| Identification | Back Directory | [Name]
Niflumic acid | [CAS]
4394-00-7 | [Synonyms]
ACTOL
UP-83
sc1332
Forenol
Landruma
niflumic
NIFLURIL
DONALGIN
Niflumate
Nifumic Acid
TOSLAB 796450
NIFLUMIC ACID
acidoniflumico
Nifluminic acid
acideniflumique
Acido niflumico
Acide niflumique
Actol, analgesic
ACIDUM NIFLUMICUM
Niflumic acid,99%
TIMTEC-BB SBB001146
LABOTEST-BB LT00451962
Niflumic acid solution,100ppm
ACIDUMNIFLUMICUM(NIFLUMICACID)
Nicotinic acid Solution, 100ppm
2-(3-TRIFLUOROMETHYLANILINO)NICOTINIC ACID
2-(α,α,α-trifluoro-m-toluidino)nicotinic acid
aza-2dimethyl-2’,3’(tetrazolyl-5)-6diphenylamino
2-[(3-TRIFLUOROMETHYLPHENYL)AMINO]NICOTINIC ACID
2-(alpha,alpha,alpha-trifluoro-m-toluidino)-nicotinicaci
2-(ALPHA,ALPHA,ALPHA-TRIFLUORO-M-TOLUIDINO)NICOTINIC ACID
Nicotinic acid, 2-(alpha,alpha,alpha-trifluoro-m-toluidino)-
2-[(3-TRIFLUOROMETHYL)PHENYL]AMINO]-3-PYRIDINECARBOXYLIC ACID
2-[(3-Trifluoromethylphenyl)amino]nicotinic Acid
Niflumic Acid
3-Pyridinecarboxylic acid, 2-[[3-(trifluoromethyl)phenyl]amino]-
Niflumic Acid:2-[(3-trifluoromethyl) phenyl] amino-3-pyridine-carboxylic acid
2-[3-(Trifluoromethyl)anilino]nicotinic acid, 2-(α,α,α-Trifluoro-m-toluidino)nicotinic acid | [EINECS(EC#)]
224-516-2 | [Molecular Formula]
C13H9F3N2O2 | [MDL Number]
MFCD00010569 | [MOL File]
4394-00-7.mol | [Molecular Weight]
282.22 |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
203-204 °C
| [Boiling point ]
378.0±42.0 °C(Predicted) | [density ]
1.3935 (estimate) | [storage temp. ]
Store at RT | [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). | [form ]
neat | [pka]
pKa 2.26 ± 0.08;4.44± 0.03(H2O,t =25±0.1,I=0.01(NaCl))(Approximate) | [color ]
Light orange to Yellow to Green | [Stability:]
Stable, but may discolour in light. Incompatible with strong oxidizing agents. Hygroscopic. | [Water Solubility ]
19mg/L(room temperature) | [Sensitive ]
Light Sensitive | [Merck ]
14,6531 | [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) |
| Hazard Information | Back Directory | [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].
| [storage]
Store at -20°C |
|
|