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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.
P S Manchand, and
R L Cerruti, and
J A Martin, and
C H Hill, and
J H Merrett, and
E Keech, and
R B Belshe, and
E V Connell, and
I S Sim
May 2006,
Bioorganic & medicinal chemistry,
P S Manchand, and
R L Cerruti, and
J A Martin, and
C H Hill, and
J H Merrett, and
E Keech, and
R B Belshe, and
E V Connell, and
I S Sim
December 2003,
Bioorganic & medicinal chemistry,
P S Manchand, and
R L Cerruti, and
J A Martin, and
C H Hill, and
J H Merrett, and
E Keech, and
R B Belshe, and
E V Connell, and
I S Sim
January 1973,
Acta microbiologica Polonica. Series A: Microbiologia generalis,
P S Manchand, and
R L Cerruti, and
J A Martin, and
C H Hill, and
J H Merrett, and
E Keech, and
R B Belshe, and
E V Connell, and
I S Sim
January 1977,
Voprosy virusologii,
P S Manchand, and
R L Cerruti, and
J A Martin, and
C H Hill, and
J H Merrett, and
E Keech, and
R B Belshe, and
E V Connell, and
I S Sim
January 1988,
Drug metabolism and disposition: the biological fate of chemicals,
P S Manchand, and
R L Cerruti, and
J A Martin, and
C H Hill, and
J H Merrett, and
E Keech, and
R B Belshe, and
E V Connell, and
I S Sim
January 1999,
Revista Argentina de microbiologia,
P S Manchand, and
R L Cerruti, and
J A Martin, and
C H Hill, and
J H Merrett, and
E Keech, and
R B Belshe, and
E V Connell, and
I S Sim
June 1968,
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan,
P S Manchand, and
R L Cerruti, and
J A Martin, and
C H Hill, and
J H Merrett, and
E Keech, and
R B Belshe, and
E V Connell, and
I S Sim
November 1987,
Acta virologica,
P S Manchand, and
R L Cerruti, and
J A Martin, and
C H Hill, and
J H Merrett, and
E Keech, and
R B Belshe, and
E V Connell, and
I S Sim
August 1999,
Bioorganic & medicinal chemistry,
P S Manchand, and
R L Cerruti, and
J A Martin, and
C H Hill, and
J H Merrett, and
E Keech, and
R B Belshe, and
E V Connell, and
I S Sim
January 1991,
Journal of natural products,
