CHEBI:42638 - flufenamic acid

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ChEBI Name flufenamic acid
ChEBI ID CHEBI:42638
Definition An aromatic amino acid consisting of anthranilic acid carrying an N-(trifluoromethyl)phenyl substituent. An analgesic and anti-inflammatory, it is used in rheumatic disorders.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42631, CHEBI:31619
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Formula C14H10F3NO2
Net Charge 0
Average Mass 281.22995
Monoisotopic Mass 281.066
InChI InChI=1S/C14H10F3NO2/c15-14(16,17)9-4-3-5-10(8-9)18-12-7-2-1-6-11(12)13(19)20/h1-8,18H,(H,19,20)
InChIKey LPEPZBJOKDYZAD-UHFFFAOYSA-N
SMILES OC(=O)c1ccccc1Nc1cccc(c1)C(F)(F)F
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 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.
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.
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ChEBI Ontology
Outgoing flufenamic acid (CHEBI:42638) has functional parent (trifluoromethyl)benzene (CHEBI:36810)
flufenamic acid (CHEBI:42638) has functional parent anthranilic acid (CHEBI:30754)
flufenamic acid (CHEBI:42638) has functional parent diphenylamine (CHEBI:4640)
flufenamic acid (CHEBI:42638) has role antipyretic (CHEBI:35493)
flufenamic acid (CHEBI:42638) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
flufenamic acid (CHEBI:42638) has role non-narcotic analgesic (CHEBI:35481)
flufenamic acid (CHEBI:42638) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
flufenamic acid (CHEBI:42638) is a aromatic amino acid (CHEBI:33856)
flufenamic acid (CHEBI:42638) is a organofluorine compound (CHEBI:37143)
flufenamic acid (CHEBI:42638) is conjugate acid of flufenamate (CHEBI:520819)
Incoming flufenamate (CHEBI:520819) is conjugate base of flufenamic acid (CHEBI:42638)
IUPAC Name
2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid
INNs Sources
acide flufénamique ChemIDplus
ácido flufenámico ChemIDplus
acidum flufenamicum ChemIDplus
flufenamic acid ChemIDplus
Synonyms Sources
2-[3-(trifluoromethyl)anilino]benzoic acid NIST Chemistry WebBook
2-[[3-(TRIFLUOROMETHYL)PHENYL]AMINO] BENZOIC ACID PDBeChem
3'-trifluoromethyldiphenylamine-2-carboxylic acid ChemIDplus
FFA KEGG COMPOUND
Flufenamic acid KEGG COMPOUND
Flufenaminsäure ChEBI
fluphenamic acid ChemIDplus
N-(3-trifluoromethylphenyl)anthranilic acid ChemIDplus
N-(α,α,α-trifluoro-m-tolyl)anthranilic acid NIST Chemistry WebBook
Brand Name Source
Achless ChemIDplus
Database Links Databases
1193 DrugCentral
C13038 KEGG COMPOUND
D01581 KEGG DRUG
DB02266 DrugBank
FLF PDBeChem
Flufenamic_acid Wikipedia
LSM-2973 LINCS
View more database links
Registry Numbers Types Sources
1327188 Gmelin Registry Number Gmelin
1996069 Beilstein Registry Number ChemIDplus
1996069 Reaxys Registry Number Reaxys
530-78-9 CAS Registry Number NIST Chemistry WebBook
530-78-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11093589 PubMed citation Europe PMC
15275834 PubMed citation Europe PMC
18436631 PubMed citation Europe PMC
20589945 PubMed citation Europe PMC
28166217 PubMed citation Europe PMC
Last Modified
15 June 2017