1109:
656:
633:
1815:
40:
1456:
31:
6919:
1608:
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.
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.
4825:
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
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".
4052:
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".
4940:
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".
278:
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
3593:
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
2416:
Nuyttens JJ, Harper J, Jenrette JM, Turrisi AT (January 2005). "Outcome of radiation therapy for renal transplant rejection refractory to chemical immunosuppression".
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.
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
6979:
4097:"Allopurinol safely and effectively optimizes tioguanine metabolites in inflammatory bowel disease patients not responding to azathioprine and mercaptopurine"
1274:
233:
4236:"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.
5053:
Murray JE, Merrill JP, Harrison JH, Wilson RE, Dammin GJ (June 1963). "Prolonged survival of human-kidney homografts by immunosuppressive drug therapy".
5129:
Henry ML, Sommer BG, Ferguson RM (November 1985). "Beneficial effects of cyclosporine compared with azathioprine in cadaveric renal transplantation".
3754:
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".
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
6726:
1626:
5164:
Modry DL, Oyer PE, Jamieson SW, Stinson EB, Baldwin JC, Reitz BA, et al. (May 1985). "Cyclosporine in heart and heart-lung transplantation".
3894:
4641:
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
6939:
1492:
1438:, the manufacturer advises not to breastfeed whilst taking azathioprine, but the "lactation risk category" reported by Thomas Hale in his book
5247:
3298:
2388:
1840:
Robert
Schwartz investigated the effect of 6-MP on the immune response in 1958 and discovered that it profoundly suppresses the formation of
1692:
127:
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
6583:
6441:
5284:
3273:
1738:(programmed cell death). Increased apoptosis of mononuclear cells is seen in inflammatory bowel disease patients treated with azathioprine.
752:
3792:
6593:
6279:
5720:
3776:
3261:
1285:
1162:
5193:"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:
1699:, one of the earlier steps in the synthesis of DNA and RNA. They achieve GPAT inhibition through a form of negative feedback called
6200:
2104:
Singer O, McCune WJ (May 2017). "Update on maintenance therapy for granulomatosis with polyangiitis and microscopic polyangiitis".
4330:
3725:
3473:"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
4742:
3589:
2028:
1068:
It was widely used for the treatment of multiple sclerosis until the first half of the 1990s. Concerns about increased risk of
6873:
4726:
4698:
4576:
4352:
3532:
3146:
2400:
1814:
905:
4146:"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.
6736:
6719:
3930:
1012:
1004:
2300:
Patel AA, Swerlick RA, McCall CO (September 2006). "Azathioprine in dermatology: the past, the present, and the future".
4913:
Elion GB, Callahan SW, Hitchings GH, Rundles RW (July 1960). "The metabolism of 2-amino-6-purine (B.W. 57-323) in man".
1050:
Azathioprine is sometimes used in systemic lupus erythematosus, requiring a maintenance dose of 15 mg or higher of
797:
178:
3452:
6949:
6143:
5513:
5090:"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"
2214:
1644:
772:
6890:
5277:
4487:
Tallent MB, Simmons RL, Najarian JS (March 1970). "Birth defects in child of male recipient of kidney transplant".
1289:
1166:
1023:
Azathioprine has been used in the management of moderate to severe chronically active Crohn's disease, to maintain
823:
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
6712:
6552:
1387:
1281:
414:
263:
159:
3425:"Pharmacogenomics in drug-metabolizing enzymes catalyzing anticancer drugs for personalized cancer chemotherapy"
1178:
870:
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
1315:
1089:
995:. The administration protocol starts either at the time of transplantation or within the following two days.
4009:
Sahasranaman S, Howard D, Roy S (August 2008). "Clinical pharmacology and pharmacogenetics of thiopurines".
5349:
3750:
1483:
968:
835:
815:
651:
532:
2052:"Inflammatory bowel disease and cancer: The role of inflammation, immunosuppression, and cancer treatment"
1982:
1027:(absence of disease activity) in corticosteroid-dependent patients, and to provide benefit in people with
6969:
6954:
5458:
5270:
4344:
3721:
3713:
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.)"
1564:
1514:
1391:
1270:
612:
6909:
5328:
5018:
Calne RY (February 1960). "The rejection of renal homografts. Inhibition in dogs by 6-mercaptopurine".
4334:
3374:"Pharmacogenetics of azathioprine in inflammatory bowel disease: a role for glutathione-S-transferase?"
1323:
957:
601:
4820:
3890:
1224:
may have increased levels of TGN metabolites and an increased risk of severe bone marrow suppression (
449:
6006:
5262:
4975:
Schwartz R, Stack J, Dameshek W (October 1958). "Effect of 6-mercaptopurine on antibody production".
4823:, G. H. Hitchings; Yonkers & G. B. Elion, "Purine Derivatives", issued 1962-10-06
3806:
Gombar VK, Enslein K, Blake BW (May 1993). "Carcinogenicity of azathioprine: an S-AR investigation".
2234:
1927:
1718:
A portion of the nucleotides is additionally phosphorylated to the triphosphate forms. These bind to
1568:
1498:
4536:
3615:
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)
6959:
6386:
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
1826:
1795:
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
953:
628:
6704:
1592:
6878:
6381:
3527:(in German) (8th ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 107, 936.
1887:
1715:) are most active in synthesizing purine, making new DNA, these cells are most strongly affected.
1300:
1133:
858:
215:
109:
3265:
1571:(TIMP) and several further intermediates. On a second path, the sulfur atom of 6-MP and TIMP is
6780:
6186:
5612:
5293:
4531:
3952:
O'Donovan P, Perrett CM, Zhang X, Montaner B, Xu YZ, Harwood CA, et al. (September 2005).
3780:
1861:
1719:
1560:
1508:
1284:
may have an excessive risk of cancers if treated with azathioprine. Epidemiological studies by
1190:
972:
355:
3471:
Relling MV, Gardner EE, Sandborn WJ, Schmiegelow K, Pui CH, Yee SW, et al. (March 2011).
3372:
Stocco G, Pelin M, Franca R, De
Iudicibus S, Cuzzoni E, Favretto D, et al. (April 2014).
929:
6944:
6775:
6373:
3666:"A common missense variant in NUDT15 confers susceptibility to thiopurine-induced leukopenia"
2204:
1883:
581:
4368:
Cleary BJ, Källén B (July 2009). "Early pregnancy azathioprine use and pregnancy outcomes".
3323:
Zaza G, Cheok M, Krynetskaia N, Thorn C, Stocco G, Hebert JM, et al. (September 2010).
1956:
4879:
4693:(in German). Vol. 2 (25th ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag.
4522:
Polifka JE, Friedman JM (May 2002). "Teratogen update: azathioprine and 6-mercaptopurine".
3965:
3216:
1853:
1296:
1008:
949:
937:
921:
843:
819:
541:
378:
2989:
Casetta I, Iuliano G, Filippini G (February 2009). "Azathioprine for multiple sclerosis".
1907:
1657:
Azathioprine is converted within tissues to 6-MP, some of which is converted, in turn, to
1360:, and spontaneous bleeding, all of which are consequences of its bone-marrow suppression.
1108:
1007:(DMARD), azathioprine has been used for the management of the signs and symptoms of adult
521:
8:
5594:
4095:
Sparrow MP, Hande SA, Friedman S, Lim WC, Reddy SI, Cao D, et al. (September 2005).
1696:
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
1062:
444:
435:
226:
4883:
4187:"Combination of thiopurines and allopurinol: adverse events and clinical benefit in IBD"
3969:
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.
6824:
6543:
5644:
5088:
Bakker RC, Hollander AA, Mallat MJ, Bruijn JA, Paul LC, de Fijter JW (September 2003).
