Triflusal

Names

[ CAS No. ]:
322-79-2

[ Name ]:
Triflusal

[Synonym ]:
Triflusal
2-(acetyloxy)-4-(trifluoromethyl)benzoic acid
α,α,α-Trifluoro-2,4-cresotic Acid Acetate
2-Acetoxy-4-trifluoromethylbenzoic acid
EINECS 206-297-5
Triflusalum [INN-Latin]
2-Acetoxy-4-trifluoromethylbenzoicacid
Benzoic acid, 2-(acetyloxy)-4-(trifluoromethyl)-
Triflusal [INN]
2-Acetoxy-4-trifluormethyl-benzoesaeure
2-Acetoxy-4-(trifluoromethyl)benzoic acid
2-Acetyloxy-4-trifluoromethylbenzoic acid
UR 1501
MFCD00866793
Disgren
Triflux

Biological Activity

[Description]:

Triflusal irreversibly inhibits the production of thromboxane-B2 in platelets by acetylating cycloxygenase-1.Target: COXTriflusal at 10 mM, 100 mM and 1 M decreases LDH efflux in rat brain slices after anoxia/reoxygenation by 24%, 35% and 49% respectively. Triflusal also reduces inducible NO synthase activity by 18%, 21% and 30% [1].Triflusal (10 mg/kg i.v.) reduces platelet deposition on subendothelium-induced primary thrombus by about 68% in rabbits. Triflusal (10 mg/kg i.v.) reduces platelet deposition on a fresh thrombus formed over tunica media by about 48% in rabbits. Triflusal (40 mg/kg p.o.) reduces platelet deposition on a primary thrombus triggered by subendothelium and tunica media by 53% in rabbits. Triflusal (40 mg/kg p.o.) significantly reduces Cox-2 mRNA levels and protein levels without influence Cox-1 mRNA levels on the vascular wall in rabbits [2]. Triflusal (600 mg/day for 5 days) results in an increase in NO production by neutrophils and an increase in endothelial nitric oxide synthase (eNOS) protein expression in neutrophils in healthy volunteers [3].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

[Target]

COX-2:280 μM (IC50)

COX-2:160 μM (IC50, in human blood)

[References]

[1]. Fernández de Arriba A, et al. Inhibition of cyclooxygenase-2 expression by 4-trifluoromethyl derivatives of salicylate, triflusal, and its deacetylated metabolite, 2-hydroxy-4-trifluoromethylbenzoic acid. Mol Pharmacol. 1999 Apr;55(4):753-60.

[2]. Duran, X., et al., Protective effects of triflusal on secondary thrombus growth and vascular cyclooxygenase-2. J Thromb Haemost, 2008. 6(8): p. 1385-92.

[3]. De Miguel, L.S., et al., A 4-trifluoromethyl derivative of salicylate, triflusal, stimulates nitric oxide production by human neutrophils: role in platelet function. Eur J Clin Invest, 2000. 30(9): p. 811-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
316.0±42.0 °C at 760 mmHg

[ Melting Point ]:
115 °C

[ Molecular Formula ]:
C₁₀H₇F₃O₄

[ Molecular Weight ]:
248.155

[ Flash Point ]:
144.9±27.9 °C

[ Exact Mass ]:
248.029648

[ PSA ]:
63.60000

[ LogP ]:
2.90

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.484

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GP4250000

CHEMICAL NAME :: 2,4-Cresotic acid, alpha,alpha,alpha-trifluoro-, acetate

CAS REGISTRY NUMBER :: 322-79-2

BEILSTEIN REFERENCE NO. :: 2945374

LAST UPDATED :: 199612

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C10-H7-F3-O4

MOLECULAR WEIGHT :: 248.17

WISWESSER LINE NOTATION :: FXFFR DVQ COV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 402 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 3,225,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 217 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 3,225,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 228 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 3,225,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 437 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 3,225,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 380 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 3,225,1978

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H317-H319-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22-36/37/38-43

[ Safety Phrases ]:
26-36/37

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
GP4250000

[ HS Code ]:
2918990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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