Niflumic acid
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
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)
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
- Ⅲ
- HS Code
- 29333999
- Toxicity
- LD50 in rats (mg/kg): 370 orally; 155 i.p. (Sorenson)
MSDS
- Language:English Provider:Niflumic acid
- Language:English Provider:ACROS
- Language:English Provider:SigmaAldrich
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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