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    Belinostat

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 414864-00-9, Pxd101, Belinostat (pxd101), 866323-14-0, Beleodaq, Pxd-101
    Molecular Formula
    C15H14N2O4S
    Molecular Weight
    318.3  g/mol
    InChI Key
    NCNRHFGMJRPRSK-MDZDMXLPSA-N
    FDA UNII
    F4H96P17NZ
    Belinostat is a novel hydroxamic acid-type histone deacetylase (HDAC) inhibitor with antineoplastic activity. Belinostat targets HDAC enzymes, thereby inhibiting tumor cell proliferation, inducing apoptosis, promoting cellular differentiation, and inhibiting angiogenesis. This agent may sensitize drug-resistant tumor cells to other antineoplastic agents, possibly through a mechanism involving the down-regulation of thymidylate synthase.
    Belinostat is a Histone Deacetylase Inhibitor. The mechanism of action of belinostat is as a Histone Deacetylase Inhibitor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (E)-N-hydroxy-3-[3-(phenylsulfamoyl)phenyl]prop-2-enamide
    2.1.2 InChI
    InChI=1S/C15H14N2O4S/c18-15(16-19)10-9-12-5-4-8-14(11-12)22(20,21)17-13-6-2-1-3-7-13/h1-11,17,19H,(H,16,18)/b10-9+
    2.1.3 InChI Key
    NCNRHFGMJRPRSK-MDZDMXLPSA-N
    2.1.4 Canonical SMILES
    C1=CC=C(C=C1)NS(=O)(=O)C2=CC=CC(=C2)C=CC(=O)NO
    2.1.5 Isomeric SMILES
    C1=CC=C(C=C1)NS(=O)(=O)C2=CC=CC(=C2)/C=C/C(=O)NO
    2.2 Other Identifiers
    2.2.1 UNII
    F4H96P17NZ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Belecodaq

    2. Pxd101

    2.3.2 Depositor-Supplied Synonyms

    1. 414864-00-9

    2. Pxd101

    3. Belinostat (pxd101)

    4. 866323-14-0

    5. Beleodaq

    6. Pxd-101

    7. (e)-n-hydroxy-3-(3-(n-phenylsulfamoyl)phenyl)acrylamide

    8. Nsc726630

    9. N-hydroxy-3-(3-phenylsulfamoylphenyl)acrylamide

    10. Pxd 101

    11. Px-105684

    12. Px105684

    13. F4h96p17nz

    14. (2e)-n-hydroxy-3-[3-(phenylsulfamoyl)phenyl]prop-2-enamide

    15. Chebi:61076

    16. N-hydroxy-3-[3-[(phenylamino)sulfonyl]phenyl]-2-propenamide

    17. 2-propenamide, N-hydroxy-3-[3-[(phenylamino)sulfonyl]phenyl]-, (2e)-

    18. N-hydroxy-3-(3-(phenylsulfamoyl)phenyl)prop-2-enamide

    19. Nsc-726630

    20. (2e)-n-hydroxy-3-[3-(phenylsulfamoyl)phenyl]acrylamide

    21. Px 105684

    22. (e)-n-hydroxy-3-[3-(phenylsulfamoyl)phenyl]prop-2-enamide

    23. 2-propenamide, N-hydroxy-3-(3-((phenylamino)sulfonyl)phenyl)-

    24. (e)-n-hydroxy-3-[3-(phenylsulfamoyl)phenyl]prop-2-enamide.

