ERASTIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C30H31ClN4O4
Molecular Weight	547.045
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC1=CC=CC=C1N2C(=O)C3=C(C=CC=C3)N=C2C(C)N4CCN(CC4)C(=O)COC5=CC=C(Cl)C=C5

InChI

InChIKey=BKQFRNYHFIQEKN-UHFFFAOYSA-N

InChI=1S/C30H31ClN4O4/c1-3-38-27-11-7-6-10-26(27)35-29(32-25-9-5-4-8-24(25)30(35)37)21(2)33-16-18-34(19-17-33)28(36)20-39-23-14-12-22(31)13-15-23/h4-15,21H,3,16-20H2,1-2H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22632970 | https://www.ncbi.nlm.nih.gov/pubmed/17568748

Erastin is antitumor agent, exhibiting selectivity for tumor cells bearing oncogenic RAS. Erastin is a ferroptosis activator; it induces oxidative, non-apoptotic cell death in tumors by acting directly on voltage-dependent anion channel 2 (VDAC2).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-dependent anion-selective channel protein 2 1 Target ID: CHEMBL6190 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17568748	Binding Agent 1076
ferroptosis 1 Target ID: ferroptosis Sources: https://www.ncbi.nlm.nih.gov/pubmed/22632970	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704666	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Caspase-independent cell death is involved in the negative effect of EGF receptor inhibitors on cisplatin in non-small cell lung cancer cells.	2013-02-15	23344263
Mitochondrial voltage-dependent anion channels (VDACs) as novel pharmacological targets for anti-cancer agents.	2008-06	18704666
Identification of genotype-selective antitumor agents using synthetic lethal chemical screening in engineered human tumor cells.	2003-03	12676586

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Erastin-induced cell death in human cancer cells involves DFO-sensitive ROS accumulation and can occur in cells lacking a functional electron transport chain (ETC). It was shown, that in erastin-treated (10 µM, 6 hrs) HT-1080 cells, observed no increase in MitoSOX-sensitive mitochondrial ROS production. KRAS-mutant 143B osteosarcoma cells incapable of ETC-dependent ROS formation, due to the depletion of mitochondrial DNA (mtDNA)-encoded transcripts, were as sensitive to erastin and RSL3 as matched mtDNA-wild-type (ρ+) cells.

Name

Type

Language

E-7781

Preferred Name

English

ERASTIN

Common Name

English

PIPERAZINE, 1-((4-CHLOROPHENOXY)ACETYL)-4-(1-(3-(2-ETHOXYPHENYL)-3,4-DIHYDRO-4-OXO-2-QUINAZOLINYL)ETHYL)-

Systematic Name

English

2-(1-(4-(2-(4-CHLOROPHENOXY)ACETYL)-1-PIPERAZINYL)ETHYL)-3-(2-ETHOXYPHENYL)-4(3H)-QUINAZOLINONE

Systematic Name

English

E7781

Code

English

2-(1-(4-(2-(4-CHLOROPHENOXY)ACETYL)PIPERAZIN-1-YL)ETHYL)-3-(2-ETHOXYPHENYL)QUINAZOLIN-4-ONE

Systematic Name

English

Code System Code Type Description

PUBCHEM

11214940