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    Entinostat

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    Also known as: 209783-80-2, Ms-275, Sndx-275, Entinostat (ms-275), Ms 275, Ms-27-275
    Molecular Formula
    C21H20N4O3
    Molecular Weight
    376.4  g/mol
    InChI Key
    INVTYAOGFAGBOE-UHFFFAOYSA-N
    FDA UNII
    1ZNY4FKK9H
    Entinostat is a synthetic benzamide derivative with potential antineoplastic activity. Entinostat binds to and inhibits histone deacetylase, an enzyme that regulates chromatin structure and gene transcription. This agent appears to exert dose-dependent effects in human leukemia cells including cyclin-dependent kinase inhibitor 1A (p21/CIP1/WAF1)-dependent growth arrest and differentiation at low drug concentrations; a marked induction of reactive oxygen species (ROS); mitochondrial damage; caspase activation; and, at higher concentrations, apoptosis. In normal cells, cyclin-dependent kinase inhibitor 1A expression has been associated with cell-cycle exit and differentiation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    pyridin-3-ylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate
    2.1.2 InChI
    InChI=1S/C21H20N4O3/c22-18-5-1-2-6-19(18)25-20(26)17-9-7-15(8-10-17)13-24-21(27)28-14-16-4-3-11-23-12-16/h1-12H,13-14,22H2,(H,24,27)(H,25,26)
    2.1.3 InChI Key
    INVTYAOGFAGBOE-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC=C(C(=C1)N)NC(=O)C2=CC=C(C=C2)CNC(=O)OCC3=CN=CC=C3
    2.2 Other Identifiers
    2.2.1 UNII
    1ZNY4FKK9H
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ms 27-275

    2. Ms 275

    3. Ms-27-275

    4. Ms-275

    5. N-(2-aminophenyl)-4-(n-(pyridin-3-ylmethoxycarbonyl)aminomethyl)benzamide

    6. Sndx-275

    2.3.2 Depositor-Supplied Synonyms

    1. 209783-80-2

    2. Ms-275

    3. Sndx-275

    4. Entinostat (ms-275)

    5. Ms 275

    6. Ms-27-275

    7. Sndx 275

    8. Pyridin-3-ylmethyl 4-((2-aminophenyl)carbamoyl)benzylcarbamate

    9. Ms 27-275

    10. Ms275

    11. Entinostat (ms-275,sndx-275)

    12. 1zny4fkk9h

    13. Bay 86-5274

    14. N-(2-aminophenyl)-4-(n-(pyridin-3-ylmethoxycarbonyl)aminomethyl)benzamide

    15. Pyridin-3-ylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate

    16. Chembl27759

    17. Pyridin-3-ylmethyl {4-[(2-aminophenyl)carbamoyl]benzyl}carbamate

    18. Nsc706995

    19. Bay86-5274

    20. Nsc-706995

    21. Pyridin-3-ylmethyl 4-(2-aminophenylcarbamoyl)benzylcarbamate

    22. Ms-275-27

    23. Carbamic Acid, N-((4-(((2-aminophenyl)amino)carbonyl)phenyl)methyl)-, 3- Pyridinylmethyl Ester

    24. Carbamic Acid, N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-, 3-pyridinylmethyl Ester

    25. Pyridin-3-ylmethyl 4-((2-aminophenyl)carbamoyl)benzylcarbamate.

    26. Pyridin-3-ylmethyl N-({4-[(2-aminophenyl)carbamoyl]phenyl}methyl)carbamate

    27. N-[[4-[(2-aminoanilino)-oxomethyl]phenyl]methyl]carbamic Acid 3-pyridinylmethyl Ester

    28. Entinostatum

    29. N-(2-aminophenyl)-4-[n-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzamide

    30. Entinostat, Free Base

    31. Entinostat [inn]

    32. Entinostat [jan]

    33. Entinostat [usan:inn]

    34. Unii-1zny4fkk9h

    35. Entinostat [usan]

    36. Ms-275 - Entinostat

    37. 3-pyridinylmethyl ((4-(((2-aminophenyl)amino)carbonyl)phenyl)methyl)carbamate

    38. Benzamide-type Inhibitor, 3

    39. Carbamic Acid, ((4-(((2-aminophenyl)amino)carbonyl)phenyl)methyl)-, 3-pyridinylmethyl Ester

    40. Entinostat [who-dd]

    41. Mls006010183

    42. Entinostat (jan/usan/inn)

    43. Schembl148309

    44. Gtpl7007

    45. Dtxsid0041068

    46. Bdbm19410

    47. Ex-a038

    48. Chebi:132082

    49. Bcpp000155

    50. Hms3426g07

    51. Hms3648k12

    52. Hms3654o11

    53. Hms3744o17

    54. Act06782

    55. Amy31163

    56. Bcp01824

    57. Zinc1488870

    58. Mfcd08272435

    59. Nsc756642

    60. S1053

    61. Entinostat (ms-275;sndx-275)

    62. 3-pyridylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate

    63. Akos024262667

    64. N-(2-aminophenyl)-4-[n-(pyridin-3-yl-methoxycarbonyl)aminomethyl]benzamide

    65. Ac-8968

    66. Bcp9000967

    67. Carbamic Acid, 3-pyridinylmethyl Ester

    68. Ccg-208680

    69. Cs-0511

    70. Db11841

    71. Entinostat (ms-275, Sndx-275)

    72. Nsc 706995

    73. Nsc-756642

    74. Sb16665

    75. Carbamic Acid, [[4-[[(2-aminophenyl)carbaonyl]phenyl]methyl]-, 3-pyridinylmethyl Ester

    76. Ncgc00165833-01

    77. Ncgc00165833-02

    78. Ncgc00165833-03

    79. Ncgc00165833-04

    80. Ncgc00165833-11

    81. Ncgc00165833-13

    82. 442532-99-2

    83. As-17906

    84. Bp-25653

    85. Hy-12163

    86. Nci60_038022

    87. Smr004458705

    88. Ms-275, A Hdac1 And Hdac3 Inhibitor

    89. Zk 244894

    90. E1454

    91. Ft-0667871

    92. Sw219667-1

    93. Ec-000.2117

    94. D09338

    95. 783m802

    96. A815057

    97. Ms-275,entinostat, Sndx-275, Ms-27-275

    98. Sr-01000946382

    99. Q1281020

    100. Sr-01000946382-1

    101. W-201831

    102. Brd-k77908580-001-02-1

    103. Brd-k77908580-001-04-7

    104. (pyridin-3-yl)methyl 4-(2-aminophenylcarbamoyl)benzylcarbamate

    105. Pyridin-3-ylmethyl4-((2-aminophenyl)carbamoyl)benzylcarbamate

    106. N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-3-pyridinylmethyl Ester, Carbamic Acid

    107. N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]carbamic Acid 3-pyridinylmethyl Ester

    108. Pyridin-3-ylmethyl ((4-((2-aminophenyl)carbamoyl)phenyl)methyl)carbamate

    109. Sndx 275;3-pyridylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 376.4 g/mol
    Molecular Formula C21H20N4O3
    XLogP32
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count7
    Exact Mass376.15354051 g/mol
    Monoisotopic Mass376.15354051 g/mol
    Topological Polar Surface Area106 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity508
    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.)

    Antineoplastic Agents

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

    4.2 ATC Code

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01X - Other antineoplastic agents

    L01XH - Histone deacetylase (hdac) inhibitors

    L01XH05 - Entinostat