E1383

Etoposide

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

• Synonym(s): 4′-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside), VP-16-213
• Empirical Formula (Hill Notation): C₂₉H₃₂O₁₃
• CAS Number: 33419-42-0
• Molecular Weight: 588.56
• NACRES: NA.77
• PubChem Substance ID: 24278178
• UNSPSC Code: 12352200
• EC Number: 251-509-1
• MDL number: MFCD00869325

Properties

• Product Name: Etoposide, synthetic, 95.0-105.0%, powder
• 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
• InChI key: VJJPUSNTGOMMGY-MRVIYFEKSA-N
• SMILES string: 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
• biological source: synthetic
• assay: 95.0-105.0%
• form: powder
• color: white to off-white
• pKa: 9.8
• mp: 236-251 °C (lit.)
• antibiotic activity spectrum: neoplastics
• mode of action: DNA synthesis | interferes; enzyme | inhibits
• originator: Teva
• Quality Level: 200
• Gene Information: human ... ABCB1(5243), CYP3A4(1576), TOP2A(7153), TOP2B(7155) ; mouse ... Abcb1a(18671), Abcb1b(18669) ; rat ... Top2a(360243)

Description

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[1]
• to incubate cells for cell viability assay[2]
• to treat neuro-2A cells to induce programmed cell death[3]

Biochem/physiol Actions

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.[4]

Features and Benefits

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.

General description

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.[5]

Etoposide is synthesised from podophyllotoxins of plants.[4]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302,H350,H361d
• pcodes: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 1B - Repr. 2
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges