ibufenac (CHEBI:76158)

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CHEBI:76158 - ibufenac

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ChEBI ID	CHEBI:76158
ChEBI Name	ibufenac
Stars
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.
Last Modified	22 February 2017
Submitter	Steve
Downloads	Molfile

Formula	C12H16O2
Net Charge	0
Average Mass	192.258
Monoisotopic Mass	192.11503
SMILES	CC(C)Cc1ccc(CC(=O)O)cc1
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

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	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. hepatotoxic agent A role played by a chemical compound exhibiting itself through the ability to induce damage to the liver in animals. non-narcotic analgesic A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
Applications:	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.

ChEBI Ontology

Outgoing Relation(s)
	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-(2-methylpropyl)phenyl]acetic acid
(4-isobutylphenyl)acetic acid

INNs	Source
ibufenac	KEGG DRUG
ibufenaco	ChemIDplus
ibufenacum	ChemIDplus

Synonyms	Source
4-(2-Methylpropyl)benzeneacetic acid	ChemIDplus
4-Isobutylphenylacetic acid	ChemIDplus
Ibunac	ChemIDplus
(p-Isobutylphenyl)acetic acid	ChemIDplus

Brand Name	Source
Dytransin	ChemIDplus

Manual Xrefs	Databases
3293	DrugCentral
D01963	KEGG DRUG
US2008014272	Patent
US2011212904	Patent
US4391814	Patent
WO2010013279	Patent

Registry Numbers	Sources
Reaxys:2046683	Reaxys
CAS:1553-60-2	ChemIDplus
CAS:1553-60-2	KEGG DRUG

Citations