Azathioprine

Azathioprine
Clinical data


Pronunciation	/ˌæzəˈθaɪəˌpriːn/
Trade names	Azasan, Imuran and others
AHFS/Drugs.com	Monograph
MedlinePlus	a682167
License data	US FDA: azathioprine
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	Mainly by mouth (sometimes initially intravenous)
ATC code	L04AX01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	60±31%
Protein binding	20–30%
Metabolism	Activated non-enzymatically, deactivated mainly by xanthine oxidase
Biological half-life	26–80 minutes (azathioprine) 3–5 hours (drug plus metabolites)
Excretion	Kidney, 98% as metabolites
Identifiers
IUPAC name 6-[(1-Methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine
CAS Number	446-86-6^Y 55774-33-9 (sodium salt)
PubChem (CID)	2265
DrugBank	DB00993^Y
ChemSpider	2178^Y
UNII	MRK240IY2L^Y
KEGG	D00238^Y
ChEBI	CHEBI:2948^Y
ChEMBL	CHEMBL1542^Y
ECHA InfoCard	100.006.525
Chemical and physical data
Formula	C₉H₇N₇O₂S
Molar mass	277.263 g/mol
3D model (Jmol)	Interactive image
Melting point	238 to 245 °C (460 to 473 °F)
SMILES [O-][N+](=O)c3ncn(c3Sc1ncnc2ncnc12)C
InChI 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

Azathioprine (AZA), sold under the brand name Imuran among others, is an immunosuppressive medication. It is used in rheumatoid arthritis, Crohn's disease, and in kidney transplants to prevent rejection. It is taken by mouth or injected into a vein.

Common side effect 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 lymphoma. Use during pregnancy may result in harm to the baby. Azathioprine is in the purine analogue and antimetabolite family of medication. 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, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 7.63 to 17.19 USD a month. The wholesale cost in the United States is about 35.34 USD per month.

Azathioprine is used alone or in combination with other immunosuppressive therapy to prevent rejection following organ transplantation, and to treat an array of autoimmune diseases, including rheumatoid arthritis, pemphigus, systemic lupus erythematosus, Behçet's disease, and other forms of vasculitis, autoimmune hepatitis, atopic dermatitis, myasthenia gravis, neuromyelitis optica (Devic's disease), restrictive lung disease, and others. It is also an important therapy and steroid-sparing agent for inflammatory bowel disease (such as Crohn's disease and ulcerative colitis) and for multiple sclerosis.