Iminocyclophosphamide as a chemically reactive metabolite of cyclophosphamide.
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.
D000818:Animals; D001711:Biotransformation; D055598:Chemical Phenomena; D002621:Chemistry; D003520:Cyclophosphamide / Q000031:analogs & derivatives* / Q000378:metabolism; D003577:Cytochrome P-450 Enzyme System; D004800:Enzymes, Immobilized; D007097:Imines / Q000378:metabolism; D013058:Mass Spectrometry; D010105:Oxygenases / Q000378:metabolism; D011817:Rabbits
D004800:Enzymes, Immobilized; D007097:Imines; D003520:Cyclophosphamide; D003577:Cytochrome P-450 Enzyme System; D010105:Oxygenases