Mercaptopurine

Mercaptopurine
Clinical data
Trade names	Purinethol, Purixan, others
Other names	6-mercaptopurine (6-MP)
AHFS/Drugs.com	Monograph
MedlinePlus	a682653
License data	US DailyMed: Mercaptopurine;
Routes of; administration	By mouth
ATC code	L01BB02 (WHO) ;
Legal status
Legal status	EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	5 to 37%
Metabolism	xanthine oxidase
Elimination half-life	60 to 120 min., longer for its active metabolites
Excretion	kidney
Identifiers
	IUPAC name 3,7-dihydropurine-6-thione;
CAS Number	50-44-2 ;
PubChem CID	667490;
IUPHAR/BPS	7226;
DrugBank	DB01033 ;
ChemSpider	580869 ;
UNII	PKK6MUZ20G;
KEGG	D04931 ;
ChEBI	CHEBI:50667 ;
ChEMBL	ChEMBL1425 ;
CompTox Dashboard (EPA)	DTXSID0020810 ;
ECHA InfoCard	100.000.035
Chemical and physical data
Formula	C5H4N4S
Molar mass	152.18 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES S=c1nc[nH]c2nc[nH]c12;
	InChI InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) ; Key:GLVAUDGFNGKCSF-UHFFFAOYSA-N ;
	(verify)

Mercaptopurine (6-MP), sold under the brand name Purinethol among others, is a medication used for cancer and autoimmune diseases. Specifically it is used to treat acute lymphocytic leukemia (ALL), acute promyelocytic leukemia (APL), Crohn's disease, and ulcerative colitis. For acute lymphocytic leukemia it is generally used with methotrexate. It is taken orally.

Common side effects include bone marrow suppression, liver toxicity, vomiting, and loss of appetite. Other serious side effects include an increased risk of future cancer and pancreatitis. Those with a genetic deficiency in thiopurine S-methyltransferase are at higher risk of side effects. Use in pregnancy may harm the baby. Mercaptopurine is in the thiopurine and antimetabolite family of medications.

Mercaptopurine was approved for medical use in the United States in 1953. It is on the World Health Organization's List of Essential Medicines.