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TABLE 14.8
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Ef cacy and Cytotoxicitya of Ether Lipid Esters of Cidofovir (CDV)
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Compound
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CIDOFOVIR SERIES
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Cidofovir
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PROPANEDIOL LINKERS
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Dodecyloxypropyl- (16)c Tetradecyloxypropyl- (18) Hexadecyloxypropyl- (20) Octadecyloxypropyl- (22) Oleyloxypropyl- (22:1)c Eicosyloxypropyl- (24)
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Octadecyloxyethyl- (21) Oleyloxyethyl- (21:1)
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Values are the mean of two or more assays standard deviation. Selectivity index (SI) CC50/EC50. c Values in parentheses are the number of atoms beyond the phosphonate oxygen; the number after the colon is the number of double bonds in the alkyl chain. Source: Adapted from Keith et al.51
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with activity declining sharply at 22 and 24 atoms. The oxyethyl analogues of CDV (ODE- and OLE-CDV) were generally more active than their oxypropyl counterparts (ODP- and OLP-CDV) even though they differ in the overall numbers of atoms by only one methylene. The enhancement in activity of the ether lipid esters appear to be due to their greater uptake into cells, resulting in a signi cant increase of intracellular levels of CDV.52 As summarized above, a number of these analogues had signi cantly enhanced activity and selectivity indices, suggesting that the best of these analogues need to be evaluated for their oral ef cacy in animal models of orthopoxvirus disease, particularly since the relative oral bioavailability of HDP-CDV and ODE-CDV ranges from 88% to 97%.53 A series of studies were then carried out by Quenelle and co-workers54 to determine the comparative ef cacy of parenteral CDV with oral HDP-CDV and ODE-CDV, on CV and VV infections of mice. Since we have reported previously that CDV is highly active in these models when given as single or multiple doses either prior to or after infection, similar studies were carried out with these analogues. In addition, we also determined the effect of oral treatment with HDP-CDV or ODE-CDV on the replication of CV or VV in important target organs. In initial experiments, HDP-CDV or ODE-CDV were administered once daily for 5 consecutive days by oral gavage to CV- or VV-infected mice beginning 24, 48, or 72 h post viral inoculation. CDV was given i.p. at similar doses and times of initiation of therapy. At the 6.7 mg/kg dose, no toxicity was observed and each compound signi cantly reduced nal mortality in CV-infected mice (p 0.01) at one or more times of initiation of therapy (Table 14.9). In mice inoculated with VV, both HDP-CDV and ODE-CDV signi cantly reduced mortality rates when treatment was initiated as late as 48 h post viral inoculation. Treatment with CDV also resulted in signi cant protection from mortality and at most times of initiation of treatment. In mice infected with ectromelia virus (mousepox), similar results were obtained to those seen above for VV and CV.48 At 10 mg/kg both analogues gave complete protection, whereas ODE-CDV was more effective at lower dosages than HDP-CDV. We have reported previously that CDV can protect mice infected with CV or VV when given as early as 5 days prior to infection.26 HDP-CDV and ODE-CDV were also evaluated for their prophylactic activity by treating mice by oral gavage beginning 5, 3, or 1 day prior to viral inoculation. The results in Table 14.10 indicated that HDP-CDV and ODE-CDV, as well as CDV, were highly protective against mortality due to CV infection when given 1 5 days prior to infection. CDV has also been reported by us and others to signi cantly reduce mortality of CV- or VV-infected mice with only one or two doses due to the long intracellular half-life of this drug.22,25,26 In a similar study, we gave HDP-CDV as a single dose on days 5, 3, or 1 prior to or on days 1 or 3 after intranasal CV inoculation. All regimens used provided signi cant protection from mortality at all times of initiation with both compounds (Table 14.11). In addition, CDV given as a single dose i.p. was also protective at all times of initiation of treatment. To determine the effect of treatment with HDP-CDV or ODE-CDV on the replication of VV in target organs of mice, animals were inoculated with VV and
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