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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
Structure of NIFLUMIC ACID

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)

HIDE SMILES / InChI

Molecular Formula C13H9F3N2O2
Molecular Weight 282.2185
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35354
Gene ID: 5743.0
Gene Symbol: PTGS2
Target Organism: Homo sapiens (Human)
0.1 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
niflamol

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Ca(2+)-activated Cl(-) channels: a newly emerging anion transport family.
2001
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
Cyclooxygenase-2 protein and prostaglandin E(2) production are up-regulated in a rat bladder inflammation model.
2001 Apr 13
Evidence for two mechanisms of amino acid osmolyte release from hippocampal slices.
2001 Aug
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
Niflumic acid reduces the hyperpolarization-activated current (I(h)) in rod photoreceptor cells.
2001 Aug
Key role for constitutive cyclooxygenase-2 of MDCK cells in basal signaling and response to released ATP.
2001 Aug
Inhibition of large-conductance calcium-activated potassium channel by 2-methoxyestradiol in cultured vascular endothelial (HUV-EC-C) cells.
2001 Aug 1
Calcium channels in Xenopus spinal neurons differ in somas and presynaptic terminals.
2001 Jul
Responses to prolonged odour stimulation in frog olfactory receptor cells.
2001 Jul 1
Niflumic acid modulates uncoupled substrate-gated conductances in the human glutamate transporter EAAT4.
2001 Jul 1
Chloride channel antagonists perturb growth and morphology of Neurospora crassa.
2001 Jul 24
Hypo-osmotic swelling-activated release of organic osmolytes in brain slices: implications for brain oedema in vivo.
2001 Jun
Role of chloride in constriction of descending vasa recta by angiotensin II.
2001 Jun
Ca(2+)-activated Cl- channels in Ehrlich ascites tumor cells are distinct from mCLCA1, 2 and 3.
2001 May
Afterhyperpolarization current in myenteric neurons of the guinea pig duodenum.
2001 May
Chloride channels regulate HIT cell volume but cannot fully account for swelling-induced insulin secretion.
2001 May
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
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Fenamates stimulate BKCa channel osteoblast-like MG-63 cells activity in the human.
2001 Nov
Characterization of action potential-evoked calcium transients in mouse postganglionic sympathetic axon bundles.
2001 Nov 15
Selective inhibition of Cl(-) conductance in toad skin by blockers of Cl(-) channels and transporters.
2001 Oct
Volume-activated trimethylamine oxide efflux in red blood cells of spiny dogfish (Squalus acanthias).
2001 Sep
Fenamates: a novel class of reversible gap junction blockers.
2001 Sep
Spontaneous Ca2+ activated Cl- currents in isolated urethral smooth muscle cells.
2001 Sep
Multiple transport functions of a red blood cell anion exchanger, tAE1: its role in cell volume regulation.
2001 Sep 1
Synthesis, spectral studies and anti-inflammatory activity of glycolamide esters of niflumic acid as potential prodrugs.
2002
The non-steroidal anti-inflammatory drug niflumic acid inhibits Candida albicans growth.
2002
Characterisation of the ionic currents in freshly isolated rat ureter smooth muscle cells: evidence for species-dependent currents.
2002 Dec
Comparative inhibitory effects of niflumic acid and novel synthetic derivatives on the rat isolated stomach fundus.
2002 Feb
Dual effect of blocking agents on Ca2+-activated Cl(-) currents in rabbit pulmonary artery smooth muscle cells.
2002 Feb 15
Stimulation of the BK(Ca) channel in cultured smooth muscle cells of human trachea by magnolol.
2002 Jan
The repolarizing effects of volatile anesthetics on porcine tracheal and bronchial smooth muscle cells.
2002 Jan
Swelling-activated taurine and creatine effluxes from rat cortical astrocytes are pharmacologically distinct.
2002 Jan 15
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
Sensitivity of the plant vacuolar malate channel to pH, Ca2+ and anion-channel blockers.
2002 Mar 1
Activation thresholds of K(V), BK andCl(Ca) channels in smooth muscle cells in pial precapillary arterioles.
2002 Mar-Apr
D2-like dopamine receptors promote interactions between calcium and chloride channels that diminish rod synaptic transfer in the salamander retina.
2002 May-Jun
Anion channels influence ECC by modulating L-type Ca(2+) channel in ventricular myocytes.
2002 Nov
Plasmalemmal voltage-activated K(+) currents in protoplasts from tobacco BY-2 cells: possible regulation by actin microfilaments?
2002 Oct
Tyrosine kinases and amino acid efflux under hyposmotic and ischaemic conditions in the chicken retina.
2002 Oct
Fenamate-induced enhancement of heterologously expressed HERG currents in Xenopus oocytes.
2002 Oct 11
Functional role of Cl- channels in acidic pH-induced contraction of the aorta of spontaneously hypertensive and Wistar Kyoto rats.
2002 Oct 25
Three electrophysiological phenotypes of cultured human umbilical vein endothelial cells.
2002 Sep
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
Characterization of norepinephrine-evoked inward currents in interstitial cells isolated from the rabbit urethra.
2002 Sep
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
The Entamoeba histolytica EhPgp5 (MDR-like) protein induces swelling of the trophozoites and alters chloride-dependent currents in Xenopus laevis oocytes.
2002 Spring
Cellular mechanisms involved in the increased contraction of portal veins from Schistosoma mansoni-infected mice.
2003 Jan
Ca2+-activated Cl- channels in corpus cavernosum smooth muscle: a novel mechanism for control of penile erection.
2003 Jan
Patents

Patents

Sample Use Guides

Unknown
Route of Administration: Oral
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 Fri Jun 25 21:10:46 UTC 2021
Edited
by admin
on Fri Jun 25 21:10:46 UTC 2021
Record UNII
4U5MP5IUD8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NIFLUMIC ACID
EP   INN   MART.   MI   WHO-DD  
INN  
Official Name English
UP-83
Code English
NIFLUGEL
Brand Name English
NIFLUMIC ACID [EP]
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
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
WHO-VATC QM01AX02
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
WHO-VATC QM01AX52
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
NCI_THESAURUS C257
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
WHO-VATC QM02AA17
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
WHO-ATC M01AX02
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
Code System Code Type Description
INN
2194
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
NCI_THESAURUS
C76807
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
PUBCHEM
4488
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
IUPHAR
2439
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
ChEMBL
CHEMBL63323
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
MESH
D009544
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
RXCUI
7418
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY RxNorm
EPA CompTox
4394-00-7
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
ECHA (EC/EINECS)
224-516-2
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
FDA UNII
4U5MP5IUD8
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
EVMPD
SUB09257MIG
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
WIKIPEDIA
NIFLUMIC ACID
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
CAS
4394-00-7
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
MERCK INDEX
M7885
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
1925
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
DRUG BANK
DB04552
Created by admin on Fri Jun 25 21:10:46 UTC 2021 , Edited by admin on Fri Jun 25 21:10:46 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY