A stereoselective assay for bupropion and oxidative, reductive, and glucuronide metabolites (16 analytes total) in human urine was developed and validated.
A trifurcated sample preparation and analysis procedure was used for chiral analysis of (a) free bupropion and primary metabolites, (b) total hydroxybupropion after hydrolysis, and (c) glucuronide metabolites.
Erythrohydrobupropion and threohydrobupropion glucuronides underwent diastereomer-specific hydrolysis by β-glucuronidase.
Stereochemistry of glucuronide standards obtained from commercial sources was found to be incorrectly labeled, and the correct stereochemistry was unequivocally reassigned.
Urine concentration of bupropion and metabolite isomers were determined from a patient who received extended release (R,S)-bupropion.