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ChemicalBook--->CAS DataBase List--->4394-00-7

4394-00-7

4394-00-7 Structure

4394-00-7 Structure
IdentificationBack 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 PropertiesBack 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.
[biological source]

synthetic (organic)
[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 InformationBack 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].

Synthesis_4394-00-7

[storage]

Store at -20°C
Safety DataBack Directory
[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)
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Niflumic acid(4394-00-7).msds
Spectrum DetailBack Directory
[Spectrum Detail]

Niflumic acid(4394-00-7)MS
Niflumic acid(4394-00-7)1HNMR
Niflumic acid(4394-00-7)13CNMR
Niflumic acid(4394-00-7)IR1
Niflumic acid(4394-00-7)IR2
Niflumic acid(4394-00-7)Raman
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