Flufenamic acid

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;Active Pharmaceutical Ingredients;Aromatics;Intermediates & Fine Chemicals;Signalling;Pharmaceuticals;API's
Mol File:530-78-9.mol
Flufenamic acid Structure
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.
form Crystalline Powder or Chunks
pkapKa 3.9 (Uncertain);3.85 (Uncertain)
color Off-white to gray-green
Water Solubility 0.0265 g/L (37 ºC)
Merck 14,4132
BRN 1996069
LogP5.25
CAS DataBase Reference530-78-9(CAS DataBase Reference)
NIST Chemistry ReferenceFlufenamic 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
ToxicityLD50 in mice: 715 mg/kg orally (Zoni)
MSDS Information
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Flufenamic acid English
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Flufenamic acid Usage And Synthesis
DescriptionFlufenamic 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 PropertiesFluomic 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.
OriginatorFlufenamic acid,AroKor Holdings Inc.
UsesFlufenamic acid is used for moderate pain and dysmenorrhea, but it should not be used for more than 1 week due to the possibility of nephrotoxicity, gastrointestinal toxicity, and anemia. It is frequently used in combination with the anticoagulant warfarin, the effect of which is strengthened when combined with flufenamic acid.
UsesAn NSAID found to be a reversible gap junction blocker
DefinitionChEBI: 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 ProcessA mixture 31.3 g of o-chlorobenzoic acid, 32.2 g of trifluoromethyl-maminobenzene, 3 g of copper powder, 13.8 g of waterless potassium carbonate and 100 ml amyl alcohol was refluxed for 4 hours. To the cooled mixture was added 25 ml of 10 N solution NaOH and the mixture was concentrated and filtrated. Addition to the filtrate hydrochloric acid and water give a sediment of 2-((3-trifluromethyl)phenyl)aminobenzoic acid. After recrystallization from hexane 2-((3-trifluromethyl)phenyl)aminobenzoic acid have melting point 134-136°C.
Brand nameArlef (Parke-Davis).
Therapeutic FunctionAntiinflammatory, Antirheumatic
Biological ActivityFlufenamic 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.
SynthesisFlufenamic 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 the presence of potassium carbonate and copper filings [78,79].Synthesis_530-78-9
storageStore at RT
Etofenamate ufenamate Hyaluronic acid 3-(Trifluoromethyl)benzoic acid METHYL 2-(3-TRIFLUOROMETHYLPHENYLAMINO)-BENZOATE TOLUALDEHYDES Ethyl 2-(Chlorosulfonyl)acetate Ascoric Acid Niflumic acid 4-Dimethylaminobenzoic acid 4-Aminobenzoic acid N-(3,5-BIS-TRIFLUOROMETHYLPHENYL)ANTHRANILIC ACID Folic acid α-Lipoic Acid Flufenamic acid 4-(Trifluoromethyl)benzoic acid Anthranilic acid Citric acid

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