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

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
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	11404844
Cyclooxygenase-2 protein and prostaglandin E(2) production are up-regulated in a rat bladder inflammation model.	2001 Apr 13	11334856
Key role for constitutive cyclooxygenase-2 of MDCK cells in basal signaling and response to released ATP.	2001 Aug	11443051
Activation of alpha 6 GABAA receptors on depolarized cerebellar parallel fibers elicits glutamate release through anion channels.	2001 Dec	11747899
The properties of the secretagogue-evoked chloride current in mouse pancreatic acinar cells.	2001 Jan	11212212
Calcium channels in Xenopus spinal neurons differ in somas and presynaptic terminals.	2001 Jul	11431508
Niflumic acid modulates uncoupled substrate-gated conductances in the human glutamate transporter EAAT4.	2001 Jul 1	11432999
Hypo-osmotic swelling-activated release of organic osmolytes in brain slices: implications for brain oedema in vivo.	2001 Jun	11413246
Role of chloride in constriction of descending vasa recta by angiotensin II.	2001 Jun	11353695
Ca(2+)-activated Cl- channels in Ehrlich ascites tumor cells are distinct from mCLCA1, 2 and 3.	2001 May	11417225
Afterhyperpolarization current in myenteric neurons of the guinea pig duodenum.	2001 May	11353011
Aluminum activates a citrate-permeable anion channel in the aluminum-sensitive zone of the maize root apex. A comparison between an aluminum- sensitive and an aluminum-resistant cultivar.	2001 May	11351102
Chloride channels regulate HIT cell volume but cannot fully account for swelling-induced insulin secretion.	2001 May	11334443
Niflumic acid and cutaneous reactions in children.	2001 May	11316692
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	11386636
Selective inhibition of Cl(-) conductance in toad skin by blockers of Cl(-) channels and transporters.	2001 Oct	11546659
Nitric oxide contracts longitudinal smooth muscle of opossum oesophagus via excitation-contraction coupling.	2001 Oct 1	11579163
Cell-to-cell communication via nitric oxide modulation of oscillatory Cl(-) currents in rat intact cerebral arterioles.	2001 Oct 1	11579157
Fenamates: a novel class of reversible gap junction blockers.	2001 Sep	11504800
Action potential afterdepolarization mediated by a Ca2+-activated cation conductance in myenteric AH neurons.	2002	12421604
The non-steroidal anti-inflammatory drug niflumic acid inhibits Candida albicans growth.	2002	11913762
Mechanism of n-butyrate uptake in the human proximal colonic basolateral membranes.	2002 Apr	11897627
Calcium and calcium-activated currents in vagotomized rat primary vagal afferent neurons.	2002 Apr 15	11956342
Stimulation of the BK(Ca) channel in cultured smooth muscle cells of human trachea by magnolol.	2002 Jan	11809993
Swelling-activated taurine and creatine effluxes from rat cortical astrocytes are pharmacologically distinct.	2002 Jan 15	11891574
Role of Ca2+-activated Cl- channels and MLCK in slow IJP in opossum esophageal smooth muscle.	2002 Jul	12065297
Presence of a calcium-activated chloride current in mouse ventricular myocytes.	2002 Jul	12063303
A comparative study of the effects of Cl(-) channel blockers on mesenteric vascular conductance in anaesthetized rat.	2002 Jul 12	12126972
Disparity between ionic mediators of volume regulation and apoptosis in N1E 115 mouse neuroblastoma cells.	2002 Jul 12	12101047
The role of prostaglandin E2 in the immunopathogenesis of experimental pulmonary tuberculosis.	2002 Jun	12047755
Does mucus hypersecretion matter in airway disease?	2002 Jun 1	12057561
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	11920772
Activation thresholds of K(V), BK andCl(Ca) channels in smooth muscle cells in pial precapillary arterioles.	2002 Mar-Apr	12011584
Inhibition of mycophenolic acid glucuronidation by niflumic acid in human liver microsomes.	2002 May	12012139
The Entamoeba histolytica EhPgp5 (MDR-like) protein induces swelling of the trophozoites and alters chloride-dependent currents in Xenopus laevis oocytes.	2002 Spring	12002645

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.

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