5000:
4666:
4618:
4593:
4469:
4308:
4265:
4211:
4186:
4126:
4077:
4034:
3986:
3953:
3867:
3842:
3690:
3665:
3641:
3616:
3497:
3472:
3400:
3373:
3349:
3324:
3240:
3188:
3107:
3082:
3058:
3033:
3014:
2971:
2928:
2916:
2885:
2841:
2793:
2768:
2703:
2678:
2659:
2610:
2524:
2499:
2480:
2363:
2175:
2148:
2129:
2078:
2051:
1779:
1700:
1304:
1295:
The various diseases requiring transplantation may in themselves increase the risks of
1149:
1039:
1024:
961:
917:
847:
831:
827:
655:
632:
189:
5031:
4797:
4772:
2959:
2769:"Azathioprine and 6-mercaptopurine for maintenance of remission in ulcerative colitis"
2744:
2727:
2468:
1622:
6964:
6767:
6548:
6538:
5339:
5297:
5251:
5214:
5191:
Woodroffe R, Yao GL, Meads C, Bayliss S, Ready A, Raftery J, et al. (May 2005).
5173:
5146:
5142:
5111:
5106:
5089:
5070:
5035:
4992:
4957:
4922:
4895:
4802:
4722:
4694:
4658:
4623:
4572:
4549:
4504:
4461:
4456:
4439:
4420:
4385:
4348:
4300:
4296:
4257:
4252:
4235:
4216:
4167:
4118:
4113:
4096:
4069:
4065:
4026:
3991:
3872:
3823:
3819:
3695:
3646:
3571:
3528:
3502:
3444:
3405:
3354:
3302:
3244:
3232:
3180:
3176:
3142:
3112:
3063:
3018:
3006:
2963:
2920:
2877:
2873:
2833:
2798:
2749:
2708:
2651:
2646:
2629:
2602:
2567:
2529:
2472:
2433:
2396:
2355:
2351:
2317:
2210:
2180:
2121:
2083:
1669:
1463:
1459:
1395:
1344:
1221:
1209:
1125:
992:
945:
941:
839:
302:
290:
151:
4746:
4670:
4473:
4081:
4038:
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:
6974:
6344:
6247:
5910:
5806:
5204:
5138:
5101:
5062:
5027:
5004:
4984:
4949:
4887:
4849:
4792:
4784:
4650:
4613:
4605:
4541:
4496:
4451:
4412:
4377:
4312:
4292:
4269:
4247:
4206:
4198:
4157:
4130:
4108:
4061:
4018:
3981:
3973:
3862:
3854:
3815:
3685:
3677:
3636:
3628:
3561:
3492:
3484:
3436:
3395:
3385:
3344:
3336:
3224:
3172:
3102:
3094:
3053:
3049:
3045:
2998:
2975:
2955:
2912:
2903:
Richman DP, Agius MA (December 2003). "Treatment of autoimmune myasthenia gravis".
2869:
2825:
2788:
2784:
2780:
2739:
2698:
2690:
2641:
2598:
2594:
2559:
2519:
2511:
2464:
2425:
2347:
2309:
2242:
2170:
2160:
2113:
2073:
2063:
1865:
1731:
1661:
by the addition of an amino group. Both 6-MP and 6-thioguanine are conjugated with
1596:
1540:
1471:
1420:
1373:
1347:. Patients taking azathioprine were found to be abnormally sensitive to UVA light.
1250:
1225:
1121:
1085:, conflicting conclusions regarding cancer, and the potential for long-term risks.
668:
456:
371:
337:
246:
57:
4283:
Oliveira A, Sanches M, Selores M (October 2011). "Azathioprine-induced pellagra".
3775:
3566:
3549:
3260:
6923:
6790:
6643:
6528:
4440:"Azathioprine, mercaptopurine and birth outcome: a population-based cohort study"
4202:
3632:
3340:
2429:
2117:
1912:
1685:
1529:
1524:
1082:
1077:
988:
882:
481:
365:
345:
6740:
5237:
5066:
3916:
3288:
6884:
6533:
6401:
6049:
5883:
5862:
5858:
5854:
5482:
5319:
5241:
4416:
4403:
Tagatz GE, Simmons RL (January 1975). "Pregnancy after renal transplantation".
4234:
Ansari A, Patel N, Sanderson J, O'Donohue J, Duley JA, Florin TH (March 2010).
3664:
Yang SK, Hong M, Baek J, Choi H, Zhao W, Jung Y, et al. (September 2014).
3440:
3292:
2829:
2563:
2313:
1873:
1830:
1477:
1435:
1288:
have provided "sufficient" evidence of azathioprine carcinogenicity in humans (
1237:
1182:
1097:
886:
4988:
4162:
4145:
4022:
3228:
2515:
6933:
6834:
6811:
6757:
6683:
6613:
6523:
6430:
6216:
5916:
5838:
5790:
5770:
5628:
5544:
5395:
5361:
4500:
3390:
3002:
2387:
2068:
1849:
1807:
1712:
1677:
1673:
1658:
1576:
1528:
azathioprine and 3–5 hours for drug plus metabolites. 20 to 30% are bound to
1380:
1340:
1246:
890:
739:
644:
315:
22:
4891:
4609:
3977:
3858:
2694:
956:, and others. It is also an important therapy and steroid-sparing agent for
6846:
6693:
6653:
6638:
6633:
6349:
6299:
6294:
6274:
6154:
6149:
6012:
5997:
5945:
5921:
5868:
5745:
5735:
5554:
5471:
5466:
5424:
5377:
5301:
5255:
5218:
5115:
5074:
5039:
4996:
4961:
4926:
4806:
4662:
4627:
4553:
4465:
4389:
4304:
4261:
4220:
4171:
4122:
4030:
3995:
3876:
3699:
3650:
3575:
3506:
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
1834:
1241:
1217:
241:
5177:
5150:
4953:
4899:
4508:
4438:
Nørgård B, Pedersen L, Fonager K, Rasmussen SN, Sørensen HT (March 2003).
4073:
3827:
3488:
3098:
2753:
2571:
6829:
6820:
6815:
6795:
6688:
6628:
6618:
6608:
6508:
6498:
6488:
6483:
6448:
6359:
6354:
6329:
6319:
6309:
6284:
6269:
6264:
6222:
6192:
6178:
6173:
6159:
6102:
6060:
6055:
6041:
6036:
6022:
6002:
5955:
5931:
5889:
5873:
5844:
5828:
5796:
5780:
5775:
5750:
5700:
5690:
5685:
5680:
5669:
5659:
5564:
5476:
5434:
5419:
5413:
5409:
5356:
4424:
3548:
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.).
1879:
1803:
1799:
1791:
1787:
1752:
1666:
1556:
1416:
1369:
1357:
1335:
1201:
1197:
1145:
1117:
851:
145:
39:
4853:
4840:
Blicke FF, Godt HC (1954). "Diuretics. I. 3-Substituted
Paraxanthines".
2247:
501:
6853:
6841:
6678:
6673:
6658:
6598:
6588:
6573:
6568:
6563:
6513:
6503:
6493:
6458:
6436:
6422:
6334:
6324:
6314:
6304:
6289:
6232:
6227:
6206:
6121:
6116:
6074:
6068:
5969:
5926:
5822:
5812:
5765:
5755:
5730:
5725:
5715:
5710:
5705:
5695:
5654:
5639:
5634:
5618:
5559:
5539:
5488:
5448:
5429:
5371:
4545:
4381:
3921:
3083:"Prednisone, azathioprine, and N-acetylcysteine for pulmonary fibrosis"
2165:
1841:
1764:
1748:
1428:
1308:
1266:
1233:
1213:
1069:
1051:
933:
846:. It is listed by the International Agency for Research on Cancer as a
704:
512:
5292:
3205:
2858:
6785:
6749:
6668:
6663:
6648:
6623:
6578:
6558:
6518:
6453:
6417:
6339:
6135:
6088:
6017:
5983:
5950:
5760:
5740:
5649:
5549:
5389:
4788:
4144:
Sparrow MP, Hande SA, Friedman S, Cao D, Hanauer SB (February 2007).
