NIFLUMIC ACID

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H9F3N2O2
Molecular Weight	282.2185
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1cc(cc(c1)Nc2c(cccn2)C(=O)O)C(F)(F)F

InChI

InChIKey=JZFPYUNJRRFVQU-UHFFFAOYSA-N

InChI=1S/C13H9F3N2O2/c14-13(15,16)8-3-1-4-9(7-8)18-11-10(12(19)20)5-2-6-17-11/h1-7H,(H,17,18)(H,19,20)

HIDE SMILES / InChI

Molecular Formula	C13H9F3N2O2
Molecular Weight	282.2185
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920213 | https://www.ncbi.nlm.nih.gov/pubmed/4556915 | https://www.ncbi.nlm.nih.gov/pubmed/21898399

Niflumic acid belongs to the group of nonsteroidal anti-inflammatory drugs (NSAIDs) and used in the treatment of rheumatoid arthritis, and joint and muscular pain. Its mechanism of action is believed to be based on selective inhibition of cycloxygenases-2 that results in antipyretic, analgesic, and anti-inflammatory effects. In addition to these effects on prostaglandin synthesis, it has been shown to act as a positive allosteric modulator on α1β2γ2 and as a negative modulator on α6β2 and α6β2γ2 (and α1β2) GABAA receptors. In addition, was reported, that niflumic acid blocked T-type calcium channels. It is available for clinical use in several European countries.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Prostaglandin G/H synthase 2 46 Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7947975	Inhibitor 7728	0.1 µM [IC50]
GABA-A receptor; alpha-1/beta-2/gamma-2 21 Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920213	Positive Allosteric Modulator 157
GABA A receptor alpha-6/beta-2/gamma-2 1 Target ID: CHEMBL2111370 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920213	Negative Allosteric Modulator 36
Voltage-gated T-type calcium channel 17 Target ID: CHEMBL2362995 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21898399	Blocker 511

