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Trichostatin A

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Also known as: 58880-19-6, Trichostatin, Trichostatin a (tsa), Tsa, (2e,4e,6r)-7-[4-(dimethylamino)phenyl]-n-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide, Antibiotic a-300

Molecular Formula

C₁₇H₂₂N₂O₃

Molecular Weight

302.37 g/mol

InChI Key

RTKIYFITIVXBLE-QEQCGCAPSA-N

FDA UNII

3X2S926L3Z

Trichostatin A is a natural derivative of dienohydroxamic acid isolated from species of the bacterial genus Streptomyces. Trichostatin A (TSA) reversibly and specifically inhibits histone deacetylases, resulting in hyperacetylation of core histones which modulate chromatin structure. The increase in histone acetylation promotes selective gene transcription and the inhibition of tumor growth. This agent is a potent inducer of tumor cell growth arrest, differentiation and apoptosis in a variety of transformed cells in culture and in tumor-bearing animals. (NCI04)

1 2D Structure

Trichostatin A

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2E,4E,6R)-7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide

2.1.2 InChI

InChI=1S/C17H22N2O3/c1-12(5-10-16(20)18-22)11-13(2)17(21)14-6-8-15(9-7-14)19(3)4/h5-11,13,22H,1-4H3,(H,18,20)/b10-5+,12-11+/t13-/m1/s1

2.1.3 InChI Key

RTKIYFITIVXBLE-QEQCGCAPSA-N

2.1.4 Canonical SMILES

CC(C=C(C)C=CC(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C

2.1.5 Isomeric SMILES

C[C@H](/C=C(\C)/C=C/C(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C

2.2 Other Identifiers

2.2.1 UNII

3X2S926L3Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2,4-heptadienamide, 7-(4-(dimethylamino)phenyl)-n-hydroxy-4,6-dimethyl-7-oxo-

2. 7-(4-(dimethylamino)phenyl)-n-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide

3. A 300

4. Tsa Antibioitc

2.3.2 Depositor-Supplied Synonyms

1. 58880-19-6

2. Trichostatin

3. Trichostatin A (tsa)

4. Tsa

5. (2e,4e,6r)-7-[4-(dimethylamino)phenyl]-n-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide

6. Antibiotic A-300

7. (r)-trichostatin A

8. Chebi:46024

9. C17h22n2o3

10. (r,2e,4e)-7-(4-(dimethylamino)phenyl)-n-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide

11. Gnf-pf-1011

12. 3x2s926l3z

13. 58880-19-6 (r-isomer)

14. 2,4-heptadienamide, 7-(4-(dimethylamino)phenyl)-n-hydroxy-4,6-dimethyl-7-oxo-

15. 7-(4-(dimethylamino)phenyl)-n-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide

16. A-300-i

17. (2e,4e,6r)-7-(4-(dimethylamino)phenyl)-n-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide

18. [r-(e,e)]-7-[4-(dimethylamino)phenyl]-n-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide

19. Trichostatin-a

20. Tricostatin A

21. 7-[4-(dimethylamino)phenyl]-n-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide

22. 2,4-heptadienamide, 7-(4-(dimethylamino)phenyl)-n-hydroxy-4,6-dimethyl-7-oxo-, (2e,4e,6r)-

23. 2,4-heptadienamide, 7-[4-(dimethylamino)phenyl]-n-hydroxy-4,6-dimethyl-7-oxo-, (2e,4e,6r)-

24. Tsn

25. Trichostatina

26. Trichostatine A

27. Unii-3x2s926l3z

28. Trichlostatin A

29. Trichostatin(s)

30. Dtxsid6037063

31. Nsc-311042

32. (2e,4e,6r)-7-(4-dimethylaminophenyl)-4,6-dimethyl-7-oxo-hepta-2,4-dienehydroxamic Acid

33. (2e,4e,6r)-7-(4-dimethylaminophenyl)-n-hydroxy-4,6-dimethyl-7-oxo-hepta-2,4-dienamide

34. Trichostatin A,tsa

35. Mfcd03848392

36. Ncgc_tsa

37. 1c3r

38. 3f0r

39. Trichostatin-a - Tsa

40. Trichostatin A [mi]

41. Schembl19886

42. Mls006011095

43. Sgcto-002

44. Schembl675951

45. Gtpl7005

46. Chebi:93196

47. Vtr-297

48. Bcpp000035

49. Hms1362l09

50. Hms1792l09

51. Hms1990l09

52. Hms3403l09

53. Hms3649o20

54. Bcp01776

55. Ex-a1665

56. Trichostatin A, Ready Made Solution

57. Bdbm50005711

58. Lmpk01000055

59. S1045

60. Trichostatin A From Streptomyces Sp.

61. Akos015899840

62. Zinc100014731

63. Ccg-208142

64. Ccg-208681

65. Cs-0499

66. Db04297

67. Nsc 311042

68. Ncgc00162453-01

69. Ncgc00162453-02

70. Ncgc00162453-03

71. Ncgc00162453-04

72. Ncgc00162453-05

73. Ncgc00162453-15

74. 3c10

75. Ac-35470

76. As-74315

77. Hy-15144

78. Smr004702883

79. A8183

80. Sw219664-1

81. T2477

82. A25618

83. M02571

84. 880t196

85. Q425894

86. Sr-05000013796

87. Q-201864

88. Sr-05000013796-3

89. Brd-k68202742-001-04-1

90. Brd-k68202742-001-05-8

91. Trichostatin A, >=98% (hplc), From Streptomyces Sp.

92. Trichostatin A, Streptomyces Sp. - Cas 58880-19-6

93. Trichostatin A??, Vetec(tm) Reagent Grade, From Streptomyces Sp., >=98%

94. (2e,4e,6r)-7-(4-(dimethylamino)phen Yl)-n-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamid E

95. (6r)-n-hydroxy-4,6-dimethyl-7-oxo-7-[4-(dimethylamino)phenyl]-2,4-heptadienamide

96. 7-[4-(dimethylamino)phenyl]-n-hydroxy-4,6r-dimethyl-7-oxo-2e,4e-heptadienamide

97. 2,4-heptadienamide, 7-(4-(dimethylamino)phenyl)-n-hydroxy-4,6-dimethyl-7-oxo-,(2e,4e,6r)-

98. 2,4-heptadienamide, 7-[4-(dimethylamino)phenyl]-n-hydroxy-4,6-dimethyl-7-oxo-, (2e,4e,6r)- (9ci)

99. 2,4-heptadienamide, 7-[4-(dimethylamino)phenyl]-n-hydroxy-4,6-dimethyl-7-oxo-, [r-(e,e)]-

100. 2,4-heptadienamide,7-[4-(dimethylamino)phenyl]-n-hydroxy-4,6-dimethyl-7-oxo-, (2e,4e,6r)-

2.4 Create Date

2005-06-01

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₂N₂O₃
Molecular Weight	302.37 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	302.16304257 g/mol
Monoisotopic Mass	302.16304257 g/mol
Topological Polar Surface Area	69.6 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	447
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal 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.)

Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

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