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Canertinib

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Synopsis

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Chemistry

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Also known as: 267243-28-7, Ci-1033, Pd-183805, Canertinib (ci-1033), Canertinib free base, N-(4-(3-chloro-4-fluorophenylamino)-7-(3-morpholinopropoxy)quinazolin-6-yl)acrylamide

Molecular Formula

C₂₄H₂₅ClFN₅O₃

Molecular Weight

485.9 g/mol

InChI Key

OMZCMEYTWSXEPZ-UHFFFAOYSA-N

FDA UNII

C78W1K5ASF

Canertinib is a pan-erbB tyrosine kinase inhibitor which work against esophageal squamous cell carcinoma in vitro and in vivo. Canertinib treatment significantly affects tumour metabolism, proliferation and hypoxia as determined by PET.

1 2D Structure

Canertinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[4-(3-chloro-4-fluoroanilino)-7-(3-morpholin-4-ylpropoxy)quinazolin-6-yl]prop-2-enamide

2.1.2 InChI

InChI=1S/C24H25ClFN5O3/c1-2-23(32)30-21-13-17-20(14-22(21)34-9-3-6-31-7-10-33-11-8-31)27-15-28-24(17)29-16-4-5-19(26)18(25)12-16/h2,4-5,12-15H,1,3,6-11H2,(H,30,32)(H,27,28,29)

2.1.3 InChI Key

OMZCMEYTWSXEPZ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C=CC(=O)NC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4

2.2 Other Identifiers

2.2.1 UNII

C78W1K5ASF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ci 1033

2. Ci-1033

3. Ci1033

2.3.2 Depositor-Supplied Synonyms

1. 267243-28-7

2. Ci-1033

3. Pd-183805

4. Canertinib (ci-1033)

5. Canertinib Free Base

6. N-(4-(3-chloro-4-fluorophenylamino)-7-(3-morpholinopropoxy)quinazolin-6-yl)acrylamide

7. N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[3-(morpholin-4-yl)propoxy]quinazolin-6-yl}prop-2-enamide

8. C78w1k5asf

9. Chembl31965

10. N-[4-(3-chloro-4-fluoroanilino)-7-(3-morpholin-4-ylpropoxy)quinazolin-6-yl]prop-2-enamide

11. Chebi:61399

12. 267243-28-7 (free Base)

13. N-(4-((3-chloro-4-fluorophenyl)amino)-7-(3-(morpholin-4-yl)propoxy)quinazolin-6-yl)prop-2-enamide

14. Ncgc00182713-01

15. Pd183805

16. Canertinib [inn]

17. Canertinib [inn:ban]

18. Sn-26606

19. Ci-1033(canertinib)

20. Ci1033

21. Unii-c78w1k5asf

22. Canetinib

23. Canertinib [mi]

24. Caneritinib; Ci-1033

25. Canertinib - Ci-1033

26. Ci-1033 (canertinib)

27. Canertinib [who-dd]

28. Dsstox_cid_28869

29. Dsstox_rid_83138

30. Dsstox_gsid_48943

31. Schembl54837

32. Mls004774146

33. Pd 183805 Dihydrochloride

34. Bdbm4779

35. Cid_156414

36. Gtpl5675

37. Dtxsid8048943

38. Ex-a078

39. Bcpp000301

40. Hms3244m17

41. Hms3244m18

42. Hms3244n17

43. Bcp01790

44. Tox21_113361

45. Nsc780019

46. Nsc801011

47. S1019

48. Zinc27439698

49. Akos005145818

50. Bcp9000481

51. Bcp9000482

52. Bcp9000525

53. Ccg-269588

54. Cs-0121

55. Db05424

56. Nsc-780019

57. Nsc-801011

58. Sb16594

59. N-(4-((3-chloro-4-fluorophenyl)amino)-7-(3-morpholinopropoxy)quinazolin-6-yl)acrylamide

60. N-[4-(3-chloro-4-fluoro-anilino)-7-(3-morpholinopropoxy)quinazolin-6-yl]prop-2-enamide

61. Ncgc00182713-02

62. Ncgc00182713-18

63. As-56189

64. Hy-10367

65. Smr003500789

66. Pd0183805

67. Cas-267243-28-7

68. Ft-0654215

69. Ec-000.2258

70. A25038

71. 499c452

72. Q5032274

73. 2-propenamide, N-(4-((3-chloro-4-fluorophenyl)amino)-7-(3-(4-morpholinyl)propoxy)-6-quinazolinyl)-

74. N-(4-(3-chloro-4-fluorophenyl)amino)-7-(3-morpholin-4-yl)propoxy)quinazolin-6-yl)prop-2-enamide

75. N-[4-(3-chloro-4-fluoro-phenyl-amino)-7-(3-morpholin-4-yl-propoxy)-quinazolin-6-yl]-acrylamide

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₂₅ClFN₅O₃
Molecular Weight	485.9 g/mol
XLogP3	3.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Exact Mass	485.1629955 g/mol
Monoisotopic Mass	485.1629955 g/mol
Topological Polar Surface Area	88.6 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	671
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 Drug and Medication Information

4.1 Drug Indication

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

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

CI-1033 effectively inhibits the growth of esophageal squamous cell carcinoma which co-expresses both EGFR and HER2 with the inhibition of phosphorylation of both MAPK and AKT. Some studies suggest that CI-1033 holds significant clinical potential in esophageal cancer.

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