File:Allopurinol_V.1.svg · Wikimedia Commons · See Wikimedia Commons
allopurinol
Sign in to saveAlso 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).
OverviewAI-generated
Allopurinol is a chemical compound with the formula C₅H₄N₄O. Its IUPAC name is 1,2-dihydropyrazolo[3,4-d]pyrimidin-4-one. The substance has a molecular mass of 136.038511 and a weight of 136.11. It possesses a charge of 0, an xlogp value of -0.5, and a topological polar surface area of 65.9. The molecule contains two hydrogen bond donors and two hydrogen bond acceptors.
The canonical SMILES notation for allopurinol is C1=C2C(=NC=NC2=O)NN1. It is associated with a Commons category titled "Allopurinol." In scientific literature, the term appears in 12167 PubMed entries. The compound is also referenced by 296 other encyclopedia articles.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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 Ų
- 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
~11 min read
Encyclopedic overview
20 sectionsContents
- 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
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).
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.
Excerpted from Wikipedia’s “allopurinol” article, available under the CC BY-SA 4.0 licence.