Daunorubicin metabolites in human urine.

We studied the human metabolism of daunorubicin (D) by isolating and identifying metabolites from urine which retained the specific fluorescence properties of D. Metabolites were extracted by adsorption to polystyrene polymeric sorbants, separated on silicic acid columns and purified by thin-layer chromatography. Structures were determined by comparative chromatography, infrared, fluorescence and mass spectroscopy, and enzymatic and chemical degradation. D metabolites identified were daunorubicinol, daunorubicinol aglycone, deoxydaunorubicin aglycone, deoxydaunorubicinol aglycone, demethyl deoxydaunorubicinol aglycone, deoxydaunorubicinol aglycone 13-O-beta-glucuronide, demethyl deoxydaunorubicinol aglycone 4-O-sulfate and demethyl deoxydaunorubicinol aglycone 4-O-beta-glucuronide. Other metabolites have been purified but not identified. Human metabolism of D involves carbonyl reduction, reductive glycosidic cleavage, O-demethylation, O-sulfation and O-glucuronidation. Since daunorubicinol has biochemical properties similar to D, the metabolites may contribute to the pharmacologic and toxicologic effects credited to D.