-6 receptor
5623:Complement component 5
4753:"Azathioprine Pathway"
4653:Nature Reviews. Cancer
4614:(Suppl 2): ii25–ii27.
4577:Hale TW (April 2010).
3939:. September 15, 2005.
3209:Analytica Chimica Acta
3137:Jasek, W, ed. (2007).
1591:Azathioprine inhibits
1561:guanosine triphosphate
1520:
1509:guanosine triphosphate
1189:), which is itself an
1113:
973:kidney transplantation
814:, among others, is an
6786:Sodium aurothiomalate
4964:10.1530/jrf.0.0040297
4831:US Patent 3056785
3535:Arzneimittelwirkungen
3499:10.1038/clpt.2010.320
3099:10.1056/NEJMoa1113354
1884:mycophenolate mofetil
1771:to 6-mercaptopurine.
1458:
1111:
932:, and other forms of
5104:Kidney International
3325:"Thiopurine pathway"
2640:(Suppl 4): 106–110.
1297:non-Hodgkin lymphoma
1161:It is listed by the
1063:third-line treatment
1009:rheumatoid arthritis
999:Rheumatoid arthritis
950:neuromyelitis optica
938:autoimmune hepatitis
922:rheumatoid arthritis
852:injected into a vein
820:rheumatoid arthritis
401:, 98% as metabolites
6749:products / DMARDs (
4894:1989Sci...244...41E
4864:10.1021/ja01643a015
4729:Medizinische Chemie
4701:Arzneistoff-Profile
3980:2005Sci...309.1871O
3974:(5742): 1871–1874.
3221:2020AcAC.1137...64P
1802:is introduced with
1751:linked to a second
1697:purine biosynthesis
1587:Mechanism of action
1501:, thioinosinic acid
1309:mesenchymal tumours
1220:for these types of
952:(Devic's disease),
918:autoimmune diseases
305:(Prescription only)
281:(Prescription only)
25:
6980:Purine antagonists
6965:Immunosuppressants
6905:Never to phase III
6835:Hydroxychloroquine
6554:Diroximel fumarate
6227:IL-2 receptor/CD25
5655:Certolizumab pegol
5308:Immunosuppressants
5182:(3): 274–80, 282.
4556:10.1002/tera.10043
4392:10.1002/bdra.20583
2593:(Suppl 2): 31–37.
2166:10.2147/ITT.S40675
1916:. Merriam-Webster.
1780:dimethyl sulfoxide
1759:derivative) via a
1747:Azathioprine is a
1701:product inhibition
1535:Azathioprine is a
1521:
1464:Active metabolites
1222:genetic variations
1210:genetic variations
1167:group 1 carcinogen
1150:Acute pancreatitis
1114:
1040:ulcerative colitis
1025:clinical remission
962:multiple sclerosis
840:kidney transplants
832:ulcerative colitis
6915:
6914:
6778:Gold preparations
6712:
6711:
6559:Efgartigimod alfa
6549:Dimethyl fumarate
6477:
6476:
6405:
6404:
6378:
6377:
5583:
5582:
5509:
5508:
5350:Mycophenolic acid
5071:(24): 1315–1323.
5036:(7121): 417–418.
4858:(14): 3653–3655.
4738:978-3-7692-3483-1
4710:978-3-7741-9846-3
4588:978-0-9823379-9-8
4505:(11): 1854–1855.
4364:978-0-85369-555-4
4301:(10): 1035–1037.
3903:. FDA. May 2011.
3818:Mutation Research
3544:978-3-8047-1763-3
3384:(13): 3534–3541.
3272:(suppl. 7): 119.
3148:978-3-85200-181-4
3093:(21): 1968–1977.
2954:(9513): 839–846.
2911:(12): 1652–1661.
2463:(9433): 503–512.
2402:978-1-58528-267-8
2062:(20): 4794–4801.
1866:heart transplants
1732:mononuclear cells
1722:-binding protein
1670:thioinosinic acid
1655:
1654:
1647:
1597:white blood cells
1466:are highlighted.
1460:Metabolic pathway
1345:ultraviolet light
1318:– a rare type of
1191:immunosuppressant
993:radiation therapy
946:myasthenia gravis
942:atopic dermatitis
805:
804:
729:Interactive image
613:CompTox Dashboard
328:
313:
300:
288:
276:
204:
171:
6997:
6932:
6931:
6930:
6923:
6739:
6732:
6725:
6716:
6355:Telimomab aritox
6258:Zolimomab aritox
6079:CD62L/L-selectin
5817:Immunoglobulin E
5610:
5601:
5592:
5520:
5326:
5297:
5290:
5283:
5274:
5269:
5233:
5232:
5222:
5198:
5192:
5191:
5171:
5165:
5164:
5136:
5130:
5129:
5119:
5110:(3): 1027–1034.
5095:
5089:
5088:
5060:
5054:
5053:
5025:
5019:
5018:
4982:
4976:
4975:
4947:
4941:
4940:
4920:
4914:
4913:
4877:
4868:
4867:
4847:
4841:
4839:
4838:
4834:
4827:
4821:
4820:
4810:
4799:10.1172/JCI18384
4793:(8): 1122–1124.
4778:
4769:
4768:
4766:
4764:
4749:
4743:
4742:
4724:
4715:
4714:
4696:
4685:
4684:
4648:
4642:
4641:
4631:
4599:
4593:
4592:
4574:
4568:
4567:
4549:
4529:
4523:
4522:
4494:
4488:
4487:
4469:
4445:
4439:
4438:
4410:
4404:
4403:
4375:
4369:
4368:
4343:) (March 2003).
4336:
4327:
4326:
4290:
4284:
4283:
4265:
4241:
4235:
4234:
4224:
4192:
4186:
4185:
4175:
4151:
4145:
4144:
4126:
4102:
4096:
4095:
4059:
4053:
4052:
4016:
4010:
4009:
3999:
3959:
3953:
3952:
3950:
3948:
3923:
3917:
3916:
3914:
3912:
3897:
3891:
3890:
3880:
3863:(8): 1055–1059.
3848:
3842:
3841:
3813:
3807:
3806:
3783:
3777:
3776:
3774:
3772:
3757:
3751:
3750:
3748:
3746:
3740:
3726:(10 June 2011).
3720:
3714:
3713:
3703:
3686:(9): 1017–1020.
3671:
3665:
3664:
3654:
3622:
3616:
3615:
3613:
3611:
3596:
3590:
3589:
3579:
3555:
3549:
3548:
3530:
3521:
3520:
3510:
3478:
3467:
3466:
3460:
3452:
3420:
3414:
3413:
3403:
3393:
3369:
3363:
3362:
3352:
3320:
3311:
3310:
3284:
3278:
3277:
3258:
3249:
3248:
3203:
3197:
3196:
3159:
3153:
3152:
3134:
3121:
3120:
3110:
3078:
3072:
3071:
3061:
3029:
3023:
3022:
2986:
2980:
2979:
2943:
2937:
2936:
2900:
2894:
2893:
2856:
2850:
2849:
2813:
2807:
2806:
2796:
2764:
2758:
2757:
2747:
2732:Gastroenterology
2723:
2717:
2716:
2706:
2689:(8): 1121–1125.
