Pulmonary inversion of 2-arylpropionic acids: influence of protein binding

Chirality. 1992;4(6):349-52. doi: 10.1002/chir.530040604.

Abstract

The possible contribution of pulmonary metabolism to the putative first-pass metabolism of 2-arylpropionic acid nonsteroidal antiinflammatory drugs has not been documented. Isolated perfused rabbit lungs, perfused with 4.5% bovine serum albumin or 5% dextran, were used to study the pulmonary elimination of (R)- and rac-ibuprofen, fenoprofen, and flurbiprofen. In the absence of protein binding, ibuprofen was metabolized via inversion and other pathways, whereas fenoprofen metabolism was essentially restricted to inversion of the (R)-enantiomer; fraction inverted (+/- SE) was 0.37 +/- 0.05 for (R)-ibuprofen and 0.85 +/- 0.03 for (R)-fenoprofen. In the presence of protein, neither ibuprofen nor fenoprofen was metabolized. Flurbiprofen did not undergo pulmonary elimination under any condition studied. This study illustrates that even though a tissue is capable of metabolism, particularly inversion of 2-arylpropionics, the quantitative importance of such elimination pathways may be minimal in the presence of the high degree of protein binding that is characteristic of these drugs.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Fenoprofen / metabolism*
  • Flurbiprofen / metabolism*
  • Ibuprofen / metabolism*
  • In Vitro Techniques
  • Lung / metabolism*
  • Male
  • Molecular Conformation
  • Protein Binding
  • Rabbits
  • Serum Albumin, Bovine / metabolism
  • Stereoisomerism

Substances

  • Serum Albumin, Bovine
  • Flurbiprofen
  • Fenoprofen
  • Ibuprofen