RT Journal Article
SR Electronic
T1 Iminocyclophosphamide as a chemically reactive metabolite of cyclophosphamide.
JF Drug Metabolism and Disposition
JO Drug Metab Dispos
FD American Society for Pharmacology and Experimental Therapeutics
SP 636
OP 640
VO 10
IS 6
A1 Fenselau, C
A1 Lehman, J P
A1 Myles, A
A1 Brandt, J
A1 Yost, G S
A1 Friedman, O M
A1 Colvin, O M
YR 1982
UL http://dmd.aspetjournals.org/content/10/6/636.abstract
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.