2674:
2668:
2667:
2649:
2625:
2619:
2618:
2582:
2576:
2575:
2547:
2538:
2537:
2527:
2495:
2489:
2488:
2451:
2442:
2441:
2413:
2407:
2406:
2385:
2372:
2371:
2335:
2326:
2325:
2297:
2278:
2277:
2275:
2273:
2259:
2253:
2252:
2250:
2231:
2225:
2224:
2200:
2189:
2188:
2178:
2168:
2144:
2138:
2137:
2101:
2092:
2091:
2081:
2071:
2047:
2041:
2040:
2038:
2036:
2021:
1998:
1997:
1995:
1993:
1979:
1973:
1972:
1970:
1968:
1953:
1947:
1946:
1944:
1942:
1932:nctr-crs.fda.gov
1924:
1918:
1917:
1904:
1817:
1650:
1643:
1639:
1636:
1630:
1610:
1609:
1602:
1593:purine synthesis
1547:cleavage of the
1541:6-mercaptopurine
1472:xanthine oxidase
1451:Pharmacokinetics
1374:xanthine oxidase
1282:alkylating agent
1251:pharmacogenetics
1226:myelosuppression
1187:Pharmacokinetics
1183:6-mercaptopurine
1173:Pharmacogenetics
1122:hypersensitivity
930:Behçet's disease
883:purine analogues
801:
800:
731:
711:
699:
693:
687:
681:
675:
658:
647:
636:
635:
621:
619:
604:
584:
564:
544:
524:
504:
484:
474:
473:
447:
382:
372:xanthine oxidase
326:
323:
318:
311:
308:
298:
295:
287:
284:
274:
271:
249:
202:
199:
181:
170:
167:
154:
140:
103:
102:
99:
98:
95:
92:
89:
86:
83:
80:
77:
74:
71:
68:
65:
62:
42:
33:
26:
24:
7005:
7004:
7000:
6999:
6998:
6996:
6995:
6994:
6970:Nitroimidazoles
6940:
6939:
6938:
6928:
6926:
6918:
6916:
6911:
6910:
6895:Clinical trials
6874:
6810:
6801:Aurothioglucose
6772:
6754:
6743:
6713:
6708:
6654:Rozanolixizumab
6539:Deucravacitinib
6473:
6401:
6374:
6263:
5912:
5906:
5614:
5579:
5536:
5515:
5505:
5463:
5403:
5394:
5330:Antimetabolites
5321:
5315:
5301:
5246:Dean L (2012).
5245:
5242:
5240:Further reading
5237:
5236:
5220:10.3310/hta9210
5200:
5199:
5195:
5173:
5172:
5168:
5138:
5137:
5133:
5097:
5096:
5092:
5062:
5061:
5057:
5027:
5026:
5022:
4984:
4983:
4979:
4949:
4948:
4944:
4922:
4921:
4917:
4888:(4900): 41–47.
4879:
4878:
4871:
4849:
4848:
4844:
4836:
4829:
4828:
4824:
4780:
4779:
4772:
4762:
4760:
4751:
4750:
4746:
4739:
4726:
4725:
4718:
4711:
4698:
4697:
4688:
4665:10.1038/nrc2292
4650:
4649:
4645:
4601:
4600:
4596:
4589:
4576:
4575:
4571:
4547:10.1.1.566.7676
4531:
4530:
4526:
4496:
4495:
4491:
4447:
4446:
4442:
4412:
4411:
4407:
4377:
4376:
4372:
4365:
4338:
4337:
4330:
4292:
4291:
4287:
4243:
4242:
4238:
4194:
4193:
4189:
4153:
4152:
4148:
4104:
4103:
4099:
4070:(8863): 83–84.
4061:
4060:
4056:
4018:
4017:
4013:
3961:
3960:
3956:
3946:
3944:
3925:
3924:
3920:
3910:
3908:
3899:
3898:
3894:
3850:
3849:
3845:
3815:
3814:
3810:
3785:
3784:
3780:
3770:
3768:
3759:
3758:
3754:
3744:
3742:
3738:
3722:
3721:
3717:
3692:10.1038/ng.3060
3680:Nature Genetics
3673:
3672:
3668:
3624:
3623:
3619:
3609:
3607:
3598:
3597:
3593:
3557:
3556:
3552:
3545:
3532:
3531:
3524:
3480:
3479:
3470:
3453:
3422:
3421:
3417:
3371:
3370:
3366:
3322:
3321:
3314:
3287:Dean L (2012).
3286:
3285:
3281:
3260:
3259:
3252:
3215:(1137): 64–73.
3205:
3204:
3200:
3161:
3160:
3156:
3149:
3136:
3135:
3124:
3080:
3079:
3075:
3044:(4): CD003982.
3031:
3030:
3026:
2988:
2987:
2983:
2945:
2944:
2940:
2902:
2901:
2897:
2858:
2857:
2853:
2815:
2814:
2810:
2779:(5): CD000478.
2766:
2765:
2761:
2725:
2724:
2720:
2676:
2675:
2671:
2627:
2626:
2622:
2584:
2583:
2579:
2549:
2548:
2541:
2510:(4): CD001461.
2497:
2496:
2492:
2453:
2452:
2445:
2415:
2414:
2410:
2403:
2387:
2386:
2375:
2337:
2336:
2329:
2299:
2298:
2281:
2271:
2269:
2261:
2260:
2256:
2233:
2232:
2228:
2217:
2203:Sami N (2016).
