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Triflusal

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Chemistry

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Also known as: 322-79-2, 2-acetoxy-4-trifluoromethylbenzoic acid, Disgren, 2-acetoxy-4-(trifluoromethyl)benzoic acid, 2-acetyloxy-4-(trifluoromethyl)benzoic acid, Triflusal [inn]

Molecular Formula

C₁₀H₇F₃O₄

Molecular Weight

248.15 g/mol

InChI Key

RMWVZGDJPAKBDE-UHFFFAOYSA-N

FDA UNII

1Z0YFI05OO

Triflusal is a 2-acetoxy-4-trifluoromethylbenzoic acid and it is an aspirin chemically-related molecule but not a derivative. The benefits of this agent are the lack of action over the arachidonic acid pathway, the driven production of nitric oxide and the increase of cyclic nucleotide concentration on endothelial cells. The latest translates into the expansion of peripheral blood vessels. It is very important as a secondary prevention of ischemic stroke by offering a lower risk of bleeding. It was developed by J. Uriach and Company and even though it is commercialized in different countries it is not approved by the FDA, EMA or HealthCanada.

1 2D Structure

Triflusal

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-acetyloxy-4-(trifluoromethyl)benzoic acid

2.1.2 InChI

InChI=1S/C10H7F3O4/c1-5(14)17-8-4-6(10(11,12)13)2-3-7(8)9(15)16/h2-4H,1H3,(H,15,16)

2.1.3 InChI Key

RMWVZGDJPAKBDE-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(=O)OC1=C(C=CC(=C1)C(F)(F)F)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

1Z0YFI05OO

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-acetoxy-4-trifluoromethylbenzoic Acid

2. Disgren

2.3.2 Depositor-Supplied Synonyms

1. 322-79-2

2. 2-acetoxy-4-trifluoromethylbenzoic Acid

3. Disgren

4. 2-acetoxy-4-(trifluoromethyl)benzoic Acid

5. 2-acetyloxy-4-(trifluoromethyl)benzoic Acid

6. Triflusal [inn]

7. 2-(acetyloxy)-4-(trifluoromethyl)benzoic Acid

8. Benzoic Acid, 2-(acetyloxy)-4-(trifluoromethyl)-

9. 1z0yfi05oo

10. Triflusal (inn)

11. Ncgc00016431-01

12. 2-acetoxy-4-trifluoromethyl-benzoic Acid

13. Cas-322-79-2

14. Triflusalum

15. Grendis

16. Aflen

17. Triflusalum [inn-latin]

18. Ur 1501

19. Drisgen

20. Triflusal [inn:ban]

21. Einecs 206-297-5

22. Unii-1z0yfi05oo

23. 4-trifluoromethylsalicylic Acid Acetate

24. Brn 2945374

25. Tecnosal

26. Triflux

27. Alpha,alpha,alpha-trifluoro-2,4-cresotic Acid Acetate

28. Prestwick_851

29. Alpha,alpha,alpha-trifluoro-2,4-creosotic Acid Acetate

30. Triflusal [mi]

31. Prestwick0_000528

32. Prestwick1_000528

33. Prestwick2_000528

34. Prestwick3_000528

35. Triflusal [mart.]

36. Triflusal [who-dd]

37. Dsstox_cid_25305

38. Dsstox_rid_80791

39. Dsstox_gsid_45305

40. Bspbio_000515

41. 4-10-00-00619 (beilstein Handbook Reference)

