| Azathioprine, sold under the brand name Imuran, among others, is an immunosuppressive medication. It is used for the treatment of rheumatoid arthritis, granulomatosis with polyangiitis, Crohn's disease, ulcerative colitis, and systemic lupus erythematosus, and in kidney transplants to prevent rejection. It is listed by the International Agency for Research on Cancer as a group 1 human carcinogen. It is taken by mouth or injected into a vein.
Common side effects include bone-marrow suppression and vomiting. Bone-marrow suppression is especially common in people with a genetic deficiency of the enzyme thiopurine S-methyltransferase. Other serious risk factors include an increased risk of certain cancers. Use during pregnancy may result in harm to the baby. Azathioprine belongs to the purine analogues subclass of antimetabolites family of medications. It works via 6-thioguanine to disrupt the making of RNA and DNA by cells.
Azathioprine was first made in 1957. It is on the World Health Organization's List of Essential Medicines. In 2018, it was the 358th most commonly prescribed medication in the United States, with more than 800,000 prescriptions. |
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immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
hepatotoxic agent
A role played by a chemical compound exhibiting itself through the ability to induce damage to the liver in animals.
antimetabolite
A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
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immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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View more via ChEBI Ontology
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6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine
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6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purine
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ChemIDplus
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6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurine
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ChemIDplus
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Imuran (TN)
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KEGG DRUG
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269
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DrugCentral
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Azathioprine
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Wikipedia
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C06837
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KEGG COMPOUND
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D00238
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KEGG DRUG
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DB00993
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DrugBank
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| View more database links |
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1225351
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Reaxys Registry Number
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Reaxys
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446-86-6
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CAS Registry Number
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KEGG DRUG
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446-86-6
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CAS Registry Number
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ChemIDplus
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