Etoposide
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MedKoo CAT#: 100330

CAS#: 33419-42-0

Description: Etoposide is a semisynthetic derivative of podophyllotoxin and a substance extracted from the mandrake root Podophyllum peltatum. Possessing potent antineoplastic properties, etoposide binds to and inhibits topoisomerase II and its function in ligating cleaved DNA molecules, resulting in the accumulation of single- or double-strand DNA breaks, the inhibition of DNA replication and transcription, and apoptotic cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Chemical Structure

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Etoposide
CAS# 33419-42-0

Theoretical Analysis

MedKoo Cat#: 100330
Name: Etoposide
CAS#: 33419-42-0
Chemical Formula: C29H32O13
Exact Mass: 588.18429
Molecular Weight: 588.55
Elemental Analysis: C, 59.18; H, 5.48; O, 35.34

Price and Availability

Size Price Availability Quantity
1.0g USD 150.0 Same day
2.0g USD 250.0 Same day
5.0g USD 450.0 Same day
10.0g USD 750.0 Same day
25.0g USD 1950.0 Same day
50.0g USD 2950.0 2 weeks
100.0g USD 4650.0 2 weeks
200.0g USD 7650.0 2 weeks
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Synonym: Demethyl Epipodophyllotoxin Ethylidine Glucoside. epipodophyllotoxin. US brand names: Toposar. VePesid. Foreign brand name: Lastet. Abbreviation: EPEG Code names: VP16; VP16213.

IUPAC/Chemical Name: (5R,5aR,8aR)-9-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

InChi Key: VJJPUSNTGOMMGY-YLLUJYJTSA-N

InChi Code: 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

SMILES Code: O=C1OC[C@]2([H])C(O[C@H]3[C@H](O)[C@@H](O)[C@]4([H])O[C@H](C)OC[C@@]4([H])O3)C5=C(C=C6OCOC6=C5)[C@@H](C7=CC(OC)=C(O)C(OC)=C7)[C@]21[H]

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 588.55 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Cardellicchio S, Bacci G, Farina S, Genitori L, Massimino M, de Martino M, Caputo R, Sardi I. Low-dose cisplatin-etoposide regimen for patients with optic pathway glioma: a report of four cases and literature review. Neuropediatrics. 2014 Feb;45(1):42-9. doi: 10.1055/s-0033-1360482. Epub 2013 Nov 22. Review. PubMed PMID: 24272769.

2: Bruserud O, Reikvam H, Kittang AO, Ahmed AB, Tvedt TH, Sjo M, Hatfield KJ. High-dose etoposide in allogeneic stem cell transplantation. Cancer Chemother Pharmacol. 2012 Dec;70(6):765-82. doi: 10.1007/s00280-012-1990-z. Epub 2012 Oct 6. Review. PubMed PMID: 23053272.

3: Kushner BH, Modak S, Kramer K, Basu EM, Roberts SS, Cheung NK. Ifosfamide, carboplatin, and etoposide for neuroblastoma: a high-dose salvage regimen and review of the literature. Cancer. 2013 Feb 1;119(3):665-71. doi: 10.1002/cncr.27783. Epub 2012 Sep 5. Review. PubMed PMID: 22951749.

4: Ezoe S. Secondary leukemia associated with the anti-cancer agent, etoposide, a topoisomerase II inhibitor. Int J Environ Res Public Health. 2012 Jul;9(7):2444-53. doi: 10.3390/ijerph9072444. Epub 2012 Jul 10. Review. PubMed PMID: 22851953; PubMed Central PMCID: PMC3407914.

5: Jiang L, Yang KH, Guan QL, Mi DH, Wang J. Cisplatin plus etoposide versus other platin-based regimens for patients with extensive small-cell lung cancer: a systematic review and meta-analysis of randomised, controlled trials. Intern Med J. 2012 Dec;42(12):1297-309. doi: 10.1111/j.1445-5994.2012.02821.x. Review. PubMed PMID: 22530708.

