E1383

Sigma-Aldrich

Etoposide

synthetic, 98.0-105.0%, powder

Synonym(s):
VP-16-213, 4′-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside)
Empirical Formula (Hill Notation):
C29H32O13
CAS Number:
Molecular Weight:
588.56
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

synthetic

assay

98.0-105.0%

form

powder

color

white to off-white

pKa 

9.8

mp

236-251 °C (lit.)

solubility

chloroform: methanol (1:1): 25 mg/mL

Mode of action

DNA synthesis | interferes
enzyme | inhibits

antibiotic activity spectrum

neoplastics

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

Looking for similar products? Visit Product Comparison Guide

General description

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

Etoposide is used in treating advanced testicular cancer, Kaposi′s sarcoma, non-small cell lung cancer (NSCLC), SCLC (small cell lung cancer) and lymphoma.
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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.
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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Certificate of Analysis

Certificate of Origin

Differential and common DNA repair pathways for topoisomerase I-and II-targeted drugs in a genetic DT40 repair cell screen panel
Maede Y, et al.
Molecular Cancer Therapeutics, 13(1), 214-220 (2014)
The latency-related gene of bovine herpesvirus 1 inhibits programmed cell death
Ciacci-Zanella J, et al.
Journal of Virology, 73(12), 9734-9740 (1999)
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)
S K Mungamuri et al.
Oncogene, 34(19), 2461-2470 (2014-07-16)
Chromatin conformation has a major role in all cellular decisions. We showed previously that P53 pro-apoptotic target promoters are enriched with H3K9me3 mark and induction of P53 abrogates this repressive chromatin conformation by downregulating SUV39H1, the writer of this mark...
Articles
We presents an article on ABC Transporters and Cancer Drug Resistance
Read More
Related Content
Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.
Read More
n proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during the synthesis (S) phase, which is followed by a second gap phase (G2) during which growth and preparation for cell division occurs. Together, these three stages comprise the interphase phase of the cell cycle. Interphase is followed by the mitotic (M) phase.
Read More
Discover Bioactive Small Molecules for ADME/Tox
Read More

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.