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E1383

Etoposide

Name: Etoposide
Brand: SIGMA

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

동의어(들):

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

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제품정보 (DICE 배송 시 비용 별도)

실험식(Hill 표기법):

C₂₉H₃₂O₁₃

CAS 번호:

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

Assay:

95.0-105.0%

Form:

powder

Quality level:

200

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속성

제품 이름

Etoposide, synthetic, 95.0-105.0%, powder

biological source

synthetic

Quality Level

200

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)

설명

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

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.

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.