2202:
2201:
2192:
2146:
2145:
2141:
2103:
2102:
2095:
2049:
2048:
2044:
2034:
2032:
2023:
2022:
2001:
1991:
1989:
1981:
1980:
1976:
1966:
1964:
1963:. 20 April 2021
1955:
1954:
1950:
1940:
1938:
1926:
1925:
1921:
1906:
1905:
1901:
1896:
1874:glucocorticoids
1823:
1745:
1651:
1640:
1634:
1631:
1623:help improve it
1620:
1611:
1607:
1589:
1563:(TGTP) and thio
1530:plasma proteins
1525:Bioavailability
1519:
1453:
1448:
1436:cytotoxic drugs
1412:
1401:
1388:nondepolarizing
1366:
1353:
1332:
1263:
1238:red blood cells
1175:
1106:
1104:Adverse effects
1083:interferon beta
1078:Cochrane review
1048:
1021:
1001:
989:corticosteroids
981:
979:Transplantation
914:
887:antimetabolites
828:Crohn's disease
796:
794:
789:
786:
781:
776:
775:
764:
761:
756:
755:
734:
709:
696:
690:
684:
678:
639:
615:
607:
587:
567:
547:
527:
507:
487:
470:
462:
448:
430:
427:
418:
417:
387:
380:
356:Protein binding
346:Bioavailability
338:Pharmacokinetic
332:
316:
253:
217:
210:
191:
184:
59:
55:
17:
12:
11:
5:
7003:
7001:
6993:
6992:
6987:
6982:
6977:
6972:
6967:
6962:
6957:
6952:
6942:
6941:
6937:
6936:
6913:
6912:
6909:
6908:
6907:
6906:
6903:
6892:
6886:
6880:
6879:
6876:
6875:
6873:
6872:
6860:
6848:
6842:
6837:
6828:
6818:
6816:
6812:
6811:
6809:
6808:
6803:
6798:
6793:
6788:
6782:
6780:
6774:
6773:
6771:
6770:
6764:
6762:
6756:
6755:
6744:
6742:
6741:
6734:
6727:
6719:
6710:
6709:
6707:
6706:
6701:
6696:
6691:
6686:
6681:
6676:
6671:
6666:
6661:
6656:
6651:
6646:
6641:
6636:
6631:
6626:
6621:
6616:
6611:
6606:
6601:
6596:
6591:
6586:
6581:
6576:
6571:
6566:
6563:+hyaluronidase
6556:
6551:
6546:
6544:Deuruxolitinib
6541:
6536:
6531:
6526:
6521:
6516:
6511:
6506:
6501:
6496:
6491:
6485:
6483:
6479:
6478:
6475:
6474:
6472:
6471:
6466:
6461:
6456:
6455:
6454:
6449:
6437:
6436:
6435:
6430:
6417:
6415:
6407:
6406:
6403:
6402:
6400:
6399:
6394:
6388:
6386:
6380:
6379:
6376:
6375:
6373:
6372:
6367:
6362:
6357:
6352:
6347:
6342:
6337:
6332:
6327:
6322:
6317:
6312:
6307:
6302:
6297:
6292:
6287:
6282:
6277:
6271:
6269:
6265:
6264:
6262:
6261:
6248:
6247:
6246:
6245:
6240:
6235:
6222:
6221:
6220:
6219:
6207:
6206:
6205:
6193:
6192:
6191:
6186:
6174:
6173:
6172:
6167:
6162:
6150:
6149:
6148:
6137:
6136:
6135:
6134:
6129:
6117:
6116:
6115:
6103:
6102:
6101:
6089:
6088:
6087:
6075:
6074:
6073:
6068:
6056:
6055:
6054:
6049:
6037:
6036:
6035:
6030:
6025:
6020:
6017:+hyaluronidase
6010:
5998:
5997:
5996:
5984:
5983:
5982:
5970:
5969:
5968:
5963:
5958:
5946:
5945:
5944:
5939:
5934:
5929:
5916:
5914:
5908:
5907:
5905:
5904:
5903:
5902:
5889:
5888:
5887:
5886:
5881:
5860:
5859:
5858:
5857:
5844:
5843:
5842:
5841:
5828:
5827:
5826:
5825:
5812:
5811:
5810:
5809:
5796:
5795:
5794:
5793:
5788:
5783:
5778:
5773:
5768:
5763:
5758:
5753:
5748:
5743:
5738:
5733:
5728:
5723:
5718:
5713:
5708:
5703:
5698:
5693:
5688:
5675:
5674:
5673:
5672:
5667:
5662:
5657:
5652:
5647:
5634:
5633:
5632:
5631:
5618:
5616:
5607:
5598:
5589:
5585:
5584:
5581:
5580:
5578:
5577:
5572:
5567:
5562:
5557:
5552:
5546:
5544:
5538:
5537:
5535:
5534:
5528:
5526:
5517:
5511:
5510:
5507:
5506:
5504:
5503:
5502:
5501:
5493:PDE4 inhibitor
5489:
5484:
5479:
5473:
5471:
5465:
5464:
5462:
5461:
5456:
5450:
5449:
5448:
5447:
5442:
5437:
5432:
5411:
5409:
5396:
5395:
5393:
5392:
5391:
5390:
5377:
5376:
5375:
5374:
5369:
5355:
5354:
5353:
5352:
5347:
5334:
5332:
5323:
5317:
5316:
5302:
5300:
5299:
5292:
5285:
5277:
5271:
5270:
5241:
5238:
5235:
5234:
5193:
5166:
5147:(5): 533–536.
5131:
5090:
5055:
5020:
4993:(1): 164–167.
4977:
4958:(3): 297–302.
4942:
4915:
4869:
4842:
4822:
4770:
4759:on 2 July 2012
4744:
4737:
4716:
4709:
4686:
4643:
4594:
4587:
4569:
4540:(5): 240–261.
4524:
4489:
4460:(6): 827–834.
4440:
4421:(1): 113–114.
4405:
4386:(7): 647–654.
4370:
4363:
4328:
4285:
4256:(6): 640–647.
4236:
4207:(4): 444–449.
4187:
4166:(2): 209–214.
4146:
4117:(5): 441–446.
4097:
4054:
4027:(8): 753–767.
4011:
3954:
3918:
3892:
3843:
3808:
3778:
3752:
3715:
3666:
3637:(6): 401–405.
3617:
3591:
3570:(5): 727–729.
3550:
3543:
3522:
3468:
3435:(6): 554–562.
3415:
3364:
3335:(9): 573–574.
3312:
3279:
3266:"Azathioprine"
3250:
3198:
3171:(8): 843–850.
3154:
3147:
3122:
3073:
3024:
2981:
2938:
2895:
2851:
2824:(3): 152–153.
2808:
2759:
2738:(4): 813–821.
2718:
2669:
2620:
2577:
2558:(234): 92–99.
2539:
2490:
2443:
2408:
2401:
2373:
2346:(2): 186–191.
2327:
2308:(3): 369–389.
2279:
2254:
2226:
2215:
2190:
2139:
2112:(3): 248–253.
2093:
2042:
2025:"Azathioprine"
1999:
1974:
1957:"Jayempi EPAR"
1948:
1919:
1908:"Azathioprine"
1898:
1897:
1895:
1892:
1831:Gertrude Elion
1822:
1819:
1744:
1741:
1740:
1739:
1716:
1689:
1653:
1652:
1614:
1612:
1605:
1588:
1585:
1518:
1517:
1511:
1505:
1502:
1495:
1489:
1486:
1480:
1478:mercaptopurine
1474:
1467:
1452:
1449:
1447:
1444:
1411:
1408:
1399:
1365:
1362:
1352:
1349:
1331:
1328:
1262:
1259:
1174:
1171:
1105:
1102:
1098:acetylcysteine
1047:
1044:
1020:
1017:
1000:
997:
980:
977:
913:
910:
803:
802:
791:
790:
788:
787:
784:
782:
779:
771:
770:
769:
766:
765:
763:
762:
759:
751:
750:
749:
746:
745:
742:
736:
735:
733:
732:
724:
722:
714:
713:
707:
701:
700:
694:
688:
682:
676:
671:
665:
664:
660:
659:
649:
641:
640:
638:
637:
624:
622:
609:
608:
606:
605:
597:
595:
589:
588:
586:
585:
577:
575:
569:
568:
566:
565:
557:
555:
549:
548:
546:
545:
537:
535:
529:
528:
526:
525:
517:
515:
509:
508:
506:
505:
497:
495:
489:
488:
486:
485:
477:
475:
464:
463:
461:
460:
440:
438:
432:
431:
429:
428:
421:
413:
412:
411:
408:
407:
403:
402:
396:
390:
389:
384:
375:
374:
368:
362:
361:
358:
352:
351:
348:
342:
341:
334:
333:
331:
330:
321:
306:
293:
282:
268:
266:
260:
259:
255:
254:
252:
251:
238:
236:
230:
229:
220:
218:administration
212:
211:
209:
208:
206:
196:
194:
186:
185:
183:
182:
164:
162:
156:
155:
148:
142:
141:
134:
124:
123:
120:
116:
115:
112:
106:
105:
53:
49:
48:
44:
43:
35:
34:
15:
13:
10:
9:
6:
4:
3:
2:
7002:
6991:
6988:
6986:
6983:
6981:
6978:
6976:
6973:
6971:
6968:
6966:
6963:
6961:
6958:
6956:
6953:
6951:
6948:
6947:
6945:
6935:
6925:
6921:
6904:
6902:
6899:
6898:
6896:
6893:
6890:
6887:
6885:
6882:
6881:
6877:
6870:
6866:
6865:
6861:
6858:
6854:
6853:
6849:
6846:
6845:Sulfasalazine
6843:
6841:
6838:
6836:
6832:
6829:
6827:
6823:
6822:Penicillamine
6820:
6819:
6817:
6813:
6807:
6804:
6802:
6799:
6797:
6794:
6792:
6789:
6787:
6784:
6783:
6781:
6779:
6775:
6769:
6768:Oxycinchophen
6766:
6765:
6763:
6761:
6757:
6752:
6748:
6747:antirheumatic
6740:
6735:
6733:
6728:
6726:
6721:
6720:
6717:
6705:
6702:
6700:
6697:
6695:
6694:Tildrakizumab
6692:
6690:
6687:
6685:
6682:
6680:
6677:
6675:
6672:
6670:
6667:
6665:
6662:
6660:
6657:
6655:
6652:
6650:
6647:
6645:
6642:
6640:
6637:
6635:
6632:
6630:
6627:
6625:
6624:Pegcetacoplan
6622:
6620:
6617:
6615:
6612:
6610:
6607:
6605:
6602:
6600:
6597:
6595:
6592:
6590:
6587:
6585:
6582:
6580:
6577:
6575:
6572:
6570:
6567:
6564:
6560:
6557:
6555:
6552:
6550:
6547:
6545:
6542:
6540:
6537:
6535:
6534:Darvadstrocel
6532:
6530:
6527:
6525:
6522:
6520:
6517:
6515:
6512:
6510:
6507:
6505:
6502:
6500:
6497:
6495:
6492:
6490:
6487:
6486:
6484:
6480:
6470:
6467:
6465:
6462:
6460:
6457:
6453:
6450:
6448:
6445:
6444:
6443:
6442:
6441:TNF inhibitor
6438:
6434:
6431:
6429:
6426:
6425:
6424:
6423:
6419:
6418:
6416:
6413:
6408:
6398:
6395:
6393:
6390:
6389:
6387:
6385:
6381:
6371:
6368:
6366:
6363:
6361:
6358:
6356:
6353:
6351:
6348:
6346:
6343:
6341:
6338:
6336:
6333:
6331:
6328:
6326:
6323:
6321:
6318:
6316:
6313:
6311:
6308:
6306:
6303:
6301:
6298:
6296:
6293:
6291:
6288:
6286:
6283:
6281:
6278:
6276:
6273:
6272:
6270:
6266:
6259:
6255:
6254:
6250:
6249:
6244:
6241:
6239:
6236:
6234:
6231:
6230:
6229:
6228:
6224:
6223:
6218:
6215:
6214:
6213:
6212:
6208:
6204:
6201:
6200:
6199:
6198:
6194:
6190:
6187:
6185:
6182:
6181:
6180:
6179:
6175:
6171:
6168:
6166:
6163:
6161:
6158:
6157:
6156:
6155:
6151:
6147:
6144:
6143:
6142:
6139:
6138:
6133:
6130:
6128:
6125:
6124:
6123:
6122:
6118:
6114:
6111:
6110:
6109:
6108:
6107:CD147/Basigin
6104:
6100:
6097:
6096:
6095:
6094:
6090:
6086:
6083:
6082:
6081:
6080:
6076:
6072:
6069:
6067:
6064:
6063:
6062:
6061:
6057:
6053:
6050:
6048:
6045:
6044:
6043:
6042:
6038:
6034:
6031:
6029:
6026:
6024:
6021:
6018:
6014:
6011:
6009:
6006:
6005:
6004:
6003:
5999:
5995:
5992:
5991:
5990:
5989:
5985:
5981:
5978:
5977:
5976:
5975:
5971:
5967:
5964:
5962:
5959:
5957:
5954:
5953:
5952:
5951:
5947:
5943:
5940:
5938:
5935:
5933:
5930:
5928:
5927:Muromonab-CD3
5925:
5924:
5923:
5922:
5918:
5917:
5915:
5909:
5901:
5898:
5897:
5896:
5895:
5891:
5890:
5885:
5882:
5880:
5877:
5876:
5875:
5874:
5870:
5866:
5862:
5861:
5856:
5853:
5852:
5851:
5850:
5846:
5845:
5840:
5837:
5836:
5835:
5834:
5830:
5829:
5824:
5821:
5820:
5819:
5818:
5814:
5813:
5808:
5805:
5804:
5803:
5802:
5801:Interleukin 5
5798:
5797:
5792:
5789:
5787:
5784:
5782:
5781:Tildrakizumab
5779:
5777:
5774:
5772:
5769:
5767:
5764:
5762:
5759:
5757:
5754:
5752:
5749:
5747:
5744:
5742:
5739:
5737:
5734:
5732:
5729:
5727:
5724:
5722:
5719:
5717:
5714:
5712:
5709:
5707:
5704:
5702:
5699:
5697:
5694:
5692:
5689:
5687:
5684:
5683:
5682:
5681:
5677:
5676:
5671:
5668:
5666:
5663:
5661:
5658:
5656:
5653:
5651:
5648:
5646:
5643:
5642:
5641:
5640:
5636:
5635:
5630:
5627:
5626:
5625:
5624:
5620:
5619:
5617:
5615:(noncellular)
5611:
5608:
5606:
5602:
5599:
5597:
5593:
5590:
5588:Extracellular
5586:
5576:
5573:
5571:
5568:
5566:
5563:
5561:
5558:
5556:
5555:Ridaforolimus
5553:
5551:
5548:
5547:
5545:
5543:
5539:
5533:
5530:
5529:
5527:
5525:
5521:
5518:
5514:Intracellular
5512:
5500:
5497:
5496:
5495:
5494:
5490:
5488:
5485:
5483:
5480:
5478:
5475:
5474:
5472:
5470:
5466:
5460:
5457:
5455:
5452:
5451:
5446:
5443:
5441:
5438:
5436:
5433:
5431:
5428:
5427:
5426:
5425:
5421:
5417:
5413:
5412:
5410:
5407:
5401:
5397:
5389:
5386:
5385:
5384:
5383:
5379:
5378:
5373:
5372:Teriflunomide
5370:
5368:
5365:
5364:
5362:
5361:
5357:
5356:
5351:
5348:
5346:
5343:
5342:
5341:
5340:
5336:
5335:
5333:
5331:
5327:
5324:
5320:Intracellular
5318:
5313:
5309:
5305:
5298:
5293:
5291:
5286:
5284:
5279:
5278:
5275:
5267:
5263:
5259:
5255:
5254:
5249:
5244:
5243:
5239:
5230:
5226:
5221:
5216:
5213:(21): 1–194.
