indoprofen (CHEBI:76162)

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ChEBI Name	indoprofen

ChEBI ID	CHEBI:76162

Definition	A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(1-oxo-1,3-dihydroisoindol-2-yl)phenyl group. Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causing severe gastrointestinal bleeding. It has been subsequently found to increase production of the survival motor neuron protein.

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

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Formula

C17H15NO3

Net Charge

Average Mass

281.30590

Monoisotopic Mass

281.10519

InChI

InChI=1S/C17H15NO3/c1-11(17(20)21)12-6-8-14(9-7-12)18-10-13-4-2-3-5-15(13)16(18)19/h2-9,11H,10H2,1H3,(H,20,21)

InChIKey

RJMIEHBSYVWVIN-UHFFFAOYSA-N

SMILES

CC(C(O)=O)c1ccc(cc1)N1Cc2ccccc2C1=O

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):	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. non-narcotic analgesic A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.

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.

ChEBI Ontology
Outgoing	indoprofen (CHEBI:76162) has functional parent propionic acid (CHEBI:30768) indoprofen (CHEBI:76162) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544) indoprofen (CHEBI:76162) has role non-narcotic analgesic (CHEBI:35481) indoprofen (CHEBI:76162) has role non-steroidal anti-inflammatory drug (CHEBI:35475) indoprofen (CHEBI:76162) is a γ-lactam (CHEBI:74222) indoprofen (CHEBI:76162) is a isoindoles (CHEBI:24897) indoprofen (CHEBI:76162) is a monocarboxylic acid (CHEBI:25384)

IUPAC Name

2-[4-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]propanoic acid

Synonyms	Sources
1-Oxo-2-(p-((alpha-methyl)carboxymethyl)phenyl)isoindoline	ChemIDplus
2-(4-(1-Carboxyethyl)phenyl)-1-isoindolinone	ChemIDplus
alpha-(4-(1-Oxo-2-isoindolinyl)phenyl)propionic acid	ChemIDplus
K 4277	ChemIDplus

Last Modified

22 February 2017