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Also known as: 1028486-01-2, Mln8237, Mln-8237, Mln 8237, Mln8237 (alisertib), 4-((9-chloro-7-(2-fluoro-6-methoxyphenyl)-5h-benzo[c]pyrimido[4,5-e]azepin-2-yl)amino)-2-methoxybenzoic acid

Molecular Formula

C₂₇H₂₀ClFN₄O₄

Molecular Weight

518.9 g/mol

InChI Key

ZLHFILGSQDJULK-UHFFFAOYSA-N

FDA UNII

T66ES73M18

Alisertib is a second-generation, orally bioavailable, highly selective small molecule inhibitor of the serine/threonine protein kinase Aurora A kinase with potential antineoplastic activity. Alisertib binds to and inhibits Aurora A kinase, which may result in disruption of the assembly of the mitotic spindle apparatus, disruption of chromosome segregation, and inhibition of cell proliferation. Aurora A kinase localizes to the spindle poles and to spindle microtubules during mitosis, and is thought to regulate spindle assembly. Aberrant expression of Aurora kinases occurs in a wide variety of cancers, including colon and breast cancers.

1 2D Structure

Alisertib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[[9-chloro-7-(2-fluoro-6-methoxyphenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino]-2-methoxybenzoic acid

2.1.2 InChI

InChI=1S/C27H20ClFN4O4/c1-36-21-5-3-4-20(29)23(21)25-19-10-15(28)6-8-17(19)24-14(12-30-25)13-31-27(33-24)32-16-7-9-18(26(34)35)22(11-16)37-2/h3-11,13H,12H2,1-2H3,(H,34,35)(H,31,32,33)

2.1.3 InChI Key

ZLHFILGSQDJULK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC1=C(C(=CC=C1)F)C2=NCC3=CN=C(N=C3C4=C2C=C(C=C4)Cl)NC5=CC(=C(C=C5)C(=O)O)OC

2.2 Other Identifiers

2.2.1 UNII

T66ES73M18

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Mln 8237

2. Mln-8237

3. Mln8237

2.3.2 Depositor-Supplied Synonyms

1. 1028486-01-2

2. Mln8237

3. Mln-8237

4. Mln 8237

5. Mln8237 (alisertib)

6. 4-((9-chloro-7-(2-fluoro-6-methoxyphenyl)-5h-benzo[c]pyrimido[4,5-e]azepin-2-yl)amino)-2-methoxybenzoic Acid

7. Alisertib [usan]

8. 4-[[9-chloro-7-(2-fluoro-6-methoxyphenyl)-5h-pyrimido[5,4-d][2]benzazepin-2-yl]amino]-2-methoxybenzoic Acid

9. Chembl483158

10. T66es73m18

11. Alisertib (usan)

12. 4-((9-chloro-7-(2-fluoro-6-methoxyphenyl)-5h-benzo[c]pyrimido-[4,5-e]azepin-2-yl)amino)-2-methoxybenzoic Acid

13. 4-{[9-chloro-7-(2-fluoro-6-methoxyphenyl)-5h-pyrimido[5,4-d][2]benzazepin-2-yl]amino}-2-methoxybenzoic Acid

14. Benzoic Acid, 4-((9-chloro-7-(2-fluoro-6-methoxyphenyl)-5h-pyrimido(5,4-d)(2)benzazepin-2-yl)amino)-2-methoxy-

15. Alisertib [usan:inn]

16. Unii-t66es73m18

17. Mln8237,alisertib

18. Kinome_3770

19. Alisertib [inn]

20. Alisertib; Mln8237

21. Alisertib (mln8237)

22. Mln8237 - Alisertib

23. Alisertib [who-dd]

24. Mls006011041

25. Schembl855823

26. Gtpl7790

27. Dtxsid30145539

28. Ex-a024

29. Min8237

30. Chebi:125628

31. Hms3654e08

32. Hms3673i07

33. Hms3743e17

34. Amy24201

35. Bcp01823

36. Bdbm50277545

37. Mfcd16621243

38. Nsc759677

39. Nsc799329

40. S1133

41. Zinc40939534

42. Akos015924647

43. Bcp9000956

44. Ccg-264832

45. Cs-0106

46. Db05220

47. Mln 8237 (contain 10% Dmso)

48. Nsc-759677

49. Nsc-799329

50. Sb16658

51. Ncgc00263271-01

52. Ncgc00263271-02

53. Ncgc00263271-10

54. 4-(9-chloro-7-(2-fluoro-6-methoxyphenyl)-5h-benzo[c]pyrimido[4,5-e]azepin-2-ylamino)-2-methoxybenzoic Acid

55. Ac-25236

56. As-17005

57. Hy-10971

58. Smr004702834

59. Ft-0672433

60. Sw219771-1

61. D10085

62. J-514220

63. Brd-k75295174-001-03-5

64. Q15633917

65. 4-((9-chloro-7-(2-fluoro-6-methoxyphenyl)-5h-benzo[c]pyrimido-[4,5-e]azepin-2-yl)amino)-2-methoxy Mln 8237 (contain 10% Dmso)

66. 4-((9-chloro-7-(2-fluoro-6-methoxyphenyl)-5h-pyrimido(5,4-d)(2)benzazepin-2-yl)amino)-2-methoxy-benzoic Acid

67. 4-(9-chloro-7-(2-fluoro-6-methoxyphenyl)-5h-benzo[e]pyrimido[5,4-c]azepin-2-ylamino)-2-methoxybenzoic Acid

68. 4-{[9-chloro-7-(2-fluoro-6-methoxyphenyl) -5h-pyrimido[5,4-d][2]benzazepin-2-yl]amino}-2-methoxybenzoic Acid

69. A5b

2.4 Create Date

2008-05-05

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₂₀ClFN₄O₄
Molecular Weight	518.9 g/mol
XLogP3	5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	6
Exact Mass	518.1157110 g/mol
Monoisotopic Mass	518.1157110 g/mol
Topological Polar Surface Area	106 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	836
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