5212:
5208:
5204:
5197:
5194:
5189:
5185:
5181:
5177:
5170:
5167:
5162:
5158:
5154:
5150:
5146:
5142:
5135:
5132:
5127:
5123:
5118:
5113:
5109:
5105:
5101:
5094:
5091:
5086:
5082:
5078:
5074:
5070:
5066:
5059:
5056:
5051:
5047:
5043:
5039:
5035:
5031:
5024:
5021:
5016:
5012:
5008:
5004:
5000:
4996:
4992:
4988:
4981:
4978:
4973:
4969:
4965:
4961:
4957:
4953:
4946:
4943:
4938:
4934:
4930:
4926:
4919:
4916:
4911:
4907:
4903:
4899:
4895:
4891:
4887:
4883:
4876:
4874:
4870:
4865:
4861:
4857:
4853:
4846:
4843:
4832:
4826:
4823:
4818:
4814:
4809:
4804:
4800:
4796:
4792:
4788:
4784:
4777:
4775:
4771:
4758:
4754:
4748:
4745:
4740:
4734:
4730:
4723:
4721:
4717:
4712:
4706:
4702:
4695:
4693:
4691:
4687:
4682:
4678:
4674:
4670:
4666:
4662:
4658:
4654:
4647:
4644:
4639:
4635:
4630:
4625:
4621:
4617:
4613:
4609:
4605:
4598:
4595:
4590:
4584:
4580:
4573:
4570:
4565:
4561:
4557:
4553:
4548:
4543:
4539:
4535:
4528:
4525:
4520:
4516:
4512:
4508:
4504:
4500:
4493:
4490:
4485:
4481:
4477:
4473:
4468:
4463:
4459:
4455:
4451:
4444:
4441:
4436:
4432:
4428:
4424:
4420:
4416:
4409:
4406:
4401:
4397:
4393:
4389:
4385:
4381:
4374:
4371:
4366:
4360:
4356:
4352:
4348:
4347:
4342:
4335:
4333:
4329:
4324:
4320:
4316:
4312:
4308:
4304:
4300:
4296:
4289:
4286:
4281:
4277:
4273:
4269:
4264:
4259:
4255:
4251:
4247:
4240:
4237:
4232:
4228:
4223:
4218:
4214:
4210:
4206:
4202:
4198:
4191:
4188:
4183:
4179:
4174:
4169:
4165:
4161:
4157:
4150:
4147:
4142:
4138:
4134:
4130:
4125:
4120:
4116:
4112:
4108:
4101:
4098:
4093:
4089:
4085:
4081:
4077:
4073:
4069:
4065:
4058:
4055:
4050:
4046:
4042:
4038:
4034:
4030:
4026:
4022:
4015:
4012:
4007:
4003:
3998:
3993:
3989:
3985:
3981:
3977:
3973:
3969:
3965:
3958:
3955:
3942:
3938:
3934:
3933:
3928:
3922:
3919:
3906:
3902:
3896:
3893:
3888:
3884:
3879:
3874:
3870:
3866:
3862:
3858:
3854:
3847:
3844:
3839:
3835:
3831:
3827:
3823:
3819:
3812:
3809:
3804:
3800:
3796:
3792:
3788:
3782:
3779:
3766:
3762:
3756:
3753:
3737:
3733:
3729:
3725:
3719:
3716:
3711:
3707:
3702:
3697:
3693:
3689:
3685:
3681:
3677:
3670:
3667:
3662:
3658:
3653:
3648:
3644:
3640:
3636:
3632:
3628:
3621:
3618:
3605:
3601:
3595:
3592:
3587:
3583:
3578:
3573:
3569:
3565:
3561:
3554:
3551:
3546:
3540:
3536:
3529:
3527:
3523:
3518:
3514:
3509:
3504:
3500:
3496:
3492:
3488:
3484:
3477:
3475:
3473:
3469:
3464:
3458:
3450:
3446:
3442:
3438:
3434:
3430:
3426:
3419:
3416:
3411:
3407:
3402:
3397:
3392:
3387:
3383:
3379:
3375:
3368:
3365:
3360:
3356:
3351:
3346:
3342:
3338:
3334:
3330:
3326:
3319:
3317:
3313:
3308:
3304:
3300:
3296:
3295:
3290:
3283:
3280:
3275:
3271:
3267:
3263:
3257:
3255:
3251:
3246:
3242:
3238:
3234:
3230:
3226:
3222:
3218:
3214:
3210:
3202:
3199:
3194:
3190:
3186:
3182:
3178:
3174:
3170:
3166:
3158:
3155:
3150:
3144:
3140:
3139:Austria-Codex
3133:
3131:
3129:
3127:
3123:
3118:
3114:
3109:
3104:
3100:
3096:
3092:
3088:
3084:
3077:
3074:
3069:
3065:
3060:
3055:
3051:
3047:
3043:
3039:
3035:
3028:
3025:
3020:
3016:
3012:
3008:
3004:
3000:
2996:
2992:
2985:
2982:
2977:
2973:
2969:
2965:
2961:
2957:
2953:
2949:
2942:
2939:
2934:
2930:
2926:
2922:
2918:
2914:
2910:
2906:
2899:
2896:
2891:
2887:
2883:
2879:
2875:
2871:
2867:
2863:
2855:
2852:
2847:
2843:
2839:
2835:
2831:
2827:
2823:
2819:
2812:
2809:
2804:
2800:
2795:
2790:
2786:
2782:
2778:
2774:
2770:
2763:
2760:
2755:
2751:
2746:
2741:
2737:
2733:
2729:
2722:
2719:
2714:
2710:
2705:
2700:
2696:
2692:
2688:
2684:
2680:
2673:
2670:
2665:
2661:
2657:
2653:
2648:
2643:
2639:
2635:
2631:
2624:
2621:
2616:
2612:
2608:
2604:
2600:
2596:
2592:
2588:
2581:
2578:
2573:
2569:
2565:
2561:
2557:
2553:
2546:
2544:
2540:
2535:
2531:
2526:
2521:
2517:
2513:
2509:
2505:
2501:
2494:
2491:
2486:
2482:
2478:
2474:
2470:
2466:
2462:
2458:
2450:
2448:
2444:
2439:
2435:
2431:
2427:
2423:
2419:
2412:
2409:
2404:
2398:
2394:
2390:
2384:
2382:
2380:
2378:
2374:
2369:
2365:
2361:
2357:
2353:
2349:
2345:
2341:
2334:
2332:
2328:
2323:
2319:
2315:
2311:
2307:
2303:
2296:
2294:
2292:
2290:
2288:
2286:
2284:
2280:
2268:
2264:
2258:
2255:
2249:
2244:
2240:
2236:
2230:
2227:
2222:
2218:
2216:9783319267289
2212:
2208:
2207:
2199:
2197:
2195:
2191:
2186:
2182:
2177:
2172:
2167:
2162:
2158:
2154:
2150:
2143:
2140:
2135:
