CAS No.50-44-2 6-Mercaptopurine

6-Mercaptopurine

Identification
Name 6-Mercaptopurine
CAS Registry Number 50-44-2
Synonyms LEUKERIN;1,7-Dihydro-6H-purine-6-thione;7H-PURINE-6-THIOL;7-mercapto-1,3,4,6-tetrazaindene;6-MERCAPTOPURINE;6-PURINETHIOL;6-THIOPURINE;6-thioxopurine
Molecular Structure 6-Mercaptopurine   50-44-2
Molecular Formula C5H4N4S
Molecular Weight 152.18
mp: 241-244℃
Safety Statements: 3249

CAS 50-44-2 Wiki / 50-44-2 MSDS

Mercaptopurine
Mercaptopurine.svg
Mercaptopurin ball-and-stick.png
Clinical data
Trade names Purinethol, others
Synonyms 6-mercaptopurine (6-MP)
AHFS/Drugs.com Monograph
MedlinePlus a682653
Pregnancy
category
  • D
Routes of
administration
by mouth
ATC code
  • L01BB02 (WHO)
Legal status
Legal status
  • In general: ℞ (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
CAS Number
  • 50-44-2 YesY
PubChem CID
  • 667490
IUPHAR/BPS
  • 7226
DrugBank
  • DB01033 YesY
ChemSpider
  • 580869 YesY
UNII
  • PKK6MUZ20G
KEGG
  • D04931 YesY
ChEBI
  • CHEBI:50667 YesY
ChEMBL
  • CHEMBL1425 YesY
ECHA InfoCard 100.000.035
Chemical and physical data
Formula C5H4N4S
Molar mass 152.177 g/mol
3D model (JSmol)
  • Interactive image
  (verify)

Mercaptopurine (6-MP), sold under the brand name Purinethol among others, is a medication used for cancer and autoimmune diseases.[1] Specifically it is used to treat acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.[1][2] For ALL it is generally used with methotrexate.[1] It is taken by mouth.[1]

Common side effects include bone marrow suppression, liver toxicity, vomiting, and loss of appetite.[1] Other serious side effects include an increased risk of future cancer and pancreatitis.[1] Those with a genetic deficiency in thiopurine S-methyltransferase are at higher risk of side effects.[1] Use in pregnancy may harm the baby.[1] Mercaptopurine is in the thiopurine and antimetabolite family of medications.[3][2]

Mercaptopurine was approved for medical use in the United States in 1953.[1] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[4] The wholesale cost in the developing world is about 18.42 to 200.16 USD a month.[5] In the United Kingdom this costs the NHS about 121.13 pounds per month.[2] In the United States the wholesale cost is about 99.16 USD per month as of 2016.[6]