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
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)
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 |
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: 5743.0 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 |
---|---|---|---|---|
Primary | niflamol Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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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 |
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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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Inhibition of large-conductance calcium-activated potassium channel by 2-methoxyestradiol in cultured vascular endothelial (HUV-EC-C) cells. | 2001 Aug 1 |
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Actions of putative chloride channel blocking agents on canine lower esophageal sphincter (LES). | 2001 Dec |
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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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Calcium channels in Xenopus spinal neurons differ in somas and presynaptic terminals. | 2001 Jul |
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Responses to prolonged odour stimulation in frog olfactory receptor cells. | 2001 Jul 1 |
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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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Hypo-osmotic swelling-activated release of organic osmolytes in brain slices: implications for brain oedema in vivo. | 2001 Jun |
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Role of chloride in constriction of descending vasa recta by angiotensin II. | 2001 Jun |
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Ca(2+)-activated Cl- channels in Ehrlich ascites tumor cells are distinct from mCLCA1, 2 and 3. | 2001 May |
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Afterhyperpolarization current in myenteric neurons of the guinea pig duodenum. | 2001 May |
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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 |
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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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Characterization of action potential-evoked calcium transients in mouse postganglionic sympathetic axon bundles. | 2001 Nov 15 |
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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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Selective inhibition of Cl(-) conductance in toad skin by blockers of Cl(-) channels and transporters. | 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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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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Osmoregulation of vasopressin secretion via activation of neurohypophysial nerve terminals glycine receptors by glial taurine. | 2001 Sep 15 |
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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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Action potential afterdepolarization mediated by a Ca2+-activated cation conductance in myenteric AH neurons. | 2002 |
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Mechanism of n-butyrate uptake in the human proximal colonic basolateral membranes. | 2002 Apr |
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Induction of cyclooxygenase-2 expression in glomeruli by aggregated protein. | 2002 Aug |
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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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Disparate effects of non-steroidal anti-inflammatory drugs on apoptosis in guinea-pig gastric mucous cells: inhibition of basal apoptosis by diclofenac. | 2002 Jan |
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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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The repolarizing effects of volatile anesthetics on porcine tracheal and bronchial smooth muscle cells. | 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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Disparity between ionic mediators of volume regulation and apoptosis in N1E 115 mouse neuroblastoma cells. | 2002 Jul 12 |
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Control of descending vasa recta pericyte membrane potential by angiotensin II. | 2002 Jun |
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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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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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Tyrosine kinases and amino acid efflux under hyposmotic and ischaemic conditions in the chicken retina. | 2002 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 |
|
Ca2+-activated Cl- current in cultured myenteric neurons from murine proximal colon. | 2003 Apr |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:56:21 UTC 2023
by
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on
Wed Jul 05 23:56:21 UTC 2023
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Record UNII |
4U5MP5IUD8
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Record Status |
Validated (UNII)
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M02AA17
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QM01AX52
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C257
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QM02AA17
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C76807
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224-516-2
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NIFLUMIC ACID
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