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Talniflumate

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Chemistry

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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

Talniflumate

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 Formula	C₂₁H₁₃F₃N₂O₄
Molecular Weight	414.3 g/mol
XLogP3	5.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	5
Exact Mass	414.08274139 g/mol
Monoisotopic Mass	414.08274139 g/mol
Topological Polar Surface Area	77.5 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	644
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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