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  • Title: Synthesis and antiviral activity of metabolites of rimantadine.
    Author: Manchand PS, Cerruti RL, Martin JA, Hill CH, Merrett JH, Keech E, Belshe RB, Connell EV, Sim IS.
    Journal: J Med Chem; 1990 Jul; 33(7):1992-5. PubMed ID: 2362279.
    Abstract:
    The hydroxy metabolites of rimantadine (3-5) were synthesized and compared to amantadine (1) and rimantadine (2) for their ability to inhibit the replication of influenza viruses in vitro. All three metabolites were inhibitory to wild-type influenza A viruses (H3N2 and H1N1). In particular, 2-hydroxyrimantadine (3) showed similar activity to amantadine, but the 3- and 4-hydroxy metabolites (4 and 5, respectively), both of which are found in rimantadine-treated patients, showed only modest inhibitory activity. A rimantadine-resistant isolate of influenza A virus exhibited cross-resistance to amantadine and to each of the metabolites 3-5. None of the compounds were effective against influenza B virus.
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