PT  - JOURNAL ARTICLE
AU  - C Fenselau
AU  - J P Lehman
AU  - A Myles
AU  - J Brandt
AU  - G S Yost
AU  - O M Friedman
AU  - O M Colvin
TI  - Iminocyclophosphamide as a chemically reactive metabolite of cyclophosphamide.
DP  - 1982 Nov 01
TA  - Drug Metabolism and Disposition
PG  - 636--640
VI  - 10
IP  - 6
4099  - http://dmd.aspetjournals.org/content/10/6/636.short
4100  - http://dmd.aspetjournals.org/content/10/6/636.full
SO  - Drug Metab Dispos1982 Nov 01; 10
AB  - 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.