4732 Azathioprine Azathioprine is only found in individuals that have used or taken this drug. It is an immunosuppressive pro-drug. It is converted into 6-mercaptopurine in the body where it blocks purine metabolism and DNA synthesis.Azathioprine antagonizes purine metabolism and may inhibit synthesis of DNA, RNA, and proteins. It may also interfere with cellular metabolism and inhibit mitosis. Its mechanism of action is likely due to incorporation of thiopurine analogues into the DNA structure, causing chain termination and cytotoxicity. 446-86-6 2265 C9H7N7O2S White powder. 243.5°C 1.07e+00 g/L Well absorbed following oral administration. Azathioprine antagonizes purine metabolism and may inhibit synthesis of DNA, RNA, and proteins. It may also interfere with cellular metabolism and inhibit mitosis. Its mechanism of action is likely due to incorporation of thiopurine analogues into the DNA structure, causing chain termination and cytotoxicity. Primarily converted to the active metabolites 6-mercaptopurine and 6-thioinosinic acid via a non-enzymatica process and glutathione transferases. Activation of 6-mercaptopurine occurs via hypoxanthine-guanine phosphoribosyltransferase (HGPRT) and a series of multi-enzymatic processes involving kinases to form 6-thioguanine nucleotides (6-TGNs) as major metabolites Route of Elimination: Both compounds are rapidly eliminated from blood and are oxidized or methylated in erythrocytes and liver; no azathioprine or mercaptopurine is detectable in urine after 8 hours. The oral LD₅₀ for single doses of azathioprine in mice and rats are 2500 mg/kg and 400 mg/kg, respectively. 1, carcinogenic to humans. (L135) Azathioprine is used alone or in combination with other immunosuppressive therapy to prevent rejection following organ transplantation, and to treat an array of autoimmune diseases, including rheumatoid arthritis, pemphigus, systemic lupus erythematosus, Behcet's disease and other forms of vasculitis, autoimmune hepatitis, atopic dermatitis, myasthenia gravis, neuromyelitis optica (Devic's disease), restrictive lung disease, and others. It is also an important therapy and steroid-sparing agent for inflammatory bowel disease (such as Crohn's disease and ulcerative colitis) and for multiple sclerosis. In the United States it is currently approved by the Food and Drug Administration (FDA) for use in kidney transplantation from human donors, and for rheumatoid arthritis. Other uses are off-label. (Wikipedia) 2014-09-11T02:04:30Z 2026-05-14T16:55:13Z http://en.wikipedia.org/wiki/Azathioprine C06837 2948 DB00993 true CN1C=NC(=C1SC1=NC=NC2=C1NC=N2)[N+]([O-])=O C9H7N7O2S 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) LMEKQMALGUDUQG-UHFFFAOYSA-N 277.263 277.038193193 Exogenous Solid 0.1 HMDB15128 CHEMBL1542 2178 CHEM003635 DTXSID4020119 NS00004945 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine 118.10000000000001 70.94619999999999 24.258830779402988 3 6 1 8.645114889803738 4.003157356049786 0 3 0.84 -2.41 1.07e+00 g/l