Mercaptopurine

Mercaptopurine

Clinical data
Trade names	Purinethol, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682653
Pregnancy category	D
Routes of administration	by mouth
ATC code	L01BB02 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	5 to 37%
Metabolism	xanthine oxidase
Biological half-life	60 to 120 min., longer for its active metabolites
Excretion	kidney
Identifiers
IUPAC name 3,7-dihydropurine-6-thione
Synonyms	6-mercaptopurine (6-MP)
CAS Number	50-44-2 Y
PubChem (CID)	667490
IUPHAR/BPS	7226
DrugBank	DB01033 Y
ChemSpider	580869 Y
UNII	PKK6MUZ20G Y
KEGG	D04931 Y
ChEBI	CHEBI:50667 Y
ChEMBL	CHEMBL1425 Y
ECHA InfoCard	100.000.035
Chemical and physical data
Formula	C5H4N4S
Molar mass	152.177 g/mol
3D model (Jmol)	Interactive image
SMILES S=C2/N=C\Nc1ncnc12
InChI InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) Y Key:GLVAUDGFNGKCSF-UHFFFAOYSA-N Y

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), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis. For ALL it is generally used with methotrexate. It is taken by mouth.

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 is 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, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 18.42 to 200.16 USD a month. In the United Kingdom this costs the NHS about 121.13 pounds per month. In the United States the wholesale cost is about 99.16 USD per month as of 2016.

It is used to treat acute lymphocytic leukemia, Crohn's disease, and ulcerative colitis.