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Also known as: Azd5363, 1143532-39-1, Azd-5363, Azd 5363, (s)-4-amino-n-(1-(4-chlorophenyl)-3-hydroxypropyl)-1-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide, 4-amino-n-[(1s)-1-(4-chlorophenyl)-3-hydroxypropyl]-1-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

Molecular Formula

C₂₁H₂₅ClN₆O₂

Molecular Weight

428.9 g/mol

InChI Key

JDUBGYFRJFOXQC-KRWDZBQOSA-N

FDA UNII

WFR23M21IE

Capivasertib is a novel pyrrolopyrimidine derivative, and an orally available inhibitor of the serine/threonine protein kinase AKT (protein kinase B) with potential antineoplastic activity. Capivasertib binds to and inhibits all AKT isoforms. Inhibition of AKT prevents the phosphorylation of AKT substrates that mediate cellular processes, such as cell division, apoptosis, and glucose and fatty acid metabolism. A wide range of solid and hematological malignancies show dysregulated PI3K/AKT/mTOR signaling due to mutations in multiple signaling components. By targeting AKT, the key node in the PIK3/AKT signaling network, this agent may be used as monotherapy or combination therapy for a variety of human cancers.

1 2D Structure

Capivasertib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-N-[(1S)-1-(4-chlorophenyl)-3-hydroxypropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

2.1.2 InChI

InChI=1S/C21H25ClN6O2/c22-15-3-1-14(2-4-15)17(6-12-29)27-20(30)21(23)7-10-28(11-8-21)19-16-5-9-24-18(16)25-13-26-19/h1-5,9,13,17,29H,6-8,10-12,23H2,(H,27,30)(H,24,25,26)/t17-/m0/s1

2.1.3 InChI Key

JDUBGYFRJFOXQC-KRWDZBQOSA-N

2.1.4 Canonical SMILES

C1CN(CCC1(C(=O)NC(CCO)C2=CC=C(C=C2)Cl)N)C3=NC=NC4=C3C=CN4

2.1.5 Isomeric SMILES

C1CN(CCC1(C(=O)N[C@@H](CCO)C2=CC=C(C=C2)Cl)N)C3=NC=NC4=C3C=CN4

2.2 Other Identifiers

2.2.1 UNII

WFR23M21IE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-amino-n-(1-(4-chlorophenyl)-3-hydroxypropyl)-1-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)piperidine-4-carboxamide

2. Azd5363

2.3.2 Depositor-Supplied Synonyms

1. Azd5363

2. 1143532-39-1

3. Azd-5363

4. Azd 5363

5. (s)-4-amino-n-(1-(4-chlorophenyl)-3-hydroxypropyl)-1-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

6. 4-amino-n-[(1s)-1-(4-chlorophenyl)-3-hydroxypropyl]-1-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

7. Wfr23m21ie

8. 4-piperidinecarboxamide, 4-amino-n-[(1s)-1-(4-chlorophenyl)-3-hydroxypropyl]-1-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-

9. 4-amino-n-[(1s)-1-(4-chlorophenyl)-3-hydroxypropyl]-1-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4-piperidinecarboxamide

10. Unii-wfr23m21ie

11. Chembl2325741

12. Cc-638

13. Capivasertib?

14. 4-amino-n-(1-(4-chlorophenyl)-3-hydroxypropyl)-1-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)piperidine-4-carboxamide

15. 4-piperidinecarboxamide, 4-amino-n-((1s)-1-(4-chlorophenyl)-3-hydroxypropyl)-1-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-

16. Capivasertib (jan/usan)

17. Capivasertib [inn]

18. Capivasertib [jan]

19. Capivasertib [usan]

20. Capivasertib (azd5363)

21. Mls006011179

22. Capivasertib [who-dd]

23. Schembl390243

24. Gtpl7709

25. Azc5363

26. Dtxsid40150710

27. Ex-a285

28. Us10654855, Example 9

29. Bdbm443385

30. Mfcd22628785

31. Nsc764039

32. Nsc782347

33. Nsc799347

34. S8019

35. Zinc43204023

36. Akos027323693

37. Bcp9000365

38. Ccg-268989

39. Cs-1284

40. Db12218

41. Nsc-764039

42. Nsc-782347

43. Nsc-799347

44. Ncgc00345795-01

45. Ncgc00345795-04

46. Ac-32685

47. Hy-15431

48. Smr004702948

49. Bcp0726000111

50. A1387

51. Sw220158-1

52. D11371

53. J-514447

54. Q27074756

55. 0xz

56. 4-amino-n-((1s)-1-(4-chlorophenyl)-3-hydroxypropyl)-1- (1h-pyrrolo(2,3-d)pyrimidin-4-yl)piperidine-4-carboxamide

57. Alternative Route 1: (s)-4-amino-n-(1-(4-chlorophenyl)-3-hydroxypropyl)-1-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

2.4 Create Date

2009-04-28

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₅ClN₆O₂
Molecular Weight	428.9 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	428.1727518 g/mol
Monoisotopic Mass	428.1727518 g/mol
Topological Polar Surface Area	120 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	580
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