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Vol. 29, Issue 12, 1525-1528, December 2001
Drug Metabolism and Drug Disposition The formation of the N1-glucuronide metabolite
of each nicotine enantiomer was studied in pooled human liver
microsomes (n = 6). The metabolite formed from
natural S(
Group,
College of
Pharmacy and Nutrition,
University of Saskatchewan,
Saskatoon,
Saskatchewan, Canada
)-nicotine was identified by comparison of
the high-pressure liquid chromatography (HPLC) retention time and
positive ion electrospray ionization-mass spectral characteristics with
a synthetic reference standard. A radiometric HPLC method was used to
quantify the metabolite. The specificity of the assay method was
demonstrated by experiments in which 
-glucuronidase treatment of
incubated assay samples resulted in elimination of the peak due to the
N1-glucuronide metabolite. The glucuronides of
S()- and R(+)-nicotine were formed by
one-enzyme kinetics, with Km values of 0.11 and 0.23 mM and Vmax values of 132 and 70 pmol/min/mg of protein, respectively. There is marked stereoselectivity in the apparent intrinsic clearance values
(Vmax/Km) in that
the value for S()-nicotine is 4 times greater than for
the R(+)-isomer (1.2 versus 0.31 µl/min/mg of protein).
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