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E1383

Sigma-Aldrich

Etoposide

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

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About This Item

Empirical Formula (Hill Notation):
C29H32O13
CAS Number:
33419-42-0
Molecular Weight:
588.56
EC Number:
251-509-1
MDL number:
MFCD00869325
UNSPSC Code:
12352200
PubChem Substance ID:
24278178
NACRES:
NA.77

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)

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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

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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H350,H361d

Hazard Classifications

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Etoposide
Reyhanoglu G and Tadi P
StatPearls [Internet] (2023)
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)
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