FLUFENAMIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H10F3NO2
Molecular Weight	281.2299
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CC=CC=C1NC2=CC(=CC=C2)C(F)(F)F

InChI

InChIKey=LPEPZBJOKDYZAD-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C14H10F3NO2
Molecular Weight	281.2299
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB02266
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/flufenamic-acid.html | https://www.ncbi.nlm.nih.gov/pubmed/22263837 | https://www.ncbi.nlm.nih.gov/pubmed/23454516 | https://www.ncbi.nlm.nih.gov/pubmed/23356979 | https://www.ncbi.nlm.nih.gov/pubmed/26384458

Flufenamic acid is a member of the anthranilic acid derivatives class of NSAID drugs. Like other members of the class, it is a COX inhibitor and prevents the formation of prostaglandins. Flufenamic acid is known to bind to and reduce the activity of prostaglandin F synthase and activate TRPC6.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22263837	Inhibitor 8504		16.0 nM [IC50]
Cyclooxygenase-1 131 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23454516	Inhibitor 8504		3.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Soft tissue Injuries 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2076623	Primary		Phase III 665	Unknown Approved Use Unknown
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4895007	Primary		Not Provided 511	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
7.85 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400059_1141004F1086_1_009_1F.pdf#page=15	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		FLUFENAMIC ACID blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
47.54 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400059_1141004F1086_1_009_1F.pdf#page=15	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		FLUFENAMIC ACID blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h REVIEW https://www.sciencedirect.com/science/article/pii/S0099542808602683	single, oral		FLUFENAMIC ACID plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg 4 times / day multiple, oral Studied dose Dose: 100 mg, 4 times / day Route: oral Route: multiple Dose: 100 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7021261/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7021261/	Disc. AE: Cramps leg, Nausea... AEs leading to discontinuation/dose reduction: Cramps leg (2.9%) Nausea (2.9%) Headache (2.9%) Sources: https://pubmed.ncbi.nlm.nih.gov/7021261/
200 mg 3 times / day multiple, oral Studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/75392/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/75392/	Sources: https://pubmed.ncbi.nlm.nih.gov/75392/

AEs

AE	Significance	Dose	Population
Cramps leg	2.9% Disc. AE	100 mg 4 times / day multiple, oral Studied dose Dose: 100 mg, 4 times / day Route: oral Route: multiple Dose: 100 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7021261/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7021261/
Headache	2.9% Disc. AE	100 mg 4 times / day multiple, oral Studied dose Dose: 100 mg, 4 times / day Route: oral Route: multiple Dose: 100 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7021261/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7021261/
Nausea	2.9% Disc. AE	100 mg 4 times / day multiple, oral Studied dose Dose: 100 mg, 4 times / day Route: oral Route: multiple Dose: 100 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7021261/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7021261/

