Chemicals and Drugs

Teniposide

A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Teniposide 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 cells from entering into the mitotic phase of the cell cycle, and lead to cell death. Teniposide acts primarily in the G2 and S phases of the cycle.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Teniposide 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 cells from entering into the mitotic phase of the cell cycle, and lead to cell death. Teniposide acts primarily in the G2 and S phases of the cycle.

Chemical Identity

Chemical Information

Molecular Formula
C32H32O13S
Molecular Weight
656.7 g/mol
CAS Registry No.
29767-20-2
IUPAC Name
(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-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
NRUKOCRGYNPUPR-QBPJDGROSA-N
SMILES
COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)O[C@H]6[C@@H]([C@H]([C@H]7[C@H](O6)CO[C@H](O7)C8=CC=CS8)O)O
MeSH Unique ID
D013713
Source
PubChem CID 452548

MeSH Record

Classification

Broader headings

Related Concepts

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

9 entry terms
  • Demethyl Epipodophyllotoxin Thenylidine Glucoside
  • NSC-122819
  • Teniposide, (5a alpha,9 alpha(S*))-Isomer
  • VM-26
  • Vumon
  • NSC 122819
  • NSC122819
  • VM 26
  • VM26

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

91(81); was see under PODOPHYLLOTOXIN 1981-90; was VM 26 see under PODOPHYLLOTOXIN 1976-80

MeSH Record

Previous Indexing

  • Glucosides (1975)
  • Glycosides (1973-1974)
  • Podophyllotoxin (1973-1974)

MeSH Hierarchy

Tree Number

  1. D09w.408w.348w.800w

AMA Style

References

  1. National Library of Medicine. Teniposide. Medical Subject Headings (MeSH). 2026. Unique ID D013713. http://id.nlm.nih.gov/mesh/2026/D013713
  2. Teniposide. In: Wikipedia. https://en.wikipedia.org/wiki/Teniposide
  3. Teniposide. In: Wikidata. https://www.wikidata.org/wiki/Q417555
  4. Teniposide. In: PubChem Compound. CID 452548. https://pubchem.ncbi.nlm.nih.gov/compound/452548