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    Technical details about Cediranib, learn more about the structure, uses, toxicity, action, side effects and more

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    Cediranib

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    DIGITAL CONTENT

    PharmaCompass

    Inke S.A: APIs manufacturing plant.

    ChemWerth works in generic API development & supply, non-infringement patent strategy development and regulatory support.

    2D Structure
    1. 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

    2D Structure

    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 Weight 450.5 g/mol
    Molecular Formula C25H27FN4O3
    XLogP34.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count8
    Exact Mass450.20671890 g/mol
    Monoisotopic Mass450.20671890 g/mol
    Topological Polar Surface Area72.5 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity625
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.

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