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    Linsitinib

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    Also known as: 867160-71-2, Osi-906, Linsitinib(osi-906), Osi906, Osi 906, Osi-906aa
    Molecular Formula
    C26H23N5O
    Molecular Weight
    421.5  g/mol
    InChI Key
    PKCDDUHJAFVJJB-UHFFFAOYSA-N
    FDA UNII
    15A52GPT8T
    Linsitinib is an orally bioavailable small molecule inhibitor of the insulin-like growth factor 1 receptor (IGF-1R) with potential antineoplastic activity. Linsitinib selectively inhibits IGF-1R, which may result in the inhibition of tumor cell proliferation and the induction of tumor cell apoptosis. Overexpressed in a variety of human cancers, IGF-1R stimulates cell proliferation, enables oncogenic transformation, and suppresses apoptosis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutan-1-ol
    2.1.2 InChI
    InChI=1S/C26H23N5O/c1-26(32)14-19(15-26)25-30-22(23-24(27)28-11-12-31(23)25)18-8-7-17-9-10-20(29-21(17)13-18)16-5-3-2-4-6-16/h2-13,19,32H,14-15H2,1H3,(H2,27,28)
    2.1.3 InChI Key
    PKCDDUHJAFVJJB-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1(CC(C1)C2=NC(=C3N2C=CN=C3N)C4=CC5=C(C=C4)C=CC(=N5)C6=CC=CC=C6)O
    2.2 Other Identifiers
    2.2.1 UNII
    15A52GPT8T
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3-(8-amino-1-(2-phenylquinolin-7-yl)imidazo(1,5-a)pyrazin-3-yl)-1-methylcyclobutanol

    2. Osi 906

    3. Osi-906

    4. Osi906

    2.3.2 Depositor-Supplied Synonyms

    1. 867160-71-2

    2. Osi-906

    3. Linsitinib(osi-906)

    4. Osi906

    5. Osi 906

    6. Osi-906aa

    7. Osi-906 (linsitinib)

    8. Asp-7487

    9. 3-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutan-1-ol

    10. 15a52gpt8t

    11. Chembl1091644

    12. Mmv676605

    13. Cis-3-(8-amino-1-(2-phenyl-7-quinolinyl)imidazo(1,5-a)pyrazin-3-yl)-1-methylcyclobutanol

    14. (1r,3r)-3-(8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol.

    15. Linsitinib [usan]

    16. Kinome_3532

    17. Linsitinib [usan:inn]

    18. Unii-15a52gpt8t

    19. Cis-3-(8-amino-1-(2-phenylquinolin-7-yl)imidazo(1,5-a)pyrazin-3-yl)-1-methylcyclobutan-1-ol

    20. Cis-3-(8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutan-1-ol

    21. Linsitinib; Osi-906

    22. Linsitinib [inn]

    23. Linsitinib (usan/inn)

    24. Linsitinib (osi-906)

    25. Linsitinib [who-dd]

    26. Mls006010304

    27. Schembl400369

    28. Schembl400734

    29. Schembl400735

    30. Gtpl7423

    31. Chembl1996234

    32. Schembl10255925

    33. Chebi:91402

    34. Ex-a719

    35. Bcpp000137

    36. Bdbm185150

    37. Dtxsid401007055

    38. Dtxsid901121553

    39. Hms3295g15

    40. Hms3654c19

    41. Bcp01831

    42. Bdbm50315887

    43. Mfcd12912153

    44. Nsc756652

    45. Nsc800784

    46. S1091

    47. Zinc53239527

    48. Akos024464740

    49. Zinc100071817

    50. Zinc113742575

    51. Bcp9001035

    52. Ccg-264815

    53. Cs-0242

    54. Db06075

    55. Nsc-756652

    56. Nsc-800784

    57. Pb22643

    58. Ncgc00250375-02

    59. Ncgc00250375-03

    60. Ncgc00250375-11

    61. Ncgc00250375-14

    62. Ac-26953

    63. As-16999

    64. Hy-10191

    65. Smr004700744

    66. Ft-0670821

    67. Sw218150-2

    68. D09925

    69. Sr-05000022538

    70. J-520074

    71. Q6554803

    72. Sr-05000022538-1

    73. Brd-k07667918-001-01-3

    74. Q27163260

    75. 3-[8-amino-1-(2-phenyl-7-quinolinyl)-3-imidazo[1,5-a]pyrazinyl]-1-methyl-1-cyclobutanol

    76. (1s,3s)-3-(8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol

    77. 1356958-77-4

    78. 3-(8-amino-1-(2-phenylquinolin-7-yl)-2,3-dihydroimidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol

    79. 3-[8-amino-1-(2-phenyl-quinolin-7-yl)-imidazo[1,5-a]pyrazin-3-yl]-1-methyl-cyclobutanol

    80. 867160-72-3

    81. Cis-3-(8-amino-1-(2-phenylquinolin-7-yl)imidazo(1,5-a)pyrazin-3-yl)-1-methylcyclobutanol

    82. Cyclobutanol, 3-(8-amino-1-(2-phenyl-7-quinolinyl)imidazo(1,5-a)pyrazin-3-yl)-1-methyl-, Cis-

    83. Trans-3-[8-amino-1-(2-phenyl-7-quinolinyl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutanol

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 421.5 g/mol
    Molecular Formula C26H23N5O
    XLogP34.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count3
    Exact Mass421.19026037 g/mol
    Monoisotopic Mass421.19026037 g/mol
    Topological Polar Surface Area89.3 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity663
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in cancer/tumors (unspecified) and solid tumors.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    In laboratory studies of 28 human tumor cell lines, OSI-906 reduced growth of 15 cell lines representative of colorectal, lung, breast, pancreatic, and pediatric tumors and in mouse models. OSI-906 was particularly effective against tumors that are highly IGF-dependent such as colorectal cancers. According to the researchers, OSI-906 not only slowed tumor growth in mice, but decreased the size of some pre-existing tumors.

    5.2 Mechanism of Action

    IGF-1R stimulates proliferation, enables onogenic transformation, and suppresses apoptosis. Inhibitors of IGF-1R are expected to have broad utility in oncology since the over-expression of IGF-1R and/or its ligands or the down-regulation of ligand binding proteins occurs in numerous human malignancies including lung, colon, breast, prostate, brain and skin cancers. In addition, signaling through the IGF system has been implicated in protecting tumor cells from apoptosis induced by anti-cancer treatments such as cytotoxic agents and EGFR inhibitors.