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
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)
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 | Condition | Potency |
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Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7947975 |
0.1 µM [IC50] | ||
Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920213 |
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Target ID: CHEMBL2111370 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920213 |
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Target ID: CHEMBL2362995 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21898399 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | niflamol Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Cyclooxygenase-2 protein and prostaglandin E(2) production are up-regulated in a rat bladder inflammation model. | 2001 Apr 13 |
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Evidence for two mechanisms of amino acid osmolyte release from hippocampal slices. | 2001 Aug |
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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 |
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Niflumic acid reduces the hyperpolarization-activated current (I(h)) in rod photoreceptor cells. | 2001 Aug |
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Key role for constitutive cyclooxygenase-2 of MDCK cells in basal signaling and response to released ATP. | 2001 Aug |
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Activation of alpha 6 GABAA receptors on depolarized cerebellar parallel fibers elicits glutamate release through anion channels. | 2001 Dec |
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Niflumic acid modulates uncoupled substrate-gated conductances in the human glutamate transporter EAAT4. | 2001 Jul 1 |
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Chloride channel antagonists perturb growth and morphology of Neurospora crassa. | 2001 Jul 24 |
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Role of chloride in constriction of descending vasa recta by angiotensin II. | 2001 Jun |
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Afterhyperpolarization current in myenteric neurons of the guinea pig duodenum. | 2001 May |
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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 |
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Chloride channels regulate HIT cell volume but cannot fully account for swelling-induced insulin secretion. | 2001 May |
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Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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Ca2+-dependent membrane currents in vascular smooth muscle cells of the rabbit. | 2001 Oct 12 |
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Volume-activated trimethylamine oxide efflux in red blood cells of spiny dogfish (Squalus acanthias). | 2001 Sep |
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Fenamates: a novel class of reversible gap junction blockers. | 2001 Sep |
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Spontaneous Ca2+ activated Cl- currents in isolated urethral smooth muscle cells. | 2001 Sep |
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Multiple transport functions of a red blood cell anion exchanger, tAE1: its role in cell volume regulation. | 2001 Sep 1 |
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Synthesis, spectral studies and anti-inflammatory activity of glycolamide esters of niflumic acid as potential prodrugs. | 2002 |
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The non-steroidal anti-inflammatory drug niflumic acid inhibits Candida albicans growth. | 2002 |
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Enhancement of HCO(3)(-) permeability across the apical membrane of bovine corneal endothelium by multiple signaling pathways. | 2002 Apr |
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Mechanism of n-butyrate uptake in the human proximal colonic basolateral membranes. | 2002 Apr |
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Calcium and calcium-activated currents in vagotomized rat primary vagal afferent neurons. | 2002 Apr 15 |
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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 |
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Characterisation of the ionic currents in freshly isolated rat ureter smooth muscle cells: evidence for species-dependent currents. | 2002 Dec |
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TRPC4 currents have properties similar to the pacemaker current in interstitial cells of Cajal. | 2002 Dec |
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Comparative inhibitory effects of niflumic acid and novel synthetic derivatives on the rat isolated stomach fundus. | 2002 Feb |
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Dual effect of blocking agents on Ca2+-activated Cl(-) currents in rabbit pulmonary artery smooth muscle cells. | 2002 Feb 15 |
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Stimulation of the BK(Ca) channel in cultured smooth muscle cells of human trachea by magnolol. | 2002 Jan |
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Comparison of the osmolyte transport properties induced by trAE1 versus IClswell in Xenopus oocytes. | 2002 Jan 1 |
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Swelling-activated taurine and creatine effluxes from rat cortical astrocytes are pharmacologically distinct. | 2002 Jan 15 |
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Inhibition of gap junction hemichannels by chloride channel blockers. | 2002 Jan 15 |
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Role of Ca2+-activated Cl- channels and MLCK in slow IJP in opossum esophageal smooth muscle. | 2002 Jul |
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Disparity between ionic mediators of volume regulation and apoptosis in N1E 115 mouse neuroblastoma cells. | 2002 Jul 12 |
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The role of prostaglandin E2 in the immunopathogenesis of experimental pulmonary tuberculosis. | 2002 Jun |
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Control of descending vasa recta pericyte membrane potential by angiotensin II. | 2002 Jun |
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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 |
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Activation thresholds of K(V), BK andCl(Ca) channels in smooth muscle cells in pial precapillary arterioles. | 2002 Mar-Apr |
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Inhibition of mycophenolic acid glucuronidation by niflumic acid in human liver microsomes. | 2002 May |
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A Ca(2+)-inhibited non-selective cation conductance contributes to pacemaker currents in mouse interstitial cell of Cajal. | 2002 May 1 |
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D2-like dopamine receptors promote interactions between calcium and chloride channels that diminish rod synaptic transfer in the salamander retina. | 2002 May-Jun |
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[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 |
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Anion channels influence ECC by modulating L-type Ca(2+) channel in ventricular myocytes. | 2002 Nov |
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Fenamate-induced enhancement of heterologously expressed HERG currents in Xenopus oocytes. | 2002 Oct 11 |
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Characterization of norepinephrine-evoked inward currents in interstitial cells isolated from the rabbit urethra. | 2002 Sep |
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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 |
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The Entamoeba histolytica EhPgp5 (MDR-like) protein induces swelling of the trophozoites and alters chloride-dependent currents in Xenopus laevis oocytes. | 2002 Spring |
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Ca2+-activated Cl- current in cultured myenteric neurons from murine proximal colon. | 2003 Apr |
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Ca2+-activated Cl- channels in corpus cavernosum smooth muscle: a novel mechanism for control of penile erection. | 2003 Jan |
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Effects of osmotic changes on the chemoreceptor cell of rat carotid body. | 2003 Jan 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6852999
Unknown
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16528019
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.
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WHO-ATC |
M02AA17
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WHO-VATC |
QM01AX02
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WHO-VATC |
QM01AX52
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NCI_THESAURUS |
C257
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QM02AA17
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WHO-ATC |
M01AX02
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2194
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C76807
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4488
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2439
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CHEMBL63323
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D009544
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7418
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4394-00-7
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224-516-2
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SUB09257MIG
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NIFLUMIC ACID
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4394-00-7
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M7885
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1925
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DB04552
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ACTIVE MOIETY