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Chemical Characteristic

Product NameZanamivir
SynonymsRelenza, GG167
CAS No.139110-80-8
Molecular Weight 332.31
FormulaC12H20N4O7
Chemical Name(2R,3R,4S)-3-Acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
SmilesC1([C@@H]([C@H](C=C(O1)C(=O)O)NC(=N)N)NC(=O)C)[C@@H]([C@@H](CO)O)O
Chemical Structure

Biological activities

Zanamivir is a potent and selective neuraminidase inhibitor which is used in the treatment and prophylaxis of influenza caused by influenza A virus and influenza B virus. Zanamivir interacts with conserved residues in the active site of the NA enzyme.[1] Zanamivir inhibits the subtype H1N1 (N1), H3N2 (N2), and B Nas with IC50 of 0.76, 1.82, and 2.28 nM, respectively. The mean IC50s of zanamivir for the N2 viruses were 2.17 and 1.48 nM, respectively, in both of chemiluminescent and fluorescent assays while the mean zanamivir IC50s for the N1 viruses is 0.61 and 0.92 nM by the chemiluminescent and fluorescent assays, respectively. [2] In another study, viruses containing a N1 neuraminidase shows a slightly higher level of sensitivity to zanamivir than to oseltamivir carboxylate, with mean IC50 of 0.37 and 0.66 nM, respectively, while N2 strains is more sensitive to oseltamivir carboxylate with IC50 of 0.31 nM versus 1.04 nM for zanamivir.[3] Zanamivir prevented plaque-forming of all EIVs in MDCK cells with IC50 ranging from 0.016 to 89 nM. [4] Intranasally administered GG167 at doses of 0.4 and 0.01 mg/kg of body weight per dose decreased mortality, lung consolidation, and virus titers in the lung, with no virus growing back following the cessation of treatment in mice infected (day 0) with influenza A/Singapore/1/57 virus. G167 was stably metabolized, with an elimination half-life of 10 minutes post intravenous injection.[5] In another study, after intranasal injection in ferrets, GG167 is at least 100 to 1,000 times more effective than ribavirin and amantadine against influenza A and B viruses. Even though treatments are delayed until 24 hours postinfection GG167 retains activity. [6]

References

[1] Barnett JM, et al. Zanamivir susceptibility monitoring and characterization of influenza virus clinical isolates obtained during phase II clinical efficacy studies. Antimicrob Agents Chemother. 2000, 44(1): 78-87.
[2] McKimm-Breschkin J, et al. Neuraminidase sequence analysis and susceptibilities of influenza virus clinical isolates to zanamivir and oseltamivir. Antimicrob Agents Chemother. 2003, 47(7): 2264-2272.
[3] Hurt AC, et al. Susceptibility of human influenza viruses from Australasia and South East Asia to the neuraminidase inhibitors zanamivir and oseltamivir. Antiviral Res. 2004, 62(1): 37-45.
[4] Yamanaka T, et al. In vitro efficacies of oseltamivir carboxylate and zanamivir against equine influenza A viruses. J Vet Med Sci. 2006, 68(4): 405-408.
[5] Ryan DM, et al. Inhibition of influenza virus replication in mice by GG167 (4-guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid) is consistent with extracellular activity of viral neuraminidase (sialidase). Antimicrob Agents Chemother. 1994, 38(10): 2270-2275.
[6] Ryan DM, et al. GG167 (4-guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid) is a potent inhibitor of influenza virus in ferrets. Antimicrob Agents Chemother. 1995, 39(11): 2583-2584.

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