Conditions

Condition	Modality	Targets	Highest Phase	Product
Joint and muscular pain 1 Sources: http://www.ndrugs.com/?s=niflamol	Primary		Approved 8043	niflamol Approved Use Unknown
Rheumatoid arthritis 294 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4556915/	Palliative		Not Provided 492	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ca(2+)-activated Cl(-) channels: a newly emerging anion transport family.	2001	11845314
Evaluation of several solid phase extraction liquid chromatography/tandem mass spectrometry on-line configurations for high-throughput analysis of acidic and basic drugs in rat plasma.	2001	11404844
Cyclooxygenase-2 protein and prostaglandin E(2) production are up-regulated in a rat bladder inflammation model.	2001 Apr 13	11334856
Evidence for two mechanisms of amino acid osmolyte release from hippocampal slices.	2001 Aug	11512036
The disulfonic stilbene DIDS and the marine poison maitotoxin activate the same two types of endogenous cation conductance in the cell membrane of Xenopus laevis oocytes.	2001 Aug	11512026
Niflumic acid reduces the hyperpolarization-activated current (I(h)) in rod photoreceptor cells.	2001 Aug	11463484
Key role for constitutive cyclooxygenase-2 of MDCK cells in basal signaling and response to released ATP.	2001 Aug	11443051
Inhibition of large-conductance calcium-activated potassium channel by 2-methoxyestradiol in cultured vascular endothelial (HUV-EC-C) cells.	2001 Aug 1	11547343
Calcium channels in Xenopus spinal neurons differ in somas and presynaptic terminals.	2001 Jul	11431508
Responses to prolonged odour stimulation in frog olfactory receptor cells.	2001 Jul 1	11433001
Niflumic acid modulates uncoupled substrate-gated conductances in the human glutamate transporter EAAT4.	2001 Jul 1	11432999
Chloride channel antagonists perturb growth and morphology of Neurospora crassa.	2001 Jul 24	11470368
Hypo-osmotic swelling-activated release of organic osmolytes in brain slices: implications for brain oedema in vivo.	2001 Jun	11413246
Role of chloride in constriction of descending vasa recta by angiotensin II.	2001 Jun	11353695
Ca(2+)-activated Cl- channels in Ehrlich ascites tumor cells are distinct from mCLCA1, 2 and 3.	2001 May	11417225
Afterhyperpolarization current in myenteric neurons of the guinea pig duodenum.	2001 May	11353011
Chloride channels regulate HIT cell volume but cannot fully account for swelling-induced insulin secretion.	2001 May	11334443
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
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Fenamates stimulate BKCa channel osteoblast-like MG-63 cells activity in the human.	2001 Nov	11730088
Characterization of action potential-evoked calcium transients in mouse postganglionic sympathetic axon bundles.	2001 Nov 15	11711556
Selective inhibition of Cl(-) conductance in toad skin by blockers of Cl(-) channels and transporters.	2001 Oct	11546659
Volume-activated trimethylamine oxide efflux in red blood cells of spiny dogfish (Squalus acanthias).	2001 Sep	11506995
Fenamates: a novel class of reversible gap junction blockers.	2001 Sep	11504800
Spontaneous Ca2+ activated Cl- currents in isolated urethral smooth muscle cells.	2001 Sep	11490316
Multiple transport functions of a red blood cell anion exchanger, tAE1: its role in cell volume regulation.	2001 Sep 1	11533139
Synthesis, spectral studies and anti-inflammatory activity of glycolamide esters of niflumic acid as potential prodrugs.	2002	12489252
The non-steroidal anti-inflammatory drug niflumic acid inhibits Candida albicans growth.	2002	11913762
Characterisation of the ionic currents in freshly isolated rat ureter smooth muscle cells: evidence for species-dependent currents.	2002 Dec	12466949
Comparative inhibitory effects of niflumic acid and novel synthetic derivatives on the rat isolated stomach fundus.	2002 Feb	11848293
Dual effect of blocking agents on Ca2+-activated Cl(-) currents in rabbit pulmonary artery smooth muscle cells.	2002 Feb 15	11850506
Stimulation of the BK(Ca) channel in cultured smooth muscle cells of human trachea by magnolol.	2002 Jan	11809993
The repolarizing effects of volatile anesthetics on porcine tracheal and bronchial smooth muscle cells.	2002 Jan	11772806
Swelling-activated taurine and creatine effluxes from rat cortical astrocytes are pharmacologically distinct.	2002 Jan 15	11891574
Thermodynamic origin of the solubility profile of drugs showing one or two maxima against the polarity of aqueous and nonaqueous mixtures: niflumic acid and caffeine.	2002 Mar	11920772
Sensitivity of the plant vacuolar malate channel to pH, Ca2+ and anion-channel blockers.	2002 Mar 1	11891587
Activation thresholds of K(V), BK andCl(Ca) channels in smooth muscle cells in pial precapillary arterioles.	2002 Mar-Apr	12011584
D2-like dopamine receptors promote interactions between calcium and chloride channels that diminish rod synaptic transfer in the salamander retina.	2002 May-Jun	12392173
Anion channels influence ECC by modulating L-type Ca(2+) channel in ventricular myocytes.	2002 Nov	12381751
Plasmalemmal voltage-activated K(+) currents in protoplasts from tobacco BY-2 cells: possible regulation by actin microfilaments?	2002 Oct	12417939
Tyrosine kinases and amino acid efflux under hyposmotic and ischaemic conditions in the chicken retina.	2002 Oct	12397392
Fenamate-induced enhancement of heterologously expressed HERG currents in Xenopus oocytes.	2002 Oct 11	12359267
Functional role of Cl- channels in acidic pH-induced contraction of the aorta of spontaneously hypertensive and Wistar Kyoto rats.	2002 Oct 25	12398916
Three electrophysiological phenotypes of cultured human umbilical vein endothelial cells.	2002 Sep	12537354
Pituitary adenylate cyclase-activating polypeptide induces a sustained increase in intracellular free Ca(2+) concentration and catechol amine release by activating Ca(2+) influx via receptor-stimulated Ca(2+) entry, independent of store-operated Ca(2+) channels, and voltage-dependent Ca(2+) channels in bovine adrenal medullary chromaffin cells.	2002 Sep	12183654
Characterization of norepinephrine-evoked inward currents in interstitial cells isolated from the rabbit urethra.	2002 Sep	12176745
Separation of two Cl(-) currents in cultured human and murine mesangial cells: biophysical and pharmacological characteristics of I(Cl.vol) and I(Cl.Ca).	2002 Sep-Oct	12297705
The Entamoeba histolytica EhPgp5 (MDR-like) protein induces swelling of the trophozoites and alters chloride-dependent currents in Xenopus laevis oocytes.	2002 Spring	12002645
Cellular mechanisms involved in the increased contraction of portal veins from Schistosoma mansoni-infected mice.	2003 Jan	12474038
Ca2+-activated Cl- channels in corpus cavernosum smooth muscle: a novel mechanism for control of penile erection.	2003 Jan	12391071

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Niflumic acid (100 uM) inhibits not only IL-13-induced goblet cell hyperplasia but also airway hyperresponsiveness and eosinophilic infiltration. IL-13 instillation markedly enhanced the expression of MUC5AC mRNA in the lung, and niflumic acid treatment suppressed IL-13–induced overexpression of MUC5AC. Effects of niflumic acid on MUC5AC expression were also analyzed after single IL-13 instillation, and niflumic acid suppressed overexpression of MUC5AC 24 h after IL-13.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:10:46 UTC 2021` Edited by `admin` on `Fri Jun 25 21:10:46 UTC 2021`
Record UNII	4U5MP5IUD8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NIFLUMIC ACID

Official Name

English

UP-83

Code

English

NIFLUGEL

Brand Name

English

NIFLUMIC ACID [EP]

Common Name

English

NIFLUMIC ACID [EP MONOGRAPH]

Common Name

English

NIFLUMIC ACID [INN]

Common Name

English

UP 83

Code

English

NIFLUMIC ACID [MI]

Common Name

English

NSC-758196

Code

English

NIFLUMIC ACID [MART.]

Common Name

English

2-(3-(TRIFLUOROMETHYL)ANILINO)NICOTINIC ACID

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

M02AA17