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2D Structure
Also known as: 1057249-41-8, Sns 314, Sns314, N-(3-chlorophenyl)-n'-[5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl]-2-thiazolyl]urea, 1-(3-chlorophenyl)-3-[5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl]-1,3-thiazol-2-yl]urea, 802ifj0z8x
Molecular Formula
C18H15ClN6OS2
Molecular Weight
430.9  g/mol
InChI Key
FAYAUAZLLLJJGH-UHFFFAOYSA-N
FDA UNII
802IFJ0Z8X

Aurora Kinase Inhibitor SNS-314 is a synthetic small molecule Aurora kinase (AK) inhibitor with potential antineoplastic activity. Aurora kinase inhibitor SNS-314 selectively binds to and inhibits AKs A and B, which may result in the inhibition of cellular division and proliferation in tumor cells that overexpress AKs. AKs are serine-threonine kinases that play essential roles in mitotic checkpoint control during mitosis.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-(3-chlorophenyl)-3-[5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl]-1,3-thiazol-2-yl]urea
2.1.2 InChI
InChI=1S/C18H15ClN6OS2/c19-11-2-1-3-12(8-11)24-17(26)25-18-21-9-13(28-18)4-6-20-16-15-14(5-7-27-15)22-10-23-16/h1-3,5,7-10H,4,6H2,(H,20,22,23)(H2,21,24,25,26)
2.1.3 InChI Key
FAYAUAZLLLJJGH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CC(=C1)Cl)NC(=O)NC2=NC=C(S2)CCNC3=NC=NC4=C3SC=C4
2.2 Other Identifiers
2.2.1 UNII
802IFJ0Z8X
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Sns 314

2. Sns314

2.3.2 Depositor-Supplied Synonyms

1. 1057249-41-8

2. Sns 314

3. Sns314

4. N-(3-chlorophenyl)-n'-[5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl]-2-thiazolyl]urea

5. 1-(3-chlorophenyl)-3-[5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl]-1,3-thiazol-2-yl]urea

6. 802ifj0z8x

7. 1-(3-chlorophenyl)-3-{5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl]-1,3-thiazol-2-yl}urea

8. 1057249-41-8 (free Base)

9. 1-(3-chlorophenyl)-3-[5-(2-{thieno[3,2-d]pyrimidin-4-ylamino}ethyl)-1,3-thiazol-2-yl]urea

10. N-(3-chlorophenyl)-n'-[5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl]-2-thiazolyl]urea.

11. Urea, N-(3-chlorophenyl)-n'-(5-(2-(thieno(3,2-d)pyrimidin-4-ylamino)ethyl)-2-thiazolyl)-

12. Kinome_3712

13. Unii-802ifj0z8x

14. Sn-314

15. Chembl482767

16. Gtpl9397

17. Schembl3415843

18. Sns 314 [who-dd]

19. Bdbm26326

20. Chebi:94720

21. Dtxsid20147269

22. Ex-a181

23. Hms3244o17

24. Hms3244o18

25. Hms3244p17

26. Amy24207

27. Bcp01773

28. Nsc758250

29. Nsc800886

30. S8699

31. Zinc40393428

32. Ccg-269017

33. Db06134

34. Db07361

35. Nsc-758250

36. Nsc-800886

37. Sb16660

38. Compound 21 [pmid: 18678489]

39. Ncgc00242482-01

40. Ncgc00242482-11

41. Ak2

42. As-16236

43. Db-059388

44. Hy-108344

45. Cs-0028416

46. Ft-0717912

47. 249c418

48. J-503125

49. Brd-k71512533-001-01-7

50. Q27096584

2.4 Create Date
2008-10-27
3 Chemical and Physical Properties
Molecular Weight 430.9 g/mol
Molecular Formula C18H15ClN6OS2
XLogP34.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count6
Exact Mass430.0437292 g/mol
Monoisotopic Mass430.0437292 g/mol
Topological Polar Surface Area148 Ų
Heavy Atom Count28
Formal Charge0
Complexity532
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 solid tumors.


5 Pharmacology and Biochemistry
5.1 Pharmacology

SNS-314 inhibits Aurora kinases A, B, and C. Stopping Aurora kinases halts cellular division at the mitotoic phase of the cell cycle and proliferation in tumor cells that overexpress Aurora kinases.


5.2 Mechanism of Action

The process of cell division, or mitosis, plays a critical role in the uncontrolled proliferation that is a hallmark of cancer. During mitosis, a cell aligns duplicate copies of its DNA along a mitotic spindle and subdivides itself through a process called cytokinesis, creating two identical daughter cells. This process is often poorly regulated in cancer, leading to rapid proliferation and tissue growth. Aurora kinases (A, B, and C) play important, though differentiated, roles in mitosis. Aurora A controls the formation of the spindle assembly, while Aurora B ensures that the DNA is appropriately aligned and that cytokinesis proceeds successfully. Less is known about Aurora C, though it is thought to serve many of the same functions as Aurora B. Elevated expression of Aurora A has been detected in a high percentage of colon, breast, ovarian, gastric, and pancreatic tumors. Aurora B and C are also expressed at high levels in primary tumors. Given the central roles of all three Aurora kinases in regulating mitosis and the association between their overexpression and tumorigenesis, they are being evaluated as potential targets in cancer therapy. SNS-314 is a potent inhibitor of all 3 Aurora kinases. Cells treated with SNS-314 make additional copies of their DNA, but are unable to create functional spindle assemblies or replicate. As a result, these cells are unable to progress, and ultimately die by a variety of mechanisms. Since most normal cells are not undergoing mitosis in their normal settings, SNS-314 is expected to affect only highly proliferating tissues, particularly tumor tissues. SNS-314 is being tested in a Phase 1 trial in patients with advanced solid tumor malignancies.