CHEBI:76158 - ibufenac

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ChEBI Name ibufenac
ChEBI ID CHEBI:76158
Definition A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a 4-isobutylphenyl group. Although it was shown to be effective in treatment of rheumatoid arthritis, the clinical use of ibufenac was discontinued due to hepatotoxic side-effects.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C12H16O2
Net Charge 0
Average Mass 192.25420
Monoisotopic Mass 192.11503
InChI InChI=1S/C12H16O2/c1-9(2)7-10-3-5-11(6-4-10)8-12(13)14/h3-6,9H,7-8H2,1-2H3,(H,13,14)
InChIKey CYWFCPPBTWOZSF-UHFFFAOYSA-N
SMILES CC(C)Cc1ccc(CC(O)=O)cc1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
hepatotoxic agent
A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor
A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
Application(s): 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.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ibufenac (CHEBI:76158) has functional parent acetic acid (CHEBI:15366)
ibufenac (CHEBI:76158) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
ibufenac (CHEBI:76158) has role hepatotoxic agent (CHEBI:50908)
ibufenac (CHEBI:76158) has role non-narcotic analgesic (CHEBI:35481)
ibufenac (CHEBI:76158) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
ibufenac (CHEBI:76158) is a monocarboxylic acid (CHEBI:25384)
IUPAC Names
(4-isobutylphenyl)acetic acid
[4-(2-methylpropyl)phenyl]acetic acid
INNs Sources
ibufenac KEGG DRUG
ibufenaco ChemIDplus
ibufenacum ChemIDplus
Synonyms Sources
(p-Isobutylphenyl)acetic acid ChemIDplus
4-(2-Methylpropyl)benzeneacetic acid ChemIDplus
4-Isobutylphenylacetic acid ChemIDplus
Ibunac ChemIDplus
Brand Name Source
Dytransin ChemIDplus
Manual Xrefs Databases
3293 DrugCentral
D01963 KEGG DRUG
US2008014272 Patent
US2011212904 Patent
US4391814 Patent
WO2010013279 Patent
View more database links
Registry Numbers Types Sources
1553-60-2 CAS Registry Number KEGG DRUG
1553-60-2 CAS Registry Number ChemIDplus
2046683 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
1479559 PubMed citation Europe PMC
16456879 PubMed citation Europe PMC
21128314 PubMed citation Europe PMC
2585272 PubMed citation Europe PMC
3215965 PubMed citation Europe PMC
5329891 PubMed citation Europe PMC
5657238 PubMed citation Europe PMC
5748163 PubMed citation Europe PMC
5752436 PubMed citation Europe PMC
5807207 PubMed citation Europe PMC
687781 PubMed citation Europe PMC
7587932 PubMed citation Europe PMC
9061203 PubMed citation Europe PMC
Last Modified
22 February 2017