Ferroptosis-centered Drug Response Information

General Information of the Drug (ID: ferrodrug0043)
Name
Etoposide
Synonyms
etoposide; 33419-42-0; VePesid; Toposar; trans-Etoposide; Lastet; (-)-Etoposide; Zuyeyidal; Etoposidum; VP-16; Etoposido; Etoposidum [INN-Latin]; VP-16-213; Etoposide (VP16); VP 16-213; Vepesid J; Sintopozid; 4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside; NSC-141540; DTXSID5023035; Etoposide (VP-16); VP 16 (pharmaceutical); 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside); VP 16; 6PLQ3CP4P3; Epipodophyllotoxin VP-16213; CHEMBL44657; CHEBI:4911; NK 171; Demethylepipodophyllotoxin-beta-D-ethylideneglucoside; NSC 141540; 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside); Etosid; Etoposido [INN-Spanish]; (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one; (5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside; Etopophos (phosphate salt); DTXCID601473876; Etopol; VP 16213; NSC141540; (10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one; (5R,5aR,8aR,9S)-9-(((4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one; 9-((4,6-O-Ethylidine-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,4-dimethyloxyphenyl)furo(3',4'':6,7)naptho-(2,3-d)-1,3-dioxol-6(5aH)-one; SMR000112002; CCRIS 2392; Demethyl-epiodophyllotoxin ethylidene glucoside; HSDB 6517; VePESID (TN); EINECS 251-509-1; UNII-6PLQ3CP4P3; 4'-Demethylepipodophyllotoxin ethylidene-.beta.-D-glucoside; Etoposide,(S); NCGC00016821-01; (5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol -5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside; EVP; Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[[4,6-O-(1R)-ethylidene-.beta.-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-; 4'-O-Demethyl-1-O-(4,6-O-ethylidene-beta-D-glucopyranosyl)epipodophyllotoxin; Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-ethylidene-beta-D-glucopyranoside); CAS-33419-42-0; Etoposide [USAN:USP:INN:BAN:JAN]; Etoposide; VP-16; CPD000112002; Epipodophyllotoxin-beta-D-ethyliden-glucoside, 4'-demethyl-; ETOPOSIDE [INN]; ETOPOSIDE [JAN]; ETOPOSIDE [MI]; ETOPOSIDE [HSDB]; ETOPOSIDE [IARC]; ETOPOSIDE [USAN]; Prestwick3_000396; ETOPOSIDE [VANDF]; ETOPOSIDE [MART.]; Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-beta-D-glucopyranoside; ETOPOSIDE [USP-RS]; ETOPOSIDE [WHO-DD]; ETOPOSIDE [WHO-IP]; SCHEMBL4259; BSPBio_000611; 9-((4,6-O-Ethylidene-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, (5R-(5alpha,5abeta,8aalpha,9beta(R*)))-; 9-((4,6-O-Ethylidine-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4- hydroxy-3,4-dimethyloxyphenyl)furo (3',4'':6,7) naptho-(2,3-d)-1,3-dioxol-6 (5aH)-one; MLS000049957; MLS001074951; MLS001424283; MLS002153463; MLS002207239; MLS002222184; Etoposide (JP17/USP/INN); BPBio1_000673; GTPL6815; ETOPOSIDE [EP IMPURITY]; ETOPOSIDE [ORANGE BOOK]; ETOPOSIDE [EP MONOGRAPH]; ETOPOSIDE [USP IMPURITY]; ETOPOSIDE [USP MONOGRAPH]; ETOPOSIDUM [WHO-IP LATIN]; VJJPUSNTGOMMGY-MRVIYFEKSA-N; etoposide4-o-b-d-galactopyranoside; HMS2052N05; HMS2089F14; HMS2096O13; HMS2232L03; HMS3713O13; EX-A1207; Tox21_110630; Tox21_302201; BDBM50127140; s1225; Etoposide - CAS 33419-42-0; AKOS007930275; BCP9000669; CCG-101165; CS-1774; DB00773; Etoposide, synthetic, >=98%, powder; NC00415; SDCCGSBI-0050405.P002; 4'-Demethyl-epipodophyllotoxin 9-[4,6-O-(R)-ethylidene-beta-D-glucopyranoside; NCGC00179504-02; NCGC00255126-01; AS-35312; BE164434; Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 9-((4,6-O-(1R)-ethylidene-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-; Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one-, 