6: Bauters T, Vandenbroucke J, Moerloose BD, Porre JD, Benoit Y, Robays H. Etoposide in continuous infusion: practical recommendations for pediatric protocols. J Oncol Pharm Pract. 2011 Dec;17(4):453-5. doi: 10.1177/1078155210384302. Review. PubMed PMID: 22130773.

7: Lima JP, dos Santos LV, Sasse EC, Lima CS, Sasse AD. Camptothecins compared with etoposide in combination with platinum analog in extensive stage small cell lung cancer: systematic review with meta-analysis. J Thorac Oncol. 2010 Dec;5(12):1986-93. doi: 10.1097/JTO.0b013e3181f2451c. Review. PubMed PMID: 20978445.

8: Schieveen PG, Hulin A, Muret P, Royer B; Suivi Thérapeutique Pharmacologique de la Société Française de Pharmacologie et de Thérapeutique. [Level of evidence for therapeutic drug monitoring for etoposide after oral administration]. Therapie. 2010 May-Jun;65(3):207-12. doi: 10.2515/therapie/2010019. Epub 2010 Aug 11. Review. French. PubMed PMID: 20699072.

9: Gerritsen-van Schieveen P, Royer B; Therapeutic Drug Monitoring Group of the French Society of Pharmacology and Therapeutics. Level of evidence for therapeutic drug monitoring for etoposide after oral administration. Fundam Clin Pharmacol. 2011 Jun;25(3):277-82. doi: 10.1111/j.1472-8206.2010.00856.x. Review. PubMed PMID: 20608987.

10: Isoyama Y, Shioyama Y, Nomoto S, Ohga S, Nonoshita T, Onishi K, Matsuura S, Atsumi K, Terashima K, Hirata H, Honda H. Carboplatin and etoposide combined with radiotherapy for limited-stage small-cell esophageal carcinoma: three cases and review of the literature. Jpn J Radiol. 2010 Apr;28(3):181-7. doi: 10.1007/s11604-009-0403-7. Epub 2010 May 1. Review. PubMed PMID: 20437127.



Additional Information

DRUG DESCRIPTION
VePesid® (etoposide) (also commonly known as VP-16) is a semisynthetic derivative of podophyllotoxin used in the treatment of certain neoplastic diseases. It is 4'-demethylepipodophyllotoxin 9-[4,6-O-(R)-ethylidene-β-D-glucopyranoside]. It is very soluble in methanol and chloroform, slightly soluble in ethanol, and sparingly soluble in water and ether. It is made more miscible with water by means of organic solvents. It has a molecular weight of 588.56 and a molecular formula of C29H32O13. VePesid is administered orally. VePesid is available as 50 mg pink capsules. Each liquid-filled, soft gelatin capsule contains 50 mg of etoposide in a vehicle consisting of citric acid, glycerin, purified water, and polyethylene glycol 400. The soft gelatin capsules contain gelatin, glycerin, sorbitol, purified water, and parabens (ethyl and propyl) with the following dye system: iron oxide (red) and titanium dioxide; the capsules are printed with edible ink.
 
CLINICAL PHARMACOLOGY
VePesid has been shown to cause metaphase arrest in chick fibroblasts. Its main effect, however, appears to be at the G2 portion of the cell cycle in mammalian cells. Two different dose-dependent responses are seen. At high concentrations (10 µg/mL or more), lysis of cells entering mitosis is observed. At low concentrations (0.3-10 µg/mL), cells are inhibited from entering prophase. It does not interfere with microtubular assembly. The predominant macromolecular effect of etoposide appears to be the induction of DNA strand breaks by an interaction with DNA topoisomerase II or the formation of free radicals.
VePesid has been shown to cause metaphase arrest in chick fibroblasts. Its main effect, however, appears to be at the G2 portion of the cell cycle in mammalian cells. Two different dose-dependent responses are seen. At high concentrations (10 µg/mL or more), lysis of cells entering mitosis is observed. At low concentrations (0.3-10 µg/mL), cells are inhibited from entering prophase. It does not interfere with microtubular assembly. The predominant macromolecular effect of etoposide appears to be the induction of DNA strand breaks by an interaction with DNA topoisomerase II or the formation of free radicals.