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QuickView for Azathioprine (compound)
PubChem
| Name: | Azathioprine |
|---|---|
| PubChem Compound ID: | 2265 |
| Description: | An immunosuppressive agent used in combination with cyclophosphamide and hydroxychloroquine in the treatment of rheumatoid arthritis. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance has been listed as a known carcinogen. (Merck Index, 11th ed) |
| Molecular formula: | C9H7N7O2S |
| Molecular weight: | 277.264 g/mol |
| Synonyms: |
CHEBI:2948; Imurel; 1H-Purine, 6-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-; 55774-33-9; AIDS047879; 6-1'-Methyl,4'-nitro,5'-imidazolyl mercaptopurine; ZINC04258316; Imuran; CCRIS 62; Imuran (TN).
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DrugBank
Identification
| Name: | Azathioprine |
|---|---|
| Name (isomeric): | DB00993 |
| Drug Type: | small molecule |
| Description: | An immunosuppressive agent used in combination with cyclophosphamide and hydroxychloroquine in the treatment of rheumatoid arthritis. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance has been listed as a known carcinogen. (Merck Index, 11th ed) |
| Synonyms: |
Azathioprin; Azathioprine Sodium; Azothioprine; Azatioprin
|
| Brand: | Azasan, Azanin, Muran, Imurel, Imurek, Imuran, Azamun, Ccucol |
| Category: | Antimetabolites, Antimetabolites, Antineoplastic, Antirheumatic Agents, Immunosuppressive Agents |
| CAS number: | 446-86-6 |
Pharmacology
| Indication: | For use in rheumatoid arthritis, preventing renal transplant rejection, Crohn's disease, and colitis. |
|---|---|
| Pharmacology: |
Azathioprine is a chemotherapy drug, now rarely used for chemotherapy but more for immunosuppression in organ transplantation and autoimmune disease such as rheumatoid arthritis or inflammatory bowel disease or Crohn's disease. It is a pro-drug, converted in the body to the active metabolite 6-mercaptopurine. Azathioprine acts to inhibit purine syn...
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| Mechanism of Action: | 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. |
| Absorption: | Well absorbed following oral administration. |
| Protein binding: | Azathioprine and the metabolite mercaptopurine are moderately bound to serum proteins (30%). |
| Biotransformation: | Primarily converted to the active metabolites 6-mercaptopurine and 6-thioinosinic acid via a non-enzymatica process. 6-mercaptopurine is subsequently metabolized primarily by xanthine oxidase. |
| Half Life: | Approximately 5 hours for the unchanged drug and its metabolites. |
| Toxicity: | The oral LD50 for single doses of azathioprine in mice and rats are 2500 mg/kg and 400 mg/kg, respectively. Very large doses of this antimetabolite may lead to marrow hypoplasia, bleeding, infection, and death. |
| Affected organisms: | Humans and other mammals |
Interactions
| Food interaction: |
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Targets
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