Chemical Properties
Crystalline Solid
Uses
analgesic, antiinflammatory
Uses
Anti-inflammatory. Selective cyclooxygenase-2 (COX-2) inhibitor
Originator
Nifluril,U.P.S.A.,France,1968
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].
