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Niflumic acid

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Niflumic acid Basic information

Product Name:
Niflumic acid
Synonyms:
  • ACIDUM NIFLUMICUM
  • 2-(α,α,α-trifluoro-m-toluidino)nicotinic acid
  • Nicotinic acid Solution, 100ppm
  • Niflumic acid solution,100ppm
  • ACIDUMNIFLUMICUM(NIFLUMICACID)
  • 2-[(3-Trifluoromethylphenyl)amino]nicotinic Acid Niflumic Acid
  • 2-[3-(Trifluoromethyl)anilino]nicotinic acid, 2-(α,α,α-Trifluoro-m-toluidino)nicotinic acid
  • Niflumic acid,99%
CAS:
4394-00-7
MF:
C13H9F3N2O2
MW:
282.22
EINECS:
224-516-2
Product Categories:
  • Aromatics
  • Inhibitors
  • Active Pharmaceutical Ingredients
  • API intermediates
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Acids and Derivatives
  • Heterocycles
Mol File:
4394-00-7.mol
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Niflumic acid Chemical Properties

Melting point:
203-204 °C
Boiling point:
378.0±42.0 °C(Predicted)
Density 
1.3935 (estimate)
storage temp. 
2-8°C
solubility 
Soluble in ethanol (~50 mg/ml), acetone (50 mg/ml, Clear to Slightly Hazy, Yellow), methanol (~50 mg/ml), DMSO (56 mg/ml at 25°C), and acetonitrile (~50 mg/ml).
pka
pKa 2.26 ± 0.08;4.44± 0.03(H2O,t =25±0.1,I=0.01(NaCl))(Approximate)
form 
Solid
color 
Light orange to Yellow to Green
Water Solubility 
19mg/L(room temperature)
Sensitive 
Light Sensitive
Merck 
14,6531
Stability:
Stable, but may discolour in light. Incompatible with strong oxidizing agents. Hygroscopic.
InChIKey
JZFPYUNJRRFVQU-UHFFFAOYSA-N
NIST Chemistry Reference
Niflumic acid(4394-00-7)
EPA Substance Registry System
3-Pyridinecarboxylic acid, 2-[[3-(trifluoromethyl)phenyl]amino]- (4394-00-7)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
20/21/22-36/37/38
Safety Statements 
26-36-36/37/39
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
QT2999100
HazardClass 
6.1
PackingGroup 
HS Code 
29333999
Toxicity
LD50 in rats (mg/kg): 370 orally; 155 i.p. (Sorenson)

MSDS

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Niflumic acid Usage And Synthesis

Chemical Properties

Crystalline Solid

Originator

Nifluril,U.P.S.A.,France,1968

Uses

analgesic, antiinflammatory

Uses

Niflumic acid is used for the exact same indications as the drugs described above. Synonyms for this drug are actol, flunir, nifluril, and others.

Uses

Anti-inflammatory. Selective cyclooxygenase-2 (COX-2) inhibitor

Definition

ChEBI: Niflumic acid is an aromatic carboxylic acid and a member of pyridines.

Manufacturing Process

Niflumic acid is prepared as follows: Nicotinic acid, m-trifluoromethylaniline, and potassium iodide are intimately mixed and heated on an oil bath at 140°C. The mixture melts to give a dark red liquid. The temperature of the oil bath is allowed to fall to 100°C and is maintained at this temperature for an hour and a half. The mixture puffs up and forms a yellow crystalline mass. After cooling to ordinary temperature, this mass is ground up in a mortar and extracted several times with small volumes of ether to remove excess mtrifluoromethylaniline. The residue is then washed twice with 10 ml of distilled water to remove m-trifluoromethylaniline hydrochloride and potassium iodide, and finally twice with 10 ml of 95% alcohol to remove colored resinous contaminants. After drying at 100°C, 2-(m-trifluoromethylanilino)nicotinic acid is obtained as pale yellow needles (from 70% ethanol) melting at 204°C (Kofler block).

Therapeutic Function

Antiinflammatory

Trade name

Actol (Mayrhofer, Austria; Upsamedica, Spain), Donalgin (Gedeon Richter, Hungary), Livornex (Genepharm, Greece), Ni- flam (Upsamedica, Italy), Nifluril (UPSA, France; Upsamedica, Belgium, Switzerland, Portugal).

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.

Side effects

Niflumic acid has been used effectively to treat rheumatoid arthritis, psoriatic arthritis, and hypertrophic osteoarthritis of the hip and knee. Gastric complications are the chief adverse effects of this drug.

Synthesis

Niflumic acid, 2-3-(trifluoromethyl)anilino nicotinic acid (3.2.21), is synthesized either by the reaction of 2-chloronicotinic acid with 3-trifluoromethylaniline [84¨C86], or 2-aminonicotinic acid with 1-bromo-3-trifluoromethylbenzene [87].

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