3717:
3617:"Very important pharmacogene summary: thiopurine S-methyltransferase"
2767:
Timmer A, Patton PH, Chande N, McDonald JW, MacDonald JK (May 2016).
1857:
1768:
1760:
1756:
1735:
1548:
1205:
1141:
984:
925:
878:
467:
393:
131:
5209:
5192:
4654:
3954:"Azathioprine and UVA light generate mutagenic oxidative DNA damage"
3681:
3614:
6734:
6603:
6478:
6167:
5675:
5585:
5521:
5443:
4569:
Medications and
Mothers' Milk: A Manual of Lactational Pharmacology
3926:
3550:"TPMT testing in rheumatology: any better than routine monitoring?"
3483:(3). Clinical Pharmacogenetics Implementation Consortium: 387–391.
3161:
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
1580:
1403:
1383:
1319:
1200:
of 6-MP into the inactive metabolite 6-methylmercaptopurine – this
1035:
866:
862:
561:
492:
222:
173:
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:
6096:
5184:
4819:
4721:(in German). Stuttgart: Deutscher Apotheker Verlag. p. 340.
4716:
4370:
Birth
Defects Research. Part A, Clinical and Molecular Teratology
4233:
3951:
3470:
1845:
1536:
1455:
1193:
1137:
1073:
1028:
4977:
Proceedings of the Society for Experimental Biology and Medicine
3081:
Raghu G, Anstrom KJ, King TE, Lasky JA, Martinez FJ (May 2012).
865:. Bone-marrow suppression is especially common in people with a
6411:
6242:
4437:
4340:
2676:
1727:
1708:
1704:
1662:
1572:
1552:
1431:
and mycophenolate, which are contraindicated during pregnancy.
1424:
1254:
1129:
1034:
Azathioprine treatment is associated with an increased risk of
874:
592:
453:
398:
30:
983:
Azathioprine is used to prevent rejections of kidney or liver
93:
6110:
5963:
5240:. In Pratt VM, McLeod HL, Rubinstein WS, et al. (eds.).
4912:
3371:
3291:. In Pratt VM, McLeod HL, Rubinstein WS, et al. (eds.).
2415:
1852:
and Gertrude Elion in discovering the immunological basis of
1783:
1544:
1253:
being translated into routine clinical care. Missense SNP in
718:
572:
4431:
2497:
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:
6082:
6030:
5991:
5977:
5531:
5405:
5087:
5052:
4051:
3781:"Azathioprine – 5. Summary of Data Reported and Evaluation"
3712:
1723:
552:
81:
78:
69:
5166:
Canadian Journal of Surgery. Journal Canadien de Chirurgie
4870:
Elion GB (April 1989). "The purine path to chemotherapy".
2766:
1236:
for these variants. However, an assay of TPMT activity in
5939:
3547:
3322:
2233:
1935:
960:(such as Crohn's disease and ulcerative colitis) and for
898:
894:
63:
5190:
5163:
3522:
2584:
2251:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
987:, usually in conjunction with other therapies including
4143:
4094:
3031:
2988:
2453:
906:
World Health Organization's List of Essential Medicines
4688:
4684:
4682:
4680:
4486:
4282:
2049:
1442:
lists azathioprine as "L3", termed "moderately safe".
6907:
4974:
4717:
Steinhilber D, Schubert-Zsilavecz M, Roth HJ (2005).
4008:
3080:
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:
5128:
4677:
3799:
2945:
2815:
2299:
1920:
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
370:Activated non-enzymatically, deactivated mainly by
72:
3805:
3777: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
4745:. 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.
6931:
4770:
3751:"FDA: Cancer Warnings Required for TNF Blockers"
3718:"Report On Carcinogens – Twelfth Edition – 2011"
3663:
3132:
3130:
3128:
3126:
2500:"Azathioprine for treating rheumatoid arthritis"
2146:
480:
4521:
3466:
3464:
3462:
3318:
3316:
2333:
2331:
1120:administration. Side effects that are probably
443:
4766:
4764:
4712:
4710:
3840:
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
1409:
1390:muscle relaxants, but increases the effect of
1158:with respect to patient care in this respect.
6980:World Health Organization essential medicines
6720:
5278:
5248:National Center for Biotechnology Information
4402:
4184:
3891:"Imuran (azathioprine) Tablets and Injection"
3299:National Center for Biotechnology Information
3123:
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
1018:
4640:
4594:"Pharmacogenetics in the rheumatic diseases"
4367:
4227:
4002:
3843:"Risks and benefits of azathioprine therapy"
3608:
3518:
3516:
3459:
3422:
3416:
3365:
3313:
3256:
3254:
2902:
2328:
2103:
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:
4761:
4707:
3038:The Cochrane Database of Systematic Reviews
2773:The Cochrane Database of Systematic Reviews
2504:The Cochrane Database of Systematic Reviews
1949:
1583:purines, which are excreted via the urine.
1286:International Agency for Research on Cancer
1163:International Agency for Research on Cancer
6727:
6713:
5285:
5271:
4839:
4444:Alimentary Pharmacology & Therapeutics
4240:Alimentary Pharmacology & Therapeutics
4101: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:
5208:
5105:
4796:
4617:
4591:
4535:
4455:
4251:
4210:
4161:
4112:
4011:European Journal of Clinical Pharmacology
3985:
3866:
3769:
3689:
3640:
3565:
3513:
3496:
3399:
3389:
3348:
3251:
3106:
3057:
2792:
2743:
2725:
2702:
2645:
2627:
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:
5238:"Azathioprine Therapy and TPMT Genotype"
4939:
4865:
4863:
4842:Journal of the American Chemical Society
4150:Clinical Gastroenterology and Hepatology
3289:"Azathioprine Therapy and TPMT Genotype"
3136:
2862:American Journal of Clinical Dermatology
2549:
2295:
2293:
2291:
2289:
2287:
2285:
2283:
1504:MeTIMP: methyl-thioinosine monophosphate
1454:
1339:Azathioprine causes the accumulation of
1107:
4771:Maltzman JS, Koretzky GA (April 2003).
4689:Dinnendahl, V, Fricke, U, eds. (2011).
4331:Pharmaceutical Society of Great Britain
3706:
3523:Mutschler E, Schäfer-Korting M (2001).
3155:
2809:
2670:
2449:
2447:
2227:
2094:
2000:
1695:(GPAT), one of the enzymes involved in
1124:reactions include dizziness, diarrhea,
998:
744:238 to 245 °C (460 to 473 °F)
627:
500:
150:
6932:
4634:
4324:
4322:
4185:Govani SM, Higgins PD (October 2010).
3841:McGovern DP, Jewell DP (August 2005).
3477:Clinical Pharmacology and Therapeutics
2545:
2543:
2383:
2381:
2379:
2377:
2263:"Azathioprine - Drug Usage Statistics"
2191:
1665:, and then phosphorylated to form the
1586:
1532:while circulating in the bloodstream.
991:, other immunosuppressants, and local
645:
324:
296:
6940:Disease-modifying antirheumatic drugs
6708:
5266:
5017:
4942:Journal of Reproduction and Fertility
4869:
4860:
4777:The Journal of Clinical Investigation
4773:"Azathioprine: old drug, new actions"
4735:
4328:
3933:from the original on October 14, 2012
3909:
3590:"Label: Imuran - azathioprine tablet"
3034:"Azathioprine for multiple sclerosis"
2337:
2280:
2241:. Geneva: World Health Organization.