9-((4,6-O-ethylidene-beta-D-glucopyranosyl)oxy)5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl), (5R-(5alpha,5abeta,8aalpha,9beta(R*)))-; HY-13629; SBI-0051910.P002; AB00438905; EN300-97099; C01576; D00125; AB00438905-17; AB00438905-18; AB00438905_19; Q418817; SR-01000763196; SR-01000763196-3; BRD-K37798499-001-02-5; BRD-K37798499-001-05-8; BRD-K37798499-001-10-8; BRD-K37798499-001-14-0; BRD-K37798499-001-27-2; -5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside; Etoposide, British Pharmacopoeia (BP) Reference Standard; Z1304065033; Etoposide, European Pharmacopoeia (EP) Reference Standard; Etoposide, United States Pharmacopeia (USP) Reference Standard; 4''-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside); 4'-DEMETHYLEPIPODOPHYLLOTOXIN 9-(4,6-O-(R)-ETHYLIDENE-.BETA.-D-GLUCOPYRANOSIDE); Etoposide for system suitability, European Pharmacopoeia (EP) Reference Standard; (5R,5AR,8aR,9S)-9-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahy; (5R,5aR,8aR,9S)-9-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one; (5R,5AR,8AR,9S)-9-((4,6-O-((1R)-ETHANE-1,1-DIYL)-.ALPHA.-D-GLUCOPYRANOSYL)OXY)-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-5,8,8A,9-TETRAHYDRO(2)BENZOFURO(5,6-F)(1,3)BENZODIOXOL-6(5AH)-ONE; (5R,5aR,8aR,9S)-9-[[4,6-O-(1R)-Ethylidene-beta-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,3]benzodioxol-8-one; (5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3'',4'':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside; [5R-[5?,5a?,8a?,9?(R*)]]-9-[(4,6-?-Ethylidene-?-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6-(5aH)-one; 121471-01-0; 9-((4,6-O-Ethylidine-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,4-dimethyloxyphenyl)furo(3'',4'''':6,7)naptho-(2,3-d)-1,3-dioxol-6(5aH)-one; FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE-, 9-((4,6-O-ETHYLIDENE-.BETA.-D-GLUCOPYRANOSYL)OXY)5,8,8A,9-TETRAHYDRO-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL), (5R-(5.ALPHA.,5A.BETA.,8A.ALPHA.,9.BETA.(R*)))-

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Structure
Formula
C29H32O13
IUPAC Name
(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
Canonical SMILES
CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O
InChI
InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
InChIKey
VJJPUSNTGOMMGY-MRVIYFEKSA-N
PubChem CID
36462
Full List of Ferroptosis Target Related to This Drug
Unspecific Target
In total 1 item(s) under this Target
Experiment 1 Reporting the Ferroptosis-centered Drug Act on This Target [1]
Responsed Disease Breast cancer ICD-11: 2C60
 Disease Info 
Responsed Regulator Medium-chain acyl-CoA ligase ACSF2, mitochondrial (ACSF2) Driver
 Regulator Info 
Pathway Response Fatty acid metabolism hsa01212
Ferroptosis hsa04216
Cell Process Cell ferroptosis
In Vitro Model MCF-7 cells Breast carcinoma Homo sapiens CVCL_0031
MCF-10A cells Normal Homo sapiens CVCL_0598
MDA-MB-231 cells Breast adenocarcinoma Homo sapiens CVCL_0062
Response regulation The combined treatment of etoposide and erastin synergistically induced oxidative stress and lipid peroxidation, while suppressing glutathione peroxidase activity in breast cancer cells. More importantly, the combination treatment synergistically increased iron accumulation, which was associated with altered expression of IREB2/FPN1. Additionally, ferroptosis-regulating proteins ACSF2 and GPX4 were altered more potently by the combination treatment, compared to untreated cells and erastin treatment alone (p<0.05).
