Mercaptopurine

Mercaptopurine
Clinical data
Trade namesPurinethol, Purixan, others
Other names6-mercaptopurine (6-MP)
AHFS/Drugs.comMonograph
MedlinePlusa682653
License data
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • EU: Rx-only[1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability5 to 37%
Metabolismxanthine oxidase
Elimination half-life60 to 120 min., longer for its active metabolites
Excretionkidney
Identifiers
  • 3,7-dihydropurine-6-thione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.035 Edit this at Wikidata
Chemical and physical data
FormulaC5H4N4S
Molar mass152.18 g·mol−1
3D model (JSmol)
  • S=c1nc[nH]c2nc[nH]c12
  • InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) checkY
  • Key:GLVAUDGFNGKCSF-UHFFFAOYSA-N checkY
  (verify)

Mercaptopurine (6-MP), sold under the brand name Purinethol among others, is a medication used for cancer and autoimmune diseases.[2] Specifically it is used to treat acute lymphocytic leukemia (ALL), acute promyelocytic leukemia (APL), Crohn's disease, and ulcerative colitis.[2][3] For acute lymphocytic leukemia it is generally used with methotrexate.[2] It is taken orally.[2]

Common side effects include bone marrow suppression, liver toxicity, vomiting, and loss of appetite.[2] Other serious side effects include an increased risk of future cancer and pancreatitis.[2] Those with a genetic deficiency in thiopurine S-methyltransferase are at higher risk of side effects.[2] Use in pregnancy may harm the baby.[2] Mercaptopurine is in the thiopurine and antimetabolite family of medications.[4][3]

Mercaptopurine was approved for medical use in the United States in 1953.[2] It is on the World Health Organization's List of Essential Medicines.[5]

  1. ^ "Xaluprine EPAR". European Medicines Agency. 30 April 2009. Retrieved 25 June 2024.
  2. ^ a b c d e f g h i "Mercaptopurine". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  3. ^ a b British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 590. ISBN 9780857111562.
  4. ^ Sahasranaman S, Howard D, Roy S (August 2008). "Clinical pharmacology and pharmacogenetics of thiopurines". European Journal of Clinical Pharmacology. 64 (8): 753–67. doi:10.1007/s00228-008-0478-6. PMID 18506437. S2CID 27475772.
  5. ^ 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.