Abstract
The dihydropyridine ⇌ pyridinium salt redox carrier based chemical delivery system (CDS) approach was applied to the antiviral agent 2′-fluoro-5-methylarabinosyluracil (FMAU) ( 1 ). Two CDSs were examined, having the redox carrier attached to the 3′-OH functionality and the 5′-OH group esterified with hexanoic ( 2a ) and octanoic acid ( 2b ), respectively. In vitro stability and in vivo distribution studies were performed. When 2a was systemically administered to rats, sustained levels of the oxidized, trigonelline ester ( 3a ) were found in brain. The parent drug was identified beginning at 4 h post-dosing. In the case of 2b, both the oxidized form ( 3b ) and the native 1 were found in brain at relatively high concentrations. No drug ( 1 ) was detected in brain after administration of an equivalent amount (50 μ mol/kg) of FMAU.
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