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1: Med Chem. 2007 Nov;3(6):543-5.Click here to read Links

The preparation and human muscarinic receptor profiling of oxybutynin and N-desethyloxybutynin enantiomers.

Reitz AB, Gupta SK, Huang Y, Parker MH, Ryan RR.

Johnson & Johnson Pharmaceutical Research and Development, Welsh & McKean Rds., Spring House, PA 19477, USA. AReitz@PRDUS.JNJ.COM

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-CT(3)-scopolamine chloride ((3)H-NMS) binding on human cloned muscarinic m1-5 receptors. Compounds 1 and 2 potently displaced (3)H-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.

PMID: 18045203 [PubMed - indexed for MEDLINE]

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