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Variability of inversion of (R)-flurbiprofen in different species.

S Menzel-Soglowek¹, G Geisslinger, W S Beck

¹Department of Pharmacology and Toxicology, Erlangen, Germany.

Journal of Pharmaceutical Sciences

|September 1, 1992

Summary

Flurbiprofen chiral inversion varies by species. (R)-flurbiprofen converted to its S-form in dogs and guinea pigs, but not significantly in rats or gerbils. (S)-flurbiprofen did not convert to the R-form.

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Area of Science:

Pharmacology
Drug Metabolism
Chirality

Background:

The anti-inflammatory effects of 2-arylpropionic acids, such as flurbiprofen, are primarily attributed to their S-enantiomers.
A notable metabolic pathway for this drug class is chiral inversion, the conversion between enantiomers.

Purpose of the Study:

To investigate the occurrence and extent of chiral inversion of flurbiprofen enantiomers in various animal species.
To determine if administration of optically pure flurbiprofen enantiomers leads to inversion in dogs, guinea pigs, rats, and gerbils.

Main Methods:

Stereoselective high-performance liquid chromatography (HPLC) with a chiral alpha 1-acid glycoprotein column was used to quantify flurbiprofen enantiomers in plasma.
Pharmacokinetic analysis was performed using a two-compartment computer model.
Studies were conducted in dogs, guinea pigs, rats, and gerbils.

Main Results:

Significant inversion of (R)-flurbiprofen to (S)-flurbiprofen was observed in dogs (fraction inverted [Fi] = 0.39) and guinea pigs (Fi = 1.00).
Minimal inversion occurred in rats (Fi = 0.02) and gerbils (Fi = 0.05).
(R)-flurbiprofen was undetectable in plasma after intravenous administration of (S)-flurbiprofen to all tested species.

Conclusions:

Species-dependent chiral inversion of flurbiprofen is confirmed, with dogs and guinea pigs exhibiting significant inversion of the R-enantiomer.
The S-enantiomer of flurbiprofen appears to be metabolically stable, with no detectable conversion to the R-enantiomer observed across the studied species.