Metabolic chiral inversion of 2-arylpropionic acid derivatives (profens)

Abstract

2-arylpropionic acid derivatives (profens) are one of the most popular anti-inflammatory, analgesic, and antipyretic drugs. They belong to a group of nonsteroidal anti-inflammatory drugs (NSAID) and exhibit metabolic chiral inversion. Enantiomers of these chiral drugs are often characterised by different pharmacological activity. It is estimated that the values of metabolic chiral inversion of ( R )-ibuprofen in humans are between 35 and 70%, depending on the condition of the liver and the intake of other medicines, while ( R )-flurbiprofen undergoes chiral metabolic inversion to its opposed ( S ) form only in small range. The described phenomenon in the case of ( R )-ketoprofen is limited to a maximum of around 10%. The metabolic chiral inversion is associated with potentially important pharmacotherapeutic and toxicological consequences, and so an attempt was made to analyse this phenomenon for the most commonly used drugs from the profens group.