2-((3-(Trifluormethyl)phenyl)-amino)benzoesäure

Bezeichnung:2-((3-(Trifluormethyl)phenyl)-amino)benzoesäure

CAS-Nr530-78-9

Englisch Name:Flufenamic acid

CBNumberCB7118092

SummenformelC14H10F3NO2

Molgewicht281.23

MOL-Datei530-78-9.mol

Synonyma

Flufenaminsure

2-((3-(Trifluormethyl)phenyl)-amino)benzoesäure

2-((3-(Trifluormethyl)phenyl)-amino)benzoesäure physikalisch-chemischer Eigenschaften

Schmelzpunkt	132-135 °C(lit.)
Siedepunkt	373.9±42.0 °C(Predicted)
Dichte	1.3380 (estimate)
Dampfdruck	0Pa at 25℃
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit	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)
Aggregatzustand	Crystalline Powder or Chunks
Farbe	Off-white to gray-green
Wasserlöslichkeit	0.0265 g/L (37 ºC)
Merck	14,4132
BRN	1996069
LogP	5.25
CAS Datenbank	530-78-9(CAS DataBase Reference)
NIST chemische Informationen	Flufenamic acid(530-78-9)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/38
S-Sätze:	26
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	CB4375000
HazardClass	6.1(b)
PackingGroup	III
HS Code	29224999
Toxizität	LD50 in mice: 715 mg/kg orally (Zoni)

Gefahreninformationscode (GHS)

Flufenamic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/38:Reizt die Augen und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
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.
Chemische Eigenschaften
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.
Verwenden
An NSAID found to be a reversible gap junction blocker
Verwenden
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.
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.
Trademarks
Arlef (Parke-Davis, Sankyo, Japan), Ansatin (Ono, Japan), Felunamin (Hokuriko, Japan), Romafen (Biofarma, Turkey).
Therapeutic Function
Antiinflammatory, Antirheumatic
Biologische Aktivität
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.
Sicherheit(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.
Synthese
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].
Lager
Store at RT

Flufenamic acid Upstream-Materialien And Downstream Produkte

2-((3-(Trifluormethyl)phenyl)-amino)benzoesäure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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