    25. E-belinostat

    26. 2-propenamide, N-hydroxy-3-(3-((phenylamino)sulfonyl)phenyl)-, (2e)-

    27. Belinostat [usan]

    28. Belinostat [usan:inn]

    29. Unii-f4h96p17nz

    30. (2e)-n-hydroxy-3-(3-(phenylsulfamoyl)phenyl)prop-2-enamide

    31. N-hydroxy-3-(3-((phenylamino)sulfonyl)phenyl)-2-propenamide

    32. Belinostat Ph3

    33. Beleodaq (tn)

    34. N-hydroxy-3-(3-(n-phenylsulfamoyl)phenyl)acrylamide

    35. Belinostat [mi]

    36. Belinostat - Pxd101

    37. Belinostat [inn]

    38. Belinostat (usan/inn)

    39. Belinostat [vandf]

    40. N-hydroxy-3-[3-(phenylsulfamoyl)phenyl]-2-propenamide

    41. Belinostat [who-dd]

    42. N-hydroxy-3-(3-phenylsulphamoylphenyl)acrylamide

    43. Mls006011091

    44. Chembl408513

    45. Gtpl7496

    46. Belinostat [orange Book]

    47. Bdbm25150

    48. Chebi:94531

    49. Amy1792

    50. Dtxsid60194378

    51. Ex-a180

    52. (e)-3-[3-(phenylsulfamoyl)phenyl]prop-2-enehydroxamic Acid

    53. Bcpp000351

    54. Bcp01741

    55. Zinc3818726

    56. Belinostat,pxd101, Px105684

    57. Mfcd08064035

    58. Nsc758774

    59. S1085

    60. Akos025401741

    61. Bcp9000386

    62. Ccg-208758

    63. Db05015

    64. Nsc-758774

    65. Ncgc00263155-02

    66. Ncgc00263155-05

    67. Ac-25046

    68. Ac-35365

    69. As-17068

    70. Smr004702879

    71. Sw219445-1

    72. Ec-000.2286

    73. A25012

    74. D08870

    75. J-523584

    76. Q4882925

    77. Brd-k17743125-001-01-9

    78. N-hydroxy-3-[(phenylamino)sulfonyl]-trans-cinnamamide

    79. (e)-n-hydroxy-3-(3-phenylsulfamoyl-phenyl)-acrylamide

    80. 5og

    2.4 Create Date
    2006-07-28
    3 Chemical and Physical Properties
    Molecular Weight 318.3 g/mol
    Molecular Formula C15H14N2O4S
    XLogP31.7
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count5
    Exact Mass318.06742811 g/mol
    Monoisotopic Mass318.06742811 g/mol
    Topological Polar Surface Area104 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity492
    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 Information
    1 of 2  
    Drug NameBeleodaq
    PubMed HealthBelinostat (Intravenous route)
    Drug ClassesHistone Deacetylase Inhibitor
    Drug LabelBeleodaq is a histone deacetylase inhibitor with a sulfonamide-hydroxamide structure. The chemical name of belinostat is (2E)-N-hydroxy-3-[3-(phenylsulfamoyl)phenyl]prop-2-enamide. The structural formula is as follows:The molecular formula is C15H14N...
    Active IngredientBelinostat
    Dosage FormPowder
    RouteIv (infusion)
    Strength500mg/vial
    Market StatusPrescription
    CompanySpectrum Pharms

    2 of 2  
    Drug NameBeleodaq
    PubMed HealthBelinostat (Intravenous route)
    Drug ClassesHistone Deacetylase Inhibitor
    Drug LabelBeleodaq is a histone deacetylase inhibitor with a sulfonamide-hydroxamide structure. The chemical name of belinostat is (2E)-N-hydroxy-3-[3-(phenylsulfamoyl)phenyl]prop-2-enamide. The structural formula is as follows:The molecular formula is C15H14N...
    Active IngredientBelinostat
    Dosage FormPowder
    RouteIv (infusion)
    Strength500mg/vial
    Market StatusPrescription
    CompanySpectrum Pharms

    4.2 Drug Indication

    Belinostat is indicated for the treatment of patients with relapsed or refractory peripheral T-cell lymphoma (PTCL) with manageable safety profile. It is a potential alternative therapy for patients who did not experience adequate response to first-line drugs for PTCL. It can be used in patients with baseline thrombocytopenia.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Beleodaq is a histone deacetylase (HDAC) inhibitor that exhibits pan-HDAC inhibition and potent growth inhibitory and pro-apoptotic activities in a variety of tumor cells, including PTCL cells, at nanomolar concentrations. None of the trials show any clinically relevant changes caused by Beleodaq on heart rate, PR duration or QRS duration as measures of autonomic state, atrio-ventricular conduction or depolarization; there were no cases of Torsades de Pointes.

    5.2 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    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.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    BELINOSTAT
    5.3.2 FDA UNII
    F4H96P17NZ
    5.3.3 Pharmacological Classes
    Histone Deacetylase Inhibitors [MoA]; Histone Deacetylase Inhibitor [EPC]
    5.4 ATC Code

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01X - Other antineoplastic agents

    L01XH - Histone deacetylase (hdac) inhibitors

    L01XH04 - Belinostat

    5.5 Absorption, Distribution and Excretion

    Route of Elimination

    Approximately 40% of the belinostat dose is excreted renally, primarily as metabolites and less than 2% of total dose recovered as unchanged parent drug.

    Volume of Distribution

    The volume of distribution is 409 76.7 L.

    Clearance

    1240 mL/min

    5.6 Metabolism/Metabolites

    Primarily metabolized by hepatic UGT1A1. Strong UGT1A1 inhibitors are expected to increase exposure to belinostat. Belinostat also undergoes hepatic metabolism by CYP2A6, CYP2C9, and CYP3A4 enzymes to form belinostat amide and belinostat acid. The enzymes responsible for the formation of methyl belinostat and 3-(anilinosulfonyl)-benzenecarboxylic acid, (3-ASBA) are not known

    5.7 Biological Half-Life

    Displays a three-compartment pharmacokinetic property with elimination half life of 1.1 hours

    5.8 Mechanism of Action

    Belinostat inhibits the activity of histone deacetylase (HDAC) thus prevents the removal of acetyl groups from the lysine residues of histones and some non-histone proteins. In vitro, belinostat caused the accumulation of acetylated histones and other proteins, increased the expression of tumor-suppressor genes. It ultimately induces cell cycle arrest, inhibition of angiogenesis and/or apoptosis of some transformed cells.