Cabozantinib Cabozantinib

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    Cabozantinib
    Also known as: 1140909-48-3, Cabozantinib malate, Cabozantinib (s)-malate, Cabometyx, Cabozantinib malate (xl184), Xl184
    Molecular Formula
    C32H30FN3O10
    Molecular Weight
    635.6  g/mol
    InChI Key
    HFCFMRYTXDINDK-WNQIDUERSA-N
    FDA UNII
    DR7ST46X58
    Cabozantinib S-malate is the s-malate salt form of cabozantinib, an orally bioavailable, small molecule receptor tyrosine kinase (RTK) inhibitor with potential antineoplastic activity. Cabozantinib strongly binds to and inhibits several RTKs, which are often overexpressed in a variety of cancer cell types, including hepatocyte growth factor receptor (MET), RET (rearranged during transfection), vascular endothelial growth factor receptor types 1 (VEGFR-1), 2 (VEGFR-2), and 3 (VEGFR-3), mast/stem cell growth factor (KIT), FMS-like tyrosine kinase 3 (FLT-3), TIE-2 (TEK tyrosine kinase, endothelial), tropomyosin-related kinase B (TRKB) and AXL. This may result in an inhibition of both tumor growth and angiogenesis, and eventually lead to tumor regression.
    1 2D Structure

    Cabozantinib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-N-[4-(6,7-dimethoxyquinolin-4-yl)oxyphenyl]-1-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide;(2S)-2-hydroxybutanedioic acid
    2.1.2 InChI
    InChI=1S/C28H24FN3O5.C4H6O5/c1-35-24-15-21-22(16-25(24)36-2)30-14-11-23(21)37-20-9-7-19(8-10-20)32-27(34)28(12-13-28)26(33)31-18-5-3-17(29)4-6-18;5-2(4(8)9)1-3(6)7/h3-11,14-16H,12-13H2,1-2H3,(H,31,33)(H,32,34);2,5H,1H2,(H,6,7)(H,8,9)/t;2-/m.0/s1
    2.1.3 InChI Key
    HFCFMRYTXDINDK-WNQIDUERSA-N
    2.1.4 Canonical SMILES
    COC1=CC2=C(C=CN=C2C=C1OC)OC3=CC=C(C=C3)NC(=O)C4(CC4)C(=O)NC5=CC=C(C=C5)F.C(C(C(=O)O)O)C(=O)O
    2.1.5 Isomeric SMILES
    COC1=CC2=C(C=CN=C2C=C1OC)OC3=CC=C(C=C3)NC(=O)C4(CC4)C(=O)NC5=CC=C(C=C5)F.C([C@@H](C(=O)O)O)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    DR7ST46X58
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Bms 907351

    2. Bms-907351

    3. Bms907351

    4. Cabozantinib

    5. Cometriq

    6. Xl 184

    7. Xl-184

    8. Xl184 Cpd

    2.3.2 Depositor-Supplied Synonyms

    1. 1140909-48-3

    2. Cabozantinib Malate

    3. Cabozantinib (s)-malate

    4. Cabometyx

    5. Cabozantinib Malate (xl184)

    6. Xl184

    7. Cabozantinib (s-malate)

    8. Cometriq

    9. Cabozantinib S-malate [usan]

    10. Dr7st46x58

    11. Bms907351

    12. Chebi:72319

    13. N-(4-((6,7-dimethoxyquinolin-4-yl)oxy)phenyl)-n-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (s)-2-hydroxysuccinate

    14. Cabometyx (tn)

    15. Cometriq (tn)

    16. Cabozantinib Malate (jan)

    17. 1-n-[4-(6,7-dimethoxyquinolin-4-yl)oxyphenyl]-1-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide;(2s)-2-hydroxybutanedioic Acid

    18. Cabozantinib S-malate (usan)

    19. Cabozantinib Malate [jan]

    20. Unii-dr7st46x58

    21. Butanedioic Acid, 2-hydroxy-, (2s)-, Compd. With N-(4-((6,7-dimethoxy-4-quinolinyl)oxy)phenyl)-n'-(4-fluorophenyl)-1,1-cyclopropanedicarboxamide (1:1)

    22. Butanedioic Acid, 2-hydroxy-, (2s)-, Compd. With N-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl]-n'-(4-fluorophenyl)-1,1-cyclopropanedicarboxamide (1:1)

    23. Xl184 Malate

    24. Cabozantinib L-malate

    25. Bms907351 Malate

    26. Xl184(cabozantinib Malate)

    27. Mls006010951

    28. Chembl2103868

    29. Dtxsid60915949

    30. Ex-a2819

    31. Mfcd20923480

    32. S4001

    33. 1140909-48-3 (malate)

    34. Akos025401945

    35. Cabozantinib S-malate [who-dd]

    36. Ccg-270301

    37. Cs-0201

    38. (2s)-2-hydroxybutanedioic Acid Compd. With N-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl]-n'-(4-fluor

    39. (2s)-2-hydroxybutanedioic Acid Compd. With N-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl]-n'-(4-fluorophenyl)-1,1-cyclopropanedicarboxamide (1:1)

    40. Ac-27471

    41. As-75255

    42. Hy-12044

    43. Smr004702755

    44. Cabozantinib S-malate [orange Book]

    45. Sw218093-2

    46. D10095

    47. Q27139901

    48. (2s)-2-hydroxybutanedioic Acid Compd. With N-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl]-n'-(4-fluorophenyl)-1,1-cyclopropanedicarboxamide

    49. (2s)-2-hydroxybutanedioic Acid Compd. With N-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl]-n-(4-fluorophenyl)-1,1-cyclopropanedicarboxamide (1:1)

    50. (2s)-2-hydroxybutanedioic Acid; N'1-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}-n1-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

    51. 1,1-cyclopropanedicarboxamide, N'-(4-((6,7-dimethoxy-4-quinolinyl)oxy]phenyl]-n-(4- Fluorophenyl)- Mono((2s)-2-hydroxybutanedioate)

    52. Cyclopropane-1,1-dicarboxylic Acid [4-(6,7-dimethoxy-quinoline-4-yloxy)-phenyl]-amide(4-fluoro-phenyl)-amide, (s) Malate Salt

    53. N-(4-((6,7-dimethoxyquinolin-4-yl)oxy)phenyl)-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Mono((2s)-2-hydroxybutanedioate)

    54. N-(4-(6,7-dimethoxyquinolin-4-yloxy)phenyl)-n-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (s)-2-hydroxysuccinate

    55. N-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (2s)-2-hydroxybutanedioate

    2.4 Create Date
    2008-12-22
    3 Chemical and Physical Properties
    Molecular Weight 635.6 g/mol
    Molecular Formula C32H30FN3O10
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count11
    Exact Mass635.19152232 g/mol
    Monoisotopic Mass635.19152232 g/mol
    Topological Polar Surface Area194 Ų
    Heavy Atom Count46
    Formal Charge0
    Complexity924
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Indication

    * Renal Cell Carcinoma (RCC):

    Cabometyx is indicated as monotherapy for the treatment of advanced renal cell carcinoma (RCC):

    - in treatment-nave adults with intermediate or poor risk,

    - in adults following prior vascular endothelial growth factor (VEGF)-targeted therapy.

    Cabometyx, in combination with nivolumab, is indicated for the first-line treatment of advanced renal cell carcinoma in adults.

    * Hepatocellular Carcinoma (HCC):

    Cabometyx is indicated as monotherapy for the treatment of hepatocellular carcinoma (HCC) in adults who have previously been treated with sorafenib.

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    L01EX07

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