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Niflumic acid

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Niflumic acid Basic information
Product Name:Niflumic acid
Synonyms:2-[3-(Trifluoromethyl)anilino]nicotinic acid, 2-(α,α,α-Trifluoro-m-toluidino)nicotinic acid;Niflumic acid,99%;LABOTEST-BB LT00451962;DONALGIN;2-(ALPHA,ALPHA,ALPHA-TRIFLUORO-M-TOLUIDINO)NICOTINIC ACID;2-(3-TRIFLUOROMETHYLANILINO)NICOTINIC ACID;2-[(3-TRIFLUOROMETHYL)PHENYL]AMINO]-3-PYRIDINECARBOXYLIC ACID;2-[(3-TRIFLUOROMETHYLPHENYL)AMINO]NICOTINIC ACID
CAS:4394-00-7
MF:C13H9F3N2O2
MW:282.22
EINECS:224-516-2
Product Categories:API intermediates;Active Pharmaceutical Ingredients;Acids and Derivatives;Heterocycles;Pharmaceuticals;Intermediates & Fine Chemicals;Inhibitors;Aromatics
Mol File:4394-00-7.mol
Niflumic acid Structure
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).
pkapKa 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
biological sourcesynthetic (organic)
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.
InChIKeyJZFPYUNJRRFVQU-UHFFFAOYSA-N
NIST Chemistry ReferenceNiflumic acid(4394-00-7)
EPA Substance Registry System3-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 
HS Code 29333999
ToxicityLD50 in rats (mg/kg): 370 orally; 155 i.p. (Sorenson)
MSDS Information
ProviderLanguage
Niflumic acid English
SigmaAldrich English
ACROS English
Niflumic acid Usage And Synthesis
Chemical PropertiesCrystalline Solid
OriginatorNifluril,U.P.S.A.,France,1968
Usesanalgesic, antiinflammatory
UsesAnti-inflammatory. Selective cyclooxygenase-2 (COX-2) inhibitor
UsesNiflumic acid is used for the exact same indications as the drugs described above. Synonyms for this drug are actol, flunir, nifluril, and others.
DefinitionChEBI: Niflumic acid is an aromatic carboxylic acid and a member of pyridines.
Manufacturing ProcessNiflumic 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 FunctionAntiinflammatory
Trade nameActol (Mayrhofer, Austria; Upsamedica, Spain), Donalgin (Gedeon Richter, Hungary), Livornex (Genepharm, Greece), Ni- flam (Upsamedica, Italy), Nifluril (UPSA, France; Upsamedica, Belgium, Switzerland, Portugal).
Biochem/physiol ActionsNiflumic 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 effectsNiflumic 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.
SynthesisNiflumic 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

Niflumic acid Preparation Products And Raw materials
Raw materialsPotassium iodide-->3-AMINOBENZOTRIFLUORIDE-->Nicotinic acid
Tag:Niflumic acid(4394-00-7) Related Product Information
2-Aminopyridine Quinolinic acid Ethyl 2-(Chlorosulfonyl)acetate PHENYL VALERATE 3-Trifluoromethylpyridine Nicotinic acid 4-Dimethylaminopyridine CLOFENAMIC ACID 2,5-PYRIDINEDICARBOXYLIC ACID Stearic acid Hexafluorozirconic acid 3-Aminopyridine Folic acid Ammonium hexafluorozirconate Citric acid Tolfenamic acid Flufenamic acid Ascoric Acid

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