synthetic, 98.0-105.0%, powder

VP-16-213, 4′-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside)
Empirical Formula (Hill Notation):
CAS Number:
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EC Number:
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PubChem Substance ID:

Quality Level

biological source







white to off-white




236-251 °C (lit.)


chloroform: methanol (1:1): 25 mg/mL

Mode of action

DNA synthesis | interferes
enzyme | inhibits

antibiotic activity spectrum




SMILES string




InChI key


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General description

Etoposide is synthesised from podophyllotoxins of plants.


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.


Bottomless glass bottle. Contents are inside inserted fused cone.

Legal Information

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


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Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves


NONH for all modes of transport

WGK Germany


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...
We presents an article on ABC Transporters and Cancer Drug Resistance
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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.
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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.
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