1627:make it understandable to non-experts
1402:), resulting in at least one case to
1186:
600:
580:
309:
168:
136:
5235:
4566:
4336:British National Formulary, Issue 45
3596:from the original on 20 October 2014
3286:
2444:
2202:
1987:Union Register of medicinal products
1844:when given to rabbits together with
1726:, blocking synthesis of the protein
1601:
1013:Nonsteroidal anti-inflammatory drugs
1005:disease-modifying antirheumatic drug
889:family of medications. It works via
245:
5055:The New England Journal of Medicine
4319:
3834:
3087:The New England Journal of Medicine
2540:
2374:
2031:from the original on 20 August 2016
1778:-imidazole and 6-mercaptopurine in
1450:
1172:
560:
471:
13:
5229:
3917:"Skin cancer alert for organ drug"
3897: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
1103:
978:
818:. It is used for the treatment of
14:
6991:
3757:from the original on July 3, 2012
3731: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)
272:
200:
6917:
5107:10.1046/j.1523-1755.2003.00175.x
4598:Annals of the Rheumatic Diseases
4457:10.1046/j.1365-2036.2003.01537.x
4297:10.1111/j.1346-8138.2010.01189.x
4253:10.1111/j.1365-2036.2009.04221.x
4191:Journal of Crohn's & Colitis
4114:10.1111/j.1365-2036.2005.02583.x
3795: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:
5157:
5122:
5081:
5046:
5011:
4968:
4933:
4906:
4833:
4813:
4585:
4560:
4515:
4480:
4396:
4361:
4276:
4178:
4137:
4088:
4045:
3945:
3883:
3743:
3657:
3582:
3541:
3280:
3199:
3074:
3025:
2982:
2939:
2896:
2852:
2760:
2719:
2621:
2578:
2491:
2409:
2255:
2106:Current Opinion in Rheumatology
1445:
1363:
1329:
911:
785:Key:LMEKQMALGUDUQG-UHFFFAOYSA-N
114:Azasan, Imuran, Jayempi, others
4592: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
2140:
2043:
1975:
1913:Merriam-Webster.com Dictionary
1900:
1356:infections of unclear origin,
1179:thiopurine S-methyltransferase
871:thiopurine S-methyltransferase
760:Cn1cnc(N(=O)=O)c1Sc2ncnc3ncc23
697:
691:
673:
285:
1:
5032:10.1016/S0140-6736(60)90343-3
3621: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"
1893:
1488:6-MMP: 6-methylmercaptopurine
1440:Medications and Mothers' Milk
1406:and fatal medullary aplasia.
1316:hepatosplenic T-cell lymphoma
1090:idiopathic pulmonary fibrosis
5350:dihydroorotate dehydrogenase
5197:Health Technology Assessment
5143:10.1016/0002-9610(85)90431-3
4203:10.1016/j.crohns.2010.02.009
4066:10.1016/0140-6736(93)91287-V
3820:10.1016/0165-7992(93)90083-8
3633:10.1097/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
1742:
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
7:
5329:purine synthesis inhibitors
5131:American Journal of Surgery
5067:10.1056/NEJM196306132682401
4915:Cancer Chemotherapy Reports
4405:Annals of Internal Medicine
4345:British Medical Association
3785:Summaries & Evaluations
3722:National Toxicology Program
3714:National Toxicology Program
3567:10.1093/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
1350:
1271:National Toxicology Program
1140:and be more susceptible to
10:
6996:
5258:. Bookshelf ID: NBK100661.
5243:Medical Genetics Summaries
4417:10.7326/0003-4819-82-1-113
4285: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
1820:
1434:Traditionally, as for all
1324:inflammatory bowel disease
1260:
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
6868:
6804:
6766:
6748:
6471:
6399:
6372:
6257:
5900:
5602:
5593:
5584:
5577:
5530:
5514:IL-1 receptor antagonists
5512:
5503:
5457:
5388:
5318:
5309:
4989:10.3181/00379727-99-24281
4163:10.1016/j.cgh.2006.11.020
4023:10.1007/s00228-008-0478-6
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
1045:
893:to disrupt the making of
869:deficiency of the enzyme
793:
768:
748:
738:
716:
703:
667:
662:
643:
611:
591:
571:
551:
531:
511:
491:
466:
434:
410:
405:
392:
377:
364:
354:
344:
336:
262:
257:
232:
214:
188:
158:
144:
126:
118:
108:
51:
46:
37:
28:
6950:IARC Group 1 carcinogens
6387:Anti-lymphocyte globulin
4501:10.1001/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
6382:Anti-thymocyte globulin
5294:Immunosuppressive drugs
4892:10.1126/science.2649979
4610:10.1136/ard.2004.028217
4329:Mehta DK, et al. (
3978:10.1126/science.1114233
3859:10.1136/gut.2004.053231
3753:. 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
6781:Sodium aurothiosulfate
6187:Interleukin-6 receptor
5613:Complement component 5
4743:"Azathioprine Pathway"
4643:Nature Reviews. Cancer
4604:(Suppl 2): ii25–ii27.
4567:Hale TW (April 2010).
3929:. 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
6776:Sodium aurothiomalate
4954:10.1530/jrf.0.0040297
4821:US Patent 3056785
3525:Arzneimittelwirkungen
3489:10.1038/clpt.2010.320
3099:10.1056/NEJMoa1113354
1884:mycophenolate mofetil
1771:to 6-mercaptopurine.
1458:
1111:
932:, and other forms of
5094: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
6739:products / DMARDs (
4884:1989Sci...244...41E
4854:10.1021/ja01643a015
4719:Medizinische Chemie
4691:Arzneistoff-Profile
3970:2005Sci...309.1871O
3964:(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:
6970:Purine antagonists
6955:Immunosuppressants
6895:Never to phase III
6825:Hydroxychloroquine
6544:Diroximel fumarate
6217:IL-2 receptor/CD25
5645:Certolizumab pegol
5298:Immunosuppressants
5172:(3): 274–80, 282.
4546:10.1002/tera.10043
4382:10.1002/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
21:
6905:
6904:
6768:Gold preparations
6702:
6701:
6549:Efgartigimod alfa
6539:Dimethyl fumarate
6467:
6466:
6395:
6394:
6368:
6367:
5573:
5572:
5499:
5498:
5340:Mycophenolic acid
5061:(24): 1315–1323.
5026:(7121): 417–418.
4848:(14): 3653–3655.
4728:978-3-7692-3483-1
4700:978-3-7741-9846-3
4578:978-0-9823379-9-8
4495:(11): 1854–1855.
4354:978-0-85369-555-4
4291:(10): 1035–1037.
3893:. FDA. May 2011.
3808:Mutation Research
3534:978-3-8047-1763-3
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:
6987:
6922:
6921:
6920:
6913:
6729:
6722:
6715:
6706:
6705:
6345:Telimomab aritox
6248:Zolimomab aritox
6069:CD62L/L-selectin
5807:Immunoglobulin E
5600:
5599:
5591:
5590:
5582:
5581:
5510:
5509:
5316:
5315:
5287:
5280:
5273:
5264:
5263:
5259:
5223:
5222:
5212:
5188:
5182:
5181:
5161:
5155:
5154:
5126:
5120:
5119:
5109:
5100:(3): 1027–1034.
5085:
5079:
5078:
5050:
5044:
5043:
5015:
5009:
5008:
4972:
4966:
4965:
4937:
4931:
4930:
4910:
4904:
4903:
4867:
4858:
4857:
4837:
4831:
4829:
4828:
4824:
4817:
4811:
4810:
4800:
4789:10.1172/JCI18384
4783:(8): 1122–1124.
4768:
4759:
4758:
4756:
4754:
4739:
4733:
4732:
4714:
4705:
4704:
4686:
4675:
4674:
4638:
4632:
4631:
4621:
4589:
4583:
4582:
4564:
4558:
4557:
4539:
4519:
4513:
4512:
4484:
4478:
4477:
4459:
4435:
4429:
4428:
4400:
4394:
4393:
4365:
4359:
4358:
4333:) (March 2003).
4326:
4317:
4316:
4280:
4274:
4273:
4255:
4231:
4225:
4224:
4214:
4182:
4176:
4175:
4165:
4141:
4135:
4134:
4116:
4092:
4086:
4085:
4049:
4043:
4042:
4006:
4000:
3999:
3989:
3949:
3943:
3942:
3940:
3938:
3913:
3907:
3906:
3904:
3902:
3887:
3881:
3880:
3870:
3853:(8): 1055–1059.
