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 |
|---|---|---|---|
Target ID: P35354 Gene ID: 5743 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) |
0.100000000000000006 µM [IC50] | ||
Target ID: CHEMBL2095172 |
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Target ID: CHEMBL2111370 |
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Target ID: CHEMBL2362995 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | niflamol |
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| Palliative |
PubMed
| Title | Date | PubMed |
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| Ca(2+)-activated Cl(-) channels: a newly emerging anion transport family. | 2001 |
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| Actions of putative chloride channel blocking agents on canine lower esophageal sphincter (LES). | 2001 Dec |
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| Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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| Fenamates stimulate BKCa channel osteoblast-like MG-63 cells activity in the human. | 2001 Nov |
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| Role of Cl- current in endothelin-1-induced contraction in rabbit basilar artery. | 2001 Nov |
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| Identification of dual cyclooxygenase-eicosanoid oxidoreductase inhibitors: NSAIDs that inhibit PG-LX reductase/LTB(4) dehydrogenase. | 2001 Nov 9 |
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| Isovolumetric regulation mechanisms in cultured cerebellar granule neurons. | 2001 Oct |
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| Nitric oxide contracts longitudinal smooth muscle of opossum oesophagus via excitation-contraction coupling. | 2001 Oct 1 |
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| Cell-to-cell communication via nitric oxide modulation of oscillatory Cl(-) currents in rat intact cerebral arterioles. | 2001 Oct 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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| Induction of cyclooxygenase-2 expression in glomeruli by aggregated protein. | 2002 Aug |
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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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| 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 |
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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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| 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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| Presence of a calcium-activated chloride current in mouse ventricular myocytes. | 2002 Jul |
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| A comparative study of the effects of Cl(-) channel blockers on mesenteric vascular conductance in anaesthetized rat. | 2002 Jul 12 |
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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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| Does mucus hypersecretion matter in airway disease? | 2002 Jun 1 |
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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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| Sensitivity of the plant vacuolar malate channel to pH, Ca2+ and anion-channel blockers. | 2002 Mar 1 |
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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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| [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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| [Cannabis and nifluril]. | 2002 Nov-Dec |
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| Plasmalemmal voltage-activated K(+) currents in protoplasts from tobacco BY-2 cells: possible regulation by actin microfilaments? | 2002 Oct |
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| Fenamate-induced enhancement of heterologously expressed HERG currents in Xenopus oocytes. | 2002 Oct 11 |
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| Three electrophysiological phenotypes of cultured human umbilical vein endothelial cells. | 2002 Sep |
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| 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 |
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| 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 |
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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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| Anomalous effect of anthracene-9-carboxylic acid on calcium-activated chloride currents in rabbit pulmonary artery smooth muscle cells. | 2003 Jan |
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| Cellular mechanisms involved in the increased contraction of portal veins from Schistosoma mansoni-infected mice. | 2003 Jan |
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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
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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QM01AX02
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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
