VS-5584

Synopsis, Chemistry

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Also known as: Vs-5584, 1246560-33-7, Vs-5584 (sb2343), Sb2343, Sb-2343, 5-(8-methyl-2-morpholin-4-yl-9-propan-2-ylpurin-6-yl)pyrimidin-2-amine

Molecular Formula

C₁₇H₂₂N₈O

Molecular Weight

354.4 g/mol

InChI Key

QYBGBLQCOOISAR-UHFFFAOYSA-N

FDA UNII

W71J4X250V

PI3K/mTOR Kinase Inhibitor VS-5584 is a potent and selective inhibitor of both phosphatidylinositol 3 kinase (PI3K) and mammalian target of rapamycin (mTOR) kinase in the PI3K/mTOR signaling pathway, with potential antineoplastic activity. PI3K/mTOR kinase inhibitor VS-5584 inhibits mTOR kinase and all class I PI3K isoforms. Consequently, this disrupts phosphorylation of substrates downstream of PI3K and mTOR and may result in apoptosis and growth inhibition in susceptible tumor cells. Activation of the PI3K/mTOR pathway promotes cell growth, survival, and resistance to chemotherapy and radiotherapy. mTOR is a serine/threonine kinase downstream of PI3K, which also has PI3K-independent activity. Consequently, this agent may potentially be more potent than an agent that inhibits either PI3K kinase or mTOR kinase.

1 2D Structure

VS-5584

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-(8-methyl-2-morpholin-4-yl-9-propan-2-ylpurin-6-yl)pyrimidin-2-amine

2.1.2 InChI

InChI=1S/C17H22N8O/c1-10(2)25-11(3)21-14-13(12-8-19-16(18)20-9-12)22-17(23-15(14)25)24-4-6-26-7-5-24/h8-10H,4-7H2,1-3H3,(H2,18,19,20)

2.1.3 InChI Key

QYBGBLQCOOISAR-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=NC2=C(N=C(N=C2N1C(C)C)N3CCOCC3)C4=CN=C(N=C4)N

2.2 Other Identifiers

2.2.1 UNII

W71J4X250V

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-(9-isopropyl-8-methyl-2-morpholin-4-yl-9h-purin-6-yl)-pyrimidin-2-ylamine

2. Sb2343

3. Vs-5584

2.3.2 Depositor-Supplied Synonyms

1. Vs-5584

2. 1246560-33-7

3. Vs-5584 (sb2343)

4. Sb2343

5. Sb-2343

6. 5-(8-methyl-2-morpholin-4-yl-9-propan-2-ylpurin-6-yl)pyrimidin-2-amine

7. Chembl3393066

8. W71j4x250v

9. Vs5584

10. 5-[9-isopropyl-8-methyl-2-(morpholin-4-yl)purin-6-yl]pyrimidin-2-amine

11. 2-pyrimidinamine, 5-(8-methyl-9-(1-methylethyl)-2-(4-morpholinyl)-9h-purin-6-yl)-

12. 2-pyrimidinamine, 5-[8-methyl-9-(1-methylethyl)-2-(4-morpholinyl)-9h-purin-6-yl]-

13. Unii-w71j4x250v

14. Schembl539098

15. Gtpl8382

16. Dtxsid10677328

17. Ex-a288

18. Vs 5584 [who-dd]

19. Hms3652b16

20. Bcp08247

21. Wzb56033

22. Bdbm50059635

23. Mfcd25372027

24. Nsc778810

25. Nsc800991

26. S7016

27. Zinc95644685

28. 5-(9-isopropyl-8-methyl-2-morpholin-4-yl-9h-purin-6-yl)-pyrimidin-2-ylamine

29. Akos024465057

30. Ccg-268087

31. Cs-1202

32. Db12986

33. Nsc-778810

34. Nsc-800991

35. Sb 2343

36. Sb16877

37. 5-[8-methyl-2-(morpholin-4-yl)-9-(propan-2-yl)-9h-purin-6-yl]pyrimidin-2-amine

38. Ncgc00386370-03

39. Ncgc00386370-06

40. Ac-33121

41. As-80075

42. Da-46738

43. Hy-16585

44. Ft-0700143

45. Sw220201-1

46. A857790

47. J-690096

48. Q27089164

49. 5-(8-methyl-9-(1-methylethyl)-2-(4-morpholinyl)-9h-purin-6yl)-2-pyrimidinamine

50. 5-[8-methyl-9-(1-methylethyl)-2-(4-morpholinyl)-9h-purin-6-yl]-2-pyrimidinamine

2.4 Create Date

2010-10-18

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₂N₈O
Molecular Weight	354.4 g/mol
XLogP3	0.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	3
Exact Mass	354.19165736 g/mol
Monoisotopic Mass	354.19165736 g/mol
Topological Polar Surface Area	108 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	466
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