User:Mr. Ibrahem/Azathioprine
From Wikipedia, the free encyclopedia
Azathioprine (AZA), sold under the brand name Imuran among others, is an immunosuppressive medication.[2] It is used in rheumatoid arthritis, granulomatosis with polyangiitis, Crohn's disease, ulcerative colitis, systemic lupus erythematosus, and in kidney transplants to prevent rejection.[2][3][4][5] It is taken by mouth or injected into a vein.[2]
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Pronunciation | /ˌæzəˈθaɪəˌpriːn/[1] |
Trade names | Azasan, Imuran and others |
AHFS/Drugs.com | Monograph |
MedlinePlus | a682167 |
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Routes of administration | Mainly by mouth (sometimes initially intravenous) |
Drug class | Immunosuppresant |
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Pharmacokinetic data | |
Bioavailability | 60±31% |
Protein binding | 20–30% |
Metabolism | Activated non-enzymatically, deactivated mainly by xanthine oxidase |
Elimination half-life | 26–80 minutes (azathioprine) 3–5 hours (drug plus metabolites) |
Excretion | Kidney, 98% as metabolites |
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Chemical and physical data | |
Formula | C9H7N7O2S |
Molar mass | 277.26 g·mol−1 |
3D model (JSmol) | |
Melting point | 238 to 245 °C (460 to 473 °F) |
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Common side effects include bone marrow suppression and vomiting.[2] Bone marrow suppression is especially common in people with a genetic deficiency of the enzyme thiopurine S-methyltransferase.[2] Other serious risk factors include an increased risk of lymphoma.[2] Use during pregnancy may result in harm to the baby.[2] Azathioprine is in the purine analogue and antimetabolite family of medication.[2][6] It works via 6-thioguanine to disrupt the making of RNA and DNA by cells.[2][6]
Azathioprine was first made in 1957.[6] It is on the World Health Organization's List of Essential Medicines.[7] The wholesale cost in the developing world is about US$7.63–17.19 a month.[8] The wholesale cost in the United States is about US$35.34 per month.[9] As of 2023, a month supply in the UK typically costs the NHS less than £10.[10] In 2017, it was the 335th most commonly prescribed medication in the United States, with more than 800 thousand prescriptions.[11]