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    Losmapimod

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
    Xls

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    2D Structure
    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

    2D Structure

    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 Weight 383.5 g/mol
    Molecular Formula C22H26FN3O2
    XLogP33.8
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count6
    Exact Mass383.20090524 g/mol
    Monoisotopic Mass383.20090524 g/mol
    Topological Polar Surface Area71.1 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity573
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1