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    Vorolanib

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    Also known as: 1013920-15-4, Vorolanib [inn], Yp8g3i74el, Cm082, N-[(3s)-1-(dimethylcarbamoyl)pyrrolidin-3-yl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide, X-82
    Molecular Formula
    C23H26FN5O3
    Molecular Weight
    439.5  g/mol
    InChI Key
    KMIOJWCYOHBUJS-HAKPAVFJSA-N
    FDA UNII
    YP8G3I74EL
    Vorolanib is an orally available small molecule dual inhibitor targeting human vascular endothelial growth factor receptors (VEGFRs) and platelet-derived growth factor receptors (PDGFRs) with antiangiogenic and antineoplastic activities. Vorolanib inhibits all isoforms of VEGFR and PDGFR, which may result in the inhibition of tumor angiogenesis and tumor cell proliferation, and the induction of tumor cell death. Both VEGFRs and PDGFRs are receptor tyrosine kinases that may be upregulated in various tumor cell types. Vorolanib has been shown to reduce tissue toxicity by 95 percent compared with first-generation kinase inhibitors.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[(3S)-1-(dimethylcarbamoyl)pyrrolidin-3-yl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide
    2.1.2 InChI
    InChI=1S/C23H26FN5O3/c1-12-19(10-17-16-9-14(24)5-6-18(16)27-21(17)30)25-13(2)20(12)22(31)26-15-7-8-29(11-15)23(32)28(3)4/h5-6,9-10,15,25H,7-8,11H2,1-4H3,(H,26,31)(H,27,30)/b17-10-/t15-/m0/s1
    2.1.3 InChI Key
    KMIOJWCYOHBUJS-HAKPAVFJSA-N
    2.1.4 Canonical SMILES
    CC1=C(NC(=C1C(=O)NC2CCN(C2)C(=O)N(C)C)C)C=C3C4=C(C=CC(=C4)F)NC3=O
    2.1.5 Isomeric SMILES
    CC1=C(NC(=C1C(=O)N[C@H]2CCN(C2)C(=O)N(C)C)C)/C=C\3/C4=C(C=CC(=C4)F)NC3=O
    2.2 Other Identifiers
    2.2.1 UNII
    YP8G3I74EL
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cm082

    2. N-((3s)-1-(dimethylcarbamoyl)pyrrolidin-3-yl)-5-((z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide

    2.3.2 Depositor-Supplied Synonyms

    1. 1013920-15-4

    2. Vorolanib [inn]

    3. Yp8g3i74el

    4. Cm082

    5. N-[(3s)-1-(dimethylcarbamoyl)pyrrolidin-3-yl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide

    6. X-82

    7. (s,z)-n-(1-(dimethylcarbamoyl)pyrrolidin-3-yl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide

    8. 1h-pyrrole-3-carboxamide, N-((3s)-1-((dimethylamino)carbonyl)-3-pyrrolidinyl)-5-((z)-(5-fluoro-1,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl)-2,4-dimethyl-

    9. N-((3s)-1-(dimethylcarbamoyl)pyrrolidin-3-yl)-5-((z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide

    10. Unii-yp8g3i74el

    11. Vorolanib [who-dd]

    12. Schembl2439528

    13. Chembl4297587

    14. Gtpl11618

    15. Eyp-1901

    16. Cm-082

    17. S6843

    18. Db15247

    19. Example 8 [wo2008033562a2]

    20. Ac-35712

    21. Hy-109019

    22. Cs-0030517

    23. X-082

    24. Q27294638

    2.4 Create Date
    2012-08-20
    3 Chemical and Physical Properties
    Molecular Weight 439.5 g/mol
    Molecular Formula C23H26FN5O3
    XLogP31.6
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count3
    Exact Mass439.20196787 g/mol
    Monoisotopic Mass439.20196787 g/mol
    Topological Polar Surface Area97.5 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity803
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Protein Kinase Inhibitors

    Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)