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Entinostat

Entinostat structure

CAS No:
209783-80-2
Formula:
C21H20N4O3
Chemical Name:
Entinostat
Synonyms:
Carbamic acid,N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-,3-pyridinylmethyl ester;Carbamic acid,[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-,3-pyridinylmethyl ester;MS 275;MS 27-275;MS 275-27;SNDX 275;Entinostat;(Pyridin-3-yl)methyl 4-(2-aminophenylcarbamoyl)benzylcarbamate;442532-99-2
Categories:
Biochemical Engineering > Inhibitors

Description

Entinostat is an oral and selective class I HDAC inhibitor, with IC50s of 243 nM, 453 nM, and 248 nM for HDAC1, HDAC2, and HDAC3, respectively.

Entinostat is a member of the class of benzamides resulting from the formal condensation of the carboxy group of the pyridin-3-ylmethyl carbamate derivative of p-(aminomethyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an inhibitor of histone deacetylase isoform 1 (HDAC1) and isoform 3 (HDAC3). It has a role as an EC 3.5.1.98 (histone deacetylase) inhibitor, an antineoplastic agent and an apoptosis inducer. It is a member of pyridines, a carbamate ester, a substituted aniline, a primary amino compound and a member of benzamides. It derives from a 1,2-phenylenediamine.|Entinostat is under investigation for the treatment and other of Volunteers, Breast Cancer, Human Volunteers, and Normal Volunteers. Entinostat has been investigated for the treatment of Non-Small Lung Cancer, Epigenetic Therapy.|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.

Entinostat Basic Attributes

Molecular Weight：

376.4085

Exact Mass：

376.41

UNII：

1ZNY4FKK9H

NSC Number：

706995

DSSTox ID：

DTXSID0041068

NCI Thesaurus Code：

C1863

ATC Code：

L - Antineoplastic and immunomodulating agents

HScode：

29333990

Characteristics

PSA：

106

XLogP3：

Appearance：

solid

Density：

1.3±0.1 g/cm3

Melting Point：

159-160 °C

Boiling Point：

566.7°C at 760 mmHg

Flash Point：

296.6±30.1 °C

Refractive Index：

1.672

Water Solubility：

DMSO: 38 mg/mL, soluble

Storage Conditions：

−20°C

Vapor Pressure：

7.31E-13mmHg at 25°C

Safety Information

Transport codes：

UN 2811 6.1 / PGIII

wgk germany：

hazard class code：

36/37/38-62-48/25-25-61

safety instructions：

26-36-45

Marks：

Xi,T

Precautionary statement(s)：

P201-P261-P301 + P310-P305 + P351 + P338-P308 + P313

Hazard Statements：

H301-H315-H319-H335-H360

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 43 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

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

MeSH Entry Terms：

entinostat

Entinostat Use and Manufacturing

Uses

Entinostat is an emerging HDACi (histone deacetylase inhibitor). Entinostat is used for treatment of solid tumors and hematologic malignancies.

Use Classification：

Human drugs -> Rare disease (orphan)

Computed Properties

Molecular Weight:376.4
XLogP3:2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:376.15354051
Monoisotopic Mass:376.15354051
Topological Polar Surface Area:106
Heavy Atom Count:28
Complexity:508
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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