42. Schembl136423

43. 3-acetoxy-alpha,alpha,alpha-trifluoro-p-toluic Acid

44. Spbio_002436

45. Bpbio1_000567

46. Zinc2220

47. Chembl1332032

48. Dtxsid8045305

49. Triflusal [ep Monograph]

50. Chebi:94721

51. 2,4-cresotic Acid, Alpha,alpha,alpha-trifluoro-, Acetate

52. Hms1569j17

53. Hms2096j17

54. Hms3652m11

55. Hms3713j17

56. Hms3885i13

57. Bcp10024

58. Hy-b0531

59. Tox21_110436

60. Mfcd00866793

61. S3200

62. Ur1501

63. Akos015890393

64. Ac-1829

65. Ccg-220528

66. Ccg-222319

67. Db08814

68. Mb01536

69. Ur-1501

70. 2-acetoxy-4-trifluoromethyl Benzoic Acid

71. Acetyl-4-(trifluoromethyl)salicylic Acid

72. Ncgc00016431-02

73. Ncgc00016431-04

74. Ncgc00016431-11

75. As-63983

76. A5797

77. B1461

78. Ft-0601555

79. Sw196982-3

80. T3601

81. D07142

82. T72290

83. 322t792

84. Sr-01000872666

85. Q1758668

86. Sr-01000872666-1

87. W-106849

88. Brd-k71696703-001-01-2

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₇F₃O₄
Molecular Weight	248.15 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	248.02964319 g/mol
Monoisotopic Mass	248.02964319 g/mol
Topological Polar Surface Area	63.6 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	313
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Triflusal is indicated as prophylaxis of thromboembolic disorders. It has been registered in Spain and in other countries of Europe, South America and South Korea for the prevention of Stroke and myocardial infarction.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Triflusal is an antithrombotic anticoagulant. It irreversibly inhibits the production of thromboxane-B2 in platelets by acetylating cycloxygenase-1. Triflusal affects many other targets such as NF kappa B, which is a gene expression regulatory factor for cycloxygenase-a and cytokines. Numerous studies comparing the efficacy and safety profile (i.e. systemic hemorrhage) between triflusal and acetylsalsylic acid has shown either no significant difference or a better effacy and safety profile for triflusal. Triflusal has been shown to protect cerebral tissue due to its inhibition of lipid peroxidation resulting from anoxia-reoxygenation.

5.2 MeSH Pharmacological Classification

Platelet Aggregation Inhibitors

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)

5.3 ATC Code

B - Blood and blood forming organs

B01 - Antithrombotic agents

B01A - Antithrombotic agents

B01AC - Platelet aggregation inhibitors excl. heparin

B01AC18 - Triflusal

5.4 Absorption, Distribution and Excretion

Absorption

Absorbed in the small intestine with a bioavailability range from 83% to 100%. There is no significant difference between the absorption of the oral solution and capsule formulation. Triflusal displays a Cmax of 11.6 mcg/ml and a tmax of 0.88 h. The major metabolite of triflusal presents different pharmacokinetic properties by showing a Cmax and tmax of 92.7 mcg/ml and 4.96 h, respectively.

Route of Elimination

The elimination pathway of triflusal is primarily renal. Urine analysis has shown the presence of unchanged triflusal, HTB and the glycine conjugate of HTB.

Volume of Distribution

The reported volume of distribution for triflusal is of 34L.

Clearance

Renal clearance is 0.8 +/- 0.2L/h and 0.18 +/1 0.04L/h for triflusal and HTB, respectively.

5.5 Metabolism/Metabolites

In the liver, triflusal undergoes deacetylation, forming its main metabolite 2-OH-4-trifluoromethyl benzoic acid (HTB). This major metabolite seems to have marked antiplatelet properties in vitro.

5.6 Biological Half-Life

In the healthy human, the half-life is 0.5 +/- 0.1h, while that of HTB is 34.3 +/- 5.3h.

5.7 Mechanism of Action

Triflusal is chemically related to acetylsalicylic acid (ASA) and irreversibly inhibits cycloxygenase-1 (COX-1) in platelets. Acetylation of the active group of COX-1 prevents the formation of thromboxane-B2 in platelets. However, it is unique because it spares the arachidonic acid metabolic pathway in endothelial cells. In addition, it favors the production of nitric oxide, a vasodilator.

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