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Chemistry

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Also known as: Mk-1775, 955365-80-7, Mk1775, Mk 1775, Azd1775, Azd-1775

Molecular Formula

C₂₇H₃₂N₈O₂

Molecular Weight

500.6 g/mol

InChI Key

BKWJAKQVGHWELA-UHFFFAOYSA-N

FDA UNII

K2T6HJX3I3

Adavosertib is a small molecule inhibitor of the tyrosine kinase WEE1 with potential antineoplastic sensitizing activity. Adavosertib selectively targets and inhibits WEE1, a tyrosine kinase that phosphorylates cyclin-dependent kinase 1 (CDK1, CDC2) to inactivate the CDC2/cyclin B complex. Inhibition of WEE1 activity prevents the phosphorylation of CDC2 and impairs the G2 DNA damage checkpoint. This may lead to apoptosis upon treatment with DNA damaging chemotherapeutic agents. Unlike normal cells, most p53 deficient or mutated human cancers lack the G1 checkpoint as p53 is the key regulator of the G1 checkpoint and these cells rely on the G2 checkpoint for DNA repair to damaged cells. Annulment of the G2 checkpoint may therefore make p53 deficient tumor cells more vulnerable to antineoplastic agents and enhance their cytotoxic effect.

1 2D Structure

Adavosertib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[6-(2-hydroxypropan-2-yl)pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-prop-2-enylpyrazolo[3,4-d]pyrimidin-3-one

2.1.2 InChI

InChI=1S/C27H32N8O2/c1-5-13-34-25(36)21-18-28-26(29-19-9-11-20(12-10-19)33-16-14-32(4)15-17-33)31-24(21)35(34)23-8-6-7-22(30-23)27(2,3)37/h5-12,18,37H,1,13-17H2,2-4H3,(H,28,29,31)

2.1.3 InChI Key

BKWJAKQVGHWELA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(C1=NC(=CC=C1)N2C3=NC(=NC=C3C(=O)N2CC=C)NC4=CC=C(C=C4)N5CCN(CC5)C)O

2.2 Other Identifiers

2.2.1 UNII

K2T6HJX3I3

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-allyl-1-(6-(2-hydroxy-2-propanyl)-2-pyridinyl)-6-((4-(4-methyl-1-piperazinyl)phenyl)amino)-1,2-dihydro-3h-pyrazolo(3,4-d)pyrimidin-3-one

2. 3h-pyrazolo(3,4-d)pyrimidin-3-one, 1,2-dihydro-1-(6-(1-hydroxy-1-methylethyl)-2-pyridinyl)-6-((4-(4-methyl-1-piperazinyl)phenyl)amino)-2-(2-propen-1-yl)-

3. Azd 1775

4. Azd-1775

5. Azd1775

6. Mk 1775

7. Mk-1775

8. Mk1775

2.3.2 Depositor-Supplied Synonyms

1. Mk-1775

2. 955365-80-7

3. Mk1775

4. Mk 1775

5. Azd1775

6. Azd-1775

7. Azd 1775

8. 1-[6-(2-hydroxypropan-2-yl)pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-prop-2-enylpyrazolo[3,4-d]pyrimidin-3-one

9. 2-allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-((4-(4-methylpiperazin-1-yl)phenyl)amino)-1h-pyrazolo[3,4-d]pyrimidin-3(2h)-one

10. 2-allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(4-(4-methylpiperazin-1-yl)phenylamino)-1h-pyrazolo[3,4-d]pyrimidin-3(2h)-one

11. K2t6hjx3i3

12. Mfcd17215200

13. Adavosertib (usan)

14. 1-[6-(2-hydroxypropan-2-yl)pyridin-2-yl]-6-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-2-(prop-2-en-1-yl)pyrazolo[3,4-d]pyrimidin-3-one

