Etoposide Phosphate
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MedKoo CAT#: 100320

CAS#: 117091-64-2

Description: Etoposide phosphate is a phosphate salt of a semisynthetic derivative of podophyllotoxin. Etoposide binds to the enzyme topoisomerase II, inducing double-strand DNA breaks, inhibiting DNA repair, and resulting in decreased DNA synthesis and tumor cell proliferation. Cells in the S and G2 phases of the cell cycle are most sensitive to this agent.


Chemical Structure

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Etoposide Phosphate
CAS# 117091-64-2

Theoretical Analysis

MedKoo Cat#: 100320
Name: Etoposide Phosphate
CAS#: 117091-64-2
Chemical Formula: C29H33O16P
Exact Mass: 668.15062
Molecular Weight: 668.54
Elemental Analysis: C, 52.10; H, 4.98; O, 38.29; P, 4.63

Price and Availability

Size Price Availability Quantity
25.0mg USD 325.0 2 weeks
100.0mg USD 750.0 2 weeks
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Synonym: Eposin Etopophos Vepesid VP16. US brand name: Etopophos. Abbreviation: ETOP.

IUPAC/Chemical Name: [4-[(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2,6-dimethoxyphenyl] dihydrogen phosphate

InChi Key: LIQODXNTTZAGID-OCBXBXKTSA-N

InChi Code: InChI=1S/C29H33O16P/c1-11-38-9-20-27(42-11)23(30)24(31)29(43-20)44-25-14-7-17-16(40-10-41-17)6-13(14)21(22-15(25)8-39-28(22)32)12-4-18(36-2)26(19(5-12)37-3)45-46(33,34)35/h4-7,11,15,20-25,27,29-31H,8-10H2,1-3H3,(H2,33,34,35)/t11-,15+,20-,21-,22+,23-,24-,25-,27-,29+/m1/s1

SMILES Code: O=P(O)(OC1=C(OC)C=C([C@H](C2=C3C=C4OCOC4=C2)[C@@]5([H])C(OC[C@]5([H])[C@@H]3O[C@H]6[C@H](O)[C@@H](O)[C@]7([H])O[C@H](C)OC[C@@]7([H])O6)=O)C=C1OC)O

Appearance: 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 668.54 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: Hu JL, Xu G, Lei L, Zhang WL, Hu Y, Huang AL, Cai XF. Etoposide phosphate enhances the acetylation level of translation elongation factor 1A in PLC5 cells. Z Naturforsch C. 2012 May-Jun;67(5-6):327-30. PubMed PMID: 22888539.

2: Lindsay H, Gaynon P. Anaphylactic reaction to etoposide phosphate. Pediatr Blood Cancer. 2012 Oct;59(4):765. doi: 10.1002/pbc.24183. Epub 2012 Apr 22. PubMed PMID: 22522419.

3: Collier K, Schink C, Young AM, How K, Seckl M, Savage P. Successful treatment with etoposide phosphate in patients with previous etoposide hypersensitivity. J Oncol Pharm Pract. 2008 Mar;14(1):51-5. PubMed PMID: 18337441.

4: Levitt NC, Propper DJ, Madhusudan S, Braybrooke JP, Echeta C, Te Poele R, Davies SL, Flanagan E, Hickson ID, Joel S, Ganesan TS. Pharmacokinetically guided phase I trial of topotecan and etoposide phosphate in recurrent ovarian cancer. Br J Cancer. 2005 Jul 11;93(1):60-9. PubMed PMID: 15956976; PubMed Central PMCID: PMC2361471.

5: Marigny K, Aubin F, Burgot G, Le Gall E, Gandemer V. Particular cutaneous side effects with etoposide-containing courses: is VP16 or etoposide phosphate responsible? Cancer Chemother Pharmacol. 2005 Mar;55(3):244-50. Epub 2004 Nov 4. PubMed PMID: 15526203.

6: Ragozina NY, Pütz M, Heissler S, Faubel W, Pyell U. Quantification of etoposide and etoposide phosphate in human plasma by micellar electrokinetic chromatography and near-field thermal lens detection. Anal Chem. 2004 Jul 1;76(13):3804-9. PubMed PMID: 15228358.

7: Braybrooke JP, Levitt NC, Joel S, Davis T, Madhusudan S, Turley H, Wilner S, Harris AL, Talbot DC. Pharmacokinetic study of cisplatin and infusional etoposide phosphate in advanced breast cancer with correlation of response to topoisomerase IIalpha expression. Clin Cancer Res. 2003 Oct 15;9(13):4682-8. PubMed PMID: 14581337.

8: Kim KY, Cho YJ, Jeon GA, Ryu PD, Myeong JN. Membrane-bound alkaline phosphatase gene induces antitumor effect by G2/M arrest in etoposide phosphate-treated cancer cells. Mol Cell Biochem. 2003 Oct;252(1-2):213-21. PubMed PMID: 14577595.

9: Dorr RT, Briggs A, Kintzel P, Meyers R, Chow HH, List A. Comparative pharmacokinetic study of high-dose etoposide and etoposide phosphate in patients with lymphoid malignancy receiving autologous stem cell transplantation. Bone Marrow Transplant. 2003 Apr;31(8):643-9. PubMed PMID: 12692603.

10: Demperio VL. Determination of etoposide phosphate intermediates by gradient liquid chromatography using postcolumn derivatization with cuprammonium hydroxide. J Chromatogr A. 2002 Apr 5;952(1-2):283-7. PubMed PMID: 12064540.



Additional Information

According to http://en.wikipedia.org/wiki/Etoposide, Etoposide phosphate (brand names: Eposin, Etopophos, Vepesid, VP-16) is a cancer drug. It inhibits the enzyme topoisomerase II, which unwinds DNA, and by doing so causes DNA strands to break. Cancer cells are less able to repair this damage than healthy cells. It is used as a form of chemotherapy for cancers such as Ewing's sarcoma, lung cancer, testicular cancer, lymphoma, non-lymphocytic leukemia, and glioblastoma multiforme. It is often given in combination with other drugs. It is also sometimes used in a conditioning regimen prior to a bone marrow or blood stem cell transplant. Its chemical make-up derives from podophyllotoxin, a toxin found in the American Mayapple. The name "VP-16"likely comes from a compounding of the last name of the chemists who performed early work on the drug (von Wartburg and von Kuhn) and podophyllotoxin[1]. Another chemist who was integral in the development of podophyllotoxin-based chemotherapeutics was Hartmann F. Stähelin.
 
DRUG DESCRIPTION
ETOPOPHOS (etoposide phosphate) for Injection is an antineoplastic agent which is available for intravenous infusion as a sterile lyophile in single-dose vials containing etoposide phosphate equivalent to 100 mg etoposide, 32.7 mg sodium citrate USP, and 300 mg dextran 40. Etoposide phosphate is a water soluble ester of etoposide (commonly known as VP-16), a semi-synthetic derivative of podophyllotoxin. The water solubility of etoposide phosphate lessens the potential for precipitation following dilution and during intravenous administration.