Racemic and chiral sulfoxides as potential prodrugs of 4-pyrone COX-2 inhibitors.

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Caturla F, Amat M, Reinoso RF, Calaf E, Warrellow G

Racemic and chiral sulfoxides as potential prodrugs of 4-pyrone COX-2 inhibitors.

Bioorg Med Chem Lett. 2006 Jul 1;16(13):3605-8. Epub 2006 May 2.

PubMed ID

16647258 [ View in PubMed

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Abstract

The preparation of the sulfoxide analogues 7, 8, and 9 and their enantiomerically pure forms is discussed as well as their ability to act as prodrugs of the potent and selective sulfone-containing COX-2 inhibitors 1, 2, and 3. Sulfoxide derivatives 7 and 9 were shown to be rapidly transformed in vivo into the corresponding sulfone derivatives 1 and 3, after oral administration to rats.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Etoricoxib	Prostaglandin G/H synthase 2	IC 50 (nM)	810	N/A	N/A	Details
Rofecoxib	Prostaglandin G/H synthase 2	IC 50 (nM)	760	N/A	N/A	Details