3838:
3832:
3831:
3803:
3797:
3796:
3773:
3767:
3766:
3764:
3762:
3747:
3741:
3740:
3738:
3736:
3730:
3716:(10 June 2011).
3710:
3704:
3703:
3693:
3676:(9): 1017–1020.
3661:
3655:
3654:
3644:
3612:
3606:
3605:
3603:
3601:
3586:
3580:
3579:
3569:
3545:
3539:
3538:
3520:
3511:
3510:
3500:
3468:
3457:
3456:
3451:. Archived from
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:
20:
6995:
6994:
6990:
6989:
6988:
6986:
6985:
6984:
6960:Nitroimidazoles
6930:
6929:
6928:
6918:
6916:
6908:
6906:
6901:
6900:
6885:Clinical trials
6864:
6800:
6791:Aurothioglucose
6762:
6744:
6733:
6703:
6698:
6644:Rozanolixizumab
6529:Deucravacitinib
6463:
6391:
6364:
6253:
5902:
5896:
5604:
5569:
5526:
5505:
5495:
5453:
5393:
5384:
5320:Antimetabolites
5311:
5305:
5291:
5236:Dean L (2012).
5232:
5230:Further reading
5227:
5226:
5210:10.3310/hta9210
5189:
5185:
5162:
5158:
5127:
5123:
5086:
5082:
5051:
5047:
5016:
5012:
4973:
4969:
4938:
4934:
4911:
4907:
4878:(4900): 41–47.
4868:
4861:
4838:
4834:
4826:
4818:
4814:
4769:
4762:
4752:
4750:
4741:
4740:
4736:
4729:
4715:
4708:
4701:
4687:
4678:
4655:10.1038/nrc2292
4639:
4635:
4590:
4586:
4579:
4565:
4561:
4537:10.1.1.566.7676
4520:
4516:
4485:
4481:
4436:
4432:
4401:
4397:
4366:
4362:
4355:
4327:
4320:
4281:
4277:
4232:
4228:
4183:
4179:
4142:
4138:
4093:
4089:
4060:(8863): 83–84.
4050:
4046:
4007:
4003:
3950:
3946:
3936:
3934:
3915:
3914:
3910:
3900:
3898:
3889:
3888:
3884:
3839:
3835:
3804:
3800:
3774:
3770:
3760:
3758:
3749:
3748:
3744:
3734:
3732:
3728:
3711:
3707:
3682:10.1038/ng.3060
3670:Nature Genetics
3662:
3658:
3613:
3609:
3599:
3597:
3588:
3587:
3583:
3546:
3542:
3535:
3521:
3514:
3469:
3460:
3421:
3417:
3370:
3366:
3321:
3314:
3287:Dean L (2012).
3285:
3281:
3259:
3252:
3215:(1137): 64–73.
3204:
3200:
3160:
3156:
3149:
3135:
3124:
3079:
3075:
3044:(4): CD003982.
3030:
3026:
2987:
2983:
2944:
2940:
2901:
2897:
2857:
2853:
2814:
2810:
2779:(5): CD000478.
2765:
2761:
2724:
2720:
2675:
2671:
2626:
2622:
2583:
2579:
2548:
2541:
2510:(4): CD001461.
2496:
2492:
2452:
2445:
2414:
2410:
2403:
2386:
2375:
2336:
2329:
2298:
2281:
2271:
2269:
2261:
2260:
2256:
2232:
2228:
2217:
2203:Sami N (2016).
2201:
2192:
2145:
2141:
2102:
2095:
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:
6993:
6983:
6982:
6977:
6972:
6967:
6962:
6957:
6952:
6947:
6942:
6927:
6926:
6903:
6902:
6899:
6898:
6897:
6896:
6893:
6882:
6876:
6870:
6869:
6866:
6865:
6863:
6862:
6850:
6838:
6832:
6827:
6818:
6808:
6806:
6802:
6801:
6799:
6798:
6793:
6788:
6783:
6778:
6772:
6770:
6764:
6763:
6761:
6760:
6754:
6752:
6746:
6745:
6732:
6731:
6724:
6717:
6709:
6700:
6699:
6697:
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:
6561:
6556:
6553:+hyaluronidase
6546:
6541:
6536:
6534:Deuruxolitinib
6531:
6526:
6521:
6516:
6511:
6506:
6501:
6496:
6491:
6486:
6481:
6475:
6473:
6469:
6468:
6465:
6464:
6462:
6461:
6456:
6451:
6446:
6445:
6444:
6439:
6427:
6426:
6425:
6420:
6407:
6405:
6397:
6396:
6393:
6392:
6390:
6389:
6384:
6378:
6376:
6370:
6369:
6366:
6365:
6363:
6362:
6357:
6352:
6347:
6342:
6337:
6332:
6327:
6322:
6317:
6312:
6307:
6302:
6297:
6292:
6287:
6282:
6277:
6272:
6267:
6261:
6259:
6255:
6254:
6252:
6251:
6238:
6237:
6236:
6235:
6230:
6225:
6212:
6211:
6210:
6209:
6197:
6196:
6195:
6183:
6182:
6181:
6176:
6164:
6163:
6162:
6157:
6152:
6140:
6139:
6138:
6127:
6126:
6125:
6124:
6119:
6107:
6106:
6105:
6093:
6092:
6091:
6079:
6078:
6077:
6065:
6064:
6063:
6058:
6046:
6045:
6044:
6039:
6027:
6026:
6025:
6020:
6015:
6010:
6007:+hyaluronidase
6000:
5988:
5987:
5986:
5974:
5973:
5972:
5960:
5959:
5958:
5953:
5948:
5936:
5935:
5934:
5929:
5924:
5919:
5906:
5904:
5898:
5897:
5895:
5894:
5893:
5892:
5879:
5878:
5877:
5876:
5871:
5850:
5849:
5848:
5847:
5834:
5833:
5832:
5831:
5818:
5817:
5816:
5815:
5802:
5801:
5800:
5799:
5786:
5785:
5784:
5783:
5778:
5773:
5768:
5763:
5758:
5753:
5748:
5743:
5738:
5733:
5728:
5723:
5718:
5713:
5708:
5703:
5698:
5693:
5688:
5683:
5678:
5665:
5664:
5663:
5662:
5657:
5652:
5647:
5642:
5637:
5624:
5623:
5622:
5621:
5608:
5606:
5597:
5588:
5579:
5575:
5574:
5571:
5570:
5568:
5567:
5562:
5557:
5552:
5547:
5542:
5536:
5534:
5528:
5527:
5525:
5524:
5518:
5516:
5507:
5501:
5500:
5497:
5496:
5494:
5493:
5492:
5491:
5483:PDE4 inhibitor
5479:
5474:
5469:
5463:
5461:
5455:
5454:
5452:
5451:
5446:
5440:
5439:
5438:
5437:
5432:
5427:
5422:
5401:
5399:
5386:
5385:
5383:
5382:
5381:
5380:
5367:
5366:
5365:
5364:
5359:
5345:
5344:
5343:
5342:
5337:
5324:
5322:
5313:
5307:
5306:
5290:
5289:
5282:
5275:
5267:
5261:
5260:
5231:
5228:
5225:
5224:
5183:
5156:
5137:(5): 533–536.
5121:
5080:
5045:
5010:
4983:(1): 164–167.
4967:
4948:(3): 297–302.
4932:
4905:
4859:
4832:
4812:
4760:
4749:on 2 July 2012
4734:
4727:
4706:
4699:
4676:
4633:
4584:
4577:
4559:
4530:(5): 240–261.
4514:
4479:
4450:(6): 827–834.
4430:
4411:(1): 113–114.
4395:
4376:(7): 647–654.
