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    Technical details about Prestwick3_000528, learn more about the structure, uses, toxicity, action, side effects and more

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    Prestwick3_000528

    APIs // Active Pharmaceutical Ingredients

    DOSSIERs // Finished Dosage Forms

    GLOBAL SALES INFORMATION

    MARKET PLACE

    ANALYTICAL SOLUTION(s)

    PharmaCompass

    Minakem offers CDMO services for API & HPAPI, generics, regulatory expertise, track record performance & FDA & GMP certifications.

    ChemWerth works in generic API development & supply, non-infringement patent strategy development and regulatory support.

    2D Structure
    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

    2D Structure

    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 Weight 248.15 g/mol
    Molecular Formula C10H7F3O4
    XLogP32.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count3
    Exact Mass248.02964319 g/mol
    Monoisotopic Mass248.02964319 g/mol
    Topological Polar Surface Area63.6 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity313
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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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