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Chemistry

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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
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

Entinostat

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


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