4360:
4353:
4318:
4275:
4246:(6): 640–647.
4226:
4197:(4): 444–449.
4177:
4156:(2): 209–214.
4136:
4107:(5): 441–446.
4087:
4044:
4017:(8): 753–767.
4001:
3944:
3908:
3882:
3833:
3798:
3768:
3742:
3705:
3656:
3627:(6): 401–405.
3607:
3581:
3560:(5): 727–729.
3540:
3533:
3512:
3458:
3455:on 2013-01-12.
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:
9:
6:
4:
3:
2:
6992:
6981:
6978:
6976:
6973:
6971:
6968:
6966:
6963:
6961:
6958:
6956:
6953:
6951:
6948:
6946:
6943:
6941:
6938:
6937:
6935:
6925:
6915:
6914:
6911:
6894:
6892:
6889:
6888:
6886:
6883:
6880:
6877:
6875:
6872:
6871:
6867:
6860:
6856:
6855:
6851:
6848:
6844:
6843:
6839:
6836:
6835:Sulfasalazine
6833:
6831:
6828:
6826:
6822:
6819:
6817:
6813:
6812:Penicillamine
6810:
6809:
6807:
6803:
6797:
6794:
6792:
6789:
6787:
6784:
6782:
6779:
6777:
6774:
6773:
6771:
6769:
6765:
6759:
6758:Oxycinchophen
6756:
6755:
6753:
6751:
6747:
6742:
6738:
6737:antirheumatic
6730:
6725:
6723:
6718:
6716:
6711:
6710:
6707:
6695:
6692:
6690:
6687:
6685:
6684:Tildrakizumab
6682:
6680:
6677:
6675:
6672:
6670:
6667:
6665:
6662:
6660:
6657:
6655:
6652:
6650:
6647:
6645:
6642:
6640:
6637:
6635:
6632:
6630:
6627:
6625:
6622:
6620:
6617:
6615:
6614:Pegcetacoplan
6612:
6610:
6607:
6605:
6602:
6600:
6597:
6595:
6592:
6590:
6587:
6585:
6582:
6580:
6577:
6575:
6572:
6570:
6567:
6565:
6562:
6560:
6557:
6554:
6550:
6547:
6545:
6542:
6540:
6537:
6535:
6532:
6530:
6527:
6525:
6524:Darvadstrocel
6522:
6520:
6517:
6515:
6512:
6510:
6507:
6505:
6502:
6500:
6497:
6495:
6492:
6490:
6487:
6485:
6482:
6480:
6477:
6476:
6474:
6470:
6460:
6457:
6455:
6452:
6450:
6447:
6443:
6440:
6438:
6435:
6434:
6433:
6432:
6431:TNF inhibitor
6428:
6424:
6421:
6419:
6416:
6415:
6414:
6413:
6409:
6408:
6406:
6403:
6398:
6388:
6385:
6383:
6380:
6379:
6377:
6375:
6371:
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:
6271:
6268:
6266:
6263:
6262:
6260:
6256:
6249:
6245:
6244:
6240:
6239:
6234:
6231:
6229:
6226:
6224:
6221:
6220:
6219:
6218:
6214:
6213:
6208:
6205:
6204:
6203:
6202:
6198:
6194:
6191:
6190:
6189:
6188:
6184:
6180:
6177:
6175:
6172:
6171:
6170:
6169:
6165:
6161:
6158:
6156:
6153:
6151:
6148:
6147:
6146:
6145:
6141:
6137:
6134:
6133:
6132:
6129:
6128:
6123:
6120:
6118:
6115:
6114:
6113:
6112:
6108:
6104:
6101:
6100:
6099:
6098:
6097:CD147/Basigin
6094:
6090:
6087:
6086:
6085:
6084:
6080:
6076:
6073:
6072:
6071:
6070:
6066:
6062:
6059:
6057:
6054:
6053:
6052:
6051:
6047:
6043:
6040:
6038:
6035:
6034:
6033:
6032:
6028:
6024:
6021:
6019:
6016:
6014:
6011:
6008:
6004:
6001:
5999:
5996:
5995:
5994:
5993:
5989:
5985:
5982:
5981:
5980:
5979:
5975:
5971:
5968:
5967:
5966:
5965:
5961:
5957:
5954:
5952:
5949:
5947:
5944:
5943:
5942:
5941:
5937:
5933:
5930:
5928:
5925:
5923:
5920:
5918:
5917:Muromonab-CD3
5915:
5914:
5913:
5912:
5908:
5907:
5905:
5899:
5891:
5888:
5887:
5886:
5885:
5881:
5880:
5875:
5872:
5870:
5867:
5866:
5865:
5864:
5860:
5856:
5852:
5851:
5846:
5843:
5842:
5841:
5840:
5836:
5835:
5830:
5827:
5826:
5825:
5824:
5820:
5819:
5814:
5811:
5810:
5809:
5808:
5804:
5803:
5798:
5795:
5794:
5793:
5792:
5791:Interleukin 5
5788:
5787:
5782:
5779:
5777:
5774:
5772:
5771:Tildrakizumab
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:
5682:
5679:
5677:
5674:
5673:
5672:
5671:
5667:
5666:
5661:
5658:
5656:
5653:
5651:
5648:
5646:
5643:
5641:
5638:
5636:
5633:
5632:
5631:
5630:
5626:
5625:
5620:
5617:
5616:
5615:
5614:
5610:
5609:
5607:
5605:(noncellular)
5601:
5598:
5596:
5592:
5589:
5587:
5583:
5580:
5578:Extracellular
5576:
5566:
5563:
5561:
5558:
5556:
5553:
5551:
5548:
5546:
5545:Ridaforolimus
5543:
5541:
5538:
5537:
5535:
5533:
5529:
5523:
5520:
5519:
5517:
5515:
5511:
5508:
5504:Intracellular
5502:
5490:
5487:
5486:
5485:
5484:
5480:
5478:
5475:
5473:
5470:
5468:
5465:
5464:
5462:
5460:
5456:
5450:
5447:
5445:
5442:
5441:
5436:
5433:
5431:
5428:
5426:
5423:
5421:
5418:
5417:
5416:
5415:
5411:
5407:
5403:
5402:
5400:
5397:
5391:
5387:
5379:
5376:
5375:
5374:
5373:
5369:
5368:
5363:
5362:Teriflunomide
5360:
5358:
5355:
5354:
5352:
5351:
5347:
5346:
5341:
5338:
5336:
5333:
5332:
5331:
5330:
5326:
5325:
5323:
5321:
5317:
5314:
5310:Intracellular
5308:
5303:
5299:
5295:
5288:
5283:
5281:
5276:
5274:
5269:
5268:
5265:
5257:
5253:
5249:
5245:
5244:
5239:
5234:
5233:
5220:
5216:
5211:
5206:
5203:(21): 1–194.
