F. J. Bullock, R. Bruni, M. A. Asbell
Jul 1, 1972
Citations
0
Influential Citations
26
Citations
Journal
The Journal of pharmacology and experimental therapeutics
Abstract
Two new metabolites of daunomycin have been identified as 8-(1-hydroxyethyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5, 12-naphthacenedione (D x , I) and 8-acetyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5, 12-naphthacenedione (D y , II). Two similar metabolites of adriamycin have been identified as 8-hydroxyacetyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5, 12-napthacenedione (A y , IV) and 8-(1,2-dihydroxyethyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5, 12-napthacenedione (A x , V), characterized as its diacetate (III). These metabolites arise by an unusual reductive cleavage of the O-glycosidic linkage of the parent drugs. The metabolites have been identified by application of infrared spectroscopy, high resolution mass spectroscopy and, in two cases, Fourier transform proton magnetic resonance spectroscopy. The latter technique appears to be a sensitive and useful adjunct to mass spectroscopy in structure elucidation of drug metabolites.