Afuresertib

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Also known as: 1047644-62-1, Gsk-2110183, Gsk2110183c, Afuresertib [usan], Asb183, Asb-183

Molecular Formula

C₁₈H₁₇Cl₂FN₄OS

Molecular Weight

427.3 g/mol

InChI Key

AFJRDFWMXUECEW-LBPRGKRZSA-N

FDA UNII

8739X25QI3

Afuresertib is an orally bioavailable inhibitor of the serine/threonine protein kinase Akt (protein kinase B) with potential antineoplastic activity. Afuresertib binds to and inhibits the activity of Akt, which may result in inhibition of the PI3K/Akt signaling pathway and tumor cell proliferation and the induction of tumor cell apoptosis. Activation of the PI3K/Akt signaling pathway is frequently associated with tumorigenesis and dysregulated PI3K/Akt signaling may contribute to tumor resistance to a variety of antineoplastic agents.

1 2D Structure

Afuresertib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(2S)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)thiophene-2-carboxamide

2.1.2 InChI

InChI=1S/C18H17Cl2FN4OS/c1-25-16(14(19)9-23-25)13-7-15(27-17(13)20)18(26)24-12(8-22)6-10-3-2-4-11(21)5-10/h2-5,7,9,12H,6,8,22H2,1H3,(H,24,26)/t12-/m0/s1

2.1.3 InChI Key

AFJRDFWMXUECEW-LBPRGKRZSA-N

2.1.4 Canonical SMILES

CN1C(=C(C=N1)Cl)C2=C(SC(=C2)C(=O)NC(CC3=CC(=CC=C3)F)CN)Cl

2.1.5 Isomeric SMILES

CN1C(=C(C=N1)Cl)C2=C(SC(=C2)C(=O)N[C@@H](CC3=CC(=CC=C3)F)CN)Cl

2.2 Other Identifiers

2.2.1 UNII

8739X25QI3

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 1047644-62-1

2. Gsk-2110183

3. Gsk2110183c

4. Afuresertib [usan]

5. Asb183

6. Asb-183

7. Gsk 2110183c

8. Afuresertib (gsk2110183)

9. Afuresertib (usan)

10. 8739x25qi3

11. Gsk-2110183c

12. N-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)thiophene-2-carboxamide

13. 2-thiophenecarboxamide, N-((1s)-2-amino-1-((3-fluorophenyl)methyl)ethyl)-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)-

14. N-((1s)-1-(aminomethyl)-2-(3-fluorophenyl)ethyl)-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)thiophene-2-carboxamide

15. Afuresertib [usan:inn]

16. Unii-8739x25qi3

17. 2-thiophenecarboxamide, N-[(1s)-2-amino-1-[(3-fluorophenyl)methyl]ethyl]-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)-

18. N-((2s)-1-amino-3-(3-fluorophenyl)propan-2-yl)-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)thiophene-2-carboxamide

19. N-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)thiophene-2-carboxamide

20. Afuresertib [inn]

21. Afuresertib [who-dd]

22. Schembl187686

23. Gtpl7890

24. Chembl2219422

25. Dtxsid60146711

26. Chebi:131168

27. Bcp08435

28. Ex-a1574

29. Bdbm50502477

30. Nsc778305

31. Nsc781255

32. Nsc800109

33. Nsc829868

34. S7521

35. Zinc43197674

36. Ccg-268972

37. Cs-3384

38. Db11648

39. Nsc-778305

40. Nsc-781255

41. Nsc-800109

42. Nsc-829868

43. Gsk 2110183

44. Ncgc00387879-03

45. Ac-35761

46. Ba166066

47. Bs-14212

48. Hy-15727

49. A16392

50. D10381

51. D71036

52. A853608

53. Afuresertib, Gsk-2110183, Gsk-2110183b

54. Q27224945

55. N-((s)-1-amino-3-(3-fluorophenyl)propan-2-yl)-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)thiophene-2-carboxamide

56. N-((s)-1-amino-3-(3-fluorophenyl)propan-2-yl)-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)thiophene-2-carboxamide;afuresertib

57. N-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methyl-3-pyrazolyl)-2-thiophenecarboxamide

58. N-{(1s)-2-amino-1-[(3-fluorophenyl)methyl]ethyl}-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)-2-thiophenecarboxamide

2.4 Create Date

2010-08-16

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₇Cl₂FN₄OS
Molecular Weight	427.3 g/mol
XLogP3	4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	426.0484159 g/mol
Monoisotopic Mass	426.0484159 g/mol
Topological Polar Surface Area	101 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	520
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1