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


CONCLUSIONS
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.
Yang
C
C
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
He
W Y
WY
Kong
M
M
Xu
R M
RM
Zhang
S R
SR
Si
Y K
YK
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000493:pharmacokinetics / Q000652:urine*; D005260:Female; D007052:Ibuprofen / Q000493:pharmacokinetics / Q000652:urine*; D009682:Magnetic Resonance Spectroscopy; D051381:Rats; D017208:Rats, Wistar
D000894:Anti-Inflammatory Agents, Non-Steroidal; D007052:Ibuprofen