Table of Contents
Pharmaceuticals, Volume 12, Issue 1 (March 2019)
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Cover Story (view full-size image) Tolterodine is a chiral drug with muscarinic receptor antagonist activity, patented and marketed as [...] Read more. Tolterodine is a chiral drug with muscarinic receptor antagonist activity, patented and marketed as L-tartrate salt of (R)-enantiomer. The absolute configuration of tolterodine was ambiguously defined in the original patents, and only later established by X-ray analysis. We report the first chiroptical investigation of tolterodine by electronic and vibrational circular dichroism (ECD and VCD), including solvent effects and temperature dependence. The CD-based combined experimental/computational approach allows a safe assignment of the absolute configuration of a chiral drug, independent of chemical correlations with other chiral compounds. The existing literature does not ultimately prove the enantioselective calcium antagonist and anticholinergic mode of action of tolterodine, posing a question on the necessity of using this drug in its enantiomerically pure form rather than as a racemate. View this paper.