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Trichostatin A

Trichostatin A structure

CAS No:
58880-19-6
Formula:
C17H22N2O3
Chemical Name:
Trichostatin A
Synonyms:
2,4-Heptadienamide,7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-,(2E,4E,6R)-;2,4-Heptadienamide,7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-,[R-(E,E)]-;(2E,4E,6R)-7-[4-(Dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide;Trichostatin A;(R)-Trichostatin A;TSA;(R)-(+)-Trichostatin A
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Trichostatin A is a potent and specific inhibitor of HDAC class I/II, with an IC50 value of 1.8 nM for HDAC.

Trichostatin A is an antibiotic antifungal agent, a trichostatin and a hydroxamic acid. It has a role as a bacterial metabolite, a geroprotector and an EC 3.5.1.98 (histone deacetylase) inhibitor. It derives from a (R)-trichostatic acid.|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)

Trichostatin A Basic Attributes

Molecular Weight：

302.37

Exact Mass：

302.37

UNII：

3X2S926L3Z

DSSTox ID：

DTXSID6037063

NCI Thesaurus Code：

C1261

HScode：

2924299090

Characteristics

PSA：

69.6

XLogP3：

2.7

Appearance：

Off-white powder

Density：

1.1±0.1 g/cm3

Melting Point：

140-143 °C

Refractive Index：

1.578

Water Solubility：

ethanol: 1 mg/mL

Storage Conditions：

−20°C

Specific rotation：

D20.5 +62.8° ±1.1° (c = 1.007 in ethanol)

Safety Information

Transport codes：

NA 1993 / PGIII

wgk germany：

hazard class code：

20/21/22-36/37/38-43

safety instructions：

26-36

RTECS Number：

MI5215000

Marks：

Xn,Xi

Precautionary statement(s)：

P261-P280-P302 + P352 + P312-P304 + P340 + P312-P333 + P313

Hazard Statements：

H302 + H312 + H332-H315-H317-H319-H335

GHS Classification：

|Warning|H302+H312+H332 (49.52%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 315 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

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.)|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.)|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.)

MeSH Entry Terms：

2,4-Heptadienamide, 7-(4-(dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxo-

Trichostatin A Use and Manufacturing

Uses

Trichostatin A is a histone deacetylase inhibitor that enhances the cytotoxic efficacy of anticancer drugs that target DNA. Trichostatin A displays antifungal, antiprotozoan and antitumor activity

Use Classification：

Polyketides [PK] -> Linear polyketides [PK01]

Computed Properties

Molecular Weight:302.37
XLogP3:2.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:302.16304257
Monoisotopic Mass:302.16304257
Topological Polar Surface Area:69.6
Heavy Atom Count:22
Complexity:447
Defined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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