Introduction：Basic information about Niflumic acid CAS 4394-00-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Niflumic acid Basic information
| Product Name: | Niflumic acid |
| Synonyms: | ACIDUM NIFLUMICUM;2-(α,α,α-trifluoro-m-toluidino)nicotinic acid;Nicotinic acid Solution, 100ppm;Niflumic acid solution,100ppm;ACIDUMNIFLUMICUM(NIFLUMICACID);2-[(3-Trifluoromethylphenyl)amino]nicotinic AcidNiflumic Acid;2-[3-(Trifluoromethyl)anilino]nicotinic acid, 2-(α,α,α-Trifluoro-m-toluidino)nicotinic acid;Niflumic acid,99% |
| CAS: | 4394-00-7 |
| MF: | C13H9F3N2O2 |
| MW: | 282.22 |
| EINECS: | 224-516-2 |
| Product Categories: | Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;API intermediates;Active Pharmaceutical Ingredients;Acids and Derivatives;Heterocycles |
| Mol File: | 4394-00-7.mol |
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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). |
| pka | pKa 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 source | synthetic (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. |
| InChI | 1S/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) |
| InChIKey | JZFPYUNJRRFVQU-UHFFFAOYSA-N |
| SMILES | O=C(O)C1=CC=CN=C1NC2=CC(C(F)(F)F)=CC=C2 |
| NIST Chemistry Reference | Niflumic acid(4394-00-7) |
| EPA Substance Registry System | 3-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 | Ⅲ |
| HS Code | 29333999 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral
Aquatic Chronic 4 |
| Toxicity | LD50 in rats (mg/kg): 370 orally; 155 i.p. (Sorenson) |
Niflumic acid Usage And Synthesis
| Chemical Properties | Crystalline Solid |
| Originator | Nifluril,U.P.S.A.,France,1968 |
| Uses | analgesic, antiinflammatory |
| Uses | Niflumic acid is used for the exact same indications as the drugs described above. Synonyms for thisdrug are actol, flunir, nifluril, and others. |
| Uses | Anti-inflammatory. Selective cyclooxygenase-2 (COX-2) inhibitor |
| 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 at140°C. The mixture melts to give a dark red liquid. The temperature of the oilbath is allowed to fall to 100°C and is maintained at this temperature for anhour 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 andextracted several times with small volumes of ether to remove excess mtrifluoromethylaniline. The residue is then washed twice with 10 ml of distilledwater to remove m-trifluoromethylaniline hydrochloride and potassium iodide,and finally twice with 10 ml of 95% alcohol to remove colored resinouscontaminants. After drying at 100°C, 2-(m-trifluoromethylanilino)nicotinic acidis 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 totreat rheumatoid arthritis, psoriatic arthritis, andhypertrophic 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]. |
Niflumic acid Preparation Products And Raw materials
| Raw materials | Potassium iodide-->3-AMINOBENZOTRIFLUORIDE-->Nicotinic acid |
