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Flufenamic acid

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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
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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
LogP
5.25
CAS DataBase Reference
530-78-9(CAS DataBase Reference)
NIST Chemistry Reference
Flufenamic acid(530-78-9)
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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
Toxicity
LD50 in mice: 715 mg/kg orally (Zoni)

MSDS

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Flufenamic acid Usage And Synthesis

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 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.

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 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 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 flufenamate like other fenamates modifies several ion channel functions, e.g., inhibition of nonselective cation conductance, calcium-activated chloride channels, voltage-gated calcium channels and potassium channels and induces blocking of gap junctions. The relevance of these activities for the analgesic and anti-inflammatory potential of fenamates is unknown.

Clinical Use

Flufenamate is a nonsteroidal anti-inflammatory drug used for the treatment of mild to moderate pain of musculoskeletal, joint or soft-tissue origin. It was marketed in a variety of topical formulations alone or in combination with other ingredients.

Safety

Flufenamic acid is used at 600 – 800 mg/d to provide a beneficial therapeutic effect in chronic polyarthritis. 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 the presence of potassium carbonate and copper filings [78,79].

storage

Store at RT

Flufenamic acidSupplier

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