Key Documents

View All Documentation

E1383

Etoposide

Name: Etoposide
Brand: SIGMA

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

Synonym(s):

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

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₂₉H₃₂O₁₃

CAS Number:

33419-42-0

Molecular Weight:

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

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

Product Name

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)

Description

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.

Still not finding the right product?

Explore all of our products under Etoposide

pictograms

GHS08,GHS07

signalword

Danger

hcodes

H302,H350,H361d

pcodes

P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313

Hazard Classifications

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

Storage Class

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

0000481183

0000455695

0000455696

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library