CHEBI:32243 - tolfenamic acid

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ChEBI Name tolfenamic acid
ChEBI ID CHEBI:32243
Definition An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 3-chloro-2-methylphenyl group. Tolfenamic acid is used specifically for relieving the pain of migraine. It also shows anticancer activity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C14H12ClNO2
Net Charge 0
Average Mass 261.70400
Monoisotopic Mass 261.05566
InChI InChI=1S/C14H12ClNO2/c1-9-11(15)6-4-8-12(9)16-13-7-3-2-5-10(13)14(17)18/h2-8,16H,1H3,(H,17,18)
InChIKey YEZNLOUZAIOMLT-UHFFFAOYSA-N
SMILES Cc1c(Cl)cccc1Nc1ccccc1C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC 2.7.1.33 (pantothenate kinase) inhibitor
An EC 2.7.1.* (phosphotransferases with an alcohol group as acceptor) inhibitor that interferes with the action of pantothenate kinase (EC 2.7.1.33).
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.
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ChEBI Ontology
Outgoing tolfenamic acid (CHEBI:32243) has functional parent anthranilic acid (CHEBI:30754)
tolfenamic acid (CHEBI:32243) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
tolfenamic acid (CHEBI:32243) has role EC 2.7.1.33 (pantothenate kinase) inhibitor (CHEBI:77194)
tolfenamic acid (CHEBI:32243) has role non-narcotic analgesic (CHEBI:35481)
tolfenamic acid (CHEBI:32243) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
tolfenamic acid (CHEBI:32243) is a aminobenzoic acid (CHEBI:22495)
tolfenamic acid (CHEBI:32243) is a organochlorine compound (CHEBI:36683)
tolfenamic acid (CHEBI:32243) is a secondary amino compound (CHEBI:50995)
IUPAC Name
2-[(3-chloro-2-methylphenyl)amino]benzoic acid
INNs Sources
acide tolfénamique WHO MedNet
ácido tolfenámico WHO MedNet
acidum tolfenamicum ChemIDplus
tolfenamic acid KEGG DRUG
Synonyms Sources
N-(2-Methyl-3-chlorophenyl)anthranilic acid ChemIDplus
N-(3-Chloro-2-methylphenyl)anthranilic acid ChemIDplus
N-(3-Chloro-o-tolyl)-anthranilic acid ChemIDplus
Manual Xrefs Databases
1874 VSDB
2698 DrugCentral
D01183 KEGG DRUG
LSM-5612 LINCS
Tolfenamic_acid Wikipedia
US2003060465 Patent
View more database links
Registry Numbers Types Sources
13710-19-5 CAS Registry Number ChemIDplus
13710-19-5 CAS Registry Number KEGG DRUG
657821 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017