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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
Evidence for two mechanisms of amino acid osmolyte release from hippocampal slices.
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
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
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
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
Role of Cl- current in endothelin-1-induced contraction in rabbit basilar artery.
2001 Nov
Identification of dual cyclooxygenase-eicosanoid oxidoreductase inhibitors: NSAIDs that inhibit PG-LX reductase/LTB(4) dehydrogenase.
2001 Nov 9
Selective inhibition of Cl(-) conductance in toad skin by blockers of Cl(-) channels and transporters.
2001 Oct
Cell-to-cell communication via nitric oxide modulation of oscillatory Cl(-) currents in rat intact cerebral arterioles.
2001 Oct 1
Ca2+-dependent membrane currents in vascular smooth muscle cells of the rabbit.
2001 Oct 12
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
Multiple transport functions of a red blood cell anion exchanger, tAE1: its role in cell volume regulation.
2001 Sep 1
Osmoregulation of vasopressin secretion via activation of neurohypophysial nerve terminals glycine receptors by glial taurine.
2001 Sep 15
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
Calcium and calcium-activated currents in vagotomized rat primary vagal afferent neurons.
2002 Apr 15
Induction of cyclooxygenase-2 expression in glomeruli by aggregated protein.
2002 Aug
Characterisation of the ionic currents in freshly isolated rat ureter smooth muscle cells: evidence for species-dependent currents.
2002 Dec
TRPC4 currents have properties similar to the pacemaker current in interstitial cells of Cajal.
2002 Dec
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
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
Disparate effects of non-steroidal anti-inflammatory drugs on apoptosis in guinea-pig gastric mucous cells: inhibition of basal apoptosis by diclofenac.
2002 Jan
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
Comparison of the osmolyte transport properties induced by trAE1 versus IClswell in Xenopus oocytes.
2002 Jan 1
Inhibition of gap junction hemichannels by chloride channel blockers.
2002 Jan 15
The role of prostaglandin E2 in the immunopathogenesis of experimental pulmonary tuberculosis.
2002 Jun
D2-like dopamine receptors promote interactions between calcium and chloride channels that diminish rod synaptic transfer in the salamander retina.
2002 May-Jun
[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
Anion channels influence ECC by modulating L-type Ca(2+) channel in ventricular myocytes.
2002 Nov
[Cannabis and nifluril].
2002 Nov-Dec
Plasmalemmal voltage-activated K(+) currents in protoplasts from tobacco BY-2 cells: possible regulation by actin microfilaments?
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
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
Ca2+-activated Cl- current in cultured myenteric neurons from murine proximal colon.
2003 Apr
Ca2+-activated Cl- channels in corpus cavernosum smooth muscle: a novel mechanism for control of penile erection.
2003 Jan
Effects of osmotic changes on the chemoreceptor cell of rat carotid body.
2003 Jan 15
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