5202:
5198:
5194:
5187:
5179:
5175:
5171:
5167:
5160:
5152:
5148:
5144:
5140:
5136:
5132:
5125:
5117:
5113:
5108:
5103:
5099:
5095:
5091:
5084:
5076:
5072:
5068:
5064:
5060:
5056:
5049:
5041:
5037:
5033:
5029:
5025:
5021:
5014:
5006:
5002:
4998:
4994:
4990:
4986:
4982:
4978:
4971:
4963:
4959:
4955:
4951:
4947:
4943:
4936:
4928:
4924:
4920:
4916:
4909:
4901:
4897:
4893:
4889:
4885:
4881:
4877:
4873:
4866:
4864:
4855:
4851:
4847:
4843:
4836:
4822:
4816:
4808:
4804:
4799:
4794:
4790:
4786:
4782:
4778:
4774:
4767:
4765:
4748:
4744:
4738:
4730:
4724:
4720:
4713:
4711:
4702:
4696:
4692:
4685:
4683:
4681:
4672:
4668:
4664:
4660:
4656:
4652:
4648:
4644:
4637:
4629:
4625:
4620:
4615:
4611:
4607:
4603:
4599:
4595:
4588:
4580:
4574:
4570:
4563:
4555:
4551:
4547:
4543:
4538:
4533:
4529:
4525:
4518:
4510:
4506:
4502:
4498:
4494:
4490:
4483:
4475:
4471:
4467:
4463:
4458:
4453:
4449:
4445:
4441:
4434:
4426:
4422:
4418:
4414:
4410:
4406:
4399:
4391:
4387:
4383:
4379:
4375:
4371:
4364:
4356:
4350:
4346:
4342:
4338:
4337:
4332:
4325:
4323:
4314:
4310:
4306:
4302:
4298:
4294:
4290:
4286:
4279:
4271:
4267:
4263:
4259:
4254:
4249:
4245:
4241:
4237:
4230:
4222:
4218:
4213:
4208:
4204:
4200:
4196:
4192:
4188:
4181:
4173:
4169:
4164:
4159:
4155:
4151:
4147:
4140:
4132:
4128:
4124:
4120:
4115:
4110:
4106:
4102:
4098:
4091:
4083:
4079:
4075:
4071:
4067:
4063:
4059:
4055:
4048:
4040:
4036:
4032:
4028:
4024:
4020:
4016:
4012:
4005:
3997:
3993:
3988:
3983:
3979:
3975:
3971:
3967:
3963:
3959:
3955:
3948:
3932:
3928:
3924:
3923:
3918:
3912:
3896:
3892:
3886:
3878:
3874:
3869:
3864:
3860:
3856:
3852:
3848:
3844:
3837:
3829:
3825:
3821:
3817:
3813:
3809:
3802:
3794:
3790:
3786:
3782:
3778:
3772:
3756:
3752:
3746:
3727:
3723:
3719:
3715:
3709:
3701:
3697:
3692:
3687:
3683:
3679:
3675:
3671:
3667:
3660:
3652:
3648:
3643:
3638:
3634:
3630:
3626:
3622:
3618:
3611:
3595:
3591:
3585:
3577:
3573:
3568:
3563:
3559:
3555:
3551:
3544:
3536:
3530:
3526:
3519:
3517:
3508:
3504:
3499:
3494:
3490:
3486:
3482:
3478:
3474:
3467:
3465:
3463:
3454:
3450:
3446:
3442:
3438:
3434:
3430:
3426:
3419:
3411:
3407:
3402:
3397:
3392:
3387:
3383:
3379:
3375:
3368:
3360:
3356:
3351:
3346:
3342:
3338:
3334:
3330:
3326:
3319:
3317:
3308:
3304:
3300:
3296:
3295:
3290:
3283:
3275:
3271:
3267:
3263:
3257:
3255:
3246:
3242:
3238:
3234:
3230:
3226:
3222:
3218:
3214:
3210:
3202:
3194:
3190:
3186:
3182:
3178:
3174:
3170:
3166:
3158:
3150:
3144:
3140:
3139:Austria-Codex
3133:
3131:
3129:
3127:
3118:
3114:
3109:
3104:
3100:
3096:
3092:
3088:
3084:
3077:
3069:
3065:
3060:
3055:
3051:
3047:
3043:
3039:
3035:
3028:
3020:
3016:
3012:
3008:
3004:
3000:
2996:
2992:
2985:
2977:
2973:
2969:
2965:
2961:
2957:
2953:
2949:
2942:
2934:
2930:
2926:
2922:
2918:
2914:
2910:
2906:
2899:
2891:
2887:
2883:
2879:
2875:
2871:
2867:
2863:
2855:
2847:
2843:
2839:
2835:
2831:
2827:
2823:
2819:
2812:
2804:
2800:
2795:
2790:
2786:
2782:
2778:
2774:
2770:
2763:
2755:
2751:
2746:
2741:
2737:
2733:
2729:
2722:
2714:
2710:
2705:
2700:
2696:
2692:
2688:
2684:
2680:
2673:
2665:
2661:
2657:
2653:
2648:
2643:
2639:
2635:
2631:
2624:
2616:
2612:
2608:
2604:
2600:
2596:
2592:
2588:
2581:
2573:
2569:
2565:
2561:
2557:
2553:
2546:
2544:
2535:
2531:
2526:
2521:
2517:
2513:
2509:
2505:
2501:
2494:
2486:
2482:
2478:
2474:
2470:
2466:
2462:
2458:
2450:
2448:
2439:
2435:
2431:
2427:
2423:
2419:
2412:
2404:
2398:
2394:
2390:
2384:
2382:
2380:
2378:
2369:
2365:
2361:
2357:
2353:
2349:
2345:
2341:
2334:
2332:
2323:
2319:
2315:
2311:
2307:
2303:
2296:
2294:
2292:
2290:
2288:
2286:
2284:
2268:
2264:
2258:
2249:
2244:
2240:
2236:
2230:
2222:
2218:
2216:9783319267289
2212:
2208:
2207:
2199:
2197:
2195:
2186:
2182:
2177:
2172:
2167:
2162:
2158:
2154:
2150:
2143:
2135:
2131:
2127:
2123:
2119:
2115:
2111:
2107:
2100:
2098:
2089:
2085:
2080:
2075:
2070:
2065:
2061:
2057:
2053:
2046:
2030:
2026:
2020:
2018:
2016:
2014:
2012:
2010:
2008:
2006:
2004:
1988:
1984:
1978:
1962:
1958:
1952:
1937:
1933:
1929:
1923:
1915:
1914:
1909:
1903:
1899:
1891:
1889:
1885:
1881:
1877:
1875:
1869:
1867:
1863:
1859:
1855:
1851:
1850:Peter Medawar
1847:
1843:
1838:
1836:
1832:
1828:
1818:
1816:
1811:
1809:
1808:sulfuric acid
1805:
1801:
1797:
1793:
1789:
1785:
1781:
1777:
1772:
1770:
1766:
1762:
1758:
1754:
1750:
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:
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:
1443:
1441:
1437:
1432:
1430:
1426:
1422:
1418:
1407:
1405:
1397:
1393:
1389:
1385:
1382:
1381:anticoagulant
1377:
1375:
1371:
1361:
1359:
1348:
1346:
1342:
1341:6-thioguanine
1337:
1327:
1325:
1321:
1317:
1312:
1310:
1306:
1303:of the skin,
1302:
1298:
1293:
1291:
1287:
1283:
1278:
1276:
1272:
1268:
1258:
1256:
1252:
1248:
1247:myelotoxicity
1243:
1239:
1235:
1231:
1227:
1223:
1219:
1215:
1211:
1207:
1203:
1199:
1195:
1192:
1188:
1184:
1180:
1170:
1168:
1164:
1159:
1156:
1151:
1147:
1143:
1139:
1135:
1131:
1127:
1123:
1119:
1110:
1101:
1099:
1095:
1091:
1086:
1084:
1079:
1075:
1071:
1066:
1064:
1059:
1055:
1053:
1043:
1041:
1037:
1032:
1030:
1026:
1016:
1014:
1010:
1006:
996:
994:
990:
986:
976:
974:
970:
965:
963:
959:
955:
951:
947:
943:
939:
935:
931:
927:
923:
919:
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:
777:
774:
767:
758:
757:
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:
419:
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:
6945:Hepatotoxins
6859:Azathioprine
6858:
6852:
6847:Methotrexate
6840:
6694:Upadacitinib
6654:Satralizumab
6639:Ritlecitinib
6634:Risankizumab
6429:
6410:
6350:Teprotumumab
6300:Inebilizumab
6295:Fontolizumab
6275:Atorolimumab
6243:T-lymphocyte
6241:
6215:
6199:
6185:
6166:
6155:Lerdelimumab
6150:Bertilimumab
6142:
6130:
6109:
6095:
6081:
6067:
6048:
6029:
6013:Pascolizumab
5998:Obinutuzumab
5990:
5976:
5962:
5946:Clenoliximab
5938:
5922:Otelixizumab
5909:
5882:
5869:Lebrikizumab
5853:
5837:
5821:
5805:
5789:
5746:Satralizumab
5736:Risankizumab
5668:
5627:
5611:
5603:Serum target
5555:Temsirolimus
5481:
5472:Pomalidomide
5467:Lenalidomide
5425:Pimecrolimus
5404:
5378:Methotrexate
5370:
5348:
5335:Azathioprine
5334:
5327:
5312:(initiation)
5242:
5200:
5196:
5186:
5169:
5165:
5159:
5134:
5130:
5124:
5097:
5093:
5083:
5058:
5054:
5048:
5023:
5019:
5013:
4980:
4976:
4970:
4945:
4941:
4935:
4918:
4914:
4908:
4875:
4871:
4845:
4841:
4835:
4815:
4780:
4776:
4751:. Retrieved
4747:the original
4737:
4718:
4690:
4649:(1): 24–36.
4646:
4642:
4636:
4601:
4597:
4587:
4571:. Hale Pub.
4568:
4562:
4527:
4523:
4517:
4492:
4488:
4482:
4447:
4443:
4433:
4408:
4404:
4398:
4373:
4369:
4363:
4335:
4288:
4284:
4278:
4243:
4239:
4229:
4194:
4190:
4180:
4153:
4149:
4139:
4104:
4100:
4090:
4057:
4053:
4047:
4014:
4010:
4004:
3961:
3957:
3947:
3935:. Retrieved
3920:
3911:
3899:. Retrieved
3885:
3850:
3846:
3836:
3811:
3807:
3801:
3788:
3784:
3771:
3759:. Retrieved
3745:
3733:. Retrieved
3708:
3673:
3669:
3659:
3624:
3620:
3610:
3598:. Retrieved
3584:
3557:
3554:Rheumatology
3553:
3543:
3524:
3480:
3476:
3453:the original
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:
6881:from market
6830:Leflunomide
6821:Chloroquine
6816:Bucillamine
6796:Aurotioprol
6689:Tofacitinib
6629:Ravulizumab
6619:Pirfenidone
6609:Peficitinib
6509:Canakinumab
6499:Briakinumab
6489:Bimekizumab
6484:Baricitinib
6449:Aflibercept
6360:Vepalimomab
6355:Vapaliximab
6330:Rovelizumab
6320:Pexelizumab
6310:Morolimumab
6285:Cedelizumab
6270:Anifrolumab
6265:Alemtuzumab
6223:Basiliximab
6193:Tocilizumab
6179:Vedolizumab
6174:Natalizumab
6160:Metelimumab
6103:Gavilimomab
6061:Toralizumab
6056:Teneliximab
6042:Lumiliximab
6037:Gomiliximab
6023:Ublituximab
6003:Ocrelizumab
5956:Zanolimumab
5932:Visilizumab
5890:Secukinumab
5874:Ustekinumab
5845:Elsilimomab
5829:Faralimomab
5797:Mepolizumab
5781:Ustekinumab
5776:Tocilizumab
5751:Secukinumab
5701:Canakinumab
5691:Briakinumab
5686:Bimekizumab
5681:Basiliximab
5670:Interleukin
5660:Nerelimomab
5565:Zotarolimus
5506:(reception)
5477:Thalidomide
5435:Voclosporin
5420:Ciclosporin
5414:Calcineurin
5410:Cyclophilin
5357:Leflunomide
5353:inhibitors
3814:(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
6934:Categories
6854:thiopurine
6842:antifolate
6750:Quinolines
6679:Sutimlimab
6674:Spesolimab
6659:Siltuximab
6599:Olokizumab
6589:Ixekizumab
6584:Itacitinib
6574:Guselkumab
6569:Fingolimod
6564:Filgotinib
6514:Crovalimab
6504:Brodalumab
6494:Blisibimod
6459:Rilonacept
6442:Opinercept
6437:Etanercept
6423:Belatacept
6374:Polyclonal
6335:Siplizumab
6325:Reslizumab
6315:Ofatumumab
6305:Maslimomab
6290:Emapalumab
6233:Inolimomab
6228:Daclizumab
6207:Odulimomab
6122:Ruplizumab
6117:Frexalimab
6075:Aselizumab
5970:Efalizumab
5927:Teplizumab
5823:Interferon
5813:Omalizumab
5766:Spesolimab
5756:Siltuximab
5731:Rilonacept
5726:Olokizumab
5716:Ixekizumab
5711:Guselkumab
5706:Daclizumab
5696:Brodalumab
5655:Infliximab
5640:Afelimomab
5635:Adalimumab
5619:Eculizumab
5595:Monoclonal
5586:Antibodies
5560:Umirolimus
5540:Everolimus
5489:Apremilast
5449:Gusperimus
5430:Tacrolimus
5398:inhibitors
5390:Macrolides
5372:antifolate
4524:Teratology
3922:BBC Online
3600:19 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
6891:Phase III
6879:Withdrawn
6786:Auranofin
6735:Specific
6669:Sirukumab
6664:Siponimod
6649:Sarilumab
6624:Ponesimod
6594:Netakimab
6579:Iptacopan
6559:Etrasimod
6519:Danicopan
6454:Alefacept
6418:Abatacept
6340:Talizumab
6280:Begelomab
6136:Belimumab
6089:Galiximab
6018:Rituximab
5984:Erlizumab
5951:Keliximab
5761:Sirukumab
5741:Sarilumab
5721:Netakimab
5650:Golimumab
5550:Sirolimus
4921:: 47–52.
4753:31 August
4532: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
6965:Prodrugs
6924:Medicine
6604:Ozanimod
6479:Avacopan
6472:Unsorted
6258:Unsorted
6168:Integrin
5901:Cellular
5676:Anakinra
5522:Anakinra
5444:Abetimus
5296: /
5256:28520349
5250:(NCBI).
5219:15899149
5116:12911553
5075:13936775
5040:13807024
4997:13601801
4962:13980986
4927:13849699
4807:12697731
4671:23327335
4663:18097462
4628:15479867
4554:11967923
4474:25314258
4466:12641505
4390:19343728
4305:21658113
4262:20015102
4221:21122542
4172:17296529
4123:16128682
4082:13419507
4039:27475772
4031:18506437
3996:16166520
3937:June 10,
3931:Archived
3927:BBC News
3901:June 20,
3895:Archived
3877:16009676
3793:Archived
3779:(1981).
3761:June 20,
3755:Archived
3735:June 20,
3726:Archived
3700:25108385
3651:20154640
3594:Archived
3576:17255139
3507:21270794
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
6975:Purines
6400:-cept (
5178:3922606
5151:2998215
5005:8043359
4900:2649979
4880:Bibcode
4872:Science
4619:1766779
4509:4905893
4313:3396280
4270:6000856
4212:3157326
4131:9356163
4074:8100914
3987:2426755
3966:Bibcode
3958:Science
3868:1774869
3828:7683109
3691:4999337
3642:3086840
3498:3098761
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
6910:Portal
6874:WHO-EM
6412:CTLA-4
6402:Fusion
5903:target
5884:IL-17A
5861:, and
5394:other
5254:
5217:
5176:
5149:
5114:
5073:
5038:
5020:Lancet
5003:
4995:
4960:
4925:
4898:
4827:
4805:
4798:152947
4795:
4725:
4697:
4669:
4661:
4626:
4616:
4575:
4552:
4534:
4507:
4472:
4464:
4425:799904
4423:
4388:
4351:
4341:London
4311:
4303:
4268:
4260:
4219:
4209:
4170:
4129:
4121:
4080:
4072:
4054:Lancet
4037:
4029:
3994:
3984:
3875:
3865:
3826:
3791:: 47.
3698:
3688:
3649:
3639:
3574:
3531:
3505:
3495:
3447:
3408:
3398:
3357:
3347:
3305:
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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:
2522:
2483:
2475:
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