Stereoselective plasma protein binding of ibuprofen enantiomers

A. M. Evans, R. L. Nation, L. N. Sansom, F. Bochner, A. A. Somogyi

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Abstract

We have developed a novel and reproducible method for determining the plasma protein binding of the two ibuprofen enantiomers in the presence of each other. The method involves the use of radiolabelled racemic ibuprofen, equilibrium dialysis, derivatization of the enantiomers to diastereomeric amides, high-performance liquid chromatography, and radiochemical analysis. We have determined the plasma protein binding of R(-)- and S(+)-ibuprofen in 6 healthy male volunteers after the oral administration of 800 mg racemic ibuprofen. The mean time-averaged percentage unbound of the R(-)-enantiomer, 0.419 was significantly less than that of the S(+)-enantiomer, 0.643, consistent with stereoselective plasma protein binding. The percentage unbound of each ibuprofen enantiomer was concentration-dependent over the therapeutic concentration range and was influenced by the presence of its optical antipode.

Original languageEnglish
Pages (from-to)283-290
Number of pages8
JournalEuropean Journal of Clinical Pharmacology
Volume36
Issue number3
DOIs
Publication statusPublished - 1 May 1989

Keywords

  • enantiomers
  • ibuprofen
  • pharmacokinetics
  • stereoselective protein binding

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