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    Talniflumate

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    MARKET PLACE

    PharmaCompass
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    2D Structure
    Also known as: 66898-62-2, Somalgen, Lomucin, Talniflumato, Ba 7602-06, Ba-7602-06
    Molecular Formula
    C21H13F3N2O4
    Molecular Weight
    414.3  g/mol
    InChI Key
    ANMLJLFWUCQGKZ-UHFFFAOYSA-N
    FDA UNII
    JFK78S0U9S
    Talniflumate, is an anti-inflammatory molecule studied and used as a mucin regulator in the treatment of cystic fibrosis, chronic obstructive pulmonary disease (COPD) and asthma. In addition, it is used in inflammatory conditions such as rheumatoid arthritis. Phase I trials with talniflumate for the treatment of cystic fibrosis and COPD were completed in August 2001, and phase II trials were performed in Ireland for the treatment of cystic fibrosis but this research has now been discontinued. Talniflumate has been approved for approximately 20 years in Argentina other countries (excluding the United States, Europe, and Japan).
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3-oxo-1H-2-benzofuran-1-yl) 2-[3-(trifluoromethyl)anilino]pyridine-3-carboxylate
    2.1.2 InChI
    InChI=1S/C21H13F3N2O4/c22-21(23,24)12-5-3-6-13(11-12)26-17-16(9-4-10-25-17)19(28)30-20-15-8-2-1-7-14(15)18(27)29-20/h1-11,20H,(H,25,26)
    2.1.3 InChI Key
    ANMLJLFWUCQGKZ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC=C2C(=C1)C(OC2=O)OC(=O)C3=C(N=CC=C3)NC4=CC=CC(=C4)C(F)(F)F
    2.2 Other Identifiers
    2.2.1 UNII
    JFK78S0U9S
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 66898-62-2

    2. Somalgen

    3. Lomucin

    4. Talniflumato

    5. Ba 7602-06

    6. Ba-7602-06

    7. Phthalidyl 2-(3-trifluoromethylanilino)nicotinate

    8. Ba7602-06; Somalgen

    9. Jfk78s0u9s

    10. [(1r)-3-oxo-1h-2-benzofuran-1-yl] 2-[3-(trifluoromethyl)anilino]pyridine-3-carboxylate

    11. 3-phthalidyl Ester Of 2-((3-(trifluoromethyl)phenyl)amino)-3-pyridinecarboxylic Acid

    12. Ncgc00167754-01

    13. 3-ftalidilico Del Acido 2-((3-(trifluormetil)fenil)amino)-3-piridincarboxilico

    14. (3-oxo-1h-2-benzofuran-1-yl) 2-[3-(trifluoromethyl)anilino]pyridine-3-carboxylate

    15. Dsstox_cid_26740

    16. Dsstox_rid_81869

    17. Dsstox_gsid_46740

    18. 2-[[3-(trifluoromethyl)phenyl]amino]-3-pyridinecarboxylic Acid 1,3-dihydro-3-oxo-1-isobenzofuranyl Ester

    19. Talniflumatum

    20. Talniflumate [usan:inn]

    21. Talniflumatum [inn-latin]

    22. Talniflumato [inn-spanish]

    23. 3-pyridinecarboxylic Acid, 2-((3-(trifluoromethyl)phenyl)amino)-, 1,3-dihydro-3-oxo-1-isobenzofuranyl Ester

    24. Cas-66898-62-2

    25. Unii-jfk78s0u9s

    26. Brn 0503261

    27. Somalgen (tn)

    28. 3-pyridinecarboxylic Acid, 2-[[3-(trifluoromethyl)phenyl]amino]-, 1,3-dihydro-3-oxo-1-isobenzofuranyl Ester

    29. Phthalidyl 2-(alpha,alpha,alpha-trifluoro-m-toluidino)nicotinate

    30. Talniflumate [mi]

    31. Talniflumate (usan/inn)

    32. Talniflumate [inn]

    33. 2-(alpha,alpha,alpha-trifluoro-m-toluidino)nicotinic Acid Phthalidyl Ester

    34. Talniflumate [usan]

    35. 3-ftalidilico Del Acido 2-((3-(trifluormetil)fenil)amino)-3-piridincarboxilico [spanish]

    36. Schembl23691

    37. Talniflumate [mart.]

    38. Talniflumate [who-dd]

    39. Chembl1081506

    40. Dtxsid3046740

    41. Chebi:91991

    42. Hms3269m13

    43. Hms3413d19

    44. Hms3677d19

    45. Msi-1995

    46. Phthalidyl 2-(alpha,alpha,alpha,-trifluoro-m-toluidino)nicotinate

    47. Tox21_112584

    48. Mfcd00866135

    49. S6439

    50. Akos015895754

    51. Tox21_112584_1

    52. Db09295

    53. Ks-5130

    54. Nicotinic Acid, 2-(alpha,alpha,alpha-trifluoro-m-toluidino)-, Phthalidyl Ester

    55. Ncgc00167754-02

    56. Ac-14144

    57. Db-054972

    58. Hy-103370

    59. Cs-0027765

    60. Ft-0630769

    61. T3101

    62. D02701

    63. T72807

    64. 898t622

    65. A835581

    66. Brd-a98378129-001-01-4

    67. Q22075910

    68. Phthalidyl 2-(3'-trifluormethylanilino)-pyridin-3-carboxylate

    69. Phthalidyl 2-(3-trifluoromethylanilino)-3-pyridinecarboxylate

    70. Phthalidyl 2-(.alpha.,.alpha.,.alpha.-trifluoro-m-toluidino)nicotinate

    71. 2-(.alpha.,.alpha.,.alpha.-trifluoro-m-toluidino)nicotinic Acid Phthalidyl Ester

    72. 3-oxo-1,3-dihydroisobenzofuran-1-yl 2-(3-(trifluoromethyl)phenylamino)nicotinate

    73. Nicotinic Acid, 2-(.alpha.,.alpha.,.alpha.-trifluoro-m-toluidino)-, Phthalidyl Ester

    74. (3-oxo-1h-isobenzofuran-1-yl) 2-[3-(trifluoromethyl)anilino]pyridine-3-carboxylate;talniflumate

    75. 2-[[3-(trifluoromethyl)phenyl]amino]-1,3-dihydro-3-oxo-1-isobenzofuranyl 3-pyridinecarboxylic Acid Ester

    76. 2-[3-(trifluoromethyl)anilino]-3-pyridinecarboxylic Acid (3-oxo-1h-isobenzofuran-1-yl) Ester

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 414.3 g/mol
    Molecular Formula C21H13F3N2O4
    XLogP35.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count5
    Exact Mass414.08274139 g/mol
    Monoisotopic Mass414.08274139 g/mol
    Topological Polar Surface Area77.5 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity644
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Talnifumate is a phthalidyl ester of nifumic acid, which has potent analgesic and anti-inflammatory effects and is widely used to treat inflammatory disorders, such as rheumatoid arthritis and osteoarthritis, and has also been studied for the management of cystic fibrosis.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Talniflumate is metabolized to its prodrug, niflumic acid, which has several pharmacodynamic effects. Firstly, it blocks synthesis of mucin. Secondly, talniflumate blocks prostaglandin synthesis by cyclooxygenases, which aids in pain and inflammation management.

    5.2 Absorption, Distribution and Excretion

    Volume of Distribution

    In 12 subjects after a single oral administration, total plasma clearance of the main metabolite, niflumic acid, averaged 45 ml/min giving a distribution volume of 0.12 l/kg on average.

    Clearance

    This drug undergoes extensive first pass effect.

    5.3 Metabolism/Metabolites

    Extensive liver metabolism.

    5.4 Biological Half-Life

    Approximately 2h in 12 subjects

    5.5 Mechanism of Action

    Talniflumate is a strong and selective inhibitor of core mucin-synthesizing enzyme GCNT3 (core 2 b-1,6 N-acetylglucosaminyltransferase). Talniflumate decreases gene expression of GCNT3 and production of mucins in vivo and in vitro. Talniflumate improves response of pancreatic tumors to gefitinib (chemotherapy drug). Talniflumate is a strong calcium-activated chloride channel (CaCC) blocker.