Quaternary ammonium glucuronide of croconazole in rabbits

Xenobiotica. 1989 Nov;19(11):1327-36. doi: 10.3109/00498258909043184.


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. beta-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.

MeSH terms

  • Animals
  • Chromatography
  • Chromatography, High Pressure Liquid
  • Glucuronates / isolation & purification
  • Glucuronates / metabolism*
  • Glucuronates / urine
  • Imidazoles / metabolism*
  • Magnetic Resonance Spectroscopy
  • Male
  • Mass Spectrometry
  • Rabbits
  • Spectrophotometry, Infrared


  • Glucuronates
  • Imidazoles
  • croconazole