Racemic and chiral sulfoxides as potential prodrugs of the COX-2 inhibitors Vioxx and Arcoxia.

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Caturla F, Amat M, Reinoso RF, Cordoba M, Warrellow G

Racemic and chiral sulfoxides as potential prodrugs of the COX-2 inhibitors Vioxx and Arcoxia.

Bioorg Med Chem Lett. 2006 Jun 15;16(12):3209-12. Epub 2006 Apr 17.

PubMed ID
16616494 [ View in PubMed
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Abstract

The preparation of the sulfoxide analogues 2 and 4, and their enantiomeric pure forms is discussed as well as their potential to act as prodrugs to the potent and selective sulfone-containing COX-2 inhibitors rofecoxib and etoricoxib. Sulfoxides 2 and 4 were shown to be effectively transformed in vivo into rofecoxib and etoricoxib, respectively, after oral administration in rats. In the case of sulfoxide 2, both a slightly improved pharmacokinetic profile and a better pharmacological activity in an arthritis model were seen when compared with rofecoxib.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
EtoricoxibProstaglandin G/H synthase 2IC 50 (nM)810N/AN/ADetails
RofecoxibProstaglandin G/H synthase 2IC 50 (nM)760N/AN/ADetails