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    Pracinostat

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 929016-96-6, Sb939, Sb 939, Pracinostat (sb939), Sb-939, Pracinostat [inn]
    Molecular Formula
    C20H30N4O2
    Molecular Weight
    358.5  g/mol
    InChI Key
    JHDKZFFAIZKUCU-ZRDIBKRKSA-N
    FDA UNII
    GPO2JN4UON
    Pracinostat is an orally available, small-molecule histone deacetylase (HDAC) inhibitor with potential antineoplastic activity. Pracinostat inhibits HDACs, which may result in the accumulation of highly acetylated histones, followed by the induction of chromatin remodeling; the selective transcription of tumor suppressor genes; the tumor suppressor protein-mediated inhibition of tumor cell division; and, finally, the induction of tumor cell apoptosis. This agent may possess improved metabolic, pharmacokinetic and pharmacological properties compared to other HDAC inhibitors.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (E)-3-[2-butyl-1-[2-(diethylamino)ethyl]benzimidazol-5-yl]-N-hydroxyprop-2-enamide
    2.1.2 InChI
    InChI=1S/C20H30N4O2/c1-4-7-8-19-21-17-15-16(10-12-20(25)22-26)9-11-18(17)24(19)14-13-23(5-2)6-3/h9-12,15,26H,4-8,13-14H2,1-3H3,(H,22,25)/b12-10+
    2.1.3 InChI Key
    JHDKZFFAIZKUCU-ZRDIBKRKSA-N
    2.1.4 Canonical SMILES
    CCCCC1=NC2=C(N1CCN(CC)CC)C=CC(=C2)C=CC(=O)NO
    2.1.5 Isomeric SMILES
    CCCCC1=NC2=C(N1CCN(CC)CC)C=CC(=C2)/C=C/C(=O)NO
    2.2 Other Identifiers
    2.2.1 UNII
    GPO2JN4UON
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3-(2-butyl-1-(2-diethylaminoethyl)-1h-benzoimidazol-5-yl)-n-hydroxyacrylamide-hydrochloride

    2. Sb939 Compound

    2.3.2 Depositor-Supplied Synonyms

    1. 929016-96-6

    2. Sb939

    3. Sb 939

    4. Pracinostat (sb939)

    5. Sb-939

    6. Pracinostat [inn]

    7. (e)-3-(2-butyl-1-(2-(diethylamino)ethyl)-1h-benzo[d]imidazol-5-yl)-n-hydroxyacrylamide

    8. Gpo2jn4uon

    9. Chembl1851943

    10. 2-propenamide, 3-(2-butyl-1-(2-(diethylamino)ethyl)-1h-benzimidazol-5-yl)-n-hydroxy-, (2e)-

    11. Unii-gpo2jn4uon

    12. Pracinostatum

    13. (2e)-3-[2-butyl-1-[2-(diethylamino)ethyl]-1h-benzimidazol-5-yl]-n-hydroxyacrylamide

    14. (2e)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1h-benzimidazol-5-yl}-n-hydroxyacrylamide

    15. Sb939,pracinostat

    16. Pracinostat(sb939)

    17. Sb939 (pracinostat)

    18. Pracinostat [who-dd]

    19. Mls006011217

    20. Schembl833105

    21. Gtpl8365

    22. Chebi:95071

    23. Dtxsid00239196

    24. Ex-a351

    25. Bcp02073

    26. Bdbm50105330

    27. Mfcd17215206

    28. Nsc758249

    29. S1515

    30. Zinc43152558

    31. Ccg-264903

    32. Cs-0567

    33. Db05223

    34. Nsc-758249

    35. (e)-3-[2-butyl-1-[2-(diethylamino)ethyl]benzimidazol-5-yl]-n-hydroxyprop-2-enamide

    36. Ncgc00263136-04

    37. Ac-33161

    38. As-19395

    39. Hy-13322

    40. Smr004702979

    41. Sw219429-1

    42. Ec-000.2481

    43. A850037

    44. Q18344027

    45. Kaempferol 3-o-.beta.-d-(6-e-p-coumaroylglucoside)

    46. (2e)-3-[2-butyl-1-[2-(diethylamino)ethyl]-1h-benzimidazol-5-yl]-n-hydroxy-2-propenamide

    47. (e)-3-[2-butyl-1-(2-diethylaminoethyl)benzimidazol-5-yl]prop-2-enehydroxamic Acid

    48. (2e)-3-(2-butyl-1-(2-(dimethylamino)ethyl)-1h-benzimidazol-5-yl)-n-hydroxyprop-2-enamide

    49. (2e)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1h-1,3-benzodiazol-5-yl}-n-hydroxyprop-2-enamide

    50. (e)-3-(2-butyl-1-(2-diethylaminoethyl)-1h-benzimidazol-5-yl)-n-hydroxy-2-propenamide

    2.4 Create Date
    2011-02-14
    3 Chemical and Physical Properties
    Molecular Weight 358.5 g/mol
    Molecular Formula C20H30N4O2
    XLogP33.1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count10
    Exact Mass358.23687621 g/mol
    Monoisotopic Mass358.23687621 g/mol
    Topological Polar Surface Area70.4 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity453
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of various forms of cancer.

    Treatment of acute myeloid leukaemia

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    SB939 is a novel compound with superior pharmaceutical, metabolic and pharmacokinetic properties. SB939 has demonstrated excellent in vivo anti-tumour activity in various animal models with dose proportional pharmacodynamic effects. The pharmacokinetics and pharmacodynamic attributes of SB939 explain and differentiate it as the best in class HDAC inhibitor.

    5.2 Absorption, Distribution and Excretion

    Absorption

    Oral bioavailability in mice is 34%.

    5.3 Mechanism of Action

    Inhibition of HDAC activity allows for the accumulation of acetyl groups on the histone lysine residues resulting in an open chromatin structure and transcriptional activation. In vitro, SB939 causes the accumulation of acetylated histones and induces cell cycle arrest and/or apoptosis of some transformed cells. The mechanism of the antineoplastic effect of SB939 has not been fully characterized.