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Chemistry

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Also known as: 585543-15-3, Gsk-ahab, Gw856553, Gw856553x, Gw-856553, Gskahab

Molecular Formula

C₂₂H₂₆FN₃O₂

Molecular Weight

383.5 g/mol

InChI Key

KKYABQBFGDZVNQ-UHFFFAOYSA-N

FDA UNII

F2DQF16BXE

Losmapimod is an orally bioavailable inhibitor of the alpha and beta isoforms of p38 mitogen-activated protein kinase (MAPK), with potential immunomodulating and anti-inflammatory activities. Upon oral administration, losmapimod inhibits the activity of p38alpha/beta MAPK, thereby preventing p38alpha/beta MAPK-mediated signaling. This may result in the inhibition of the production of proinflammatory cytokines. p38 MAPK, a serine/threonine protein kinase, plays an important role in regulating the transcription and translation of cytokines involved in inflammation including tumor necrosis factor alpha (TNF-alpha) and interleukin (IL)-1, IL-6 and IL-8.

1 2D Structure

Losmapimod

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-N-(2,2-dimethylpropyl)pyridine-3-carboxamide

2.1.2 InChI

InChI=1S/C22H26FN3O2/c1-13-17(9-15(10-18(13)23)21(28)26-16-6-7-16)19-8-5-14(11-24-19)20(27)25-12-22(2,3)4/h5,8-11,16H,6-7,12H2,1-4H3,(H,25,27)(H,26,28)

2.1.3 InChI Key

KKYABQBFGDZVNQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C=C(C=C1F)C(=O)NC2CC2)C3=NC=C(C=C3)C(=O)NCC(C)(C)C

2.2 Other Identifiers

2.2.1 UNII

F2DQF16BXE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6-(5-((cyclopropylamino)carbonyl)-3-fluoro-2-methylphenyl)-n-(2,2-dimethylprpyl)-3-pyridinecarboxamide

2. Gsk-ahab

3. Gw856553

2.3.2 Depositor-Supplied Synonyms

1. 585543-15-3

2. Gsk-ahab

3. Gw856553

4. Gw856553x

5. Gw-856553

6. Gskahab

7. 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-(2,2-dimethylpropyl)pyridine-3-carboxamide

8. F2dqf16bxe

9. Losmapimod (gw856553x)

10. Ftx1821

11. Ftx-1821

12. Gw-856553x

13. Gsk-ahab;gw856553x;sb856553

14. 6-(5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl)-n-neopentylnicotinamide

15. 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-(2,2-dimethylpropyl)pyridine-3-carboxamide.

16. Losmapimod [usan:inn]

17. Unii-f2dqf16bxe

18. 3-pyridinecarboxamide, 6-(5-((cyclopropylamino)carbonyl)-3-fluoro-2-methylphenyl)-n-(2,2-dimethylpropyl)-

19. 3-pyridinecarboxamide, 6-[5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl]-n-(2,2-dimethylpropyl)-

20. Gw 856553x

21. Sb 856553

22. Losmapimod [inn]

23. Losmapimod (usan/inn)

24. Losmapimod [usan]

25. Losmapimod,gw-856553

26. Losmapimod [who-dd]

27. Gtpl7835

28. Schembl1070401

29. Chembl1088752

30. Dtxsid30974109

31. Ex-a486

32. Chebi:131167

33. Hms3653g19

34. Hms3673k13

35. Losmapimod Pound>>gw-856553

36. Bcp09909

37. Bdbm50418610

38. Mfcd16619322

39. Nsc785336

40. Nsc800785

41. S7215

42. Zinc35793138

43. Akos015994587

44. Ccg-268442

45. Cs-3235

46. Db12270

47. Ge-0056

48. Nsc-785336

49. Nsc-800785

50. Sb16761

51. Ncgc00386332-03

52. Ncgc00481552-01

53. Ac-35781

54. Da-33431

55. Gs856553

56. Hy-10402

57. Sb856553

58. Gw 856553

59. B4620

60. Ft-0700337

61. Sw219307-1

62. D09639

63. 543c153

64. Q6683687

65. 6-(5-cyclopropylcarbamoyl-3-fluoro-2-methyl-phenyl)-n-(2,2-dimethylpropyl)-nicotinamide

66. 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-n-(2,2-dimethylpropyl)nicotinamide

67. 6-(5-((cyclopropylamino)carbonyl)-3-fluoro-2-methylphenyl)-n-(2,2-dimethylpropyl)-3-pyridinecarboxamide

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₆FN₃O₂
Molecular Weight	383.5 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	383.20090524 g/mol
Monoisotopic Mass	383.20090524 g/mol
Topological Polar Surface Area	71.1 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	573
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