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Synthesis of a water-soluble prodrug of entacapone
J Leppänen1, J Huuskonen, J Savolainen
1Department of Pharmaceutical Chemistry, University of Kuopio, Finland. jukka.leppanen@uku.fi
Bioorganic & Medicinal Chemistry Letters
|September 15, 2000
Abstract:
Entacapone was reacted with phosphorous oxychloride in dry pyridine to yield a phosphate ester. The phosphate promoiety increased aqueous solubility of the parent drug by more than 1700- and 20-fold at pH 1.2 and 7.4, respectively. The phosphate ester provides adequate stability (t(1/2) = 2227 h; pH 7.4) towards chemical hydrolysis, and allowed for release of the parent drug via enzymatic hydrolysis in liver homogenate.