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    Lisavanbulin

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: Bal101553, Bal-101553, Lisavanbulin [inn], Lisavanbulin [usan], 1263384-43-5, 5pt0qp06x5
    Molecular Formula
    C26H29N9O3
    Molecular Weight
    515.6  g/mol
    InChI Key
    NIPZLALJRAHABJ-IBGZPJMESA-N
    FDA UNII
    5PT0QP06X5
    Lisavanbulin is an orally available, highly water-soluble lysine prodrug of the synthetic small molecule BAL27862 with potential antitumor activity. Upon administration of lisavanbulin and conversion into the active form BAL27862, this agent binds to tubulin at a site distinct from the vinca-alkaloid-binding site, and prevents tubulin polymerization and destabilizes microtubules, ultimately leading to cell cycle arrest, blockage of cell division and an induction of cell death in cancer cells.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2,6-diamino-N-[4-[2-[2-[4-(2-cyanoethylamino)-1,2,5-oxadiazol-3-yl]benzimidazol-1-yl]acetyl]phenyl]hexanamide
    2.1.2 InChI
    InChI=1S/C26H29N9O3/c27-13-4-3-6-19(29)26(37)31-18-11-9-17(10-12-18)22(36)16-35-21-8-2-1-7-20(21)32-25(35)23-24(34-38-33-23)30-15-5-14-28/h1-2,7-12,19H,3-6,13,15-16,27,29H2,(H,30,34)(H,31,37)/t19-/m0/s1
    2.1.3 InChI Key
    NIPZLALJRAHABJ-IBGZPJMESA-N
    2.1.4 Canonical SMILES
    C1=CC=C2C(=C1)N=C(N2CC(=O)C3=CC=C(C=C3)NC(=O)C(CCCCN)N)C4=NON=C4NCCC#N
    2.1.5 Isomeric SMILES
    C1=CC=C2C(=C1)N=C(N2CC(=O)C3=CC=C(C=C3)NC(=O)[C@H](CCCCN)N)C4=NON=C4NCCC#N
    2.2 Other Identifiers
    2.2.1 UNII
    5PT0QP06X5
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2s)-2,6-diamino-n-(4-(2-(2-(4-((2-cyanoethyl)amino)-1,2,5-oxadiazol-3-yl)-1h-benzimidazol-1-yl)acetyl)phenyl)hexanamide

    2. Bal101553

    2.3.2 Depositor-Supplied Synonyms

    1. Bal101553

    2. Bal-101553

    3. Lisavanbulin [inn]

    4. Lisavanbulin [usan]

    5. 1263384-43-5

    6. 5pt0qp06x5

    7. Microtubule-targeted Agent Bal101553

    8. (2s)-2,6-diamino-n-(4-(2-(2-(4-((2-cyanoethyl)amino)-1,2,5-oxadiazol-3-yl)-1h-benzimidazol-1-yl)acetyl)phenyl)hexanamide

    9. Hexanamide, 2,6-diamino-n-(4-(2-(2-(4-((2-cyanoethyl)amino)-1,2,5-oxadiazol-3-yl)-1h-benzimidazol-1-yl)acetyl)phenyl)-, (2s)-

    10. Lisavanbulin (usan/inn)

    11. Lisavanbulin [usan:inn]

    12. Unii-5pt0qp06x5

    13. Lisavanbulin [who-dd]

    14. Schembl1160313

    15. Chembl4297595

    16. Glxc-25728

    17. Ex-a4306

    18. Nsc764608

    19. Nsc789724

    20. Who 10401

    21. Bal 101553

    22. Db15224

    23. Nsc-764608

    24. Nsc-789724

    25. D11494

    26. Q27262705

    2.4 Create Date
    2010-05-03
    3 Chemical and Physical Properties
    Molecular Weight 515.6 g/mol
    Molecular Formula C26H29N9O3
    XLogP31.5
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count13
    Exact Mass515.23933582 g/mol
    Monoisotopic Mass515.23933582 g/mol
    Topological Polar Surface Area191 Ų
    Heavy Atom Count38
    Formal Charge0
    Complexity828
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Immune Checkpoint Inhibitors

    Drugs that block negative regulator IMMUNE CHECKPOINT proteins (e.g., PD-1 RECEPTOR and CTLA-4 ANTIGEN) thereby increasing suppressed immune activation in immunotherapies. (See all compounds classified as Immune Checkpoint Inhibitors.)