Azathioprine

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.

Azathioprine
Clinical data
Pronunciation/ˌæzəˈθaɪəˌpriːn/
Trade namesAzasan, Imuran, Jayempi, others
Other namesAZA
AHFS/Drugs.comMonograph
MedlinePlusa682167
License data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth, intravenous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability60±31%
Protein binding20–30%
MetabolismActivated non-enzymatically, deactivated mainly by xanthine oxidase
Elimination half-life26–80 minutes (azathioprine)
3–5 hours (drug plus metabolites)
ExcretionKidney, 98% as metabolites
Identifiers
  • 6-[(1-Methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.525
Chemical and physical data
FormulaC9H7N7O2S
Molar mass277.26 g·mol−1
3D model (JSmol)
Melting point238 to 245 °C (460 to 473 °F)
SMILES
  • Cn1cnc(N(=O)=O)c1Sc2ncnc3nc[nH]c23
  • 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) Y
  • Key:LMEKQMALGUDUQG-UHFFFAOYSA-N Y
  (verify)

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.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.