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Belinostat

Belinostat

Synopsis, Chemistry

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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

Belinostat

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 Formula	C₁₅H₁₄N₂O₄S
Molecular Weight	318.3 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	318.06742811 g/mol
Monoisotopic Mass	318.06742811 g/mol
Topological Polar Surface Area	104 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	492
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Beleodaq
PubMed Health	Belinostat (Intravenous route)
Drug Classes	Histone Deacetylase Inhibitor
Drug Label	Beleodaq 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 Ingredient	Belinostat
Dosage Form	Powder
Route	Iv (infusion)
Strength	500mg/vial
Market Status	Prescription
Company	Spectrum Pharms

2 of 2
Drug Name	Beleodaq
PubMed Health	Belinostat (Intravenous route)
Drug Classes	Histone Deacetylase Inhibitor
Drug Label	Beleodaq 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 Ingredient	Belinostat
Dosage Form	Powder
Route	Iv (infusion)
Strength	500mg/vial
Market Status	Prescription
Company	Spectrum 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.