15. Adavosertib [usan]

16. 3h-pyrazolo(3,4-d)pyrimidin-3-one, 1,2-dihydro-1-(6-(1-hydroxy-1-methylethyl)-2-pyridinyl)-6-((4-(4-methyl-1-piperazinyl)phenyl)amino)-2-(2-propen-1-yl)-

17. 1-[6-(2-hydroxypropan-2-yl)pyridin-2-yl]-6-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-2-(prop-2-en-1-yl)-1,2-dihydro-3h-pyrazolo[3,4-d]pyrimidin-3-one

18. 3h-pyrazolo[3,4-d]pyrimidin-3-one, 1,2-dihydro-1-[6-(1-hydroxy-1-methylethyl)-2-pyridinyl]-6-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-2-(2-propen-1-yl)-

19. Unii-k2t6hjx3i3

20. 8x7

21. Kinome_2656

22. Adavosertib [inn]

23. Adavosertib (mk-1775)

24. Adavosertib [who-dd]

25. Mls006011025

26. Gtpl7702

27. Schembl1504444

28. Chembl1976040

29. Chebi:91414

30. Dtxsid30241868

31. Ex-a331

32. Hms3295k03

33. Hms3654h20

34. Hms3744i13

35. Bcp01928

36. Bdbm50240826

37. Mk-1775 (wee-1)

38. Nsc754352

39. Nsc800793

40. S1525

41. Zinc63539231

42. Akos024259153

43. Mk-1775(azd-1775,adavosertib)

44. Adavosertib Pound Mk-1775 Pound(c)

45. Am90274

46. Bcp9000937

47. Ccg-264905

48. Cs-0105

49. Db11740

50. Nsc-754352

51. Nsc-800793

52. Sb16663

53. Ncgc00263183-01

54. Ncgc00263183-09

55. Ncgc00263183-10

56. 2-allyl-1-(6-(2-hydroxy-2-propanyl)-2-pyridinyl)-6-((4-(4-methyl-1-piperazinyl)phenyl)amino)-1,2-dihydro-3h-pyrazolo(3,4-d)pyrimidin-3-one

57. 2-allyl-1-[6-(2-hydroxy-2-propyl)-2-pyridyl]-6-[[4-(4-methyl-1-piperazinyl)phenyl]amino]pyrazolo[3,4-d]pyrimidin-3(2h)-one

58. Ac-28416

59. As-17001

60. Bm161385

61. Hy-10993

62. Smr004702820

63. Sy258875

64. Ft-0699265

65. Sw218122-2

66. D11361

67. Brd-k54256913-001-01-2

68. Q27074716

69. 1,2-dihydro-1-(6-(1-hydroxy-1-methylethyl)-2-pyridinyl)-6-((4-(4-methyl-1-piperazinyl)phenyl)amino)-2-(2-propen-1-yl)-3h-pyrazolo(3,4-d)pyrimidin-3-one

70. 1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(4-(4-methylpiperazin-1-yl)anilino)-2-(prop-2-en-1-yl)-1,2-dihydro-3h-pyrazolo(3,4-d)pyrimidin-3-one

71. 1075739-30-8

72. 2-allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(4-(4-methylpiperazin-1-yl)phenylamino)-1h-pyrazo

73. 2-allyl-1-[6-(1-hydroxy-1-methyl-ethyl)-pyridin-2-yl]-6-[4-(4-methyl-piperazin-1-yl)-phenylamino]-1,2-dihydro-pyrazolo[3,4-d]pyrimidin-3-one

74. 2-allyl-1-[6-(1-hydroxy-1-methylethyl)pyridin-2-yl]-6-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-1,2-dihydro-3h-pyrazolo[3,4-d]pyrimidin-3-one

2.4 Create Date

2008-07-28

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₂N₈O₂
Molecular Weight	500.6 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	7
Exact Mass	500.26482229 g/mol
Monoisotopic Mass	500.26482229 g/mol
Topological Polar Surface Area	101 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	795
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

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Drugs in Development

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Adavosertib

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