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CHEBI:76162 - indoprofen

ChEBI IDCHEBI:76162
ChEBI Nameindoprofen
Stars
DefinitionA 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 Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causing severe gastrointestinal bleeding.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.
Last Modified22 February 2017
SubmitterSteve
DownloadsMolfile
FormulaC17H15NO3
Net Charge0
Average Mass281.311
Monoisotopic Mass281.10519
SMILESCC(C(=O)O)c1ccc(N2Cc3ccccc3C2=O)cc1
InChIInChI=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)
InChIKeyRJMIEHBSYVWVIN-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
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.
Applications:
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
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 Relation(s)
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 isoindoles (CHEBI:24897)
indoprofen (CHEBI:76162) is a monocarboxylic acid (CHEBI:25384)
indoprofen (CHEBI:76162) is a γ-lactam (CHEBI:74222)
IUPAC Name 
2-[4-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]propanoic acid
INNs  Source
indoprofenKEGG DRUG
indoprofenumChemIDplus
indoprofeneChemIDplus
indoprofenoChemIDplus
Synonyms  Source
1-Oxo-2-(p-((alpha-methyl)carboxymethyl)phenyl)isoindolineChemIDplus
alpha-(4-(1-Oxo-2-isoindolinyl)phenyl)propionic acidChemIDplus
K 4277ChemIDplus
2-(4-(1-Carboxyethyl)phenyl)-1-isoindolinoneChemIDplus
Manual XrefsDatabases
D04530KEGG DRUG
WO2008011083Patent
IndoprofenWikipedia
NZ586198Patent
LSM-1564LINCS
1442DrugCentral
Registry NumbersSources
Reaxys:1543920Reaxys
CAS:31842-01-0KEGG DRUG
CAS:31842-01-0ChemIDplus
Citations