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Cediranib

Cediranib

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Also known as: 288383-20-0, Recentin, Azd2171, Cedirannib, Cediranib (azd2171), Azd 2171

Molecular Formula

C₂₅H₂₇FN₄O₃

Molecular Weight

450.5 g/mol

InChI Key

XXJWYDDUDKYVKI-UHFFFAOYSA-N

FDA UNII

NQU9IPY4K9

The novel indole-ether quinazoline Cediranib is a highly potent (IC50 < 1 nmol/L) ATP-competitive inhibitor of recombinant KDR tyrosine kinase in vitro. It is being developed clinically as a once-daily oral therapy for the treatment of cancer.

1 2D Structure

Cediranib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline

2.1.2 InChI

InChI=1S/C25H27FN4O3/c1-16-12-17-19(29-16)6-7-21(24(17)26)33-25-18-13-22(31-2)23(14-20(18)27-15-28-25)32-11-5-10-30-8-3-4-9-30/h6-7,12-15,29H,3-5,8-11H2,1-2H3

2.1.3 InChI Key

XXJWYDDUDKYVKI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC2=C(N1)C=CC(=C2F)OC3=NC=NC4=CC(=C(C=C43)OC)OCCCN5CCCC5

2.2 Other Identifiers

2.2.1 UNII

NQU9IPY4K9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-((4-fluoro-2-methyl-1h-indol-5-yl)oxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline

2. 4-((4-fluoro-2-methyl-1h-indol-5-yl)oxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (2z)-but-2-enedioate

3. 4-((4-fluoro-2-methyl-1h-indol-5-yl)oxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (2z)-but-2-enedioate (1:1)

4. Azd 2171

5. Azd-2171

6. Azd-2171 Maleate

7. Azd2171

8. Azd2171 Maleate

9. Cediranib Maleate

10. Recentin

2.3.2 Depositor-Supplied Synonyms

1. 288383-20-0

2. Recentin

3. Azd2171

4. Cedirannib

5. Cediranib (azd2171)

6. Azd 2171

7. Azd-2171

8. 4-((4-fluoro-2-methyl-1h-indol-5-yl)oxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline

9. Cediranib Free Base

10. 4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxy-7-[3-(pyrrolidin-1-yl)propoxy]quinazoline

11. Cediranib (azd217)

12. Azd-2171 Maleate

13. 4-[(4-fluoro-2-methyl-1h-indol-5-yl)oxy]-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline

14. Nqu9ipy4k9

15. Zd-2171

16. 4-[(4-fluoro-2-methyl-1h-indol-5-yl)oxy]-6-methoxy-7-[3-(pyrrolidin-1-yl)propoxy]quinazoline

17. Chembl491473

18. 288383-20-0 (free Base)

19. Nsc-732208

20. 4-(4-fluoro-2-methyl-1h-indol-5-yloxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline

21. Cediranib [inn]

22. Quinazoline, 4-((4-fluoro-2-methyl-1h-indol-5-yl)oxy)-6-methoxy-7-(3-(1-pyrrolidinyl)propoxy)-

23. Kinome_3318

24. Cediranib (usan/inn)

25. Unii-nqu9ipy4k9

26. Cediranib [usan:inn:ban]

27. 4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline

28. 4-((4-fluoro-2-methyl-1h-indol-5-yl)oxy)-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline

29. Cediranib,azd2171

30. Cediranib Dihydrochloride

31. Azd2171, Cediranib

32. Cediranib [usan]

33. Cediranib - Azd2171

34. Cediranib [mart.]

35. Cediranib [who-dd]

36. Schembl63147

37. Mls006010063

38. Gtpl5664

39. Chebi:94782

40. Dtxsid10183035

41. Bcpp000295

42. Hms3654g05

43. Hms3674g17

44. Hms3744o21

45. Amy16021

46. Bcp01378

47. Ex-a2039

48. Zinc3948085

49. Bdbm50331096

50. Mfcd09954115

51. Nsc755606

52. Nsc800069

53. S1017

54. Akos005145767

55. Bcp9000500

56. Ccg-264679

57. Cs-0119

58. Db04849

59. Es-0052

60. Nsc-755606

61. Nsc-800069

62. Sb16536

63. Zd 2171

64. Ncgc00263097-01

65. Ncgc00263097-09

66. Ac-25033

67. Hy-10205

68. Quinazoline,4-[(4-fluoro-2-methyl-1h-indol-5-yl)oxy]-6-methoxy-7-[3-(1-pyrrolidinyl)propoxy]-

69. Smr004701223

70. Ft-0751000

71. Sw219261-1

72. Ec-000.2328

73. A24280

74. D08881

75. Q-101399

76. Q5057052

77. Brd-k86930074-001-01-9

78. 4-(4-fluoro-2-methyl-1h-indol-5-yloxy)-6-methoxy-7-(3-pyrrolidin-1-yl-propoxy)-quinazoline

79. Av3

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₂₇FN₄O₃
Molecular Weight	450.5 g/mol
XLogP3	4.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	8
Exact Mass	450.20671890 g/mol
Monoisotopic Mass	450.20671890 g/mol
Topological Polar Surface Area	72.5 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	625
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

For the treatment of liver cancer, advanced non-small cell lung cancer (NSCLC), advanced colorectal cancer (CRC) and other solid tumors.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cediranib is a once-daily, orally available, highly potent and selective VEGF signalling inhibitor that inhibits all three VEGF receptors. The preclinical profile of Cediranib indicates that it has the potential to be the 'best in class' VEGF signalling inhibitor. Phase I data indicate that Cediranib is generally well tolerated, with the most common dose related adverse events being diarrhoea, hoarseness, headache and hypertension.

5.2 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.)

5.3 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01E - Protein kinase inhibitors

L01EK - Vascular endothelial growth factor receptor (vegfr) tyrosine kinase inhibitors

L01EK02 - Cediranib

5.4 Absorption, Distribution and Excretion

Absorption

Available following oral administration.

5.5 Biological Half-Life

12 to 35 hours

5.6 Mechanism of Action

Cediranib inhibits vacular endothelial growth factor (VEGF) receptor tyrosine kinase (RTK). By forming a blockade at the VEGF receptors, Cediranib limits the growth of new blood vessels, which are essential to supporting tumor growth. Thus, lacking sufficient blood supply, tumor cells become starved for nutrients, slowing or halting growth and potentially improving the efficacy of other treatments. Preclinical evidence indicated that the drug had a high affinity at these sites, and was well tolerated and efficacious in animal studies.