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Isolation and characterization of the four antipyrine glucuronides and determination of their urinary excretion pattern in man by a reversed-phase h.p.l.c. assay.

A large-scale procedure for the isolation of four urinary glucuronides in antipyrine metabolism is described; the isolated compounds are used as standards in a direct h.p.l.c. assay. The four glucuronides were characterized by u.v. and 1H-n.m.r. spectroscopy, and after hydrolysis by a t.l.c. assay of the corresponding aglycones. A reversed-phase h.p.l.c. assay procedure has been developed for the direct quantification of the four antipyrine glucuronides; this separates 3-hydroxymethyl-antipyrine glucuronide, 4,4'-dihydroxy-antipyrine glucuronide, norantipyrine glucuronide and 4-hydroxy-antipyrine glucuronide in a single run. Urinary elimination patterns of these glucuronides have been determined in five female and five male volunteers after antipyrine (1200 mg) administration. The direct assay of urinary glucuronides enables the simultaneous determination of glucuronidation activities and four different phase-I metabolites of antipyrine in vivo.