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Linsitinib

Linsitinib

Synopsis, Chemistry

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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

Linsitinib

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 Formula	C₂₆H₂₃N₅O
Molecular Weight	421.5 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	421.19026037 g/mol
Monoisotopic Mass	421.19026037 g/mol
Topological Polar Surface Area	89.3 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	663
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

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.