flunoxaprofen (CHEBI:76154)

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ChEBI Name	flunoxaprofen

ChEBI ID	CHEBI:76154

Definition	A monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group (the S-enantiomer). Although it was shown to be effective in treatment of rheumatoid arthritis and osteoarthritis, the clinical use of flunoxaprofen was discontinued due to possible hepatotoxic side-effects.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C16H12FNO3

Net Charge

Average Mass

285.26980

Monoisotopic Mass

285.08012

InChI

InChI=1S/C16H12FNO3/c1-9(16(19)20)11-4-7-14-13(8-11)18-15(21-14)10-2-5-12(17)6-3-10/h2-9H,1H3,(H,19,20)/t9-/m0/s1

InChIKey

ARPYQKTVRGFPIS-VIFPVBQESA-N

SMILES

C[C@H](C(O)=O)c1ccc2oc(nc2c1)-c1ccc(F)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):	hepatotoxic agent A role played by a chemical compound exhibiting itself through the ability to induce damage to the liver in animals. protein kinase C agonist An agonist that selectively binds to and activates a protein kinase C receptor

Application(s):	antirheumatic drug A drug used to treat rheumatoid arthritis. 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.

ChEBI Ontology
Outgoing	flunoxaprofen (CHEBI:76154) has functional parent propionic acid (CHEBI:30768) flunoxaprofen (CHEBI:76154) has role antirheumatic drug (CHEBI:35842) flunoxaprofen (CHEBI:76154) has role hepatotoxic agent (CHEBI:50908) flunoxaprofen (CHEBI:76154) has role non-steroidal anti-inflammatory drug (CHEBI:35475) flunoxaprofen (CHEBI:76154) has role protein kinase C agonist (CHEBI:64018) flunoxaprofen (CHEBI:76154) is a 1,3-benzoxazoles (CHEBI:51548) flunoxaprofen (CHEBI:76154) is a monocarboxylic acid (CHEBI:25384) flunoxaprofen (CHEBI:76154) is a organofluorine compound (CHEBI:37143)

IUPAC Name

(2S)-2-[2-(4-fluorophenyl)-1,3-benzoxazol-5-yl]propanoic acid

Synonyms	Sources
(+)-2-(p-Fluorophenyl)-alpha-methyl-5-benzoxazoleacetic acid	ChemIDplus
(S)-(+)-Flunoxaprofen	ChemIDplus
(S)-2-(4-Fluorophenyl)-alpha-methyl-5-benzoxazoleacetic acid	ChemIDplus

Last Modified

22 February 2017