117091-64-2

Basic information

• Product Name: Etoposide phosphate
• Synonyms: ETOPOPHOS;ETOPOSIDE PHOSPHATE;ETOPOSIDE PHOSPHONATE;ETOPOSIDE PHOSPHONATE, ETOPOPHOS;Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5-[3,5-dimethoxy-4-(phosphonooxy)phenyl]-9-[[4,6-O-(1R)-ethylidene-b-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-, (5R,5aR,8aR,9S)-;ETOPOSIDEPHOSPHATE,ETOPOPHOS;Etoposide 4'-Phosphate;(5R,5aR,8aR,9S)-5-[3,5-DiMethoxy-4-(phosphonooxy)phenyl]-9-[[4,6-O-(1R)-ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
• CAS NO: 117091-64-2
• Molecular Formula: C29H33O16P
• Molecular Weight: 668.54
• EINECS: 1312995-182-4
• Product Categories: Carbohydrates & Derivatives;Drug Analogues;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Antineoplastic
• Mol File: 117091-64-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 798.1 °C at 760 mmHg
• Flash Point: 263.6 °C
• Appearance: /
• Density: 1.55 g/cm³
• Storage Temp.: -20°C
• PKA: 1.13±0.50(Predicted)
• CAS DataBase Reference: Etoposide phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Etoposide phosphate(117091-64-2)
• EPA Substance Registry System: Etoposide phosphate(117091-64-2)

Safety Data

• Hazardous Substances Data: 117091-64-2(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Uses

As a bioequivalent prodrug of the DNA topoisomerase II inhibitor Etoposide (E933750), Etoposide phosphate can be used in the treatment of a wide variety of hematological malignancies and solid tumors.

Brand name

Etopophos (Bristol-Myers Squibb).

Upstream product

• 6559-91-7 4'-demethylepipodophyllotoxin 
• 33419-42-0 etoposide 
• 18623-11-5 octadecyl silane 

Related news

Short communicationDetermination of Etoposide phosphate (cas 117091-64-2) intermediates by gradient liquid chromatography using postcolumn derivatization with cuprammonium hydroxide09/03/2019

Allyl 4,6-O-ethylidene-β-d-glucopyranoside is an intermediate used in the synthesis of etoposide phosphate, a water-soluble derivative of the antineoplastic drug etoposide. In this paper, a method for the determination of allyl 4,6-O-ethylidene-β-d-glucopyranoside and related glucopyranosides ...detailed

RESEARCHPhysical and Chemical Stability of Etoposide phosphate (cas 117091-64-2) Solutions09/01/2019

ObjectiveTo evaluate the physical and chemical stability of etoposide phosphate solutions over 7 days at 32°C and 31 days at 4°C and 23°C: (1) at etoposide concentrations of 0.1 and 10 mg/mL as phosphate in 0.9% sodium chloride injection and 5% dextrose injection and (2) at etoposide concentr...detailed

Short communicationPhase I and pharmacokinetic study of a water-soluble etoposide prodrug, Etoposide phosphate (cas 117091-64-2) (BMY-40481)08/31/2019

Etoposide phosphate is a water-soluble prodrug of etoposide. A phase I and pharmacokinetic study has been performed over the dose range 25–110 mg/m2/day for 5 days (etoposide equivalent doses). The maximum tolerated dose (MTD) was 110 mg/m2/day for 5 days every 3 weeks and the dose-limiting tox...detailed

Etoposide phosphate (cas 117091-64-2) or etoposide with cisplatin in the treatment of small cell lung cancer: Randomized Phase II trial08/29/2019

Etoposide phosphate, a water soluble prodrug of etoposide, has several potential advantages including easier and more rapid administration, avoidance of large fluid loads, and elimination of hypersensitivity reactions and other problems related to the solubilizer. This randomized Phase II study ...detailed

Research ArticlePharmaceutics, Drug Delivery and Pharmaceutical TechnologyTransdermal Delivery of Etoposide phosphate (cas 117091-64-2) II: In Vitro In Vivo Correlations (IVIVC)08/26/2019

A dependable in vitro in vivo correlation (IVIVC) is a vital tool to optimize drug formulation and expedite product development time. Although many IVIVC examples are available for oral delivery systems, IVIVC for transdermal delivery is far less common, especially for electrical-assisted delive...detailed

Research ArticlePharmaceutics, Drug Delivery and Pharmaceutical TechnologyTransdermal Delivery of Etoposide phosphate (cas 117091-64-2) I: In Vitro and In Vivo Evaluation08/25/2019

Cancer chemotherapy frequently requires long periods of multiple intravenous infusions that often results in patients opting out of treatment. The main purpose of this study was to investigate the feasibility of delivering one of these anticancer agents: etoposide phosphate (ETP) transdermally u...detailed

Relevant articles and documents

Efficient synthesis of the anticancer drug etoposide 4′-phosphate: Use of benzylic ether-protecting groups on the carbohydrate segment

The prodrug etoposide phosphate 2 is synthesized efficiently in three steps in 54.6% overall yield from 4′-demethylepipodophyllotoxin 3. The strategy pursued in the synthesis of 2 places the phosphate on 3 prior to coupling with the sugar and employs benzyl ether-protecting groups on both the phosphate and the sugar, allowing easy removal in one step. The importance of solvent, steric effects, and electronic effects in the coupling reaction is demonstrated. Two features of the synthesis are an unusual thermal anomerization of the carbohydrate component 5a and completely diastereoselective, one-pot crystallization of the coupled product 6a-β. The process has been demonstrated on multi-kilogram scale.

Antibody-enzyme conjugates in combination with prodrugs for the delivery of cytotoxic agents to tumor cells

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