[Use of high-field nulear magnetic resonance spectroscopy for the analysis of stereoselective metabolites of ibuprofen (R)-enantiomer in rat urine].

AIM: To study the metabolic chiral inversion and chiral metabolites of R-(-)-ibuprofen. METHODS: Following administration of R-(-)-ibuprofen (250 mg.kg-1), analysis was performed on rat urine purified extracts obtained by solid phase extraction onto C-18 bonded silica gel, then the metabolites of ibuprofen were detected and identified by 1HNMR spectroscopy. RESULTS: Except for a little ibuprofen, there were 2'-hydroxy-ibuprofen and its glucuronide, 1'-carboxy-ibuprofen glucuronide and ibuprofen glucuronide in rat urine. 2'-hydroxy-ibuprofen is the main metabolite. 1'-carboxy-ibuprofen glucuronide and ibuprofen glucuronide were diastereoisomers. CONCLUSION: There was the phenomenon of metabolic chiral inversion, whereby the R-enantiomer is transformed in vivo to its active S-antipode via an unusual process.