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    Tinostamustine

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    2D Structure
    Also known as: Edo-s101, 1236199-60-2, Minomustine, Edo-s 101, Edo-s-101, Tinostamustine [usan]
    Molecular Formula
    C19H28Cl2N4O2
    Molecular Weight
    415.4  g/mol
    InChI Key
    GISXTRIGVCKQBX-UHFFFAOYSA-N
    FDA UNII
    29DKI2H2NY
    Tinostamustine is an alkylating histone-deacetylase inhibitor (HDACi) fusion molecule composed of the alkylating agent bendamustine fused to the pan-HDACi vorinostat, with potential bi-functional antineoplastic activity. Upon administration of tinostamustine the vorinostat moiety targets and binds to HDACs. This leads to an accumulation of highly acetylated histones, which results in an induction of chromatin remodeling, a modulation of gene expression, an inhibition of tumor cell division and the induction of tumor cell apoptosis. The bendamustine moiety binds to, alkylates and crosslinks macromolecules, inhibiting DNA, RNA and protein synthesis, which also results in tumor cell apoptosis. Thus, tinostamustine shows superior efficacy compared to the activity of either agent alone. In addition, the inhibition of HDAC6 activity by tinostamustine induces the activation of inositol-requiring enzyme 1 (IRE-1), the key regulatory protein for the unfolded protein response (UPR). Induction of the UPR increases the sensitivity of certain cancer cell types to certain chemotherapeutic agents, such as proteasome inhibitors. Therefore, tinostamustine may work synergistically with proteasome inhibitors. HDACs, enzymes that deacetylate chromatin histone proteins, are overexpressed in various cancers and play a key role in proliferation and resistance of tumor cells.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    7-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]-N-hydroxyheptanamide
    2.1.2 InChI
    InChI=1S/C19H28Cl2N4O2/c1-24-17-9-8-15(25(12-10-20)13-11-21)14-16(17)22-18(24)6-4-2-3-5-7-19(26)23-27/h8-9,14,27H,2-7,10-13H2,1H3,(H,23,26)
    2.1.3 InChI Key
    GISXTRIGVCKQBX-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1C2=C(C=C(C=C2)N(CCCl)CCCl)N=C1CCCCCCC(=O)NO
    2.2 Other Identifiers
    2.2.1 UNII
    29DKI2H2NY
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Edo-s101

    2.3.2 Depositor-Supplied Synonyms

    1. Edo-s101

    2. 1236199-60-2

    3. Minomustine

    4. Edo-s 101

    5. Edo-s-101

    6. Tinostamustine [usan]

    7. Tinostamustine(edo-s101)

    8. 29dki2h2ny

    9. 7-(5-(bis(2-chloroethyl)amino)-1-methyl-1h-benzo[d]imidazol-2-yl)-n-hydroxyheptanamide

    10. 7-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]-n-hydroxyheptanamide

    11. 1h-benzimidazole-2-heptanamide, 5-[bis(2-chloroethyl)amino]-n-hydroxy-1-methyl-

    12. 1h-benzimidazole-2-heptanamide, 5-(bis(2-chloroethyl)amino)-n-hydroxy-1-methyl-

    13. Starbld0018955

    14. Unii-29dki2h2ny

    15. Tinostamustine (usan/inn)

    16. Tinostamustine [inn]

    17. Schembl7915449

    18. Tinostamustine [who-dd]

    19. Chembl3989941

    20. Bcp20331

    21. Ex-a1322

    22. Bdbm50569838

    23. Zinc68244536

    24. Cs-6484

    25. Db15147

    26. Sb19172

    27. Be170657

    28. Hy-101780

    29. S8769

    30. D11182

    31. E76854

    32. 7-(5-(bis(2-chloroethyl)amino)-1-methyl-1h-benzimidazol-2-yl)-n-hydroxyheptanamide

    2.4 Create Date
    2010-08-09
    3 Chemical and Physical Properties
    Molecular Weight 415.4 g/mol
    Molecular Formula C19H28Cl2N4O2
    XLogP33.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count12
    Exact Mass414.1589315 g/mol
    Monoisotopic Mass414.1589315 g/mol
    Topological Polar Surface Area70.4 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity438
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1