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Enzastaurin

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Chemistry

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Also known as: 170364-57-5, Ly317615, Enzastaurin (ly317615), 3-(1-methyl-1h-indol-3-yl)-4-(1-(1-(pyridin-2-ylmethyl)piperidin-4-yl)-1h-indol-3-yl)-1h-pyrrole-2,5-dione, Ly-317615, 3-(1-methylindol-3-yl)-4-[1-[1-(pyridin-2-ylmethyl)piperidin-4-yl]indol-3-yl]pyrrole-2,5-dione

Molecular Formula

C₃₂H₂₉N₅O₂

Molecular Weight

515.6 g/mol

InChI Key

AXRCEOKUDYDWLF-UHFFFAOYSA-N

FDA UNII

UC96G28EQF

Enzastaurin, an investigational, targeted, oral agent, will be evaluated at more than 100 sites worldwide for the treatment of relapsed glioblastoma multiforme (GBM), an aggressive and malignant form of brain cancer.

1 2D Structure

Enzastaurin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(1-methylindol-3-yl)-4-[1-[1-(pyridin-2-ylmethyl)piperidin-4-yl]indol-3-yl]pyrrole-2,5-dione

2.1.2 InChI

InChI=1S/C32H29N5O2/c1-35-19-25(23-9-2-4-11-27(23)35)29-30(32(39)34-31(29)38)26-20-37(28-12-5-3-10-24(26)28)22-13-16-36(17-14-22)18-21-8-6-7-15-33-21/h2-12,15,19-20,22H,13-14,16-18H2,1H3,(H,34,38,39)

2.1.3 InChI Key

AXRCEOKUDYDWLF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1C=C(C2=CC=CC=C21)C3=C(C(=O)NC3=O)C4=CN(C5=CC=CC=C54)C6CCN(CC6)CC7=CC=CC=N7

2.2 Other Identifiers

2.2.1 UNII

UC96G28EQF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ly317615.hcl

2.3.2 Depositor-Supplied Synonyms

1. 170364-57-5

2. Ly317615

3. Enzastaurin (ly317615)

4. 3-(1-methyl-1h-indol-3-yl)-4-(1-(1-(pyridin-2-ylmethyl)piperidin-4-yl)-1h-indol-3-yl)-1h-pyrrole-2,5-dione

5. Ly-317615

6. 3-(1-methylindol-3-yl)-4-[1-[1-(pyridin-2-ylmethyl)piperidin-4-yl]indol-3-yl]pyrrole-2,5-dione

7. Db102

8. Uc96g28eqf

9. Ly 317615

10. Chembl300138

11. Db-102

12. Dsstox_cid_24029

13. Dsstox_rid_80101

14. Dsstox_gsid_44029

15. 3-(1-methyl-1h-indol-3-yl)-4-(1-(1-(pyridin-2-ylmethyl)-piperidin-4-yl)-1h-indol-3-yl)-1h-pyrrole-2,5-dione

16. 1h-pyrrole-2,5-dione, 3-(1-methyl-1h-indol-3-yl)-4-(1-(1-(2-pyridinylmethyl)-4-piperidinyl)-1h-indol-3-yl)-

17. 3-(1-methyl-1h-indol-3-yl)-4-(1-(1-(2-pyridinylmethyl)-4-piperidinyl)-1h-indol-3-yl)-1h-pyrrole-2,5-dione

18. 3-(1-methyl-1h-indol-3-yl)-4-{1-[1-(pyridin-2-ylmethyl)piperidin-4-yl]-1h-indol-3-yl}-1h-pyrrole-2,5-dione

19. Enzastaurin [inn]

20. Cas-170364-57-5

21. Unii-uc96g28eqf

22. 3-(1-methyl-1h-indol-3-yl)-4-[1-[1-(2-pyridinylmethyl)-4-piperidinyl]-1h-indol-3-yl]-1h-pyrrole-2,5-dione

23. Le-0014

24. Enzastaurin [mi]

25. Enzastaurin [usan:inn]

26. Enzastaurin,ly317615

27. Enzastaurin [usan]

28. Enzastaurin; Ly317615

29. Enzastaurin [who-dd]

30. Ly317615 - Enzastaurin

31. Schembl678748

32. Gtpl5693

33. Dtxsid5044029

34. Chebi:91368

35. Amy7827

36. Bcpp000241

37. Hms3265m05

38. Hms3265m06

39. Hms3265n05

40. Hms3265n06

41. Hms3654a13

42. Hms3748e03

43. Bcp02703

44. Ex-a1055

45. Who 8426

46. Zinc1494900

47. Tox21_113367

48. Bdbm50128285

49. Mfcd11040980

50. Nsc767124

51. Nsc800096

52. S1055

53. Akos015994764

54. Tox21_113367_1

55. Ac-5900

56. Bcp9000648

57. Ccg-264797

58. Cs-0132

59. Db06486

60. Nsc-767124

61. Nsc-800096

62. Sb16481

63. Ncgc00238452-01

64. Ncgc00238452-02

65. Ncgc00238452-03

66. Ncgc00238452-11

67. Hy-10342

68. Db-064781

69. Ft-0667873

70. Sw219797-1

71. Ec-000.2315

72. 364e575

73. J-510442

74. Q5381479

75. Brd-k79404599-001-01-0

76. 3-(1-methyl-1h-indol-3-yl)-4-(1-(1-(2-pyridinylmethyl)-4-piperidinyl)-1h-indol-3-yl)-1h-pyrrole-2,5-

77. 3-(1-methyl-1h-indol-3-yl)-4-[1-(1-pyridin-2-ylmethyl-piperidin-4-yl)-1h-indol-3-yl]-pyrrole-2,5-dione

78. 3-(1-methyl-1h-indol-3-yl)-4-{1-[1-(pyridin-2-ylmethyl)piperidin-4-yl]-1h-indol-3-yl}-2,5-dihydro-1h-pyrrole-2,5-dione

2.4 Create Date

2005-08-09

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₂₉N₅O₂
Molecular Weight	515.6 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	515.23212518 g/mol
Monoisotopic Mass	515.23212518 g/mol
Topological Polar Surface Area	72.2 Å²
Heavy Atom Count	39
Formal Charge	0
Complexity	974
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 brain cancer, lymphoma (non-hodgkin's), and lung cancer.

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

Enzastaurin is an oral serine-threonine kinase inhibitor that is designed to suppress tumor growth through multiple mechanisms. Preclinical data indicate it may reduce the cell's ability to reproduce (cell proliferation), increase the natural death of the tumor cells (apoptosis), and inhibit tumor- induced blood supply (angiogenesis). Enzastaurin has been shown to inhibit signaling through the PKC-B and PI3K/AKT pathways. These pathways have been shown to be activated in a wide variety of cancers. In addition to glioblastoma, enzastaurin is also being studied in multiple other tumor types, including non-Hodgkin's lymphoma, colorectal cancer, non-small cell lung cancer, pancreatic cancer, and mantle cell lymphoma.

Drugs in Development