synthesis and early development of hexadecyloxypropyl-cidofovir an oral antipoxvirus nucleoside phosphonate合成和早期发展hexadecyloxypropyl-cidofovir口服antipoxvirus核苷膦酸酯.pdfVIP

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synthesis and early development of hexadecyloxypropyl-cidofovir an oral antipoxvirus nucleoside phosphonate合成和早期发展hexadecyloxypropyl-cidofovir口服antipoxvirus核苷膦酸酯.pdf

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synthesis and early development of hexadecyloxypropyl-cidofovir an oral antipoxvirus nucleoside phosphonate合成和早期发展hexadecyloxypropyl-cidofovir口服antipoxvirus核苷膦酸酯

Viruses 2010, 2, 2213-2225; doi:10.3390/v2102213 OPEN ACCESS viruses ISSN 1999-4915 /journal/viruses Review Synthesis and Early Development of Hexadecyloxypropyl- cidofovir: An Oral Antipoxvirus Nucleoside Phosphonate Karl Y. Hostetler 1,2 1 Department of Medicine, Division of Infectious Disease, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0676, USA; E-Mail: khostetler@; Tel.: +1-858-552-8585; Fax +1-858-534-6133 2 Veterans Medical Research Foundation, San Diego, CA 92161, USA Received: 26 August 2010; in revised form: 8 September 2010 / Accepted: 8 September 2010 / Published: 30 September 2010 Abstract: Hexadecyloxypropyl-cidofovir (HDP-CDV) is a novel ether lipid conjugate of (S)-1-(3-hydroxy-2-phosphonoylmethoxypropyl)-cytosine (CDV) which exhibits a remarkable increase in antiviral activity against orthopoxviruses compared with CDV. In contrast to CDV, HDP-CDV is orally active and lacks the nephrotoxicity of CDV itself. Increased oral bioavailability and increased cellular uptake is facilitated by the lipid portion of the molecule which is responsible for the improved activity profile. The lipid portion of HDP-CDV is cleaved in the cell, releasing CDV which is converted to CDV diphosphate, the active metabolite. HDP-CDV is a highly effective agent against a variety of orthopoxvirus infections in animal models of disease including vaccinia, cowpox, rabbitpox and ectromelia.