E1383

Etoposide

synthetic, 95.0-105.0%, powder

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

Properties

• Quality Level: 200
• 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 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 used in treating advanced testicular cancer, Kaposi′s sarcoma, non-small cell lung cancer (NSCLC), SCLC (small cell lung cancer) and lymphoma.

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.

Features and Benefits

This compound was developed by Teva. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• Pictograms: GHS07,GHS08
• 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