NIFLUMIC ACID

Possibly Marketed Outside US

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

Molecular Formula	C13H9F3N2O2
Molecular Weight	282.218
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 47 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 8228	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 534

Conditions

Condition	Modality	Targets	Highest Phase	Product
Joint and muscular pain 1 Sources: http://www.ndrugs.com/?s=niflamol	Primary		Approved 8360	niflamol Approved Use Unknown
Rheumatoid arthritis 313 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4556915/	Palliative		Not Provided 503	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
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
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
Actions of putative chloride channel blocking agents on canine lower esophageal sphincter (LES).	2001 Dec	11824935
Activation of alpha 6 GABAA receptors on depolarized cerebellar parallel fibers elicits glutamate release through anion channels.	2001 Dec	11747899
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
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
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
Isovolumetric regulation mechanisms in cultured cerebellar granule neurons.	2001 Oct	11595766
Selective inhibition of Cl(-) conductance in toad skin by blockers of Cl(-) channels and transporters.	2001 Oct	11546659
Nitric oxide contracts longitudinal smooth muscle of opossum oesophagus via excitation-contraction coupling.	2001 Oct 1	11579163
Cell-to-cell communication via nitric oxide modulation of oscillatory Cl(-) currents in rat intact cerebral arterioles.	2001 Oct 1	11579157
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
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
Osmoregulation of vasopressin secretion via activation of neurohypophysial nerve terminals glycine receptors by glial taurine.	2001 Sep 15	11549721
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
Mechanism of n-butyrate uptake in the human proximal colonic basolateral membranes.	2002 Apr	11897627
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
Disparate effects of non-steroidal anti-inflammatory drugs on apoptosis in guinea-pig gastric mucous cells: inhibition of basal apoptosis by diclofenac.	2002 Jan	11815376
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
Inhibition of gap junction hemichannels by chloride channel blockers.	2002 Jan 15	11891568
Presence of a calcium-activated chloride current in mouse ventricular myocytes.	2002 Jul	12063303
Disparity between ionic mediators of volume regulation and apoptosis in N1E 115 mouse neuroblastoma cells.	2002 Jul 12	12101047
Control of descending vasa recta pericyte membrane potential by angiotensin II.	2002 Jun	11997323
Sensitivity of the plant vacuolar malate channel to pH, Ca2+ and anion-channel blockers.	2002 Mar 1	11891587
A Ca(2+)-inhibited non-selective cation conductance contributes to pacemaker currents in mouse interstitial cell of Cajal.	2002 May 1	11986370
Tyrosine kinases and amino acid efflux under hyposmotic and ischaemic conditions in the chicken retina.	2002 Oct	12397392
The Entamoeba histolytica EhPgp5 (MDR-like) protein induces swelling of the trophozoites and alters chloride-dependent currents in Xenopus laevis oocytes.	2002 Spring	12002645
Ca2+-activated Cl- current in cultured myenteric neurons from murine proximal colon.	2003 Apr	12456397

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 `Wed Jul 05 23:56:21 UTC 2023` Edited by `admin` on `Wed Jul 05 23:56:21 UTC 2023`
Record UNII	4U5MP5IUD8
Record Status	`Validated (UNII)`
Record Version

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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