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=C(NC2=CC=CC(=C2)C(F)(F)F)C=CC=C1

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-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22263837	Inhibitor 8297		16.0 nM [IC50]
Cyclooxygenase-1 127 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23454516	Inhibitor 8297		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 656	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4895007	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Letter: Aspirin sensitivity: other drugs.	1975 Feb	1115460
[Levofloxacin-induced neurological adverse effects such as convulsion, involuntary movement (tremor, myoclonus and chorea like), visual hallucination in two elderly patients].	1999 Mar	10388331
Enhancement of low density lipoprotein catabolism by non-steroidal anti-inflammatory drugs in cultured HepG2 cells.	1999 May 21	10395027
A nonsteroidal anti-inflammatory drug, flufenamic acid, inhibits the expression of the androgen receptor in LNCaP cells.	1999 Nov	10537180
Two opposing effects of non-steroidal anti-inflammatory drugs on the expression of the inducible cyclooxygenase. Mediation through different signaling pathways.	2000 Sep 8	10866999
Regulation of prostaglandin synthesis and cell adhesion by a tryptophan catabolizing enzyme.	2001	11375052
The transient receptor potential protein homologue TRP6 is the essential component of vascular alpha(1)-adrenoceptor-activated Ca(2+)-permeable cation channel.	2001 Feb 16	11179201
Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation.	2001 May-Jun	11386636
A study of the conditions of the supercritical fluid extraction in the analysis of selected anti-inflammatory drugs in plasma.	2002 Feb	11902653
Flufenamic acid: growth modulating effects on human aortic smooth muscle cells in vitro.	2002 Jan	11788700
Characterization of a Ca2+-activated nonselective cation channel during dedifferentiation of cultured rat ventricular cardiomyocytes.	2002 Jul 15	12172638
Synthesis, stability and in vitro dermal evaluation of aminocarbonyloxymethyl esters as prodrugs of carboxylic acid agents.	2002 Mar	11814870
Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone.	2003 Feb 1	12604236
Ca(2+)- and voltage-dependent gating of Ca(2+)- and ATP-sensitive cationic channels in brain capillary endothelium.	2003 Jul	12829486
Calcium-activated cationic channel in rat sensory neurons.	2003 Jun	12823470
Thiram and ziram stimulate non-selective cation channel and induce apoptosis in PC12 cells.	2003 Jun	12782107
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	12736069
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	12597989
Functional hemichannels in astrocytes: a novel mechanism of glutamate release.	2003 May 1	12736329
Diclofenac inhibition of sodium currents in rat dorsal root ganglion neurons.	2003 Nov 28	14604780
Interactions of benzylpenicillin and non-steroidal anti-inflammatory drugs with the sodium-dependent dicarboxylate transporter NaDC-3.	2004	15319545
Synthesis of new 2-arylamino-6-trifluoromethylpyridine-3-carboxylic acid derivatives and investigation of their analgesic activity.	2004 Aug 1	15246093
Detergents profoundly affect inhibitor potencies against both cyclo-oxygenase isoforms.	2004 Feb 1	14510637
Analysis of ketorolac and its related impurities by capillary electrochromatography.	2004 Jul 30	15354451
Differential contribution of pacemaker properties to the generation of respiratory rhythms during normoxia and hypoxia.	2004 Jul 8	15233921
Inverse gene expression patterns for macrophage activating hepatotoxicants and peroxisome proliferators in rat liver.	2004 Jun 1	15135310
Calcium-dependent subthreshold oscillations determine bursting activity induced by N-methyl-D-aspartate in rat subthalamic neurons in vitro.	2004 Mar	15016087
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	15013815
Analysis of slow hyperpolarizing potentials in frog taste cells induced by glossopharyngeal nerve stimulation.	2004 Oct	15466810

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 `Fri Dec 15 17:12:11 GMT 2023` Edited by `admin` on `Fri Dec 15 17:12:11 GMT 2023`
Record UNII	60GCX7Y6BH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLUFENAMIC ACID

Official Name

English

FLUFENAMIC ACID [MART.]

Common Name

English

CN-27554

Code

English

Flufenamic acid [WHO-DD]

Common Name

English

ARLEF

Brand 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