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Details

Stereochemistry ACHIRAL
Molecular Formula C14H10F3NO2
Molecular Weight 281.2304
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUFENAMIC ACID

SMILES

c1ccc(c(c1)C(=O)O)Nc2cccc(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

Description
Curator's Comment:: 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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Effects of some pharmacological agents on the survival of unipedicled venous flaps: an experimental study.
2001
Comparative study of etofenamate and fentanyl for outpatient extracorporeal shockwave lithotripsy.
2001 Dec
Non-selective cation channels and oxidative stress-induced cell swelling.
2002
An improved resazurin-based cytotoxicity assay for hepatic cells.
2002
Effects of anion and cation inhibitors and carbonic anhydrase inhibitors upon the activity of the gypsy moth (Lepidoptera: Lymantriidae) nucleo-polyhedrovirus.
2002 Apr
Chloride transport in rabbit esophageal epithelial cells.
2002 Apr
Correlation between stratum corneum/water-partition coefficient and amounts of flufenamic acid penetrated into the stratum corneum.
2002 Aug
Anti-inflammatory fibrosis suppression in threatened trabeculectomy bleb failure produces good long term control of intraocular pressure without risk of sight threatening complications.
2002 Dec
Flufenamic acid blocks depolarizing afterpotentials and phasic firing in rat supraoptic neurones.
2002 Dec 1
TRPC6 is a candidate channel involved in receptor-stimulated cation currents in A7r5 smooth muscle cells.
2002 Feb
Flufenamic acid: growth modulating effects on human aortic smooth muscle cells in vitro.
2002 Jan
Inhibition of gap junction hemichannels by chloride channel blockers.
2002 Jan 15
Human skin penetration of flufenamic acid: in vivo/in vitro correlation (deeper skin layers) for skin samples from the same subject.
2002 Mar
Synthesis, stability and in vitro dermal evaluation of aminocarbonyloxymethyl esters as prodrugs of carboxylic acid agents.
2002 Mar
Intercellular calcium signaling in astrocytes via ATP release through connexin hemichannels.
2002 Mar 22
A validated high-performance liquid chromatographic method for the determination of glibenclamide in human plasma and its application to pharmacokinetic studies.
2002 May 15
ATP release from human airway epithelial cells studied using a capillary cell culture system.
2002 Nov 15
Renal papillary necrosis.
2002 Nov-Dec
Fenamate-induced enhancement of heterologously expressed HERG currents in Xenopus oocytes.
2002 Oct 11
Androgen receptors in prostate cancer.
2002 Sep
Allergic contact dermatitis from etofenamate without cross-sensitization to other anthranilic acid derivatives.
2003
The history of tocolysis.
2003 Apr
TRPC5 as a candidate for the nonselective cation channel activated by muscarinic stimulation in murine stomach.
2003 Apr
A novel, voltage-dependent nonselective cation current activated by insulin in guinea pig isolated ventricular myocytes.
2003 Apr 18
Fulfenamic acid sensitive, Ca(2+)-dependent inward current induced by nicotinic acetylcholine receptors in dopamine neurons.
2003 Aug
Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone.
2003 Feb 1
Effects of non-steroidal anti-inflammatory drugs on the methotrexate transport in rat small intestine.
2003 Jan
Storage and release of ATP from astrocytes in culture.
2003 Jan 10
Ca(2+)- and voltage-dependent gating of Ca(2+)- and ATP-sensitive cationic channels in brain capillary endothelium.
2003 Jul
Calcium-activated cationic channel in rat sensory neurons.
2003 Jun
Thiram and ziram stimulate non-selective cation channel and induce apoptosis in PC12 cells.
2003 Jun
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 Jun
Non-steroidal anti-inflammatory drugs affect the methotrexate transport in IEC-6 cells.
2003 Jun 13
Inactivation of creatine kinase during the interaction of mefenamic acid with horseradish peroxidase and hydrogen peroxide: participation by the mefenamic acid radical.
2003 Mar 14
Functional hemichannels in astrocytes: a novel mechanism of glutamate release.
2003 May 1
Pharmacological sensitivity of ATP release triggered by photoliberation of inositol-1,4,5-trisphosphate and zero extracellular calcium in brain endothelial cells.
2003 Nov
Fundamental role of ClC-3 in volume-sensitive Cl- channel function and cell volume regulation in AGS cells.
2003 Nov
Involvement of transient receptor potential-like channels in responses to mGluR-I activation in midbrain dopamine neurons.
2003 Oct
Role of Ca2+-activated Cl- channels in the mechanism of apoptosis induced by cyclosporin A in a human hepatoma cell line.
2003 Sep 19
Micellar electrokinetic chromatography for the simultaneous determination of ketorolac tromethamine and its impurities. Multivariate optimization and validation.
2004 Apr 2
Amyloidosis: a clinico-pathophysiological synopsis.
2004 Feb
Epigallocatechin-3-gallate increases intracellular [Ca2+] in U87 cells mainly by influx of extracellular Ca2+ and partly by release of intracellular stores.
2004 Feb
Detergents profoundly affect inhibitor potencies against both cyclo-oxygenase isoforms.
2004 Feb 1
Functional characterization of a Ca(2+)-activated non-selective cation channel in human atrial cardiomyocytes.
2004 Jul 1
Selective binding to transthyretin and tetramer stabilization in serum from patients with familial amyloidotic polyneuropathy by an iodinated diflunisal derivative.
2004 Jul 15
Analysis of ketorolac and its related impurities by capillary electrochromatography.
2004 Jul 30
Inverse gene expression patterns for macrophage activating hepatotoxicants and peroxisome proliferators in rat liver.
2004 Jun 1
Crystal structures of prostaglandin D(2) 11-ketoreductase (AKR1C3) in complex with the nonsteroidal anti-inflammatory drugs flufenamic acid and indomethacin.
2004 Mar 1
Enzymology of a carbonyl reduction clearance pathway for the HIV integrase inhibitor, S-1360: role of human liver cytosolic aldo-keto reductases.
2004 Mar 15
Analysis of slow hyperpolarizing potentials in frog taste cells induced by glossopharyngeal nerve stimulation.
2004 Oct
Patents

Sample Use Guides

Flufenamic acid, (3% gel) were used 2 to 6 times daily, as required
Route of Administration: Topical
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
Name Type Language
FLUFENAMIC ACID
INN   JAN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
FLUFENAMIC ACID [MART.]
Common Name English
CN-27554
Code English
ARLEF
Brand Name English
N-(.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-M-TOLYL)ANTHRANILIC ACID
Systematic Name English
CI-440
Code 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
FLUFENAMIC ACID [WHO-DD]
Common Name English
FLUFENAMIC ACID [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC M01AG03
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
WHO-VATC QM01AG03
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
Code System Code Type Description
MESH
D005439
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
PUBCHEM
3371
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
NCI_THESAURUS
C166882
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
RXCUI
618272
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
ALTERNATIVE
EVMPD
SUB07686MIG
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
INN
1495
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
CAS
530-78-9
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
FDA UNII
60GCX7Y6BH
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
WIKIPEDIA
FLUFENAMIC ACID
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
RXCUI
4453
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-494-1
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
MERCK INDEX
M5433
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY Merck Index
EPA CompTox
530-78-9
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
DRUG BANK
DB02266
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
ChEMBL
CHEMBL23588
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY
DRUG CENTRAL
1193
Created by admin on Sat Jun 26 08:46:52 UTC 2021 , Edited by admin on Sat Jun 26 08:46:52 UTC 2021
PRIMARY