Ifosfamide stereoselective dichloroethylation and neurotoxicity

Wainer, Irving W.; Ducharme, Julie; Granvil, Camille; Trudeau, Marc; Leyland‐Jones, Brian

doi:10.1016/s0140-6736(94)90109-0

Cited by 32 publications

(15 citation statements)

References 5 publications

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“…Since IF-related CNS toxicity has been associated with increased production of (R)-3-DCl-IF [9,16], the enantioselective resolution of (R,S)-3-DCl-IF was one of the key acceptance criteria for the bioanalytical assay. One of the advantages of the Chirabiotic T CSP is that it has been shown to achieve enantioselective separations in reversed phase, normal phase and polar organic modes [29].…”

Section: Optimization Of the Chromatographic Conditionsmentioning

confidence: 99%

“…The hepatic metabolism of IF has been extensively studied and occurs in the liver by two major pathways, Fig. 1 [6][7][8][9][10][11]. One pathway involves the 4-hydroxylation of IF and eventually leads to the production of the cytotoxic isophosphoramide mustard [6].…”

Section: Introductionmentioning

confidence: 99%

“…Clinically, the N-dechloroethylation pathway has been associated with treatment-ending central nervous system (CNS) toxicity [5,[7][8][9]. The N-dechloroethylation pathway is regioselective and enantioselective [10,11] and, as a result, (R)-IF and (S)-IF have distinct efficacy and toxicity profiles.…”

Section: Introductionmentioning

confidence: 99%

“…The N-dechloroethylation pathway is regioselective and enantioselective [10,11] and, as a result, (R)-IF and (S)-IF have distinct efficacy and toxicity profiles. Clinical studies and in in vitro experiments have demonstrated that (S)-IF is more extensively cleared by N-dechloroethylation than (R)-IF [9,[14][15][16][17]. In addition, clinical studies have indicated that treatment related CNS toxicities were associated with inter-patient variations in the cumulative urinary excretion of the (S)-IF metabolite (R)-3-DCl-IF [9,16].…”

Section: Introductionmentioning

confidence: 99%

“…Clinical studies and in in vitro experiments have demonstrated that (S)-IF is more extensively cleared by N-dechloroethylation than (R)-IF [9,[14][15][16][17]. In addition, clinical studies have indicated that treatment related CNS toxicities were associated with inter-patient variations in the cumulative urinary excretion of the (S)-IF metabolite (R)-3-DCl-IF [9,16]. Thus, it is important that clinical studies include an enantioselective determination of the disposition of (R)-and (S)-IF as well as a measurement of the relative concentrations of their N-decholorethylated metabolites [16,17].…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective liquid chromatography–mass spectrometry assay for the determination of ifosfamide and identification of the N-dechloroethylated metabolites of ifosfamide in human plasma

Oliveira

Onorato

Siluk

et al. 2007

Journal of Pharmaceutical and Biomedical Analysis

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The lower limit of detection (LLOD) was 5.00 ng/ml. The inter-and intra-day precision ranged from 3.63 to 15.8 % relative standard deviation (RSD) and 10.1 to 14.3 % RSD, respectively, and the accuracy ranged from 89.2 to 101.5 % of the nominal values. The method was applied to the analysis of plasma samples obtained from a cancer patient who received 3.75 g/m 2 /d dose of (R,S)-ifosfamide as a 96-h continuous infusion.

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Section: Optimization Of the Chromatographic Conditionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Enantioselective liquid chromatography–mass spectrometry assay for the determination of ifosfamide and identification of the N-dechloroethylated metabolites of ifosfamide in human plasma

Oliveira

Onorato

Siluk

et al. 2007

Journal of Pharmaceutical and Biomedical Analysis

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The therapeutic promise of single enantiomers: introduction

Wainer

2001

Hum. Psychopharmacol. Clin. Exp.

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This review uses several examples drawn from the literature to show how using active enantiomers as therapeutic agents may yield several benefits, including more predictable pharmacokinetics, more accurate drug monitoring and enhanced tolerability. As a result of these benefits, the therapeutic use of single enantiomers will become increasingly important not only in psychopharmacology, but in medicine generally. Indeed, over the early years of the new millennium, the therapeutic use of single active enantiomers is set to redefine the benefit-risk ratio in the management of many common conditions. Copyright 2001 John Wiley & Sons, Ltd.

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High-Performance Liquid Chromatographic–Fluorescent Method to Determine Chloroacetaldehyde, a Neurotoxic Metabolite of the Anticancer Drug Ifosfamide, in Plasma and in Liver Microsomal Incubations

Huang

Waxman

1999

Analytical Biochemistry

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Ifosfamide stereoselective dichloroethylation and neurotoxicity

Cited by 32 publications

References 5 publications

Enantioselective liquid chromatography–mass spectrometry assay for the determination of ifosfamide and identification of the N-dechloroethylated metabolites of ifosfamide in human plasma

Enantioselective liquid chromatography–mass spectrometry assay for the determination of ifosfamide and identification of the N-dechloroethylated metabolites of ifosfamide in human plasma

The therapeutic promise of single enantiomers: introduction

High-Performance Liquid Chromatographic–Fluorescent Method to Determine Chloroacetaldehyde, a Neurotoxic Metabolite of the Anticancer Drug Ifosfamide, in Plasma and in Liver Microsomal Incubations

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