University of North Florida
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Stuart Chalk, Ph.D.
Department of Chemistry
University of North Florida
Phone: 1-904-620-1938
Fax: 1-904-620-3535
Email: schalk@unf.edu
Website: @unf

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Etoposide

  • IUPAC Name: (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]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
  • Molecular Formula: C29H32O13
  • CAS Registry Number: 33419-42-0
  • InChI: 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

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Citations 4

"Online Electrochemical Derivatization Combined With Diode Array Detection In Flow Injection Analysis. Rapid Determination Of Etoposide And Teniposide In Blood Plasma"
Anal. Chim. Acta 1987 Volume 202, Issue 1 Pages 35-47
M. A. J. Van Opstal, J. S. Blauw, J. J. M. Holthuis, W. P. Van Bennekom and A. Bult

Abstract: The cited antineoplastic agents (I and II, respectively) are oxidized electrochemically in a flow-through cell equipped with two porous-graphite working electrodes, followed by spectrophotometric detection of the respective o-quinone compounds at 365 nm. Plasma (1 ml) is extracted with 2 mL of 1,2-dichloroethane and, after centrifuging for 2 min at 2500 g, 1 mL of the organic layer is evaporated to dryness. The residue is dissolved in 100 to 200 µL of carrier solution [Britton - Robinson buffer solution (pH 4) - methanol (1:1)] and a 25 µL portion of this solution is injected into the carrier stream (0.2 mL min-1). The optimum oxidation potentials for I and II were +500 and +450 mV (vs. a proprietary reference electrode), respectively. Calibration graphs were rectilinear in the range 1 to 50 µg mL-1 of I or II, and the limit of detection was 6 ng for each compound. For 2.5 and 25 µg mL-1 of I or II, the coefficient of variation were 6.5 and 3.2%, respectively. Recovery of 10 µg mL-1 of I or II was 95.7 ± 2.7% (n = 6) and the max. injection frequency was 40 h-1. Potential interference from catecholamines and metabolites is discussed.
Blood Plasma Clinical analysis Spectrophotometry Electrode Electrochemical product conversion Interferences Optimization

"Comparison Of Flow Injection Analysis With High Performance Liquid Chromatography For The Determination Of Etoposide In Plasma"
J. Chromatogr. B 1988 Volume 432, Issue 1 Pages 395-400
M. A. J. Van Opstal and P. Krabbenborg, J. J. M. Holthuis, W. P. Van Bennekom and A. Bult

Abstract: HPLC was performed with use of a guard column (2 cm x 3.9 mm) of LiChrosorb RP-18 (5 to 10 µm), an analytical column (7.5 cm x 3.9 mm) of Novapak phenyl and an electrochemical detector; the mobile phase (1 mL min-1) was 10 mM phosphate buffer (pH 7) - methanol (9:11). The apparatus and conditions for flow injection analysis were as described previously (Anal. Abstr., 1988, 50, 8D97). Both methods produced rectilinear calibration graphs but flow injection analysis had high blank responses due to interfering plasma components. Detection limits were 1.5 and 0.15 µg mL-1 by flow injection analysis and HPLC, respectively. Flow injection analysis is a good alternative to HPLC for determination of I in plasma for >1.5 µg mL-1.
Blood Plasma HPLC Interferences Method comparison

"Online FIA System Based On Electrochemical Derivatization And Spectrophotometric And Fluorimetric Detections"
J. Flow Injection Anal. 1991 Volume 8, Issue 1 Pages 49-49
T. Yamane

Abstract: A brief review is presented, with 4 references, of the development of online FIA systems with use of electrochemical derivatization and spectrophotometric and fluorimetric detection methods. Applications discussed include the dermination of etoposide, teniposide, homovanillic acid and thiamine in biological materials.
Biological Fluorescence Spectrophotometry Review Electrochemical product generation

"Current Status Of Bioanalysis Of Etoposide And Related Compounds"
J. Food Drug Anal. 1995 Volume 3, Issue 4 Pages 209-232
KUO-HSIUNG LEE AND HUI-KANG WANG

Abstract: Etoposide (VP16 or VP16-213) which was approved by the United States FDA for testicular cancer in 1983, is one of the most effective anticancer agents in the treatment of testicular teratoma, Hodgkin's and non-Hodgkin's lymphomas, small-cell lung cancer, and a variety of other malignancies. Development of bioanalytical methods for VP16 and its metabolites is critical for pharmacokinetic and metabolic studies as well as for mechanisms of action studies. In this review, the current status of the bioanalysis of VP16 and its metabolites are discussed. Recent progress in mechanism of action and metabolism studies is also presented. A number of HPLC methods employing UV, fluorescence, or electrochemical detection are available for the bioanalysis of VP16 and its metabolites. Most of these HPLC methods are sensitive and reliable enough for determining the parent drugs and their metabolites in biological fluids. In addition to radioimmunoassay, enzyme-linked immunosorbent assay (ELISA) for VP16, which is the most sensitive assay method to date, has been developed based on modern immunoassay technology. The primary pharmacological and pharmacokinetic data of GL331, a new derivative of epipodophyllotoxin discovered and developed in author's laboratory, which has shown superior antitumor activity to that of VP16, are also discussed. (FIA is used!)
Pharmaceutical HPLC Fluorescence Review