SRT-1720

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H23N7OS
Molecular Weight	469.561
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C(NC1=C(C=CC=C1)C2=CN3C(CN4CCNCC4)=CSC3=N2)C5=CN=C6C=CC=CC6=N5

InChI

InChIKey=IASPBORHOMBZMY-UHFFFAOYSA-N

InChI=1S/C25H23N7OS/c33-24(22-13-27-20-7-3-4-8-21(20)28-22)29-19-6-2-1-5-18(19)23-15-32-17(16-34-25(32)30-23)14-31-11-9-26-10-12-31/h1-8,13,15-16,26H,9-12,14H2,(H,29,33)

HIDE SMILES / InChI

Molecular Formula	C25H23N7OS
Molecular Weight	469.561
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18046409
Curator's Comment: description was created based on several sources, including: http://www.xconomy.com/boston/2013/03/12/glaxosmithkline-shuts-down-sirtris-five-years-after-720m-buyout/ | https://www.ncbi.nlm.nih.gov/pubmed/20061378 | https://www.ncbi.nlm.nih.gov/pubmed/21950728

SRT1720 is a small-molecule compound, which has the ability of activating the sirtuin subtype SIRT1. It’s not a direct activation. SRT1720 exhibits multiple off-target activities against receptors, enzymes, transporters, and ion channels. SRT1720 affects mitochondrial respiration in a Sirt1- and PGC-1α-dependent manner. SRT1720 has been demonstrated to enhance insulin sensitivity and improve measures of mitochondrial capacity and oxidative metabolism. SRT1720 also significantly inhibits VEGF-dependent multiple myeloma cell migration. SRT1720 is an experimental drug that was studied by Sirtris Pharmaceuticals. At 2013 year, GlaxoSmithKline was closed down Cambridge, MA-based Sirtris Pharmaceuticals.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
NAD-dependent deacetylase sirtuin 1 16 Target ID: CHEMBL4506 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18046409	Activator 1430	0.16 µM [EC50]
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20061378	Inhibitor 8297
Adenosine A3 receptor 24 Target ID: CHEMBL256 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20061378	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18046409	Primary	Preclinical	Unknown Approved Use Unknown
Multiple myeloma 159 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21950728	Primary	Preclinical	Unknown Approved Use Unknown
Metabolic disease 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22355589 https://www.ncbi.nlm.nih.gov/pubmed/18046409 https://www.ncbi.nlm.nih.gov/pubmed/19046567	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Specific SIRT1 activation mimics low energy levels and protects against diet-induced metabolic disorders by enhancing fat oxidation.	2008 Nov	19046567

Patents

Sample Use Guides

In Vivo Use Guide

Mouse: 100 mg/kg once daily

Route of Administration: Oral

In Vitro Use Guide

IC50 for multiple myeloma cells of SRT1720 is at concentrations that do not significantly affect viability of normal lymphocytes. Higher concentrations of SRT1720 (15 uM) induced a modest (10–20%) decrease in normal cell viability.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:11:34 GMT 2023` Edited by `admin` on `Sat Dec 16 11:11:34 GMT 2023`
Record UNII	DX3FHY76FZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SRT-1720

Code

English

N-(2-(3-(1-PIPERAZINYLMETHYL)IMIDAZO(2,1-B)THIAZOL-6-YL)PHENYL)-2-QUINOXALINECARBOXAMIDE

Systematic Name

English

2-QUINOXALINECARBOXAMIDE, N-(2-(3-(1-PIPERAZINYLMETHYL)IMIDAZO(2,1-B)THIAZOL-6-YL)PHENYL)-

Systematic Name

English

SRT1720

Code

English

Code System Code Type Description

FDA UNII

DX3FHY76FZ