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Chemistry

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Also known as: 257933-82-7, Ekb-569, Pelitinib (ekb-569), Way-ekb 569, Ekb 569, Way-ekb-569
Molecular Formula
C24H23ClFN5O2
Molecular Weight
467.9  g/mol
InChI Key
WVUNYSQLFKLYNI-AATRIKPKSA-N
FDA UNII
X5DWL380Z6

Pelitinib
Pelitinib is a 3-cyanoquinoline pan-ErbB tyrosine kinase inhibitor with potential antineoplastic activity. Pelitinib irreversibly binds covalently to epidermal growth factor receptors (EGFR) ErbB-1, -2 and -4, thereby inhibiting receptor phosphorylation and signal transduction and resulting in apoptosis and suppression of proliferation in tumor cells that overexpress these receptors.
1 2D Structure

Pelitinib

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(E)-N-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide
2.1.2 InChI
InChI=1S/C24H23ClFN5O2/c1-4-33-22-12-20-17(11-21(22)30-23(32)6-5-9-31(2)3)24(15(13-27)14-28-20)29-16-7-8-19(26)18(25)10-16/h5-8,10-12,14H,4,9H2,1-3H3,(H,28,29)(H,30,32)/b6-5+
2.1.3 InChI Key
WVUNYSQLFKLYNI-AATRIKPKSA-N
2.1.4 Canonical SMILES
CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=CC(=C(C=C3)F)Cl)C#N)NC(=O)C=CCN(C)C
2.1.5 Isomeric SMILES
CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=CC(=C(C=C3)F)Cl)C#N)NC(=O)/C=C/CN(C)C
2.2 Other Identifiers
2.2.1 UNII
X5DWL380Z6
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (2e)-n-(4-((3-chloro-4-fluorophenyl)amino)-3-cyano-7-ethoxy-6-quinolinyl)-4-(dimethylamino)-2-butenamide

2. Ekb 569

3. Ekb-569

4. Eki 569

5. Eki-569

2.3.2 Depositor-Supplied Synonyms

1. 257933-82-7

2. Ekb-569

3. Pelitinib (ekb-569)

4. Way-ekb 569

5. Ekb 569

6. Way-ekb-569

7. 326894-84-2

8. (e)-n-(4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide

9. (e)-n-(4-((3-chloro-4-fluorophenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide

10. X5dwl380z6

11. (2e)-n-(4-((3-chloro-4-fluorophenyl)amino)-3-cyano-7-ethoxy-6-quinolinyl)-4-(dimethylamino)-2-butenamide

12. (2e)-n-{4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxyquinolin-6-yl}-4-(dimethylamino)but-2-enamide

13. Chebi:38927

14. (e)-n-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide

15. Mfcd09837868

16. (e)-n-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide

17. (e)-n-[4-[(3-chloranyl-4-fluoranyl-phenyl)amino]-3-cyano-7-ethoxy-quinolin-6-yl]-4-(dimethylamino)but-2-enamide

18. 2-butenamide, N-(4-((3-chloro-4-fluorophenyl)amino)-3-cyano-7-ethoxy-6-quinolinyl)-4-(dimethylamino)-, (2e)-

19. Pelitinib [usan]

20. Eki-569

21. Pelitinib [usan:inn]

22. Unii-x5dwl380z6

23. Ekb569

24. Eki 569

25. (2e)-n-(4-((3-chloro-4-fluorophenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide

26. (2e)-n-[4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide

27. 93j

28. Pelitinib [inn]

29. Pelitinib (usan/inn)

30. Pelitinib - Ekb-569

31. 2-butenamide, (e)-,

32. Pelitinib [who-dd]

33. Schembl93756

34. Schembl93757

35. Mls006010062

36. Chembl607707

37. Gtpl7644

38. Bdbm31090

39. Cid_6445562

40. Ex-a061

41. Bcpp000118

42. Bcpp000119

43. Zinc602803

44. Bcp02376

45. Nsc729742

46. Nsc800841

47. S1392

48. Akos005146343

49. Ccg-264890

50. Db05524

51. Nsc-729742

52. Nsc-800841

53. Way-172569

54. Ncgc00263103-09

55. Ncgc00263103-10

56. (e)-n-[4-(3-chloro-4-fluoro-anilino)-3-cyano-7-ethoxy-6-quinolyl]-4-(dimethylamino)but-2-enamide

57. Ac-24700

58. Ac-25029

59. As-16280

60. Hy-32718

61. Smr004701222

62. Pelitinib (ekb-569; Way-ekb 569)

63. P2529

64. Sw219267-1

65. Ec-000.2259

66. D05399

67. 933p827

68. A818030

69. Q-101404

70. Brd-k08799216-001-01-2

71. Q27088290

72. (2e)-n-(-((3-chloro-4-fluorophenyl)amino)3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide

73. (2e)-n-(4-((3-chloro-4-fluorophenyl)amino)-3-cyano-7-ethoxy-6-quinolinyl)-4-(dimethylamino)-2-butenamide Pelitinib

74. (2e)-n-[4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxy-6-quinolinyl]-4-dimethylamino-2-butenamide

75. (e)-n-[3-cyano-4-[(4-fluoro-3-chlorophenyl)amino]-7-ethoxyquinoline-6-yl]-4-(dimethylamino)-2-buteneamide

76. (e)-n-[4-(3-chloro-4-fluoroanilino)-cyano-7-ethoxyquinolin-6-yl]-4-(dimethlyamino)but-2-enamide, (iupac)

77. (e)-n-[4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxyquinolin-6-yl]-4-dimethylaminobut-2-enamide

78. 3-cyano-4-[(3-chloro-4-fluorophenyl)amino]-6-[[4-(n,n-dimethylamino)-1-oxo-2-buten-1-yl]amino]-7-ethoxyquinoline

79. 4-dimethylaminobut-2-enoic Acid, [4-(3-chloro-4-fluoro Phenylamino)-3-cyano-7-ethoxyquinoline-6-yl]amide

2.4 Create Date
2006-04-29
3 Chemical and Physical Properties
Molecular Weight 467.9 g/mol
Molecular Formula C24H23ClFN5O2
XLogP34.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count8
Exact Mass467.1524308 g/mol
Monoisotopic Mass467.1524308 g/mol
Topological Polar Surface Area90.3 Ų
Heavy Atom Count33
Formal Charge0
Complexity729
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Investigated for use/treatment in colorectal cancer and lung cancer.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Protein Kinase Inhibitors

Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)


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