Flufenamic acid CAS 530-78-9
Introduction：Basic information about Flufenamic acid CAS 530-78-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Flufenamic acid Basic information
| Product Name: | Flufenamic acid |
| Synonyms: | ci440;CN-27,554;CN-27544;Flufacid;Flufenaminsaeure;Fluore-200;Fluphenamic acid;fluphenamicacid |
| CAS: | 530-78-9 |
| MF: | C14H10F3NO2 |
| MW: | 281.23 |
| EINECS: | 208-494-1 |
| Product Categories: | ARLEF;Other APIs;Signalling;Active Pharmaceutical Ingredients;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;API's |
| Mol File: | 530-78-9.mol |
Flufenamic acid Chemical Properties
| Melting point | 132-135 °C(lit.) |
| Boiling point | 373.9±42.0 °C(Predicted) |
| density | 1.3380 (estimate) |
| vapor pressure | 0Pa at 25℃ |
| storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
| solubility | soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide. The solubility of flufenamic acid in these solvents is approximately 11, 39, and 59 mg/ml, respectively. |
| pka | pKa 3.9 (Uncertain);3.85 (Uncertain) |
| form | Crystalline Powder or Chunks |
| color | Off-white to gray-green |
| Water Solubility | 0.0265 g/L (37 ºC) |
| Merck | 14,4132 |
| BRN | 1996069 |
| Major Application | forensics and toxicology pharmaceutical (small molecule) veterinary |
| InChI | 1S/C14H10F3NO2/c15-14(16,17)9-4-3-5-10(8-9)18-12-7-2-1-6-11(12)13(19)20/h1-8,18H,(H,19,20) |
| InChIKey | LPEPZBJOKDYZAD-UHFFFAOYSA-N |
| SMILES | OC(=O)c1ccccc1Nc2cccc(c2)C(F)(F)F |
| LogP | 5.25 |
| CAS DataBase Reference | 530-78-9(CAS DataBase Reference) |
| NIST Chemistry Reference | Flufenamic acid(530-78-9) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22-36/38 |
| Safety Statements | 26 |
| RIDADR | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | CB4375000 |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 29224999 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral Eye Irrit. 2 Skin Irrit. 2 |
| Toxicity | LD50 in mice: 715 mg/kg orally (Zoni) |
| Description | Flufenamic acid (FFA), namely N-(alpha,alpha,alpha-trifluorom-tolyl) anthranilic acid (CI-440), is an aromatic amino acid consisting of anthranilic acid carrying an N-(trifluoromethyl)phenyl substituent. It is an effective drug in the treatment of special types of migraine. Its anti-inflammatory and analgesic effects were recognized in the 1960s (Winder et al., 1963) and thus FFA is included in the family of non-steroidal anti-inflammatory drugs (NSAIDs) with mefenamic, meclofenamic (MFA) and niflumic acids (NA). Anti-inflammatory actions occur mainly through reduction of prostaglandin synthesis from arachidonic acid by inhibiting the cyclo-oxygenases. |
| Chemical Properties | Fluomic acid is a Pale-Yellow or light yellow-green crystal or crystalline powder with bitter taste. It is almost insoluble in water and can be dissolved in 50% ethanol. It is a non-hormonal anti-inflammatory and analgesic drug. It was prepared by photolysis of the corresponding benzotriazinone. |
| Originator | Flufenamic acid,AroKor Holdings Inc. |
| Uses | Flufenamic acid is used for moderate pain and dysmenorrhea, but it should not be used formore than 1 week due to the possibility of nephrotoxicity, gastrointestinal toxicity, andanemia. It is frequently used in combination with the anticoagulant warfarin, the effect ofwhich is strengthened when combined with flufenamic acid. |
| Uses | An NSAID found to be a reversible gap junction blocker |
