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    Abexinostat

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 783355-60-2, Pci-24781, Pci 24781, Cra-024781, Cra 024781, Cra-02478
    Molecular Formula
    C21H23N3O5
    Molecular Weight
    397.4  g/mol
    InChI Key
    MAUCONCHVWBMHK-UHFFFAOYSA-N
    FDA UNII
    IYO470654U
    Abexinostat is an orally bioavailable hydroxamate-based pan-inhibitor of histone deacetylase (HDAC), with potential antineoplastic and radiosensitizing activities. Upon administration, abexinostat inhibits HDAC, resulting in an accumulation of highly acetylated histones, followed by the induction of chromatin remodeling; the selective transcription of tumor suppressor genes; and the tumor suppressor protein-mediated inhibition of tumor cell division and induction of tumor cell apoptosis. In addition, abexinostat decreases the expression of the DNA-repair protein RAD51, thereby reducing the RAD51 protein, preventing repair of DNA double-strand breaks and increasing sensitivity of tumor cells to DNA damaging agents. HDAC, upregulated in many tumor types, is an enzyme that is responsible for the deacetylation of chromatin histone proteins.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-[(dimethylamino)methyl]-N-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide
    2.1.2 InChI
    InChI=1S/C21H23N3O5/c1-24(2)13-17-16-5-3-4-6-18(16)29-19(17)21(26)22-11-12-28-15-9-7-14(8-10-15)20(25)23-27/h3-10,27H,11-13H2,1-2H3,(H,22,26)(H,23,25)
    2.1.3 InChI Key
    MAUCONCHVWBMHK-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN(C)CC1=C(OC2=CC=CC=C21)C(=O)NCCOC3=CC=C(C=C3)C(=O)NO
    2.2 Other Identifiers
    2.2.1 UNII
    IYO470654U
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cra 024781

    2. Cra-024781

    3. Cra024781

    4. Pci 24781

    5. Pci-24781

    6. Pci24781

    2.3.2 Depositor-Supplied Synonyms

    1. 783355-60-2

    2. Pci-24781

    3. Pci 24781

    4. Cra-024781

    5. Cra 024781

    6. Cra-02478

    7. Pci24781

    8. Cra 24781

    9. Abexinostat [usan]

    10. 3-((dimethylamino)methyl)-n-(2-(4-(hydroxycarbamoyl)phenoxy)ethyl)benzofuran-2-carboxamide

    11. Abexinostat (pci-24781)

    12. Pci-24781 (abexinostat)

    13. Pci-24781 (cra-024781)

    14. S78454

    15. Iyo470654u

    16. Pzp115891

    17. 3-((dimethylamino)methyl)-n-(2-(4-(hydroxycarbamoyl)-phenoxy)ethyl)benzofuran-2-carboxamide

    18. Abexinostat (usan)

    19. Pzp-115891

    20. 3-(dimethylaminomethyl)-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide

    21. 3-[(dimethylamino)methyl]-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide

    22. S-78454

    23. 3-[(dimethylamino)methyl]-n-[2-[4-[(hydroxyamino)carbonyl]phenoxy]ethyl]-2-benzofurancarboxamide

    24. 3-[(dimethylamino)methyl]-n-{2-[4-(hydroxycarbamoyl)phenoxy]ethyl}-1-benzofuran-2-carboxamide

    25. 2-benzofurancarboxamide, 3-((dimethylamino)methyl)-n-(2-(4-((hydroxyamino)carbonyl)phenoxy)ethyl)-

    26. Abexinostat [usan:inn]

    27. Unii-iyo470654u

    28. 3-((dimethylamino)methyl)-n-(2-(4-(hydroxycarbamoyl)phenoxy)ethyl)-1-benzofuran-2-carboxamide

    29. Cra024781

    30. Abexinostat [inn]

    31. Abexinostat(pci-24781)

    32. Abexinostat [who-dd]

    33. Mls006011097

    34. Schembl444280

    35. Gtpl8366

    36. Chembl2103863

    37. Bdbm24622

    38. Chebi:92223

    39. Dtxsid30229005

    40. Bcpp000128

    41. Hms3654a19

    42. Ex-a2123

    43. Zinc6716700

    44. Cra-24781

    45. Fd5037

    46. Mfcd10565969

    47. Nsc764136

    48. Akos025149423

    49. Bcp9001054

    50. Ccg-264814

    51. Cs-0478

    52. Db12565

    53. Nsc-764136

    54. Sb16670

    55. Ncgc00346486-01

    56. Ncgc00346486-05

    57. Ac-26866

    58. Bs-18153

    59. Hy-10990

    60. Smr004702885

    61. Db-075461

    62. Pci-24781,cra-024781

    63. Ft-0673532

    64. Sw218266-2

    65. Ec-000.2348

    66. D10060

    67. J-511438

    68. Q4667249

    69. Brd-k12867552-001-01-3

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 397.4 g/mol
    Molecular Formula C21H23N3O5
    XLogP32.2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count8
    Exact Mass397.16377084 g/mol
    Monoisotopic Mass397.16377084 g/mol
    Topological Polar Surface Area104 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity550
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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

    Histone Deacetylase Inhibitors

    Compounds that inhibit HISTONE DEACETYLASES. This class of drugs may influence gene expression by increasing the level of acetylated HISTONES in specific CHROMATIN domains. (See all compounds classified as Histone Deacetylase Inhibitors.)

    4.2 Mechanism of Action

    Abexinostat is a novel histone deacetylase (HDAC) inhibitor. HDAC inhibitors target HDAC enzymes and inhibit the proliferation of cancer cells and induce cancer cell death, or apoptosis. Histone deacetylation is carried out by a family of related HDAC enzymes. Inhibition of these enzymes causes changes to chromatin structure and to gene expression patterns, which results in the inhibition of proliferation of cancer cells, and induction of apoptosis.