NIFLUMIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H9F3N2O2
Molecular Weight	282.218
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CC=CN=C1NC2=CC(=CC=C2)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 48 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 8297	0.1 µM [IC50]
GABA-A receptor; alpha-1/beta-2/gamma-2 27 Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920213	Positive Allosteric Modulator 179
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 42
Voltage-gated T-type calcium channel 17 Target ID: CHEMBL2362995 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21898399	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Joint and muscular pain 1 Sources: http://www.ndrugs.com/?s=niflamol	Primary		Approved 8429	niflamol Approved Use Unknown
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4556915/	Palliative		Not Provided 504	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
Functional role of sodium-calcium exchange in the regulation of renal vascular resistance.	2001 Jan	11133525
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
Vasopressin-induced contraction in the rat basilar artery in vitro.	2001 Mar 23	11282120
Afterhyperpolarization current in myenteric neurons of the guinea pig duodenum.	2001 May	11353011
Aluminum activates a citrate-permeable anion channel in the aluminum-sensitive zone of the maize root apex. A comparison between an aluminum- sensitive and an aluminum-resistant cultivar.	2001 May	11351102
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
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
Fenamates: a novel class of reversible gap junction blockers.	2001 Sep	11504800
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
Induction of cyclooxygenase-2 expression in glomeruli by aggregated protein.	2002 Aug	12233815
Characterisation of the ionic currents in freshly isolated rat ureter smooth muscle cells: evidence for species-dependent currents.	2002 Dec	12466949
TRPC4 currents have properties similar to the pacemaker current in interstitial cells of Cajal.	2002 Dec	12388058
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
Stimulation of the BK(Ca) channel in cultured smooth muscle cells of human trachea by magnolol.	2002 Jan	11809993
Comparison of the osmolyte transport properties induced by trAE1 versus IClswell in Xenopus oocytes.	2002 Jan 1	11891564
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
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
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
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
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

Niflumic acid [WHO-DD]

Common Name

English

UP-83

Code

English

NIFLUGEL

Brand Name

English

NIFLUMIC ACID [EP IMPURITY]

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