Product Name

Zanamivir

CAS Number

139110-80-8

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Product Name:
Zanamivir
CAS Number:
139110-80-8
Indication:
For the prevention and treatment of influenza A and B.
Mode of Action:

The proposed mechanism of action of zanamivir is via inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release. By binding and inhibiting the neuraminidase protein, the drug renders the influenza virus unable to escape its host cell and infect others.

Pharmacodynamics:

Zanamivir, an antiviral agent, is a neuraminidase inhibitor indicated for treatment of uncomplicated acute illness due to influenza A and B virus in adults and pediatric patients 7 years and older who have been symptomatic for no more than 2 days. Zanamivir has also been shown to significantly inhibit the human sialidases NEU3 and NEU2 in the micromolar range (Ki 3.7 +/-0.48 and 12.9+/-0.07 microM, respectively), which could account for some of the rare side effects of zanamivir.

Metabolism:

Not metabolized

IUPAC:
(2R, 3R, 4S)-4-[(diaminomethylidene)amino]-3-acetamido-2-[(1R, 2R)-1, 2, 3-trihydroxypropyl]-3, 4-dihydro-2H-pyran-6-carboxylic acid
ATC:
J05AH01
PubChem:
60855
DrugBank:
DB00558 (APRD00378)
Formula:
C17H13ClN4
Molecular Mass:
332.3098
Synonyms:
GANA GNA Modified sialic acid Zanamavir ZMR
SMILES:
CC(=O)N[C@@H]1[C@H](C=C(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O)N=C(N)N
AHFS Code:
08:18.3
InChi:
ARAIBEBZBOPLMB-UFGQHTETSA-N
General Reference:
General Reference:

  1. Meindl P, Bodo G, Palese P, Schulman J, Tuppy H: Inhibition of neuraminidase activity by derivatives of 2-deoxy-2, 3-dehydro-N-acetylneuraminic acid. Virology. 1974 Apr;58(2):457-63. Pubmed
  2. von Itzstein M, Wu WY, Kok GB, Pegg MS, Dyason JC, Jin B, Van Phan T, Smythe ML, White HF, Oliver SW, et al.: Rational design of potent sialidase-based inhibitors of influenza virus replication. Nature. 1993 Jun 3;363(6428):418-23. Pubmed
  3. Hata K, Koseki K, Yamaguchi K, Moriya S, Suzuki Y, Yingsakmongkon S, Hirai G, Sodeoka M, von Itzstein M, Miyagi T: Limited Inhibitory Effects of Oseltamivir and Zanamivir on Human Sialidases. Antimicrob Agents Chemother. 2008 Aug 11. Pubmed
  4. Sugaya N, Tamura D, Yamazaki M, Ichikawa M, Kawakami C, Kawaoka Y, Mitamura K: Comparison of the clinical effectiveness of oseltamivir and zanamivir against influenza virus infection in children. Clin Infect Dis. 2008 Aug 1;47(3):339-45. Pubmed

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