PubMed

Title	Date	PubMed
Compounds exhibiting selective efficacy for different beta subunits of human recombinant gamma-aminobutyric acid A receptors.	2004-11	15210837
Analysis of slow hyperpolarizing potentials in frog taste cells induced by glossopharyngeal nerve stimulation.	2004-10	15466810
Flufenamic acid is a pH-dependent antagonist of TRPM2 channels.	2004-09	15275834
Topical NSAIDs for chronic musculoskeletal pain: systematic review and meta-analysis.	2004-08-19	15317652
Synthesis of new 2-arylamino-6-trifluoromethylpyridine-3-carboxylic acid derivatives and investigation of their analgesic activity.	2004-08-01	15246093
Activation of a calcium-activated cation current during epileptiform discharges and its possible role in sustaining seizure-like events in neocortical slices.	2004-08	15277598
Discovery of glycine hydrazide pore-occluding CFTR inhibitors: mechanism, structure-activity analysis, and in vivo efficacy.	2004-08	15277574
Analysis of ketorolac and its related impurities by capillary electrochromatography.	2004-07-30	15354451
Selective binding to transthyretin and tetramer stabilization in serum from patients with familial amyloidotic polyneuropathy by an iodinated diflunisal derivative.	2004-07-15	15080795
Differential contribution of pacemaker properties to the generation of respiratory rhythms during normoxia and hypoxia.	2004-07-08	15233921
Substance P induces inward current and regulates pacemaker currents through tachykinin NK1 receptor in cultured interstitial cells of Cajal of murine small intestine.	2004-07-08	15219818
Functional characterization of a Ca(2+)-activated non-selective cation channel in human atrial cardiomyocytes.	2004-07-01	15121803
Effects of various vehicles on the penetration of flufenamic acid into human skin.	2004-07	15207545
Inverse gene expression patterns for macrophage activating hepatotoxicants and peroxisome proliferators in rat liver.	2004-06-01	15135310
Native state stabilization by NSAIDs inhibits transthyretin amyloidogenesis from the most common familial disease variants.	2004-05	14968122
Micellar electrokinetic chromatography for the simultaneous determination of ketorolac tromethamine and its impurities. Multivariate optimization and validation.	2004-04-02	15065803
Enzymology of a carbonyl reduction clearance pathway for the HIV integrase inhibitor, S-1360: role of human liver cytosolic aldo-keto reductases.	2004-03-15	15013815
Human cytosolic 3alpha-hydroxysteroid dehydrogenases of the aldo-keto reductase superfamily display significant 3beta-hydroxysteroid dehydrogenase activity: implications for steroid hormone metabolism and action.	2004-03-12	14672942
Crystal structures of prostaglandin D(2) 11-ketoreductase (AKR1C3) in complex with the nonsteroidal anti-inflammatory drugs flufenamic acid and indomethacin.	2004-03-01	14996743
Transient receptor potential-like channels mediate metabotropic glutamate receptor EPSCs in rat dopamine neurones.	2004-03-01	14724196
Mechanism of apoptosis induced by diazoxide, a K+ channel opener, in HepG2 human hepatoma cells.	2004-03	15089036
Calcium-dependent subthreshold oscillations determine bursting activity induced by N-methyl-D-aspartate in rat subthalamic neurons in vitro.	2004-03	15016087
Evidence of a role for TRPC channels in VEGF-mediated increased vascular permeability in vivo.	2004-03	14551041
Detergents profoundly affect inhibitor potencies against both cyclo-oxygenase isoforms.	2004-02-01	14510637
Amyloidosis: a clinico-pathophysiological synopsis.	2004-02	15036205
Epigallocatechin-3-gallate increases intracellular [Ca2+] in U87 cells mainly by influx of extracellular Ca2+ and partly by release of intracellular stores.	2004-02	14647974
Interactions of benzylpenicillin and non-steroidal anti-inflammatory drugs with the sodium-dependent dicarboxylate transporter NaDC-3.	2004	15319545
Diclofenac inhibition of sodium currents in rat dorsal root ganglion neurons.	2003-11-28	14604780
In situ monitoring of wet granulation using online X-ray powder diffraction.	2003-11	14661932
Pharmacological sensitivity of ATP release triggered by photoliberation of inositol-1,4,5-trisphosphate and zero extracellular calcium in brain endothelial cells.	2003-11	14502560
Fundamental role of ClC-3 in volume-sensitive Cl- channel function and cell volume regulation in AGS cells.	2003-11	12842831
Involvement of transient receptor potential-like channels in responses to mGluR-I activation in midbrain dopamine neurons.	2003-10	14622174
Role of Ca2+-activated Cl- channels in the mechanism of apoptosis induced by cyclosporin A in a human hepatoma cell line.	2003-09-19	12951048
[Characterization of pacemaking currents in cultured interstitial cells of Cajal from mice small intestine].	2003-08	14532716
Fulfenamic acid sensitive, Ca(2+)-dependent inward current induced by nicotinic acetylcholine receptors in dopamine neurons.	2003-08	12871768
Antimonial-induced increase in intracellular Ca2+ through non-selective cation channels in the host and the parasite is responsible for apoptosis of intracellular Leishmania donovani amastigotes.	2003-07-04	12707265
Ca(2+)- and voltage-dependent gating of Ca(2+)- and ATP-sensitive cationic channels in brain capillary endothelium.	2003-07	12829486
Non-steroidal anti-inflammatory drugs affect the methotrexate transport in IEC-6 cells.	2003-06-13	12759138
Calcium-activated cationic channel in rat sensory neurons.	2003-06	12823470
Thiram and ziram stimulate non-selective cation channel and induce apoptosis in PC12 cells.	2003-06	12782107
Closure of gap junction channels by arylaminobenzoates.	2003-06	12761350
Comprehensive study of the luminescent properties and lifetimes of Eu(3+) and Tb(3+) chelated with various ligands in aqueous solutions: influence of the synergic agent, the surfactant and the energy level of the ligand triplet.	2003-06	12736069
Functional hemichannels in astrocytes: a novel mechanism of glutamate release.	2003-05-01	12736329
Differential connexin expression, gap junction intercellular coupling, and hemichannel formation in NT2/D1 human neural progenitors and terminally differentiated hNT neurons.	2003-05-01	12692906
A novel, voltage-dependent nonselective cation current activated by insulin in guinea pig isolated ventricular myocytes.	2003-04-18	12637365
The history of tocolysis.	2003-04	12763121
Low mortality rates related to respiratory virus infections after bone marrow transplantation.	2003-04	12692610
TRPC5 as a candidate for the nonselective cation channel activated by muscarinic stimulation in murine stomach.	2003-04	12631560
Effects of non-steroidal anti-inflammatory drugs on the methotrexate transport in rat small intestine.	2003-01	12608463
Allergic contact dermatitis from etofenamate without cross-sensitization to other anthranilic acid derivatives.	2003	12771478

Patents

Sample Use Guides

In Vivo Use Guide

Flufenamic acid, (3% gel) were used 2 to 6 times daily, as required

Route of Administration: Topical

In Vitro Use Guide

Relaxation of phenylephrine-precontracted arteries by increasing doses of Flufenamic acid (FFA). After a normalization period, blood vessels were allowed to equilibrate for 30 min. Each experiment started with two Kþ-induced contractions separated by a washout. Both large and small femoral arteries were exposed to sub-maximal phenylephrine dose(10 mM) and FFA were applied in increasing concentrations 0.01-10mkM in 2–3 min interval

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:41:53 GMT 2025` Edited by `admin` on `Mon Mar 31 18:41:53 GMT 2025`
Record UNII	60GCX7Y6BH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARLEF

Preferred Name

English

FLUFENAMIC ACID

Official Name

English

FLUFENAMIC ACID [MART.]

Common Name

English

CN-27554

Code

English

Flufenamic acid [WHO-DD]

Common Name

English

N-(.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-M-TOLYL)ANTHRANILIC ACID

Systematic Name

English

CI-440

Code

English

ETOFENAMATE IMPURITY A [EP IMPURITY]

Common Name

English

CI 440

Code

English

FLUFENAMIC ACID [JAN]

Common Name

English

FLUFENAMIC ACID [USAN]

Common Name

English

CN-27,554

Code

English

flufenamic acid [INN]

Common Name

English

NSC-219007

Code

English

INF-1837

Code

English

NSC-82699

Code

English

FLUFENAMATE

Common Name

English

BENZOIC ACID, 2-((3-(TRIFLUOROMETHYL)PHENYL)AMINO)-

Common Name

English

2-[[3-(trifluoromethyl)phenyl]amino]benzoic acid

Systematic Name

English

FLUFENAMIC ACID [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

M01AG03