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E1383

Sigma-Aldrich

Etoposide

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

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C29H32O13
Numéro CAS:
Poids moléculaire :
588.56
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

product name

Etoposide, synthetic, 95.0-105.0%, powder

Source biologique

synthetic

Niveau de qualité

Pureté

95.0-105.0%

Forme

powder

Couleur

white to off-white

pKa  

9.8

Pf

236-251 °C (lit.)

Spectre d'activité de l'antibiotique

neoplastics

Mode d’action

DNA synthesis | interferes
enzyme | inhibits

Auteur

Teva

Chaîne SMILES 

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

Clé InChI

VJJPUSNTGOMMGY-MRVIYFEKSA-N

Informations sur le gène

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Description générale

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogrammes

Health hazardExclamation mark

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

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

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
Pharmacology and Therapeutics for Dentistry - E-Book, 700-700 (2010)
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)
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)
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

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