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    Chemistry

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    Also known as: 497833-27-9, Itf2357, Givinostat [inn], Givinostat free base, Itf-2357, [6-(diethylaminomethyl)naphthalen-2-yl]methyl n-[4-(hydroxycarbamoyl)phenyl]carbamate
    Molecular Formula
    C24H27N3O4
    Molecular Weight
    421.5  g/mol
    InChI Key
    YALNUENQHAQXEA-UHFFFAOYSA-N
    FDA UNII
    5P60F84FBH
    Givinostat
    Givinostat is an orally bioavailable hydroxymate inhibitor of histone deacetylase (HDAC) with potential anti-inflammatory, anti-angiogenic, and antineoplastic activities. Givinostat inhibits class I and class II HDACs, resulting in an accumulation of highly acetylated histones, followed by the induction of chromatin remodeling and an altered pattern of gene expression. At low, nonapoptotic concentrations, this agent inhibits the production of pro-inflammatory cytokines such as tumor necrosis factor- (TNF-), interleukin-1 (IL-1), IL-6 and interferon-gamma. Givinostat has also been shown to activate the intrinsic apoptotic pathway, inducing apoptosis in hepatoma cells and leukemic cells. This agent may also exhibit anti-angiogenic activity, inhibiting the production of angiogenic factors such as IL-6 and vascular endothelial cell growth factor (VEGF) by bone marrow stromal cells.
    1 2D Structure

    Givinostat

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [6-(diethylaminomethyl)naphthalen-2-yl]methyl N-[4-(hydroxycarbamoyl)phenyl]carbamate
    2.1.2 InChI
    InChI=1S/C24H27N3O4/c1-3-27(4-2)15-17-5-7-21-14-18(6-8-20(21)13-17)16-31-24(29)25-22-11-9-19(10-12-22)23(28)26-30/h5-14,30H,3-4,15-16H2,1-2H3,(H,25,29)(H,26,28)
    2.1.3 InChI Key
    YALNUENQHAQXEA-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCN(CC)CC1=CC2=C(C=C1)C=C(C=C2)COC(=O)NC3=CC=C(C=C3)C(=O)NO
    2.2 Other Identifiers
    2.2.1 UNII
    5P60F84FBH
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 497833-27-9

    2. Itf2357

    3. Givinostat [inn]

    4. Givinostat Free Base

    5. Itf-2357

    6. [6-(diethylaminomethyl)naphthalen-2-yl]methyl N-[4-(hydroxycarbamoyl)phenyl]carbamate

    7. 5p60f84fbh

    8. Chembl1213492

    9. 497833-27-9 (free Base)

    10. (6-((diethylamino)methyl)naphthalen-2-yl)methyl (4-(hydroxycarbamoyl)phenyl)carbamate

    11. (6-((diethylamino)methyl)naphthalen-2-yl)methyl(4-(hydroxycarbamoyl)phenyl)carbamate

    12. [4-[(hydroxyamino)carbonyl]phenyl]carbamic Acid [6-[(diethylamino)methyl]-2-naphthalenyl]methyl Ester

    13. Gavinostat

    14. 4-[(hydroxyamino)carbonyl]phenyl]carbamic Acid [6-[(diethylamino)methyl]-2-naphthalenyl]methyl Ester

    15. Unii-5p60f84fbh

    16. {6-[(diethylamino)methyl]naphthalen-2-yl}methyl [4-(hydroxycarbamoyl)phenyl]carbamate

    17. Gavinostat;itf-2357

    18. Gtpl7490

    19. Schembl1555814

    20. Chebi:94187

    21. Dtxsid70198049

    22. Bcp29856

    23. Zinc3820616

    24. Bdbm50105329

    25. Cs-4727

    26. Db12645

    27. Ex-5958

    28. [6-(diethylaminomethyl)-2-naphthyl]methyl N-[4-(hydroxycarbamoyl)phenyl]carbamate

    29. Ac-31380

    30. Bcb04_000011

    31. Hy-14842

    32. Ec-000.2471

    33. 833h279

    34. A923985

    35. Q426257

    36. Gavinostat; Itf-2357; Itf2357; Itf 2357

    37. Brd-k13810148-001-01-3

    38. Carbamic Acid, (4-((hydroxyamino)carbonyl)phenyl)-, (6-((diethylamino)methyl)-2-naphthalenyl)methyl Ester

    39. Qcm

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 421.5 g/mol
    Molecular Formula C24H27N3O4
    XLogP33.6
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count9
    Exact Mass421.20015635 g/mol
    Monoisotopic Mass421.20015635 g/mol
    Topological Polar Surface Area90.9 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity575
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Juvenile idiopathic arthritis

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