cis-trans-Isomerization of [E]-5-(2-bromovinyl)-2,2′-anhydrouridine in vivo in rats

I. Szinai Central Research Institute for Chemistry of the Hungarian Academy of Sciences, H-1525, Budapest, PO Box 17, Hungary

Zs. Veres Central Research Institute for Chemistry of the Hungarian Academy of Sciences, H-1525, Budapest, PO Box 17, Hungary

A. Szabolcs Central Research Institute for Chemistry of the Hungarian Academy of Sciences, H-1525, Budapest, PO Box 17, Hungary

E. Gács-Baitz Central Research Institute for Chemistry of the Hungarian Academy of Sciences, H-1525, Budapest, PO Box 17, Hungary

K. Ujszászy Central Research Institute for Chemistry of the Hungarian Academy of Sciences, H-1525, Budapest, PO Box 17, Hungary

G. Dénes Central Research Institute for Chemistry of the Hungarian Academy of Sciences, H-1525, Budapest, PO Box 17, Hungary

Abstract

1. [E]-5-(2-bromovinyl)-2,2′-anhydrouridine ([E]BVANUR) has considerable antiviral activity against herpes simplex virus type 1 (HSV-1).

2. [E]BVANUR is not a substrate of pyrimidine nucleoside phosphorylases, but it is an inhibitor of uridine phosphorylase (K_i=450 nM).

3. [E]BVANUR (trans-isomer, parent compound) undergoes isomerization to [Z]BVANUR (cis-isomer), the only metabolite in rat, which was identified by h.p.l.c., mass spectra and n.m.r. spectroscopy.

4. Absorption of the drug from the gastrointestinal tract after oral administration is minimal. Absorption of [E]BVANUR from the abdominal cavity after i.p. administration was slow.

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cis-trans-Isomerization of [E]-5-(2-bromovinyl)-2,2′-anhydrouridine in vivo in rats

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cis-trans-Isomerization of [E]-5-(2-bromovinyl)-2,2′-anhydrouridine in vivo in rats

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