Solute carrier family 40 member 1 (SLC40A1)
 Target Info 
In total 1 item(s) under this Target
Experiment 1 Reporting the Ferroptosis-centered Drug Act on This Target [1]
Target for Ferroptosis Suppressor
Responsed Disease Breast cancer ICD-11: 2C60
 Disease Info 
Pathway Response Fatty acid metabolism hsa01212
Ferroptosis hsa04216
Cell Process Cell ferroptosis
In Vitro Model MCF-7 cells Breast carcinoma Homo sapiens CVCL_0031
MCF-10A cells Normal Homo sapiens CVCL_0598
MDA-MB-231 cells Breast adenocarcinoma Homo sapiens CVCL_0062
Response regulation The combined treatment of etoposide and erastin synergistically induced oxidative stress and lipid peroxidation, while suppressing glutathione peroxidase activity in breast cancer cells. More importantly, the combination treatment synergistically increased iron accumulation, which was associated with altered expression of IREB2/FPN1. Additionally, ferroptosis-regulating proteins ACSF2 and GPX4 were altered more potently by the combination treatment, compared to untreated cells and erastin treatment alone (p<0.05).
Phospholipid hydroperoxide glutathione peroxidase (GPX4)
 Target Info 
In total 1 item(s) under this Target
Experiment 1 Reporting the Ferroptosis-centered Drug Act on This Target [1]
Target for Ferroptosis Suppressor
Responsed Disease Breast cancer ICD-11: 2C60
 Disease Info 
Pathway Response Fatty acid metabolism hsa01212
Ferroptosis hsa04216
Cell Process Cell ferroptosis
In Vitro Model MCF-7 cells Breast carcinoma Homo sapiens CVCL_0031
MCF-10A cells Normal Homo sapiens CVCL_0598
MDA-MB-231 cells Breast adenocarcinoma Homo sapiens CVCL_0062
Response regulation The combined treatment of etoposide and erastin synergistically induced oxidative stress and lipid peroxidation, while suppressing glutathione peroxidase activity in breast cancer cells. More importantly, the combination treatment synergistically increased iron accumulation, which was associated with altered expression of IREB2/FPN1. Additionally, ferroptosis-regulating proteins ACSF2 and GPX4 were altered more potently by the combination treatment, compared to untreated cells and erastin treatment alone (p<0.05).
Iron-responsive element-binding protein 2 (IREB2)
 Target Info 
In total 1 item(s) under this Target
Experiment 1 Reporting the Ferroptosis-centered Drug Act on This Target [1]
Target for Ferroptosis Driver
Responsed Disease Breast cancer ICD-11: 2C60
 Disease Info 
Pathway Response Fatty acid metabolism hsa01212
Ferroptosis hsa04216
Cell Process Cell ferroptosis
In Vitro Model MCF-7 cells Breast carcinoma Homo sapiens CVCL_0031
MCF-10A cells Normal Homo sapiens CVCL_0598
MDA-MB-231 cells Breast adenocarcinoma Homo sapiens CVCL_0062
Response regulation The combined treatment of etoposide and erastin synergistically induced oxidative stress and lipid peroxidation, while suppressing glutathione peroxidase activity in breast cancer cells. More importantly, the combination treatment synergistically increased iron accumulation, which was associated with altered expression of IREB2/FPN1. Additionally, ferroptosis-regulating proteins ACSF2 and GPX4 were altered more potently by the combination treatment, compared to untreated cells and erastin treatment alone (p<0.05).
References
Ref 1 Etoposide in combination with erastin synergistically altered iron homeostasis and induced ferroptotic cell death through regulating IREB2/FPN1 expression in estrogen receptor positive-breast cancer cells. Life Sci. 2023 Jan 1;312:121222. doi: 10.1016/j.lfs.2022.121222. Epub 2022 Nov 25.