CHEBI:76172 - loxoprofen

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ChEBI Name loxoprofen
ChEBI ID CHEBI:76172
Definition A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-[(2-oxocyclopentyl)methyl]phenyl group. A prodrug that is rapidly converted into its active trans-alcohol metabolite following oral administration.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H18O3
Net Charge 0
Average Mass 246.30160
Monoisotopic Mass 246.12559
InChI InChI=1S/C15H18O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13H,2-4,9H2,1H3,(H,17,18)
InChIKey YMBXTVYHTMGZDW-UHFFFAOYSA-N
SMILES CC(C(O)=O)c1ccc(CC2CCCC2=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.
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.
antipyretic
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing loxoprofen (CHEBI:76172) has functional parent propionic acid (CHEBI:30768)
loxoprofen (CHEBI:76172) has role antipyretic (CHEBI:35493)
loxoprofen (CHEBI:76172) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
loxoprofen (CHEBI:76172) has role non-narcotic analgesic (CHEBI:35481)
loxoprofen (CHEBI:76172) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
loxoprofen (CHEBI:76172) has role prodrug (CHEBI:50266)
loxoprofen (CHEBI:76172) is a cyclopentanones (CHEBI:36140)
loxoprofen (CHEBI:76172) is a monocarboxylic acid (CHEBI:25384)
loxoprofen (CHEBI:76172) is conjugate acid of loxoprofen(1−) (CHEBI:76199)
Incoming (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid (CHEBI:76204) has functional parent loxoprofen (CHEBI:76172)
loxoprofen(1−) (CHEBI:76199) is conjugate base of loxoprofen (CHEBI:76172)
IUPAC Name
2-{4-[(2-oxocyclopentyl)methyl]phenyl}propanoic acid
INNs Sources
loxoprofen KEGG DRUG
loxoprofene ChemIDplus
loxoprofeno ChemIDplus
loxoprofenum ChemIDplus
Synonym Source
(±)-((2-oxocyclopentyl)methyl)hydratropic acid ChemIDplus
Manual Xrefs Databases
1615 DrugCentral
D08149 KEGG DRUG
EP1767218 Patent
HMDB0041920 HMDB
Loxoprofen Wikipedia
LSM-5054 LINCS
WO2008020270 Patent
View more database links
Registry Numbers Types Sources
2860055 Reaxys Registry Number Reaxys
68767-14-6 CAS Registry Number ChemIDplus
68767-14-6 CAS Registry Number KEGG DRUG
Last Modified
28 April 2020