E1383

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
• Formule empirique (notation de Hill) : C₂₉H₃₂O₁₃
• Numéro CAS: 33419-42-0
• Poids moléculaire : 588.56
• Numéro CE : 251-509-1
• Numéro MDL: MFCD00869325
• Code UNSPSC : 12352200
• ID de substance PubChem : 24278178
• Nomenclature NACRES : NA.77

Propriétés

• Nom du produit: Etoposide, synthetic, 95.0-105.0%, powder
• Source biologique: synthetic
• Essai: 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: human ... ABCB1(5243) , CYP3A4(1576) , TOP2A(7153) , TOP2B(7155) ; mouse ... Abcb1a(18671) , Abcb1b(18669) ; rat ... Top2a(360243)

Description

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.[1]

Etoposide is synthesised from podophyllotoxins of plants.[2]

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[3]
• to incubate cells for cell viability assay[4]
• to treat neuro-2A cells to induce programmed cell death[5]

Actions biochimiques/physiologiques

Antitumor agent that complexes with topoisomerase II and DNA to enhance double-strand and single-strand cleavage of DNA and reversibly inhibit religation.

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.[2]

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.

Informations sur la sécurité

• Pictogrammes: GHS08,GHS07
• Mention d'avertissement: Danger
• Mentions de danger: H302,H350,H361d
• Conseils de prudence: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• 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