PMID: 7086655Apr 1, 1982Paper

O-Methylhydroxylamine as a new trapping reagent for quantitative studies of 4-hydroxycyclophosphamide and aldophosphamide

Journal of Pharmaceutical Sciences
G ZonL R Phillips


31P- and 1H-NMR spectroscopy were used to demonstrate that the primary metabolites of the anticancer drug cyclophosphamide (4-hydroxycyclophosphamide and its acyclic tautomer, aldophosphamide) are quantitatively converted by O-methylhydroxylamine, at pH 7.4 and 37 degrees, into the E and Z isomers of aldophosphamide O-methyl oxime. These trapping products are readily extracted from aqueous media with either chloroform or ethyl acetate, are stable at pH 6-8 toward oxime hydrolysis and elimination of phosphoramide mustard (a secondary metabolite of cyclophosphamide), and showed no evidence for transoximination with either ketone or aldehyde acceptors. All of these features support the use of aldophosphamide O-methyl oxime in quantitative studies related to cyclophosphamide metabolism.


May 19, 1995·Journal of Chromatography. B, Biomedical Applications·L W AndersonJ M Strong
Jul 20, 1999·Journal of Chromatography. B, Biomedical Sciences and Applications·F BaumannR Preiss

Related Concepts

Methoxyamine hydrochloride
4-hydroxycyclophosphamide, (trans)-isomer
Cyclophosphamide, (S)-Isomer
Drug Stability
In Vivo NMR Spectroscopy
Phosphoramide Mustards

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