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Pracinostat

Pracinostat structure

CAS No:
929016-96-6
Formula:
C20H30N4O2
Chemical Name:
Pracinostat
Synonyms:
2-Propenamide,3-[2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl]-N-hydroxy-,(2E)-;(2E)-3-[2-Butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl]-N-hydroxy-2-propenamide;SB 939;(E)-3-[2-Butyl-1-(2-diethylaminoethyl)-1H-benzimidazol-5-yl]-N-hydroxy-2-propenamide;Pracinostat;(2E)-3-[2-Butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl]-N-hydroxyacrylamide
Categories:
Biochemical Engineering > Inhibitors

Description

Pracinostat is a potent histone deacetylase (HDAC) inhibitor, with IC50s of 40-140 nM, used for cancer research.

Pracinostat is a hydroxamic acid that is N-hydroxyacrylamide which is substituted at position 3 by a 2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl group (the E isomer). An orally available pan-histone deacetylase inhibitor with demonstrated activity in the treatment of advanced solid tumours. It has a role as an EC 3.5.1.98 (histone deacetylase) inhibitor, an antineoplastic agent, an apoptosis inducer and an antimalarial. It is an olefinic compound, a hydroxamic acid, a benzimidazole and a tertiary amino compound.|Pracinostat is a novel HDAC inhibitor with improved in vivo properties compared to other HDAC inhibitors currently in clinical trials, allowing oral dosing. Data demonstrate that Pracinostat is a potent and effective anti-tumor drug with potential as an oral therapy for a variety of human hematological and solid tumors.|Pracinostat is an orally available, small-molecule histone deacetylase (HDAC) inhibitor with potential antineoplastic activity. Pracinostat inhibits HDACs, which may result in the accumulation of highly acetylated histones, followed by the induction of chromatin remodeling; the selective transcription of tumor suppressor genes; the tumor suppressor protein-mediated inhibition of tumor cell division; and, finally, the induction of tumor cell apoptosis. This agent may possess improved metabolic, pharmacokinetic and pharmacological properties compared to other HDAC inhibitors.

Pracinostat Basic Attributes

Molecular Weight：

358.4778

Exact Mass：

358.48

UNII：

GPO2JN4UON

DSSTox ID：

DTXSID00239196

NCI Thesaurus Code：

C71708

Characteristics

PSA：

70.4

XLogP3：

3.1

Density：

1.1±0.1 g/cm3

Refractive Index：

1.568

Drug Information

Drug Indication：

For the treatment of various forms of cancer.|Treatment of acute myeloid leukaemia

Pharmacology：

SB939 is a novel compound with superior pharmaceutical, metabolic and pharmacokinetic properties. SB939 has demonstrated excellent in vivo anti-tumour activity in various animal models with dose proportional pharmacodynamic effects. The pharmacokinetics and pharmacodynamic attributes of SB939 explain and differentiate it as the best in class HDAC inhibitor.

Absorption：

Oral bioavailability in mice is 34%.

Mechanism of Action：

Inhibition of HDAC activity allows for the accumulation of acetyl groups on the histone lysine residues resulting in an open chromatin structure and transcriptional activation. In vitro, SB939 causes the accumulation of acetylated histones and induces cell cycle arrest and/or apoptosis of some transformed cells. The mechanism of the antineoplastic effect of SB939 has not been fully characterized.

MeSH Entry Terms：

3-(2-butyl-1-(2-diethylaminoethyl)-1H-benzoimidazol-5-yl)-N-hydroxyacrylamide-hydrochloride

Pracinostat Use and Manufacturing

Uses

Pracinostat is a potent and orally active histone deacetylase (HDAC) inhibitor with high tumor exposure and efficacy in mouse models of colorectal cancer. The selectivity of Pracinostat for tumor tissues makes it a promising therapeutic candidate for use in patients with advanced solid malignancies.

Use Classification：

Human drugs -> Rare disease (orphan)|Human Drugs -> EU pediatric investigation plans

Computed Properties

Molecular Weight:358.5
XLogP3:3.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:10
Exact Mass:358.23687621
Monoisotopic Mass:358.23687621
Topological Polar Surface Area:70.4
Heavy Atom Count:26
Complexity:453
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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SB 939

CAS No.: 929016-96-6

Content: 98%

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