Structure via PubChem · Public domain (PubChem)
mercaptopurine
Sign in to saveAlso known as 6-mercaptopurine, Purinethol®, mercaptopurine anhydrous, Mercaptopurine anhydrous, 6-Thiohypoxanthine, Mercaptopurina, 6-Thioxopurine, 6-Mercaptopurine
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.
Key facts
- Drug.verifiedrevid
- 462248688
- Drug.image
- Mercaptopurine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.image2
- Mercaptopurin ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Purinethol, Purixan, others
- Drug.synonyms
- 6-mercaptopurine (6-MP)
- Drug.MedlinePlus
- a682653
- Drug.DailyMedID
- Mercaptopurine
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- L01
- Drug.ATC_suffix
- BB02
- Drug.legal_AU
- S4
- Drug.legal_EU
- Rx-only
- Drug.legal_status
- Rx-only
- Drug.bioavailability
- 5 to 37%
- Drug.metabolism
- xanthine oxidase
via Wikipedia infobox
Chemical data
- Formula
- C5H4N4S
- Molecular weight
- 152.18 g/mol
- IUPAC name
- 3,7-dihydropurine-6-thione
- SMILES
- C1=NC2=C(N1)C(=S)N=CN2
- InChIKey
- GLVAUDGFNGKCSF-UHFFFAOYSA-N
- XLogP
- 0
- Polar surface area
- 85.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1953
- Admin. routes
- oral
via ChEMBL · EBI
Research
23,039 papers- Why more 6-mercaptopurine?Seminars in hematology · 1991
- The clinical pharmacology of 6-mercaptopurine.European journal of clinical pharmacology · 1992
- The genetic toxicology of 6-mercaptopurine.Mutation research · 1993
- Mercaptopurine and Metabolites in Breast Milk.Breastfeeding medicine : the official journal of the Academy of Breastfeeding Medicine · 2020
- Thioguanine, mercaptopurine: their analogs and nucleosides as antimetabolites.Current pharmaceutical design · 2003
via PubMed
Wikidata facts
- Subclass of
- thiopurine
- Mass
- 152.016
- Has use
- medication
Show 7 more facts
- subject has role
- essential medicine
- found in taxon
- Allium ampeloprasum
- chemical formula
- C₅H₄N₄S
- Commons category
- Mercaptopurine
- medical condition treated
- chronic lymphocytic leukemia
- canonical SMILES
- C1=NC2=C(N1)C(=S)N=CN2
- MCN code
- 2933.59.35
via Wikidata · CC0
~10 min read
Encyclopedic overview
9 sectionsContents
- Medical uses
- Side effects
- Precautions
- Drug interactions
- Mechanisms of action
- Pharmacogenetics
- History
- References
- Further reading
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.
Excerpted from Wikipedia’s “mercaptopurine” article, available under the CC BY-SA 4.0 licence.