Sympathomimetic enantiomers and asthma

Chiral analysis of bambuterol, its intermediate and active drug in human plasma by liquid chromatography–tandem mass spectrometry: Application to a pharmacokinetic study

“…Optically pure individual enantiomers of bambuterol have been successfully produced by asymmetric synthesis [7][8]. Previous study has demonstrated that S-bambuterol (distomer) was less active and caused adverse cardiac toxic effects, while R-bambuterol (eutomer) displayed high anti-bronchospasm effects [9][10]. It is generally known that the enantiomers of a chiral drug usually display pharmacological and pharmacokinetic processes in an enantioselective manner [11][12].…”

Validation of a chiral HPLC assay for (R)-salbutamol sulfate

“…This is the case of (±)-salbutamol, in which the R-isomer is the most active enantiomer, responsible for all bronchial airway benefits [4] while the S-isomer induces hypersensitivity in the airways [5] and is metabolized more slowly than the R-isomer [6].…”

Development of safer molecules through chirality

“…[12] To add to this, later studies have found that the S enantiomer is not completely inert; it rather induces airway hyper-reactivity, eventually contributing to increased morbidity and mortality in patients with asthma. [13,14] Clinical studies have shown that it is at least twice as potent as the racemate. [15,16] Esketamine: Anesthesia with smoother recovery In vitro and in vivo anesthetic and analgesic pharmacological studies have shown that S ketamine is two to three times more potent than racemic ketamine.…”