CAS： 4394-00-7
MF： C13H9F3N2O2
Appearance： Pale yellow crystalline powder
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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). |
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Therapeutic Function |
Antiinflammatory |
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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. |
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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 [84–86], or 2-aminonicotinic acid with 1-bromo-3-trifluoromethylbenzene [87]. |
InChI:InChI=1/C13H9F3N2O2/c14-13(15,16)8-3-1-4-9(7-8)18-11-10(12(19)20)5-2-6-17-11/h1-7H,(H,17,18)(H,19,20)/p-1
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methyl 2-((3-(trifluoromethyl)phenyl)amino)nicotinate
Niflumic Acid
| Conditions | Yield |
|---|---|
|
With water; sodium hydroxide; In methanol; at 80 ℃;
|
82% |
2-chloronicotinic acid
3-trifluoromethylaniline
Niflumic Acid
| Conditions | Yield |
|---|---|
|
With pyridine; toluene-4-sulfonic acid; In water; Heating;
|
|
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With potassium iodide; at 100 - 140 ℃; for 1.5h;
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2-chloronicotinic acid
3-trifluoromethylaniline
1-(3'-trifluoromethylphenyl)-2-methyl-4H-1,2-dihydro-pyrido-<2,3-d>-<1,3>-oxazin-4-one
1-(3'-trifluoromethylphenyl)-4H-1,2-dihydro-pyrido-<2,3-d>-<1,3>-oxazin-4-one
talniflumate
1-(3'-trifluoromethylphenyl)-4H-1,2-dihydro-pyrido-<2,3-d>-<1,3>-oxazin-4-one
2-<<3-(trifluormetil)fenil>amino>-3-piridincarboxilato de pivaloiloximetilo
1-(3'-trifluoromethylphenyl)-2-methyl-4H-1,2-dihydro-pyrido-<2,3-d>-<1,3>-oxazin-4-one