2131:
2127:
2123:
2119:
2115:
2111:
2107:
2100:
2098:
2094:
2089:
2085:
2080:
2075:
2070:
2065:
2061:
2057:
2053:
2046:
2043:
2030:
2026:
2020:
2018:
2016:
2014:
2012:
2010:
2008:
2006:
2004:
2000:
1988:
1984:
1978:
1975:
1962:
1958:
1952:
1949:
1937:
1933:
1929:
1923:
1920:
1915:
1914:
1909:
1903:
1900:
1893:
1891:
1889:
1885:
1881:
1877:
1875:
1869:
1867:
1863:
1859:
1855:
1851:
1850:Peter Medawar
1847:
1843:
1838:
1836:
1832:
1828:
1820:
1818:
1816:
1811:
1809:
1808:sulfuric acid
1805:
1801:
1797:
1793:
1789:
1785:
1781:
1777:
1772:
1770:
1766:
1762:
1758:
1754:
1750:
1742:
1737:
1733:
1729:
1725:
1721:
1717:
1714:
1713:immune system
1710:
1706:
1702:
1698:
1694:
1690:
1687:
1683:
1682:
1681:
1679:
1678:guanylic acid
1675:
1674:inosinic acid
1671:
1668:
1664:
1660:
1659:6-thioguanine
1649:
1646:
1638:
1635:December 2014
1628:
1624:
1618:
1615:This section
1613:
1604:
1603:
1600:
1598:
1594:
1586:
1584:
1582:
1578:
1577:thiouric acid
1574:
1570:
1566:
1562:
1558:
1554:
1550:
1546:
1542:
1538:
1533:
1531:
1526:
1516:
1512:
1510:
1506:
1503:
1500:
1496:
1494:
1490:
1487:
1485:
1481:
1479:
1475:
1473:
1469:
1468:
1465:
1461:
1457:
1450:
1445:
1443:
1441:
1437:
1432:
1430:
1426:
1422:
1418:
1409:
1407:
1405:
1397:
1393:
1389:
1385:
1382:
1381:anticoagulant
1377:
1375:
1371:
1363:
1361:
1359:
1350:
1348:
1346:
1342:
1341:6-thioguanine
1337:
1329:
1327:
1325:
1321:
1317:
1312:
1310:
1306:
1303:of the skin,
1302:
1298:
1293:
1291:
1287:
1283:
1278:
1276:
1272:
1268:
1260:
1258:
1256:
1252:
1248:
1247:myelotoxicity
1243:
1239:
1235:
1231:
1227:
1223:
1219:
1215:
1211:
1207:
1203:
1199:
1195:
1192:
1188:
1184:
1180:
1172:
1170:
1168:
1164:
1159:
1156:
1151:
1147:
1143:
1139:
1135:
1131:
1127:
1123:
1119:
1110:
1103:
1101:
1099:
1095:
1091:
1086:
1084:
1079:
1075:
1071:
1066:
1064:
1059:
1055:
1053:
1045:
1043:
1041:
1037:
1032:
1030:
1026:
1018:
1016:
1014:
1010:
1006:
998:
996:
994:
990:
986:
978:
976:
974:
970:
965:
963:
959:
955:
951:
947:
943:
939:
935:
931:
927:
923:
919:
911:
909:
907:
902:
900:
896:
892:
891:6-thioguanine
888:
884:
880:
877:. Use during
876:
872:
868:
864:
860:
855:
853:
849:
845:
841:
837:
833:
829:
825:
821:
817:
813:
809:
799:
792:
783:
778:
774:
767:
758:
754:
747:
743:
741:
740:Melting point
737:
730:
726:
725:
723:
720:
715:
708:
706:
702:
672:
670:
666:
661:
657:
653:
650:
648:
646:ECHA InfoCard
642:
634:
630:
629:DTXSID4020119
626:
625:
623:
614:
610:
603:
599:
598:
596:
594:
590:
583:
579:
578:
576:
574:
570:
563:
559:
558:
556:
554:
550:
543:
539:
538:
536:
534:
530:
523:
519:
518:
516:
514:
510:
503:
499:
498:
496:
494:
490:
483:
479:
478:
476:
469:
465:
458:
455:
451:
446:
442:
441:
439:
437:
433:
425:
420:
416:
409:
404:
400:
397:
395:
391:
385:
383:
376:
373:
369:
367:
363:
359:
357:
353:
349:
347:
343:
339:
335:
329: Rx-only
322:
319:
307:
304:
294:
292:
283:
280:
270:
269:
267:
265:
261:
256:
248:
243:
240:
239:
237:
235:
231:
228:
224:
221:
219:
213:
207:
198:
197:
195:
193:
187:
180:
175:
166:
165:
163:
161:
157:
153:
149:
147:
143:
139:
135:
133:
129:
125:
121:
117:
113:
111:
107:
101:
54:
52:Pronunciation
50:
47:Clinical data
45:
41:
36:
32:
27:
19:
6955:Hepatotoxins
6869:Azathioprine
6868:
6862:
6857:Methotrexate
6850:
6704:Upadacitinib
6664:Satralizumab
6649:Ritlecitinib
6644:Risankizumab
6439:
6420:
6360:Teprotumumab
6310:Inebilizumab
6305:Fontolizumab
6285:Atorolimumab
6253:T-lymphocyte
6251:
6225:
6209:
6195:
6176:
6165:Lerdelimumab
6160:Bertilimumab
6152:
6140:
6119:
6105:
6091:
6077:
6058:
6039:
6023:Pascolizumab
6008:Obinutuzumab
6000:
5986:
5972:
5956:Clenoliximab
5948:
5932:Otelixizumab
5919:
5892:
5879:Lebrikizumab
5863:
5847:
5831:
5815:
5799:
5756:Satralizumab
5746:Risankizumab
5678:
5637:
5621:
5613:Serum target
5565:Temsirolimus
5491:
5482:Pomalidomide
5477:Lenalidomide
5435:Pimecrolimus
5414:
5388:Methotrexate
5380:
5358:
5345:Azathioprine
5344:
5337:
5322:(initiation)
5252:
5210:
5206:
5196:
5179:
5175:
5169:
5144:
5140:
5134:
5107:
5103:
5093:
5068:
5064:
5058:
5033:
5029:
5023:
4990:
4986:
4980:
4955:
4951:
4945:
4928:
4924:
4918:
4885:
4881:
4855:
4851:
4845:
4825:
4790:
4786:
4761:. Retrieved
4757:the original
4747:
4728:
4700:
4659:(1): 24–36.
