CHEBI:31225 - antipyrine

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ChEBI Name antipyrine
Definition A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C11H12N2O
Net Charge 0
Average Mass 188.22580
Monoisotopic Mass 188.09496
InChI InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
SMILES Cc1cc(=O)n(-c2ccccc2)n1C
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): cyclooxygenase 3 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 3.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
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ChEBI Ontology
Outgoing antipyrine (CHEBI:31225) has role antipyretic (CHEBI:35493)
antipyrine (CHEBI:31225) has role cyclooxygenase 3 inhibitor (CHEBI:73263)
antipyrine (CHEBI:31225) has role environmental contaminant (CHEBI:78298)
antipyrine (CHEBI:31225) has role non-narcotic analgesic (CHEBI:35481)
antipyrine (CHEBI:31225) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
antipyrine (CHEBI:31225) has role xenobiotic (CHEBI:35703)
antipyrine (CHEBI:31225) is a pyrazolone (CHEBI:83328)
Incoming 1-(4-sulfophenyl)-3-carboxy-4-amino-5-oxopyrazole (CHEBI:59995) has functional parent antipyrine (CHEBI:31225)
3-hydroxymethylantipyrine (CHEBI:145210) has functional parent antipyrine (CHEBI:31225)
4-(5-carboxypentanamido)antipyrine (CHEBI:59041) has functional parent antipyrine (CHEBI:31225)
4-(methylamino)antipyrine (CHEBI:73261) has functional parent antipyrine (CHEBI:31225)
4-acetamidoantipyrine (CHEBI:83513) has functional parent antipyrine (CHEBI:31225)
4-aminoantipyrine (CHEBI:59026) has functional parent antipyrine (CHEBI:31225)
metamizole (CHEBI:62088) has functional parent antipyrine (CHEBI:31225)
propyphenazone (CHEBI:135538) has functional parent antipyrine (CHEBI:31225)
INNs Sources
fenazona WHO MedNet
phénazone WHO MedNet
phenazone KEGG DRUG
phenazonum WHO MedNet
Synonyms Sources
1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one ChemIDplus
2,3-Dimethyl-1-phenyl-5-pyrazolone ChemIDplus
Antipyrine KEGG DRUG
Manual Xrefs Databases
861 DrugCentral
Antipyrine Wikipedia
DB01435 DrugBank
HMDB0015503 HMDB
View more database links
Registry Numbers Types Sources
157775 Beilstein Registry Number Beilstein
157775 Reaxys Registry Number Reaxys
60-80-0 CAS Registry Number ChemIDplus
60-80-0 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
24345239 PubMed citation Europe PMC
25038548 PubMed citation Europe PMC
25435228 PubMed citation Europe PMC
25631541 PubMed citation Europe PMC
26703262 PubMed citation Europe PMC
3425858 PubMed citation Europe PMC
Last Modified
07 February 2022
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag