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

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
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
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
Role of Cl- current in endothelin-1-induced contraction in rabbit basilar artery.	2001 Nov	11668078
Characterization of action potential-evoked calcium transients in mouse postganglionic sympathetic axon bundles.	2001 Nov 15	11711556
Identification of dual cyclooxygenase-eicosanoid oxidoreductase inhibitors: NSAIDs that inhibit PG-LX reductase/LTB(4) dehydrogenase.	2001 Nov 9	11688989
Ca2+-dependent membrane currents in vascular smooth muscle cells of the rabbit.	2001 Oct 12	11693254
Volume-activated trimethylamine oxide efflux in red blood cells of spiny dogfish (Squalus acanthias).	2001 Sep	11506995
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
Action potential afterdepolarization mediated by a Ca2+-activated cation conductance in myenteric AH neurons.	2002	12421604
The non-steroidal anti-inflammatory drug niflumic acid inhibits Candida albicans growth.	2002	11913762
Enhancement of HCO(3)(-) permeability across the apical membrane of bovine corneal endothelium by multiple signaling pathways.	2002 Apr	11923259
Calcium and calcium-activated currents in vagotomized rat primary vagal afferent neurons.	2002 Apr 15	11956342
The DC electrical-field-induced Ca(2+) response and growth stimulation of multicellular tumor spheroids are mediated by ATP release and purinergic receptor stimulation.	2002 Aug 15	12140258
Characterisation of the ionic currents in freshly isolated rat ureter smooth muscle cells: evidence for species-dependent currents.	2002 Dec	12466949
Differential activation of ion channels by inositol 1,4,5-trisphosphate (IP3)- and ryanodine-sensitive calcium stores in rat basilar artery vasomotion.	2002 Dec 1	12456838
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
Comparison of the osmolyte transport properties induced by trAE1 versus IClswell in Xenopus oocytes.	2002 Jan 1	11891564
Swelling-activated taurine and creatine effluxes from rat cortical astrocytes are pharmacologically distinct.	2002 Jan 15	11891574
Inhibition of gap junction hemichannels by chloride channel blockers.	2002 Jan 15	11891568
Role of Ca2+-activated Cl- channels and MLCK in slow IJP in opossum esophageal smooth muscle.	2002 Jul	12065297
Presence of a calcium-activated chloride current in mouse ventricular myocytes.	2002 Jul	12063303
A comparative study of the effects of Cl(-) channel blockers on mesenteric vascular conductance in anaesthetized rat.	2002 Jul 12	12126972
Disparity between ionic mediators of volume regulation and apoptosis in N1E 115 mouse neuroblastoma cells.	2002 Jul 12	12101047
The role of prostaglandin E2 in the immunopathogenesis of experimental pulmonary tuberculosis.	2002 Jun	12047755
Control of descending vasa recta pericyte membrane potential by angiotensin II.	2002 Jun	11997323
Does mucus hypersecretion matter in airway disease?	2002 Jun 1	12057561
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
[BK channels play an important role as a negative feedback mechanism in the regulation of spontaneous rhythmic contraction of urinary bladder smooth muscles].	2002 Nov	12491797
Anion channels influence ECC by modulating L-type Ca(2+) channel in ventricular myocytes.	2002 Nov	12381751
[Cannabis and nifluril].	2002 Nov-Dec	12484364
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
Oscillatory chloride efflux at the pollen tube apex has a role in growth and cell volume regulation and is targeted by inositol 3,4,5,6-tetrakisphosphate.	2002 Sep	12215517
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
Ca2+-activated Cl- current in cultured myenteric neurons from murine proximal colon.	2003 Apr	12456397
Anomalous effect of anthracene-9-carboxylic acid on calcium-activated chloride currents in rabbit pulmonary artery smooth muscle cells.	2003 Jan	12522070
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
Effects of osmotic changes on the chemoreceptor cell of rat carotid body.	2003 Jan 15	12527733

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.

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