| Definition | ChEBI: flufenamic acid is an aromatic amino acid consisting of anthranilic acid carrying an N-(trifluoromethyl)phenyl substituent. An analgesic and anti-inflammatory, it is used in rheumatic disorders. It has a role as an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, a non-steroidal anti-inflammatory drug, a non-narcotic analgesic and an antipyretic. It is an aromatic amino acid and an organofluorine compound. It derives from a diphenylamine, an anthranilic acid and a (trifluoromethyl)benzene. It is a conjugate acid of a flufenamate. |
| Manufacturing Process | A mixture 31.3 g of o-chlorobenzoic acid, 32.2 g of trifluoromethyl-maminobenzene,3 g of copper powder, 13.8 g of waterless potassiumcarbonate and 100 ml amyl alcohol was refluxed for 4 hours. To the cooledmixture was added 25 ml of 10 N solution NaOH and the mixture wasconcentrated and filtrated. Addition to the filtrate hydrochloric acid and watergive a sediment of 2-((3-trifluromethyl)phenyl)aminobenzoic acid. Afterrecrystallization from hexane 2-((3-trifluromethyl)phenyl)aminobenzoic acidhave melting point 134-136°C. |
| Brand name | Arlef (Parke-Davis, Sankyo, Japan), Ansatin (Ono, Japan), Felunamin (Hokuriko, Japan),Romafen (Biofarma, Turkey). |
| Therapeutic Function | Antiinflammatory, Antirheumatic |
| Biological Activity | Flufenamic acid is a nonsteroidal anti-inflammatory drug (NSAID). Inhibits calcium-activated chloride channels (CaCCs). Also increases currents through TRPC6 channels and inhibits currents through TRPC3 and TRPC7 channels. |
| Mechanism of action | In addition to COX inhibition flufenamatelike other fenamates modifies several ion channelfunctions, e.g., inhibition of nonselectivecation conductance, calcium-activatedchloride channels, voltage-gated calciumchannels and potassium channels andinduces blocking of gap junctions. The relevanceof these activities for the analgesic andanti-inflammatory potential of fenamates is unknown. |
| Clinical Use | Flufenamate is a nonsteroidalanti-inflammatory drug used for the treatment ofmild to moderate pain of musculoskeletal, jointor soft-tissue origin. It was marketed in a varietyof topical formulations alone or in combinationwith other ingredients. |
| Safety | Flufenamic acid is used at 600 – 800 mg/d toprovide a beneficial therapeutic effect in chronicpolyarthritis. The adverse effects most often encountered are gastrointestinal disturbances. |
| Synthesis | Flufenamic acid, N-(|á,|á,|á-trifluoro-m-tolyl)anthranylic acid (3.2.18),is synthesized by the reaction of 2-chlorobenzoic acid with 3-trifluoromethylaniline in thepresence of potassium carbonate and copper filings [78,79]. |
| storage | Store at RT |
| References | [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 5, p. 1464 - 1468 [2] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2311 - 2323 [3] Patent: US9271961, 2016, B2. Location in patent: Page/Page column 58; 59 [4] Patent: US5462952, 1995, A |
Flufenamic acid Preparation Products And Raw materials
| Raw materials | Ethanol-->Hydrochloric acid-->N,N-Dimethylformamide-->Potassium hydroxide-->Bromoethane-->Copper-->Morpholine-->N,N-Dimethylacetamide-->2-Chlorobenzoic acid-->3-Aminobenzotrifluoride-->Copper(II) acetate-->2-Iodobenzoic acid-->Potassium carbonate-->sodium 2-[[3-(trifluoromethyl)phenyl]amino]benzoate-->2-(3-TRIFLUOROMETHYL-PHENYLAMINO)-BENZONITRILE-->2-Pyrrolidinecarboxamide,N,N-diethyl-,(2S)-(9CI)-->(S)-2-amino-1-morpholino-3-phenylpropan-1-one-->Benzoic acid,2-[[3-(trifluoromethyl)phenyl]amino]-, methyl ester |
| Preparation Products | 2-(Trifluoromethyl)phenothiazine-->N-phenyl-3-(trifluoromethyl)aniline |
