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Journal of Pharmacology And Experimental Therapeutics, Vol. 182, Issue 1, 70-76, 1972
Copyright © 1972 by American Society for Pharmacology and Experimental Therapeutics

IDENTIFICATION OF NEW METABOLITES OF DAUNOMYCIN AND ADRIAMYCIN

F. J. BULLOCK 1, R. J. BRUNI 1, and M. A. ASBELL 1

1 Life Sciences Division, Arthur D. Little, Inc., Acorn Park, Cambridge, Massachusetts

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 (Dx, I) and 8-acetyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5, 12-naphthacenedione (Dy, 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 (Ay, IV) and 8-(1,2-dihydroxyethyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5, 12-napthacenedione (Ax, 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.

Submitted on November 19, 1971
Accepted on April 4, 1972






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