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ACTIVE PHARMA INGREDIENTS

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Synopsis

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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 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 Formula	C₂₄H₂₃ClFN₅O₂
Molecular Weight	467.9 g/mol
XLogP3	4.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	8
Exact Mass	467.1524308 g/mol
Monoisotopic Mass	467.1524308 g/mol
Topological Polar Surface Area	90.3 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	729
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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