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    Afuresertib

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 1047644-62-1, Gsk-2110183, Gsk2110183c, Afuresertib [usan], Asb183, Asb-183
    Molecular Formula
    C18H17Cl2FN4OS
    Molecular Weight
    427.3  g/mol
    InChI Key
    AFJRDFWMXUECEW-LBPRGKRZSA-N
    FDA UNII
    8739X25QI3
    Afuresertib is an orally bioavailable inhibitor of the serine/threonine protein kinase Akt (protein kinase B) with potential antineoplastic activity. Afuresertib binds to and inhibits the activity of Akt, which may result in inhibition of the PI3K/Akt signaling pathway and tumor cell proliferation and the induction of tumor cell apoptosis. Activation of the PI3K/Akt signaling pathway is frequently associated with tumorigenesis and dysregulated PI3K/Akt signaling may contribute to tumor resistance to a variety of antineoplastic agents.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[(2S)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)thiophene-2-carboxamide
    2.1.2 InChI
    InChI=1S/C18H17Cl2FN4OS/c1-25-16(14(19)9-23-25)13-7-15(27-17(13)20)18(26)24-12(8-22)6-10-3-2-4-11(21)5-10/h2-5,7,9,12H,6,8,22H2,1H3,(H,24,26)/t12-/m0/s1
    2.1.3 InChI Key
    AFJRDFWMXUECEW-LBPRGKRZSA-N
    2.1.4 Canonical SMILES
    CN1C(=C(C=N1)Cl)C2=C(SC(=C2)C(=O)NC(CC3=CC(=CC=C3)F)CN)Cl
    2.1.5 Isomeric SMILES
    CN1C(=C(C=N1)Cl)C2=C(SC(=C2)C(=O)N[C@@H](CC3=CC(=CC=C3)F)CN)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    8739X25QI3
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 1047644-62-1

    2. Gsk-2110183

    3. Gsk2110183c

    4. Afuresertib [usan]

    5. Asb183

    6. Asb-183

    7. Gsk 2110183c

    8. Afuresertib (gsk2110183)

    9. Afuresertib (usan)

    10. 8739x25qi3

    11. Gsk-2110183c

    12. N-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)thiophene-2-carboxamide

    13. 2-thiophenecarboxamide, N-((1s)-2-amino-1-((3-fluorophenyl)methyl)ethyl)-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)-

    14. N-((1s)-1-(aminomethyl)-2-(3-fluorophenyl)ethyl)-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)thiophene-2-carboxamide

    15. Afuresertib [usan:inn]

    16. Unii-8739x25qi3

    17. 2-thiophenecarboxamide, N-[(1s)-2-amino-1-[(3-fluorophenyl)methyl]ethyl]-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)-

    18. N-((2s)-1-amino-3-(3-fluorophenyl)propan-2-yl)-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)thiophene-2-carboxamide

    19. N-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)thiophene-2-carboxamide

    20. Afuresertib [inn]

    21. Afuresertib [who-dd]

    22. Schembl187686

    23. Gtpl7890

    24. Chembl2219422

    25. Dtxsid60146711

    26. Chebi:131168

    27. Bcp08435

    28. Ex-a1574

    29. Bdbm50502477

    30. Nsc778305

    31. Nsc781255

    32. Nsc800109

    33. Nsc829868

    34. S7521

    35. Zinc43197674

    36. Ccg-268972

    37. Cs-3384

    38. Db11648

    39. Nsc-778305

    40. Nsc-781255

    41. Nsc-800109

    42. Nsc-829868

    43. Gsk 2110183

    44. Ncgc00387879-03

    45. Ac-35761

    46. Ba166066

    47. Bs-14212

    48. Hy-15727

    49. A16392

    50. D10381

    51. D71036

    52. A853608

    53. Afuresertib, Gsk-2110183, Gsk-2110183b

    54. Q27224945

    55. N-((s)-1-amino-3-(3-fluorophenyl)propan-2-yl)-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)thiophene-2-carboxamide

    56. N-((s)-1-amino-3-(3-fluorophenyl)propan-2-yl)-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)thiophene-2-carboxamide;afuresertib

    57. N-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methyl-3-pyrazolyl)-2-thiophenecarboxamide

    58. N-{(1s)-2-amino-1-[(3-fluorophenyl)methyl]ethyl}-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)-2-thiophenecarboxamide

    2.4 Create Date
    2010-08-16
    3 Chemical and Physical Properties
    Molecular Weight 427.3 g/mol
    Molecular Formula C18H17Cl2FN4OS
    XLogP34
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count6
    Exact Mass426.0484159 g/mol
    Monoisotopic Mass426.0484159 g/mol
    Topological Polar Surface Area101 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity520
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1