Chemicals and Drugs

Etoposide

A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle.

Chemical Identity

Chemical Information

Molecular Formula
C29H32O13
Molecular Weight
588.6 g/mol
CAS Registry No.
33419-42-0
IUPAC Name
(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
InChIKey
VJJPUSNTGOMMGY-MRVIYFEKSA-N
SMILES
C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O
MeSH Unique ID
D005047
Source
PubChem CID 36462

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

Loading graph…

Drag nodes to rearrange; hover to trace links; click a node to open its page.

Drug Class

Pharmacological Action

MeSH Record

Synonyms

35 entry terms
  • Demethyl Epipodophyllotoxin Ethylidine Glucoside
  • Eposide
  • Celltop
  • Eposin
  • Eto-GRY
  • Etomedac
  • Etopos
  • Etoposide Pierre Fabre
  • Etoposide Teva
  • Etoposide, (5S)-Isomer
  • Etoposide, (5a alpha)-Isomer
  • Etoposide, (5a alpha,9 alpha)-Isomer
  • Etoposide, alpha-D-Glucopyranosyl Isomer
  • Etoposido Ferrer Farma
  • Exitop
  • Lastet
  • NSC-141540
  • Onkoposid
  • Riboposid
  • Toposar
  • VP 16-213
  • VP-16
  • Vepesid
  • Vépéside-Sandoz
  • Eto GRY
  • Etoposide, alpha D Glucopyranosyl Isomer
  • NSC 141540
  • NSC141540
  • Teva, Etoposide
  • VP 16
  • VP 16 213
  • VP 16213
  • VP16
  • Vépéside Sandoz
  • alpha-D-Glucopyranosyl Isomer Etoposide

MeSH Record

Aspects Covered

25 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

87(81); was see under PODOPHYLLOTOXIN 1981-86; was VP 16-213 see under PODOPHYLLOTOXIN 1976-80

MeSH Record

Previous Indexing

  • Glucosides (1975)
  • Glycosides (1973-1974)
  • Podophyllotoxin (1973-1974)/analogs & derivatives (1975)

MeSH Hierarchy

Tree Numbers

  1. D02w.455w.426w.559w.847w.638.960.675w.250w
  2. D04w.615w.638.960.675w.250w
  3. D09w.408w.348w.275w

MeSH Record

NLM Classification

QV 269

AMA Style

References

  1. National Library of Medicine. Etoposide. Medical Subject Headings (MeSH). 2026. Unique ID D005047. http://id.nlm.nih.gov/mesh/2026/D005047
  2. Etoposide. In: Wikipedia. https://en.wikipedia.org/wiki/Etoposide
  3. Etoposide. In: Wikidata. https://www.wikidata.org/wiki/Q418817
  4. Etoposide. In: PubChem Compound. CID 36462. https://pubchem.ncbi.nlm.nih.gov/compound/36462