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E1383

Etoposide

95.0-105.0% (anhydrous basis), powder, topoisomerase II inhibitor

Synonyme(s) :

4′-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside), VP-16-213

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A propos de cet article

Formule empirique (notation de Hill) :
C29H32O13
Numéro CAS:
33419-42-0
Poids moléculaire :
588.56
NACRES:
NA.77
PubChem Substance ID:
24278178
UNSPSC Code:
12352200
EC Number:
251-509-1
MDL number:
MFCD00869325
Assay:
95.0-105.0%
Form:
powder
Quality level:
200
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Nom du produit

Etoposide, synthetic, 95.0-105.0%, powder

biological source

synthetic

Quality Level

200

assay

95.0-105.0%

form

powder

color

white to off-white

pKa 

9.8

mp

236-251 °C (lit.)

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes, enzyme | inhibits

originator

Teva

SMILES string

COc1cc(cc(OC)c1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]4O)c6cc7OCOc7cc26

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

InChI key

VJJPUSNTGOMMGY-MRVIYFEKSA-N

Gene Information

human ... ABCB1(5243), CYP3A4(1576), TOP2A(7153), TOP2B(7155)
mouse ... Abcb1a(18671), Abcb1b(18669)
rat ... Top2a(360243)

General description

Etoposide belongs to the class of medications known as topoisomerase II inhibitors. This semi-synthetic compound is derived from Podophyllum peltatum, and Podophyllum emodi. The complex formed between etoposide and topoisomerase II initiates a mutagenic and cell death pathway, demonstrating optimal efficacy in tumor cells with elevated levels of topoisomerase II enzymes. Etoposide is administered as an oral or intravenous chemotherapy agent.
Etoposide is synthesised from podophyllotoxins of plants.

Application

Etoposide has been used:
  • to prepare drug stock solution in dimethyl sulfoxide (DMSO) and also to profile and compare the sensitivity of DT40 mutant cells
  • to incubate cells for cell viability assay
  • to treat neuro-2A cells to induce programmed cell death

Biochem/physiol Actions

Antitumor agent that complexes with topoisomerase II and DNA to enhance double-strand and single-strand cleavage of DNA and reversibly inhibit religation.
Etoposide is an antitumor agent that complexes with topoisomerase II and DNA to enhance double-strand and single-strand cleavage of DNA and reversibly inhibit religation. Blocks the cell cycle in in S-phase and G2-phase of the cell cycle; induces apoptosis in normal and tumor cell lines; inhibits synthesis of the oncoprotein Mdm2 and induces apoptosis in tumor lines that overexpress Mdm2.
Etoposide is used in treating advanced testicular cancer, Kaposi′s sarcoma, non-small cell lung cancer (NSCLC), SCLC (small cell lung cancer) and lymphoma.

Features and Benefits

This compound is a featured product for ADME Tox and Apoptosis research. Discover more featured ADME Tox and Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Teva. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Repr. 2

Classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificats d'analyse (COA)

Lot/Batch Number
0000481183
0000481183
0000455695
0000455695
0000455696

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Consulter la Bibliothèque de documents

Etoposide
Reyhanoglu G and Tadi P
StatPearls [Internet] (2023)
Loss of TBL1XR1 disrupts glucocorticoid receptor recruitment to chromatin and results in glucocorticoid resistance in a B-lymphoblastic leukemia model
Jones CL, et al.
Test, jbc-M114 (2014)
Pharmacology and Therapeutics for Dentistry - E-Book, 700-700 (2010)
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