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The Preparation and Human Muscarinic Receptor Profiling of Oxybutynin and N-Desethyloxybutynin Enantiomers

[ Vol. 3 , Issue. 6 ]


Allen B. Reitz, Suneel K. Gupta, Yifang Huang, Michael H. Parker and Richard R. Ryan   Pages 543 - 545 ( 3 )


Oxybutynin (1) is a non-selective muscarinic receptor antagonist that is used clinically for the treatment of urinary incontinence. The major metabolite of oxybutynin in humans is desethyloxybutynin (2). We have prepared the enantiomers of 1 and 2 and evaluated their ability to displace N-CT3-scopolamine chloride (3H-NMS) binding on human cloned muscarinic m1-5 receptors. Compounds 1 and 2 potently displaced 3H-NMS binding at m1, m3 and m4 receptors, but were less potent at the m2 and m5 subtypes. However, metabolite 2 was more potent than the parent compound 1 in the binding assay. In general the R enantiomers were more potent than their respective S enantiomers. Therefore, we suggest that the cholinergic side effects associated with 2 may be due to its greater apparent potency with m1 and m3 receptors, especially of its R-enantiomer, when compared with parent drug 1.


CHO cells, muscarinic receptors, desethyloxybutynin, oxybutynin therapy, binding assay


Johnson&Johnson Pharmaceutical Research and Development, Welsh&McKean Rds., Spring House, PA 19477, USA.

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