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
• EC Number: 251-509-1
• MDL number: MFCD00869325
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278178
• NACRES: NA.77

Properties

• product name: Etoposide, synthetic, 95.0-105.0%, powder
• 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
• 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
• 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
• Gene Information: human ... ABCB1(5243) , CYP3A4(1576) , TOP2A(7153) , TOP2B(7155) ; mouse ... Abcb1a(18671) , Abcb1b(18669) ; rat ... Top2a(360243)

Description

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.

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

Biochem/physiol Actions

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.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H302,H350,H361d
• Precautionary Statements: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 1B - Repr. 2
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves