Azathioprine

Azathioprine
Clinical data
Pronunciation/ˌæzəˈθaɪəˌpriːn/[1]
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
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 Edit this at Wikidata
Chemical and physical data
FormulaC9H7N7O2S
Molar mass277.26 g·mol−1
3D model (JSmol)
Melting point238 to 245 °C (460 to 473 °F)
  • 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) checkY
  • Key:LMEKQMALGUDUQG-UHFFFAOYSA-N checkY
  (verify)

Azathioprine, sold under the brand name Imuran, among others, is an immunosuppressive medication.[5] 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.[5][6][7][8] It is taken by mouth or injected into a vein.[5]

Common side effects include bone-marrow suppression and vomiting.[5] Bone-marrow suppression is especially common in people with a genetic deficiency of the enzyme thiopurine S-methyltransferase.[5] Other serious risk factors include an increased risk of certain cancers.[5] Use during pregnancy may result in harm to the baby.[5] Azathioprine belongs to the purine analogues subclass of antimetabolites family of medications.[5][9] It works via 6-thioguanine to disrupt the making of RNA and DNA by cells.[5][9]

Azathioprine was first made in 1957.[9] It is on the World Health Organization's List of Essential Medicines.[10] In 2018, it was the 358th most commonly prescribed medication in the United States, with more than 800,000 prescriptions.[11]

  1. ^ "Azathioprine". Merriam-Webster.com Dictionary. Merriam-Webster.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  3. ^ "Jayempi EPAR". European Medicines Agency. 20 April 2021. Retrieved 4 March 2023.
  4. ^ "Jayempi Product information". Union Register of medicinal products. Retrieved 3 March 2023.
  5. ^ a b c d e f g h i "Azathioprine". The American Society of Health-System Pharmacists. Archived from the original on 20 August 2016. Retrieved 8 December 2016.
  6. ^ Axelrad JE, Lichtiger S, Yajnik V (May 2016). "Inflammatory bowel disease and cancer: The role of inflammation, immunosuppression, and cancer treatment". World Journal of Gastroenterology (Review). 22 (20): 4794–4801. doi:10.3748/wjg.v22.i20.4794. PMC 4873872. PMID 27239106.
  7. ^ Singer O, McCune WJ (May 2017). "Update on maintenance therapy for granulomatosis with polyangiitis and microscopic polyangiitis". Current Opinion in Rheumatology. 29 (3): 248–253. doi:10.1097/BOR.0000000000000382. PMID 28306595. S2CID 35805200.
  8. ^ Jordan N, D'Cruz D (2016). "Current and emerging treatment options in the management of lupus". ImmunoTargets and Therapy. 5: 9–20. doi:10.2147/ITT.S40675. PMC 4970629. PMID 27529058.
  9. ^ a b c Sami N (2016). Autoimmune Bullous Diseases: Approach and Management. Springer. p. 83. ISBN 9783319267289. Archived from the original on 2016-12-21.
  10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  11. ^ "Azathioprine - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.