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=C(C=CC=C1)N2C(=O)C3=CC=CC=C3N=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

Molecular Formula	C30H31ClN4O4
Molecular Weight	547.045
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 1064
ferroptosis 1 Target ID: ferroptosis Sources: https://www.ncbi.nlm.nih.gov/pubmed/22632970	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18704666	Primary		Basic research	Unknown Approved Use Unknown

PubMed

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

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:56:56 GMT 2023` Edited by `admin` on `Sat Dec 16 16:56:56 GMT 2023`
Record UNII	ZJA3NS42T9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

E-7781

Code

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