title: 5-ethyl-5-phenylhydantoin N-glucuronide, the major urinary metabolite of 5-ethyl-5-phenylhydantoin (Nirvanol) in the dog.
abstract: A water-soluble metabolite, isolated from the urine of dogs given (S)-5-ethyl-5-phenylhydantoin [(S)-EPH], has been identified as 1-deoxy-1-[(5S)-5-ethyl-5-phenylhydantoin-3-yl] beta-D-glucopyranuronate [(S)-EPH N-glucuronide]. EPH N-glucuronide did not release the aglycone upon acid or beta-glucuronidase treatment, but incubation in alkaline solution (pH 12-13) readily formed 2-ethyl-2-phenylhydantoic acid (EPHA). The EPHA so formed could be quantitatively cyclized to EPH. With the knowledge of the conversion efficiency of EPH N-glucuronide to EPHA, a quantitative GLC assay for the metabolite was developed. EPH N-glucuronide was found to be the major urinary metabolite after administration to dogs of either (R)-, (S)-, or (RS)-EPH.
mesh_terms: D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D004285:Dogs; D005260:Female; D006827:Hydantoins / Q000378:metabolism* / Q000652:urine*; D008617:Mephenytoin / Q000031:analogs & derivatives / Q000378:metabolism* / Q000652:urine*; D013057:Spectrum Analysis / Q000379:methods
chemical_list: D006827:Hydantoins; C014544:ethylphenylhydantoin; C036947:5-ethyl-5-phenylhydantoin-N-glucuronide; D008617:Mephenytoin