Erastin

Erastin
Legal status
Legal status	Experimental;
Identifiers
	IUPAC name 2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone;
CAS Number	571203-78-6;
PubChem CID	11214940;
ChemSpider	9390002;
KEGG	C21478;
Chemical and physical data
Formula	C30H31ClN4O4
Molar mass	547.05 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1N(C2=CC=CC=C2OCC)C(C(C)N3CCN(C(COC4=CC=C(Cl)C=C4)=O)CC3)=NC5=CC=CC=C51;
	InChI 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; Key:BKQFRNYHFIQEKN-UHFFFAOYSA-N;

Erastin is named from 'Eradicator of RAS and ST-expressing cells' in 2003^[1].

Erastin is a small molecule capable of initiating ferroptotic cell death.^[2] Erastin binds and activates voltage-dependent anion channels (VDAC) by reversing tubulin's inhibition on VDAC2 and VDAC3,^[3] and functionally inhibits the cystine-glutamate antiporter system X_c⁻.^[4] Cells treated with erastin are deprived of cysteine and are unable to synthesize the antioxidant glutathione. Depletion of glutathione eventually leads to excessive lipid peroxidation and cell death.

References[]

^ "Identification of genotype-selective antitumor agents using synthetic lethal chemical screening in engineered human tumor cells". Cancer Cell. 3 (3): 285–296. 2003-03-01. doi:10.1016/S1535-6108(03)00050-3. ISSN 1535-6108.
^ Dixon SJ, Lemberg KM, Lamprecht MR, Skouta R, Zaitsev EM, Gleason CE, et al. (May 2012). "Ferroptosis: an iron-dependent form of nonapoptotic cell death". Cell. 149 (5): 1060–72. doi:10.1016/j.cell.2012.03.042. PMC 3367386. PMID 22632970.
^ Yagoda N, von Rechenberg M, Zaganjor E, Bauer AJ, Yang WS, Fridman DJ, et al. (June 2007). "RAS-RAF-MEK-dependent oxidative cell death involving voltage-dependent anion channels". Nature. 447 (7146): 864–8. Bibcode:2007Natur.447..865Y. doi:10.1038/nature05859. PMC 3047570. PMID 17568748.
^ Dixon SJ, Patel DN, Welsch M, Skouta R, Lee ED, Hayano M, et al. (May 2014). "Pharmacological inhibition of cystine-glutamate exchange induces endoplasmic reticulum stress and ferroptosis". eLife. 3: e02523. doi:10.7554/elife.02523. PMC 4054777. PMID 24844246.

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[1] "Identification of genotype-selective antitumor agents using synthetic lethal chemical screening in engineered human tumor cells". Cancer Cell. 3 (3): 285–296. 2003-03-01. doi:10.1016/S1535-6108(03)00050-3. ISSN 1535-6108.

[2] Dixon SJ, Lemberg KM, Lamprecht MR, Skouta R, Zaitsev EM, Gleason CE, et al. (May 2012). "Ferroptosis: an iron-dependent form of nonapoptotic cell death". Cell. 149 (5): 1060–72. doi:10.1016/j.cell.2012.03.042. PMC 3367386. PMID 22632970.

[3] Yagoda N, von Rechenberg M, Zaganjor E, Bauer AJ, Yang WS, Fridman DJ, et al. (June 2007). "RAS-RAF-MEK-dependent oxidative cell death involving voltage-dependent anion channels". Nature. 447 (7146): 864–8. Bibcode:2007Natur.447..865Y. doi:10.1038/nature05859. PMC 3047570. PMID 17568748.

[4] Dixon SJ, Patel DN, Welsch M, Skouta R, Lee ED, Hayano M, et al. (May 2014). "Pharmacological inhibition of cystine-glutamate exchange induces endoplasmic reticulum stress and ferroptosis". eLife. 3: e02523. doi:10.7554/elife.02523. PMC 4054777. PMID 24844246.

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Legal status

Legal status	Experimental
Identifiers
IUPAC name 2-[1-[4-[2-(4-Chlorophenoxy)acetyl]-1-piperazinyl]ethyl]-3-(2-ethoxyphenyl)-4(3H)-Quinazolinone
CAS Number	571203-78-6
PubChem CID	11214940
ChemSpider	9390002
KEGG	C21478
Chemical and physical data
Formula	C₃₀H₃₁ClN₄O₄
Molar mass	547.05 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C1N(C2=CC=CC=C2OCC)C(C(C)N3CCN(C(COC4=CC=C(Cl)C=C4)=O)CC3)=NC5=CC=CC=C51
InChI 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 Key:BKQFRNYHFIQEKN-UHFFFAOYSA-N