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N0630

Sigma-Aldrich

Niflumic acid

Synonym(s):

2-(α,α,α-Trifluoro-m-toluidino)nicotinic acid, 2-[3-(Trifluoromethyl)anilino]nicotinic acid

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About This Item

Empirical Formula (Hill Notation):
C13H9F3N2O2
CAS Number:
4394-00-7
Molecular Weight:
282.22
EC Number:
224-516-2
MDL number:
MFCD00010569
UNSPSC Code:
12352106
PubChem Substance ID:
24278582
NACRES:
NA.77

biological source

synthetic (organic)

Assay

≥98% (HPLC)

form

powder

mp

203-204 °C

solubility

acetone: 50 mg/mL, clear to slightly hazy, yellow

SMILES string

O=C(O)C1=CC=CN=C1NC2=CC(C(F)(F)F)=CC=C2

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)

InChI key

JZFPYUNJRRFVQU-UHFFFAOYSA-N

Gene Information

human ... PTGS1(5742)

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Application

Niflumic acid has been used:
  • as a chloride channel blocker in mouse olfactory epithelium for odor-induced electroolfactograms (EOGs) measurements, to test its analgesic effect on rat dorsal root ganglion neurons post γ-aminobutyric acid induction
  • as a calcium-activated chloride channel (CaCC) inhibitor in C2C12 myoblasts and also to test its effect on volume-regulated anion channel (VRAC)
  • as an inhibitor of voltage-dependent potassium channel in human embryonic kidney (HEK 293) phoenix cells

Biochem/physiol Actions

Niflumic acid (NFA), a γ-aminobutyric acid type A receptor (GABAARs) antagonist is a non-steroidal anti-inflammatory drug (NSAID) and it belongs to the fenamate class. It is also a blocker of chloride ion channel and a calcium-activated chloride channel (CaCC) inhibitor. NFA possesses anti-inflammatory property and is useful in treating rheumatic disorders. It is also an inhibitor of N-methyl-D-aspartate receptor and glycine receptor. NFA also inhibits enzymes associated with the prostaglandins synthesis.
Selective cyclooxygenase-2 (COX-2) inhibitor.

Features and Benefits

This compound is featured on the Chloride Channels and Potassium Channels pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H413

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 4

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Michele Dibattista et al.
The Journal of general physiology, 140(1), 3-15 (2012-06-27)
The rodent vomeronasal organ plays a crucial role in several social behaviors. Detection of pheromones or other emitted signaling molecules occurs in the dendritic microvilli of vomeronasal sensory neurons, where the binding of molecules to vomeronasal receptors leads to the
Galyna Maleeva et al.
Frontiers in molecular neuroscience, 10, 125-125 (2017-06-01)
Niflumic acid (NFA) is a member of the fenamate class of nonsteroidal anti-inflammatory drugs. This compound and its derivatives are used worldwide clinically for the relief of chronic and acute pain. NFA is also a commonly used blocker of voltage-gated
Luis Alvarez et al.
The Journal of cell biology, 196(5), 653-663 (2012-03-01)
During chemotaxis and phototaxis, sperm, algae, marine zooplankton, and other microswimmers move on helical paths or drifting circles by rhythmically bending cell protrusions called motile cilia or flagella. Sperm of marine invertebrates navigate in a chemoattractant gradient by adjusting the
Juraj Rievaj et al.
Pflugers Archiv : European journal of physiology, 463(3), 497-509 (2011-12-16)
Protease-activated receptor 2 (PAR-2) is a G protein-coupled receptor possibly involved in the pathogenesis of asthma. PAR-2 also modulates ion transport in cultured epithelial cells, but these effects in native airways are controversial. The influence of allergic inflammation on PAR-2-induced
Tero M Viitanen et al.
Journal of cellular physiology, 228(4), 814-823 (2012-09-29)
The initial step in a synthesis of thyroid hormones is the uptake of iodide from the circulation. Iodide (I(-)) is transported into thyroid cells via a Na(+)/I(-) symporter (NIS), which is electrogenic and thus sensitive to alterations in membrane potential
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