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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

Molecular Formula C14H10F3NO2
Molecular Weight 281.2304
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Non-selective cation channels and oxidative stress-induced cell swelling.
2002
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
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
Low mortality rates related to respiratory virus infections after bone marrow transplantation.
2003 Apr
TRPC5 as a candidate for the nonselective cation channel activated by muscarinic stimulation in murine stomach.
2003 Apr
[Characterization of pacemaking currents in cultured interstitial cells of Cajal from mice small intestine].
2003 Aug
Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone.
2003 Feb 1
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
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 Jul 4
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
Closure of gap junction channels by arylaminobenzoates.
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
Differential connexin expression, gap junction intercellular coupling, and hemichannel formation in NT2/D1 human neural progenitors and terminally differentiated hNT neurons.
2003 May 1
In situ monitoring of wet granulation using online X-ray powder diffraction.
2003 Nov
Fundamental role of ClC-3 in volume-sensitive Cl- channel function and cell volume regulation in AGS cells.
2003 Nov
Diclofenac inhibition of sodium currents in rat dorsal root ganglion neurons.
2003 Nov 28
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
Activation of a calcium-activated cation current during epileptiform discharges and its possible role in sustaining seizure-like events in neocortical slices.
2004 Aug
Discovery of glycine hydrazide pore-occluding CFTR inhibitors: mechanism, structure-activity analysis, and in vivo efficacy.
2004 Aug
Synthesis of new 2-arylamino-6-trifluoromethylpyridine-3-carboxylic acid derivatives and investigation of their analgesic activity.
2004 Aug 1
Topical NSAIDs for chronic musculoskeletal pain: systematic review and meta-analysis.
2004 Aug 19
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
Effects of various vehicles on the penetration of flufenamic acid into human skin.
2004 Jul
Functional characterization of a Ca(2+)-activated non-selective cation channel in human atrial cardiomyocytes.
2004 Jul 1
Analysis of ketorolac and its related impurities by capillary electrochromatography.
2004 Jul 30
Differential contribution of pacemaker properties to the generation of respiratory rhythms during normoxia and hypoxia.
2004 Jul 8
Inverse gene expression patterns for macrophage activating hepatotoxicants and peroxisome proliferators in rat liver.
2004 Jun 1
Calcium-dependent subthreshold oscillations determine bursting activity induced by N-methyl-D-aspartate in rat subthalamic neurons in vitro.
2004 Mar
Evidence of a role for TRPC channels in VEGF-mediated increased vascular permeability in vivo.
2004 Mar
Crystal structures of prostaglandin D(2) 11-ketoreductase (AKR1C3) in complex with the nonsteroidal anti-inflammatory drugs flufenamic acid and indomethacin.
2004 Mar 1
Transient receptor potential-like channels mediate metabotropic glutamate receptor EPSCs in rat dopamine neurones.
2004 Mar 1
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 Mar 12
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
Native state stabilization by NSAIDs inhibits transthyretin amyloidogenesis from the most common familial disease variants.
2004 May
Compounds exhibiting selective efficacy for different beta subunits of human recombinant gamma-aminobutyric acid A receptors.
2004 Nov
Flufenamic acid is a pH-dependent antagonist of TRPM2 channels.
2004 Sep
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:46:52 UTC 2021
Edited
by admin
on Sat Jun 26 08:46:52 UTC 2021
Record UNII
60GCX7Y6BH
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY