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CHEBI:40279 - allopurinol

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name allopurinol
ChEBI ID CHEBI:40279
Definition A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40276, CHEBI:2601
Supplier Information
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Formula C5H4N4O
Net Charge 0
Average Mass 136.11150
Monoisotopic Mass 136.039
InChI InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
InChIKey OFCNXPDARWKPPY-UHFFFAOYSA-N
SMILES Oc1ncnc2[nH]ncc12
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Role(s): antimetabolite
A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
EC 1.17.3.2 (xanthine oxidase) inhibitor
An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).
Application(s): gout suppressant
A drug that increases uric acid excretion by the kidney (uricosuric drug), decreases uric acid production (antihyperuricemic), or alleviates the pain and inflammation of acute attacks of gout.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing allopurinol (CHEBI:40279) has parent hydride 1H-pyrazolo[4,3-d]pyrimidine (CHEBI:50092)
allopurinol (CHEBI:40279) has role antimetabolite (CHEBI:35221)
allopurinol (CHEBI:40279) has role EC 1.17.3.2 (xanthine oxidase) inhibitor (CHEBI:35634)
allopurinol (CHEBI:40279) has role gout suppressant (CHEBI:35845)
allopurinol (CHEBI:40279) has role radical scavenger (CHEBI:48578)
allopurinol (CHEBI:40279) is a nucleobase analogue (CHEBI:67142)
allopurinol (CHEBI:40279) is a organic heterobicyclic compound (CHEBI:27171)
Incoming allopurinol riboside (CHEBI:74074) has functional parent allopurinol (CHEBI:40279)
IUPAC Name
1H-pyrazolo[3,4-d]pyrimidin-4-ol
Synonyms Sources
1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidin-4-one ChemIDplus
1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidine-4-one ChemIDplus
1H-Pyrazolo(3,4-d)pyrimidin-4-ol ChemIDplus
4'-Hydroxypyrazolol(3,4-d)pyrimidine ChemIDplus
4-HPP NIST Chemistry WebBook
4-Hydroxy-1H-pyrazolo(3,4-d)pyrimidine ChemIDplus
4-Hydroxy-3,4-pyrazolopyrimidine ChemIDplus
4-Hydroxypyrazolo(3,4-d)pyrimidine ChemIDplus
4-Hydroxypyrazolopyrimidine ChemIDplus
4-Hydroxypyrazolyl(3,4-d)pyrimidine ChemIDplus
4H-Pyrazolo(3,4-d)pyrimidin-4-one ChemIDplus
AL-100 ChemIDplus
Allopurinol KEGG DRUG
Allopurinolum ChemIDplus
Alopurinol ChemIDplus
Zyloprim (TN) KEGG DRUG
Database Links Databases
Allopurinol Wikipedia
D00224 KEGG DRUG
DB00437 DrugBank
LSM-5919 LINCS
View more database links
Registry Numbers Types Sources
315-30-0 CAS Registry Number ChemIDplus
315-30-0 CAS Registry Number KEGG DRUG
315-30-0 CAS Registry Number NIST Chemistry WebBook
608611 Beilstein Registry Number Beilstein
608611 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11333159 PubMed citation Europe PMC
16650385 PubMed citation Europe PMC
24395556 PubMed citation Europe PMC
24590210 PubMed citation Europe PMC
24591375 PubMed citation Europe PMC
7602118 PubMed citation Europe PMC
Last Modified
25 February 2016