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    Sabizabulin

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: Veru-111, 1332881-26-1, 37l1jx37j5, (2-(1h-indol-3-yl)-1h-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone, [2-(1h-indol-3-yl)-1h-imidazol-5-yl]-(3,4,5-trimethoxyphenyl)methanone, [2-(1h-indol-3-yl)-1h-imidazol-5-yl](3,4,5-trimethoxyphenyl)methanone
    Molecular Formula
    C21H19N3O4
    Molecular Weight
    377.4  g/mol
    InChI Key
    WQGVHOVEXMOLOK-UHFFFAOYSA-N
    FDA UNII
    37L1JX37J5
    Sabizabulin is an orally bioavailable, small molecule tubulin inhibitor, with potential antineoplastic, antiviral and anti-inflammatory activities. Upon oral administration, sabizabulin binds to the colchicine-binding site of alpha- and beta-tubulin subunits of microtubules and crosslinks the microtubules, thereby inhibiting microtubule polymerization in tumor blood vessel endothelial cells and tumor cells. This blocks the formation of the mitotic spindle and leads to cell cycle arrest at the G2/M phase. As a result, this agent disrupts the tumor vasculature, tumor blood flow, deprives tumor cells of nutrients, and induces apoptosis. In addition, as microtubules plays an important role in intracellular transport, the inhibition of its polymerization may disrupt the transport of the androgen receptor (AR) into the cell nucleus, as well as virus trafficking around the cell. This may decrease viral replication and assembly. Inhibition of tubulin polymerization may also inhibit the release of pro-inflammatory cytokines and disrupt inflammatory cell activities. Sabizabulin is not a substrate of P-glycoprotein (Pgp), an efflux pump that when overexpressed, may confer resistance to taxane agents.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [2-(1H-indol-3-yl)-1H-imidazol-5-yl]-(3,4,5-trimethoxyphenyl)methanone
    2.1.2 InChI
    InChI=1S/C21H19N3O4/c1-26-17-8-12(9-18(27-2)20(17)28-3)19(25)16-11-23-21(24-16)14-10-22-15-7-5-4-6-13(14)15/h4-11,22H,1-3H3,(H,23,24)
    2.1.3 InChI Key
    WQGVHOVEXMOLOK-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    COC1=CC(=CC(=C1OC)OC)C(=O)C2=CN=C(N2)C3=CNC4=CC=CC=C43
    2.2 Other Identifiers
    2.2.1 UNII
    37L1JX37J5
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2-(1h-indol-3-yl)-1h-imidazol-5-yl)-(3,4,5-trimethoxyphenyl)methanone

    2. Methanone, (2-(1h-indol-3-yl)-1h-imidazol-5-yl)(3,4,5-trimethoxyphenyl)-

    3. Veru-111

    2.3.2 Depositor-Supplied Synonyms

    1. Veru-111

    2. 1332881-26-1

    3. 37l1jx37j5

    4. (2-(1h-indol-3-yl)-1h-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone

    5. [2-(1h-indol-3-yl)-1h-imidazol-5-yl]-(3,4,5-trimethoxyphenyl)methanone

    6. [2-(1h-indol-3-yl)-1h-imidazol-5-yl](3,4,5-trimethoxyphenyl)methanone

    7. Methanone, (2-(1h-indol-3-yl)-1h-imidazol-5-yl)(3,4,5-trimethoxyphenyl)-

    8. (2-(1h-indol-3-yl)-1h-imidazol-5-yl)(3,4,5-trimethoxyphenyl)methanone

    9. Sabizabulin [inn]

    10. Sabizabulin [who-dd]

    11. Veru111

    12. Schembl724794

    13. Unii-37l1jx37j5

    14. Chembl2163631

    15. Schembl20850747

    16. Gtpl11422

    17. Abi-231

    18. Hy-120599

    19. Cs-0078414

    20. S6772

    21. Kum

    2.4 Create Date
    2011-10-11
    3 Chemical and Physical Properties
    Molecular Weight 377.4 g/mol
    Molecular Formula C21H19N3O4
    XLogP33.4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count6
    Exact Mass377.13755610 g/mol
    Monoisotopic Mass377.13755610 g/mol
    Topological Polar Surface Area89.2 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity534
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1