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U.S. Department of Health and Human Services

Scientific Publications by FDA Staff

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J Pharm Sci 1982 Apr;71(4):443-6

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

Zon G, Ludeman SM, Sweet EM, Egan W, Phillips LR


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.

Category: Journal Article
PubMed ID: #7086655 DOI: 10.1002/jps.2600710417
Includes FDA Authors from Scientific Area(s): Biologics
Entry Created: 2012-12-09