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
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100330
Name: Etoposide
CAS#: 33419-42-0
Chemical Formula: C29H32O13
Exact Mass: 588.18
Molecular Weight: 588.550
Elemental Analysis: C, 59.18; H, 5.48; O, 35.34

Price and Availability

Size Price Availability Quantity
100mg USD 55 Ready to Ship
1g USD 150 Ready to ship
2g USD 250 Ready to ship
5g USD 550 Ready to ship
10g USD 950 Ready to ship
20g USD 1650 Ready to ship
100g USD 6450 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

More Info: 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.

Biological target: Etoposide (VP-16, VP-16213) is a semisynthetic derivative of podophyllotoxin, which inhibits DNA synthesis via topoisomerase II inhibition activity.
In vitro activity: In RIN-m5F cells (a β-cell-derived cell line), the number of viable cells was significantly decreased after 24h of etoposide treatment and underwent mitochondria-dependent apoptotic signals accompanied by mitochondrial dysfunction, and increases in the population of sub-G1 hypodiploid cells and apoptotic cells, caspase-3 activity, and the activation of caspase cascades. Etoposide also increased the phosphorylation levels of glycogen synthase kinase (GSK)-3α/β in treated RIN-m5F cells. Pretreatment with LiCl, a GSK-3 inhibitor, prevented etoposide-induced mitochondria-dependent apoptosis and GSK-3 protein phosphorylation in RIN-m5F cells. Furthermore, exposure of the cells to etoposide induced the phosphorylation of c-Jun N-terminal kinase (JNK) and extracellular signal-related kinase (ERK)1/2 but not p38-MAPK. Reference: Toxicol In Vitro. 2016 Oct;36:142-152. https://linkinghub.elsevier.com/retrieve/pii/S0887-2333(16)30147-3
In vivo activity: Of C57B1/6 mice injected with 10(6) Lewis lung cancer (3LL) cells followed by treatment with a single 50 mg/kg dose of etoposide (VP-16), 60% survived over 60 days, in contrast to untreated control mice which died within 30 days. Approximately 40% of surviving mice rejected a subsequent challenge with 3LL. Their splenocytes protected naive mice injected with 3LL. To test if VP-16 treatment produced alterations in 3LL cells, which induce host immunity, leading to tumor rejection, C57B1/6 mice were injected with 3LL cells that had survived an 80-90% lethal concentration of VP-16 in vitro. These cells killed 75% of recipient mice but 60% of the surviving mice rejected challenge with 3LL. Splenocytes harvested from tumor-rejecting mice protected naive mice injected with 3LL. Reference: Cancer Chemother Pharmacol. 2001 Oct;48(4):327-32. https://dx.doi.org/10.1007/s002800100357

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 169.91

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
Formulation protocol: 1. Lee KI, Su CC, Yang CY, Hung DZ, Lin CT, Lu TH, Liu SH, Huang CF. Etoposide induces pancreatic β-cells cytotoxicity via the JNK/ERK/GSK-3 signaling-mediated mitochondria-dependent apoptosis pathway. Toxicol In Vitro. 2016 Oct;36:142-152. doi: 10.1016/j.tiv.2016.07.018. Epub 2016 Jul 27. PMID: 27473919. 2. Slater LM, Stupecky M, Sweet P, Osann K, Eklof A, Arquilla ER. Etoposide induction of tumor immunity in Lewis lung cancer. Cancer Chemother Pharmacol. 2001 Oct;48(4):327-32. doi: 10.1007/s002800100357. PMID: 11710634.
In vitro protocol: 1. Lee KI, Su CC, Yang CY, Hung DZ, Lin CT, Lu TH, Liu SH, Huang CF. Etoposide induces pancreatic β-cells cytotoxicity via the JNK/ERK/GSK-3 signaling-mediated mitochondria-dependent apoptosis pathway. Toxicol In Vitro. 2016 Oct;36:142-152. doi: 10.1016/j.tiv.2016.07.018. Epub 2016 Jul 27. PMID: 27473919.
In vivo protocol: 1. Slater LM, Stupecky M, Sweet P, Osann K, Eklof A, Arquilla ER. Etoposide induction of tumor immunity in Lewis lung cancer. Cancer Chemother Pharmacol. 2001 Oct;48(4):327-32. doi: 10.1007/s002800100357. PMID: 11710634.

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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.

1. Rasmus Blaaholm Nielsen, René Holm, Ils Pijpers, Jan Snoeys, Ulla Gro Nielsen, Carsten Uhd Nielsen, Oral etoposide and zosuquidar bioavailability in rats: Effect of co-administration and in vitro-in vivo correlation of P-glycoprotein inhibition, International Journal of Pharmaceutics: X, Volume 3, 2021, 100089, ISSN 2590-1567, https://doi.org/10.1016/j.ijpx.2021.100089. (https://www.sciencedirect.com/science/article/pii/S2590156721000189).

2. .Jochems F, Thijssen B, De Conti G, Jansen R, Pogacar Z, Groot K, Wang L, Schepers A, Wang C, Jin H, Beijersbergen RL, Leite de Oliveira R, Wessels LFA, Bernards R. The Cancer SENESCopedia: A delineation of cancer cell senescence. Cell Rep. 2021 Jul 27;36(4):109441. doi: 10.1016/j.celrep.2021.109441. PMID: 34320349.