Defactinib

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Also known as: 1073154-85-4, Pf-04554878, Vs-6063, 1345713-71-4, Defactinib (vs-6063, pf-04554878), N-methyl-4-((4-(((3-(n-methylmethylsulfonamido)pyrazin-2-yl)methyl)amino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzamide

Molecular Formula

C₂₀H₂₁F₃N₈O₃S

Molecular Weight

510.5 g/mol

InChI Key

FWLMVFUGMHIOAA-UHFFFAOYSA-N

FDA UNII

53O87HA2QU

Defactinib is an orally bioavailable, small-molecule focal adhesion kinase (FAK) inhibitor with potential antiangiogenic and antineoplastic activities. Defactinib inhibits FAK, which may prevent the integrin-mediated activation of several downstream signal transduction pathways, including those involving RAS/MEK/ERK and PI3K/Akt, thus inhibiting tumor cell migration, proliferation, survival, and tumor angiogenesis. The tyrosine kinase FAK, a signal transducer for integrins, is normally activated by binding to integrins in the extracellular matrix (ECM) but may be upregulated and constitutively activated in various tumor cell types.

1 2D Structure

Defactinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-methyl-4-[[4-[[3-[methyl(methylsulfonyl)amino]pyrazin-2-yl]methylamino]-5-(trifluoromethyl)pyrimidin-2-yl]amino]benzamide

2.1.2 InChI

InChI=1S/C20H21F3N8O3S/c1-24-18(32)12-4-6-13(7-5-12)29-19-28-10-14(20(21,22)23)16(30-19)27-11-15-17(26-9-8-25-15)31(2)35(3,33)34/h4-10H,11H2,1-3H3,(H,24,32)(H2,27,28,29,30)

2.1.3 InChI Key

FWLMVFUGMHIOAA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CNC(=O)C1=CC=C(C=C1)NC2=NC=C(C(=N2)NCC3=NC=CN=C3N(C)S(=O)(=O)C)C(F)(F)F

2.2 Other Identifiers

2.2.1 UNII

53O87HA2QU

2.3 Synonyms

2.3.1 MeSH Synonyms

1. N-methyl-4-((4-(((3-methyl(methylsulfonyl)aminopyrazin-2-yl)methyl)amino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzamide

2. Pf-04554878

3. Vs-6063

2.3.2 Depositor-Supplied Synonyms

1. 1073154-85-4

2. Pf-04554878

3. Vs-6063

4. 1345713-71-4

5. Defactinib (vs-6063, Pf-04554878)

6. N-methyl-4-((4-(((3-(n-methylmethylsulfonamido)pyrazin-2-yl)methyl)amino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzamide

7. N-methyl-4-[[4-[[3-[methyl(methylsulfonyl)amino]pyrazin-2-yl]methylamino]-5-(trifluoromethyl)pyrimidin-2-yl]amino]benzamide

8. 53o87ha2qu

9. Vs 6063

10. Benzamide, N-methyl-4-((4-(((3-(methyl(methylsulfonyl)amino)-2-pyrazinyl)methyl)amino)-5-(trifluoromethyl)-2-pyrimidinyl)amino)-

11. Vs6063

12. N-methyl-4-((4-(((3-(methyl(methylsulfonyl)amino)pyrazin-2-yl)methyl)amino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzamide

13. N-methyl-4-((4-(((3-methyl(methylsulfonyl)aminopyrazin-2-yl)methyl)amino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzamide

14. Defactinib [usan:inn]

15. Unii-53o87ha2qu

16. Defactinib [usan]

17. Defactinib [inn]

18. Defactinib (usan/inn)

19. Pf 04554878

20. Defactinib [who-dd]

21. Gtpl7910

22. Schembl1627234

23. Chembl3137331

24. Bdbm418817

25. Dtxsid901025937

26. Hms3740o13

27. Amy42170

28. Bcp11299

29. Ex-a1037

30. Ex-a1049

31. Mfcd25977806

32. Nsc778364

33. Nsc781450

34. Nsc782549

35. Nsc800089

36. S7654

37. Us10450297, Example 317

38. Us10450297, Example 318

39. Akos026750300

40. Zinc103297739

41. Ccg-269780

42. Cs-3410

43. Db12282

44. Nsc-778364

45. Nsc-781450

46. Nsc-782549

47. Nsc-800089

48. Sb17060

49. Ncgc00386425-06

50. Ncgc00386425-11

51. Ac-35820

52. As-17045

53. Da-34914

54. Da-45890

55. Hy-12289

56. Ft-0706351

57. Ft-0721609

58. J3.502.756d

59. D10618

60. A887883

61. J-690021

62. Q27077009

63. 7kd

64. N-methyl-4-({4-[({3- [methyl(methylsulfonyl)amino]pyrazin-2- Yl}methyl)amino]-5- (trifluoromethyl)pyrimidin-2- Yl}amino)benzamide (317)

65. N-methyl-4-(4-((3-(n-methylmethylsulfonamido)pyrazin-2-yl)methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)benzamide

2.4 Create Date

2009-01-19

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₁F₃N₈O₃S
Molecular Weight	510.5 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	8
Exact Mass	510.14094222 g/mol
Monoisotopic Mass	510.14094222 g/mol
Topological Polar Surface Area	151 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	804
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