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Xenobiotica
the fate of foreign compounds in biological systems
Volume 19, 1989 - Issue 11
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Research Article

Quaternary ammonium glucuronide of croconazole in rabbits

, , , , , & show all
Pages 1327-1336 | Received 10 Mar 1989, Accepted 05 May 1989, Published online: 22 Sep 2008
 

Abstract

1. A water-soluble croconazole glucuronide was isolated from the urine of rabbits dosed intravenously with croconazole, using XAD-2 column chromatography, reversed-phase RP-8 column chromatography and h.p.l.c.

2. β-Glucuronidase hydrolysis liberated unchanged croconazole from the glucuronide.

3. Secondary ion mass spectra, i.r. and n.m.r. spectroscopic studies, including two-dimensional n.m.r. techniques (ROESY and HETCOR), showed the metabolite to be a quaternary ammonium glucuronide of croconazole: i.e. a chemical bond exists between a nitrogen, having sp2 type orbital, in the imidazole ring of croconazole and the anomeric carbon of glucuronic acid.

4. The urinary excretion of the glucuronide amounted to 2.8±0.7% of dose (mean±SD, n =4) in rabbits.

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