Active Ingredient History

NOW
  • Now
Azathioprine remains one of the most important and widely prescribed drugs for immunosuppression/immunomodulation in autoimmune disease over 30 years after its introduction. Azathioprine is licensed for the treatment of only a limited range of autoimmune disorders, which is probably a reflection on the age of the drug. Widening the license for a drug is both costly and time consuming, and it would make no commercial sense for manufacturers to do so, at this late stage of life, for azathioprine. However, azathioprine is now so well established as an immunomodulating drug in autoimmune disorders that it represents the gold standard by which other drugs are compared. Azathioprine is indicated as an adjunct for the prevention of rejection in renal homotransplantation. It is also indicated for the management of active rheumatoid arthritis to reduce signs and symptoms. The combined use of azathioprine tablets with disease modifying anti-rheumatic drugs (DMARDs) has not been studied for either added benefit or unexpected adverse effects. The use of azathioprine tablets with these agents cannot be recommended. Azathioprine is a pro-drug, converted in the body to the active metabolite 6-mercaptopurine. Azathioprine acts to inhibit purine synthesis necessary for the proliferation of cells, especially leukocytes and lymphocytes. It is a safe and effective drug used alone in certain autoimmune diseases, or in combination with other immunosuppressants in organ transplantation. Its most severe side effect is bone marrow suppression, and it should not be given in conjunction with purine analogues such as allopurinol. The enzyme thiopurine S-methyltransferase (TPMT) deactivates 6-mercaptopurine. Genetic polymorphisms of TPMT can lead to excessive drug toxicity, thus assay of serum TPMT may be useful to prevent this complication. Azathioprine is metabolized to 6-mercaptopurine (6-MP). 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. 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.   NCATS

  • SMILES: Cn1cnc(c1Sc2ncnc3nc[nH]c23)[N+](=O)[O-]
  • InChIKey: LMEKQMALGUDUQG-UHFFFAOYSA-N
  • Mol. Mass: 277.27
  • ALogP: 1.15
  • ChEMBL Molecules:
More Chemistry
  • Mechanisms of Action:
  • Multi-specific: Missing data
  • Black Box: Yes
  • Availability: Prescription Only
  • Delivery Methods: Oral, Parenteral
  • Pro Drug: Yes

Drug Pricing (per unit)

Australia

$0.0943 - $0.1606

United States

$0.2146 - $226.1300
More Pricing Detail

Note: This drug pricing data is preliminary, incomplete, and may contain errors.

6-((1-methyl-4-nitro-1h-imidazol-5-yl)thio)-1h-purine | 6-(1'-methyl-4'-nitro-5'-imidazolyl)-mercaptopurine | azamune | azanin | azapress | azasan | azathioprene | azathioprin | azathioprine | azathioprine sodium | azathioprine sulfate | azathropine | azothioprine | berkaprine | bw 57-322 | bw-57-322 | immunoprin 50 | imuran | imuran (tn) | kentaprine | oprisine 50

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