U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of NIFLUMIC ACID

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)

HIDE SMILES / InChI
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
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
Niflumic acid reduces the hyperpolarization-activated current (I(h)) in rod photoreceptor cells.
2001 Aug
Inhibition of large-conductance calcium-activated potassium channel by 2-methoxyestradiol in cultured vascular endothelial (HUV-EC-C) cells.
2001 Aug 1
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
Hypo-osmotic swelling-activated release of organic osmolytes in brain slices: implications for brain oedema in vivo.
2001 Jun
Application of f--f luminescence of terbium ion for determination of non-steroidal anti-inflammatory drug-niflumic acid.
2001 Mar
Regulation of an outwardly rectifying chloride conductance in renal epithelial cells by external and internal calcium.
2001 Mar 1
Vasopressin-induced contraction in the rat basilar artery in vitro.
2001 Mar 23
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
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
Isovolumetric regulation mechanisms in cultured cerebellar granule neurons.
2001 Oct
Nitric oxide contracts longitudinal smooth muscle of opossum oesophagus via excitation-contraction coupling.
2001 Oct 1
Cell-to-cell communication via nitric oxide modulation of oscillatory Cl(-) currents in rat intact cerebral arterioles.
2001 Oct 1
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
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
Action potential afterdepolarization mediated by a Ca2+-activated cation conductance in myenteric AH neurons.
2002
The non-steroidal anti-inflammatory drug niflumic acid inhibits Candida albicans growth.
2002
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
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
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
Swelling-activated taurine and creatine effluxes from rat cortical astrocytes are pharmacologically distinct.
2002 Jan 15
Inhibition of gap junction hemichannels by chloride channel blockers.
2002 Jan 15
Role of Ca2+-activated Cl- channels and MLCK in slow IJP in opossum esophageal smooth muscle.
2002 Jul
Presence of a calcium-activated chloride current in mouse ventricular myocytes.
2002 Jul
The role of prostaglandin E2 in the immunopathogenesis of experimental pulmonary tuberculosis.
2002 Jun
Does mucus hypersecretion matter in airway disease?
2002 Jun 1
Sensitivity of the plant vacuolar malate channel to pH, Ca2+ and anion-channel blockers.
2002 Mar 1
Plasmalemmal voltage-activated K(+) currents in protoplasts from tobacco BY-2 cells: possible regulation by actin microfilaments?
2002 Oct
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
Ca2+-activated Cl- current in cultured myenteric neurons from murine proximal colon.
2003 Apr
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
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.
Name Type Language
NIFLUMIC ACID
EP   INN   MART.   MI   WHO-DD  
INN  
Official Name English
Niflumic acid [WHO-DD]
Common Name English
UP-83
Code English
NIFLUGEL
Brand Name English
NIFLUMIC ACID [EP IMPURITY]
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 Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
WHO-VATC QM01AX02
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
WHO-VATC QM01AX52
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
NCI_THESAURUS C257
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
WHO-VATC QM02AA17
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
WHO-ATC M01AX02
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
Code System Code Type Description
INN
2194
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
NCI_THESAURUS
C76807
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
PUBCHEM
4488
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
IUPHAR
2439
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
ChEMBL
CHEMBL63323
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
MESH
D009544
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
NSC
758196
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
RXCUI
7418
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID1023368
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
ECHA (EC/EINECS)
224-516-2
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
FDA UNII
4U5MP5IUD8
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
EVMPD
SUB09257MIG
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
SMS_ID
100000083867
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
WIKIPEDIA
NIFLUMIC ACID
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
CAS
4394-00-7
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
MERCK INDEX
M7885
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY Merck Index
DRUG CENTRAL
1925
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY
DRUG BANK
DB04552
Created by admin on Wed Jul 05 23:56:21 UTC 2023 , Edited by admin on Wed Jul 05 23:56:21 UTC 2023
PRIMARY