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Fenselau C, Lehman JP, Myles A, Brandt J, Yost GS, Friedman OM, Colvin OM: Iminocyclophosphamide as a chemically reactive metabolite of cyclophosphamide. Drug Metab Dispos. 1982 Nov-Dec;10(6):636-40.
Iminocyclophosphamide has been identified among the metabolites produced by incubation of cyclophosphamide with cytochrome P-450 mono-oxygenase immobilized on beaded Sepharose. The reactive imine was trapped by addition of hydrogen cyanide, and the product, 4-cyanocyclophosphamide, was identified by comparison of its chromatographic and mass-spectral properties with those of a synthetic standard. Iminocyclophosphamide was also generated chemically from 4-hydroperoxycyclophosphamide and characterized both by addition of hydrogen cyanide and by reduction with sodium borodeuteride. The synthesis of authentic 4-cyanocyclophosphamide is also reported. |
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