allopurinol

Also known as Aloprim®, BW-56-158, BW-56158, Zyloprim®, AL-100, 4H-Pyrazolo(3,4-d)pyrimidin-4-one, 4-Hydroxypyrazolyl(3,4-d)pyrimidine, 4-Hydroxypyrazolopyrimidine

Allopurinol is a medication used to decrease high blood uric acid levels. It is specifically used to prevent gout, prevent specific types of kidney stones and for the high uric acid levels that can occur with chemotherapy. It is taken orally (by mouth) or intravenously (injected into a vein).

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 477318043
Drug.image: Allopurinol V.1.svg
Drug.image_class: skin-invert-image
Drug.width: 150
Drug.image2: Allopurinol_3d_structure.png
Drug.image_class2: bg-transparent
Drug.tradename: Zyloprim, Caplenal, Zyloric, others
Drug.MedlinePlus: a682673
Drug.DailyMedID: Allopurinol
Drug.pregnancy_AU: B2
Drug.routes_of_administration: Oral, intravenous
Drug.ATC_prefix: M04
Drug.ATC_suffix: AA01
Drug.legal_AU: S4
Drug.legal_UK: POM
Drug.legal_US: Rx-only
Drug.bioavailability: 78±20%

via Wikipedia infobox

Chemical data

Formula: C5H4N4O
Molecular weight: 136.11 g/mol
IUPAC name: 1,2-dihydropyrazolo[3,4-d]pyrimidin-4-one
SMILES: C1=C2C(=NC=NC2=O)NN1
InChIKey: OFCNXPDARWKPPY-UHFFFAOYSA-N
XLogP: -0.5
Polar surface area: 65.9 Å²
H-bond donors: 2
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

12,167 papers

What Is Allopurinol Failure and What Should We Do About It?The Journal of rheumatology · 2024
Febuxostat compared with allopurinol in patients with hyperuricemia and gout.The New England journal of medicine · 2005
Allopurinol hypersensitivity: Pathogenesis and prevention.Best practice & research. Clinical rheumatology · 2020
Allopurinol in dermatology.American journal of clinical dermatology · 2010
Allopurinol-induced DRESS syndrome.The Israel Medical Association journal : IMAJ · 2005

via PubMed

Wikidata facts

Mass: 136.038511

Show 4 more facts

chemical formula: C₅H₄N₄O
World Health Organisation international non-proprietary name: allopurinol
canonical SMILES: C1=C2C(=NC=NC2=O)NN1
Commons category: Allopurinol

Sources (5)

via Wikidata · CC0

~11 min read

Article

20 sections

Contents

Medical uses
Gout
Tumor lysis syndrome
Inflammatory bowel disease
Psychiatric disorders
Cardiovascular disease
Veterinary use
Side effects
Drug interactions
Pharmacology
Mechanism of action
Pharmacogenetics
History
Society and culture
Formulations
Brands
See also
References
Further reading
External links

Common side effects when used orally include itchiness and rash. Common side effects when used by injection include vomiting and kidney problems. While not recommended historically, starting allopurinol during an attack of gout appears to be safe. In those already on the medication, it should be continued even during an acute gout attack. While use during pregnancy does not appear to result in harm, this use has not been well studied. Allopurinol is in the xanthine oxidase inhibitor family of medications.