NIFLUMIC ACID

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 Search

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920213 | https://www.ncbi.nlm.nih.gov/pubmed/4556915 | https://www.ncbi.nlm.nih.gov/pubmed/21898399

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	Potency
Prostaglandin G/H synthase 2 51 Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7947975	Inhibitor 8504	0.1 µM [IC50]
GABA-A receptor; alpha-1/beta-2/gamma-2 28 Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920213	Positive Allosteric Modulator 186
GABA A receptor alpha-6/beta-2/gamma-2 1 Target ID: CHEMBL2111370 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12920213	Negative Allosteric Modulator 43
Voltage-gated T-type calcium channel 19 Target ID: CHEMBL2362995 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21898399	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Joint and muscular pain 1 Sources: http://www.ndrugs.com/?s=niflamol	Primary		Approved 8583	niflamol Approved Use Unknown
Rheumatoid arthritis 320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4556915/	Palliative		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ca2+-activated Cl- current in cultured myenteric neurons from murine proximal colon.	2003-04	12456397
Effects of osmotic changes on the chemoreceptor cell of rat carotid body.	2003-01-15	12527733
Anomalous effect of anthracene-9-carboxylic acid on calcium-activated chloride currents in rabbit pulmonary artery smooth muscle cells.	2003-01	12522070
Cellular mechanisms involved in the increased contraction of portal veins from Schistosoma mansoni-infected mice.	2003-01	12474038
Ca2+-activated Cl- channels in corpus cavernosum smooth muscle: a novel mechanism for control of penile erection.	2003-01	12391071
[Cannabis and nifluril].	2002-12-18	12484364
Differential activation of ion channels by inositol 1,4,5-trisphosphate (IP3)- and ryanodine-sensitive calcium stores in rat basilar artery vasomotion.	2002-12-01	12456838
Characterisation of the ionic currents in freshly isolated rat ureter smooth muscle cells: evidence for species-dependent currents.	2002-12	12466949
TRPC4 currents have properties similar to the pacemaker current in interstitial cells of Cajal.	2002-12	12388058
[BK channels play an important role as a negative feedback mechanism in the regulation of spontaneous rhythmic contraction of urinary bladder smooth muscles].	2002-11	12491797
Anion channels influence ECC by modulating L-type Ca(2+) channel in ventricular myocytes.	2002-11	12381751
Functional role of Cl- channels in acidic pH-induced contraction of the aorta of spontaneously hypertensive and Wistar Kyoto rats.	2002-10-25	12398916
D2-like dopamine receptors promote interactions between calcium and chloride channels that diminish rod synaptic transfer in the salamander retina.	2002-10-24	12392173
Fenamate-induced enhancement of heterologously expressed HERG currents in Xenopus oocytes.	2002-10-11	12359267
Plasmalemmal voltage-activated K(+) currents in protoplasts from tobacco BY-2 cells: possible regulation by actin microfilaments?	2002-10	12417939
Tyrosine kinases and amino acid efflux under hyposmotic and ischaemic conditions in the chicken retina.	2002-10	12397392
Separation of two Cl(-) currents in cultured human and murine mesangial cells: biophysical and pharmacological characteristics of I(Cl.vol) and I(Cl.Ca).	2002-09-26	12297705
Three electrophysiological phenotypes of cultured human umbilical vein endothelial cells.	2002-09	12537354
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.	2002-09	12215517
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.	2002-09	12183654
Characterization of norepinephrine-evoked inward currents in interstitial cells isolated from the rabbit urethra.	2002-09	12176745
The DC electrical-field-induced Ca(2+) response and growth stimulation of multicellular tumor spheroids are mediated by ATP release and purinergic receptor stimulation.	2002-08-15	12140258
Induction of cyclooxygenase-2 expression in glomeruli by aggregated protein.	2002-08	12233815
A comparative study of the effects of Cl(-) channel blockers on mesenteric vascular conductance in anaesthetized rat.	2002-07-12	12126972
Disparity between ionic mediators of volume regulation and apoptosis in N1E 115 mouse neuroblastoma cells.	2002-07-12	12101047
Role of Ca2+-activated Cl- channels and MLCK in slow IJP in opossum esophageal smooth muscle.	2002-07	12065297
Presence of a calcium-activated chloride current in mouse ventricular myocytes.	2002-07	12063303
Does mucus hypersecretion matter in airway disease?	2002-06-01	12057561
The role of prostaglandin E2 in the immunopathogenesis of experimental pulmonary tuberculosis.	2002-06	12047755
Control of descending vasa recta pericyte membrane potential by angiotensin II.	2002-06	11997323
Activation thresholds of K(V), BK andCl(Ca) channels in smooth muscle cells in pial precapillary arterioles.	2002-05-16	12011584
A Ca(2+)-inhibited non-selective cation conductance contributes to pacemaker currents in mouse interstitial cell of Cajal.	2002-05-01	11986370
Inhibition of mycophenolic acid glucuronidation by niflumic acid in human liver microsomes.	2002-05	12012139
Calcium and calcium-activated currents in vagotomized rat primary vagal afferent neurons.	2002-04-15	11956342
Enhancement of HCO(3)(-) permeability across the apical membrane of bovine corneal endothelium by multiple signaling pathways.	2002-04	11923259
Mechanism of n-butyrate uptake in the human proximal colonic basolateral membranes.	2002-04	11897627
Sensitivity of the plant vacuolar malate channel to pH, Ca2+ and anion-channel blockers.	2002-03-01	11891587
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.	2002-03	11920772
Dual effect of blocking agents on Ca2+-activated Cl(-) currents in rabbit pulmonary artery smooth muscle cells.	2002-02-15	11850506
Comparative inhibitory effects of niflumic acid and novel synthetic derivatives on the rat isolated stomach fundus.	2002-02	11848293
Swelling-activated taurine and creatine effluxes from rat cortical astrocytes are pharmacologically distinct.	2002-01-15	11891574
Inhibition of gap junction hemichannels by chloride channel blockers.	2002-01-15	11891568
Comparison of the osmolyte transport properties induced by trAE1 versus IClswell in Xenopus oocytes.	2002-01-01	11891564
Disparate effects of non-steroidal anti-inflammatory drugs on apoptosis in guinea-pig gastric mucous cells: inhibition of basal apoptosis by diclofenac.	2002-01	11815376
Synthesis, spectral studies and anti-inflammatory activity of glycolamide esters of niflumic acid as potential prodrugs.	2002	12489252
Action potential afterdepolarization mediated by a Ca2+-activated cation conductance in myenteric AH neurons.	2002	12421604
The Entamoeba histolytica EhPgp5 (MDR-like) protein induces swelling of the trophozoites and alters chloride-dependent currents in Xenopus laevis oocytes.	2002	12002645
The non-steroidal anti-inflammatory drug niflumic acid inhibits Candida albicans growth.	2002	11913762
Actions of putative chloride channel blocking agents on canine lower esophageal sphincter (LES).	2001-12	11824935
Ca(2+)-activated Cl(-) channels: a newly emerging anion transport family.	2001	11845314

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

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 `Mon Mar 31 18:29:53 GMT 2025` Edited by `admin` on `Mon Mar 31 18:29:53 GMT 2025`
Record UNII	4U5MP5IUD8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NIFLUGEL

Preferred Name

English

NIFLUMIC ACID

Official Name

English

Niflumic acid [WHO-DD]

Common Name

English

UP-83

Code

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