4656:
4652:
4646:
4611:
4607:
4597:
4581:. Hale Pub.
4578:
4572:
4537:
4533:
4527:
4502:
4498:
4492:
4457:
4453:
4443:
4418:
4414:
4408:
4383:
4379:
4373:
4345:
4298:
4294:
4288:
4253:
4249:
4239:
4204:
4200:
4190:
4163:
4159:
4149:
4114:
4110:
4100:
4067:
4063:
4057:
4024:
4020:
4014:
3971:
3967:
3957:
3945:. Retrieved
3930:
3921:
3909:. Retrieved
3895:
3860:
3856:
3846:
3821:
3817:
3811:
3798:
3794:
3781:
3769:. Retrieved
3755:
3743:. Retrieved
3718:
3683:
3679:
3669:
3634:
3630:
3620:
3608:. Retrieved
3594:
3567:
3564:Rheumatology
3563:
3553:
3534:
3490:
3486:
3457:cite journal
3432:
3428:
3418:
3381:
3377:
3367:
3332:
3328:
3293:
3282:
3269:
3212:
3208:
3201:
3168:
3164:
3157:
3138:
3090:
3086:
3076:
3041:
3037:
3027:
2994:
2990:
2984:
2951:
2947:
2941:
2908:
2904:
2898:
2868:(2): 85–92.
2865:
2861:
2854:
2821:
2817:
2811:
2776:
2772:
2762:
2735:
2731:
2721:
2686:
2682:
2672:
2637:
2633:
2623:
2590:
2586:
2580:
2555:
2551:
2507:
2503:
2493:
2460:
2456:
2424:(1): 17–19.
2421:
2417:
2411:
2392:
2343:
2339:
2305:
2301:
2270:. Retrieved
2266:
2257:
2248:10665/325771
2238:
2229:
2205:
2156:
2152:
2142:
2109:
2105:
2059:
2055:
2045:
2033:. Retrieved
1990:. Retrieved
1986:
1977:
1965:. Retrieved
1960:
1951:
1939:. Retrieved
1931:
1922:
1911:
1902:
1878:
1870:
1839:
1835:chemotherapy
1824:
1812:
1790:and diethyl
1775:
1773:
1746:
1656:
1641:
1632:
1616:
1590:
1581:hydroxylated
1567:(TdGTP) via
1534:
1522:
1513:TdGTP: thio-
1446:Pharmacology
1439:
1433:
1413:
1392:depolarizing
1378:
1367:
1364:Interactions
1358:mouth ulcers
1354:
1333:
1330:Skin cancers
1313:
1294:
1279:
1264:
1242:genetic test
1229:
1218:heterozygous
1176:
1160:
1154:
1115:
1093:
1087:
1067:
1060:
1056:
1049:
1033:
1022:
1002:
982:
966:
920:, including
915:
912:Medical uses
903:
885:subclass of
856:
811:
808:Azathioprine
807:
806:
795:
423:
379:Elimination
264:Legal status
258:Legal status
179:Azathioprine
160:License data
23:Azathioprine
18:
6891:from market
6840:Leflunomide
6831:Chloroquine
6826:Bucillamine
6806:Aurotioprol
6699:Tofacitinib
6639:Ravulizumab
6629:Pirfenidone
6619:Peficitinib
6519:Canakinumab
6509:Briakinumab
6499:Bimekizumab
6494:Baricitinib
6459:Aflibercept
6370:Vepalimomab
6365:Vapaliximab
6340:Rovelizumab
6330:Pexelizumab
6320:Morolimumab
6295:Cedelizumab
6280:Anifrolumab
6275:Alemtuzumab
6233:Basiliximab
6203:Tocilizumab
6189:Vedolizumab
6184:Natalizumab
6170:Metelimumab
6113:Gavilimomab
6071:Toralizumab
6066:Teneliximab
6052:Lumiliximab
6047:Gomiliximab
6033:Ublituximab
6013:Ocrelizumab
5966:Zanolimumab
5942:Visilizumab
5900:Secukinumab
5884:Ustekinumab
5855:Elsilimomab
5839:Faralimomab
5807:Mepolizumab
5791:Ustekinumab
5786:Tocilizumab
5761:Secukinumab
5711:Canakinumab
5701:Briakinumab
5696:Bimekizumab
5691:Basiliximab
5680:Interleukin
5670:Nerelimomab
5575:Zotarolimus
5516:(reception)
5487:Thalidomide
5445:Voclosporin
5430:Ciclosporin
5424:Calcineurin
5420:Cyclophilin
5367:Leflunomide
5363:inhibitors
3824:(1): 7–12.
1880:Cyclosporin
1800:nitro group
1788:methylamine
1753:heterocycle
1686:replication
1667:nucleotides
1557:glutathione
1417:miscarriage
1370:allopurinol
1336:skin cancer
1202:methylation
1198:methylation
1185:(6-MP; see
1177:The enzyme
1146:blood count
1118:intravenous
1029:fistulizing
971:for use in
842:to prevent
712: g·mol
652:100.006.525
406:Identifiers
227:intravenous
146:MedlinePlus
119:Other names
110:Trade names
6944:Categories
6864:thiopurine
6852:antifolate
6760:Quinolines
6689:Sutimlimab
6684:Spesolimab
6669:Siltuximab
6609:Olokizumab
6599:Ixekizumab
6594:Itacitinib
6584:Guselkumab
6579:Fingolimod
6574:Filgotinib
6524:Crovalimab
6514:Brodalumab
6504:Blisibimod
6469:Rilonacept
6452:Opinercept
6447:Etanercept
6433:Belatacept
6384:Polyclonal
6345:Siplizumab
6335:Reslizumab
6325:Ofatumumab
6315:Maslimomab
6300:Emapalumab
6243:Inolimomab
6238:Daclizumab
6217:Odulimomab
6132:Ruplizumab
6127:Frexalimab
6085:Aselizumab
5980:Efalizumab
5937:Teplizumab
5833:Interferon
5823:Omalizumab
5776:Spesolimab
5766:Siltuximab
5741:Rilonacept
5736:Olokizumab
5726:Ixekizumab
5721:Guselkumab
5716:Daclizumab
5706:Brodalumab
5665:Infliximab
5650:Afelimomab
5645:Adalimumab
5629:Eculizumab
5605:Monoclonal
5596:Antibodies
5570:Umirolimus
5550:Everolimus
5499:Apremilast
5459:Gusperimus
5440:Tacrolimus
5408:inhibitors
5400:Macrolides
5382:antifolate
4534:Teratology
3932:BBC Online
3610:19 October
2058:(Review).
2035:8 December
1894:References
1842:antibodies
1769:hydrolyzes
1765:lipophilic
1749:thiopurine
1573:methylated
1543:(6-MP) by
1507:TGTP: thio
1429:tacrolimus
1398:(vitamin B
1372:, inhibit
1267:carcinogen
1240:or a TPMT
1234:homozygous
1214:homozygous
1070:malignancy
1052:prednisone
985:allografts
934:vasculitis
901:by cells.
717:3D model (
705:Molar mass
602:ChEMBL1542
582:CHEBI:2948
542:MRK240IY2L
513:ChemSpider
450:55774-33-9
436:CAS Number
415:IUPAC name
366:Metabolism
6901:Phase III
6889:Withdrawn
6796:Auranofin
6745:Specific
6679:Sirukumab
6674:Siponimod
6659:Sarilumab
6634:Ponesimod
6604:Netakimab
6589:Iptacopan
6569:Etrasimod
6529:Danicopan
6464:Alefacept
6428:Abatacept
6350:Talizumab
6290:Begelomab
6146:Belimumab
6099:Galiximab
6028:Rituximab
5994:Erlizumab
5961:Keliximab
5771:Sirukumab
5751:Sarilumab
5731:Netakimab
5660:Golimumab
5560:Sirolimus
4931:: 47–52.
4763:31 August
4542:CiteSeerX
3245:225287631
3019:207001537
2905:Neurology
2272:7 October
1858:Roy Calne
1854:rejection
1761:thioether
1757:imidazole
1743:Chemistry
1736:apoptosis
1549:thioether
1545:reductive
1314:Cases of
1206:cytotoxic
1142:infection
1076:. A 2007
926:pemphigus
879:pregnancy
844:rejection
838:; and in
394:Excretion
381:half-life
216:Routes of
190:Pregnancy
138:Monograph
132:Drugs.com
6975:Prodrugs
6934:Medicine
6614:Ozanimod
6489:Avacopan
6482:Unsorted
6268:Unsorted
6178:Integrin
5911:Cellular
5686:Anakinra
5532:Anakinra
5454:Abetimus
5306: /
5266:28520349
5260:(NCBI).
5229:15899149
5126:12911553
5085:13936775
5050:13807024
5007:13601801
4972:13980986
4937:13849699
4817:12697731
4681:23327335
4673:18097462
4638:15479867
4564:11967923
4484:25314258
4476:12641505
4400:19343728
4315:21658113
4272:20015102
4231:21122542
4182:17296529
4133:16128682
4092:13419507
4049:27475772
4041:18506437
4006:16166520
3947:June 10,
3941:Archived
3937:BBC News
3911:June 20,
3905:Archived
3887:16009676
3803:Archived
3789:(1981).
3771:June 20,
3765:Archived
3745:June 20,
3736:Archived
3710:25108385
3661:20154640
3604:Archived
3586:17255139
3517:21270794
3449:17691917
3410:24707136
3359:19952870
3307:28520349
3301:(NCBI).
3274:Archived
3264:(1987).
3237:33153610
3193:21873238
3185:15479355
3117:22607134
3068:17943809
3011:19151017
2968:16530578
2933:24755812
2925:14694025
2890:10699017
2882:17428113
2846:71558242
2838:11315344
2803:27192092
2713:16009685
2664:71968695
2656:15352905
2615:23554085
2607:12786610
2534:11034720
2485:22033113
2477:15302193
2438:15683663
2368:34015182
2360:15228163
2322:16908341
2267:ClinCalc
2237:(2019).
2221:Archived
2185:27529058
2159:: 9–20.
2134:35805200
2126:28306595
2088:27239106
2029:Archived
1846:antigens
1476:6-MP: 6-
1404:pellagra
1384:warfarin
1351:Overdose
1320:lymphoma
1036:lymphoma
1003:Being a
863:vomiting
798:(verify)
493:DrugBank
445:446-86-6
234:ATC code
223:By mouth
192:category
174:DailyMed
6985:Purines
6410:-cept (
5188:3922606
5161:2998215
5015:8043359
4910:2649979
4890:Bibcode
4882:Science
4629:1766779
4519:4905893
4323:3396280
4280:6000856
4222:3157326
4141:9356163
4084:8100914
3997:2426755
3976:Bibcode
3968:Science
3878:1774869
3838:7683109
3701:4999337
3652:3086840
3508:3098761
3401:3974520
3350:3098750
3217:Bibcode
3108:3422642
3059:6823213
2976:1616660
2794:7034525
2754:9753482
2704:1774897
2572:9515759
2525:8406472
2176:4970629
2079:4873872
1992:3 March
1967:4 March
1821:History
1792:oxalate
1711:of the
1709:B cells
1705:T cells
1621:Please
1537:prodrug
1425:animals
1386:and of
1290:group 1
1261:Cancers
1194:prodrug
1138:anaemia
1126:fatigue
1074:relapse
875:cancers
867:genetic
669:Formula
502:DB00993
468:PubChem
426:-purine
320:Rx-only
317:WARNING
289::
250:)
244: (
242:L04AX01
205: D
176::
152:a682167
6920:Portal
6884:WHO-EM
6422:CTLA-4
6412:Fusion
5913:target
5894:IL-17A
5871:, and
5404:other
5264:
5227:
5186:
5159:
5124:
5083:
5048:
5030:Lancet
5013:
5005:
4970:
4935:
4908:
4837:
4815:
4808:152947
4805:
4735:
4707:
4679:
4671:
4636:
4626:
4585:
4562:
4544:
4517:
4482:
4474:
4435:799904
4433:
4398:
4361:
4351:London
4321:
4313:
4278:
4270:
4229:
4219:
4180:
4139:
4131:
4090:
4082:
4064:Lancet
4047:
4039:
4004:
3994:
3885:
3875:
3836:
3801:: 47.
3708:
3698:
3659:
3649:
3584:
3541:
3515:
3505:
3447:
3408:
3398:
3357:
3347:
3305:
3243:
3235:
3191:
3183:
3145:
3115:
3105:
3066:
3056:
3017:
3009:
2974:
2966:
2948:Lancet
2931:
2923:
2888:
2880:
2844:
2836:
2801:
2791:
2752:
2711:
2701:
2662:
2654:
2613:
2605:
2570:
2532:
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