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SML0492

Sigma-Aldrich

Zanamivir

≥98% (HPLC)

Synonym(s):

4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid, 4-Guanidino-Neu5Ac2en

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About This Item

Empirical Formula (Hill Notation):
C12H20N4O7
CAS Number:
139110-80-8
Molecular Weight:
332.31
MDL number:
MFCD00866966
UNSPSC Code:
12352200
PubChem Substance ID:
329825442
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +30 to +40°, c = 1 in H2O

color

white to beige

solubility

H2O: 10 mg/mL, clear

storage temp.

room temp

SMILES string

CC(=O)N[C@@H]1[C@@H](NC(N)=N)C=C(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O

InChI

1S/C12H20N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h2,5-6,8-10,17,19-20H,3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16)/t5-,6+,8+,9+,10+/m0/s1

InChI key

ARAIBEBZBOPLMB-UFGQHTETSA-N

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Application

Zanamivir has been used:
  • as a neuraminidase inhibitor to study its effects on influenza A virus (IAV) like particles
  • as a neuraminidase inhibitor to study its effects on lipopolysaccharide (LPS)-mediated pathology in sepsis
  • as an antiviral to study its effects on influenza B virus by plaque reduction assay

Biochem/physiol Actions

Zanamivir exhibits therapeutic effects against influenza caused by influenza virus A and B.
Zanamivir is an influenza viral neuraminidase inhibitor.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mila B Ortigoza et al.
mBio, 15(2), e0220323-e0220323 (2024-01-11)
The ongoing transmission of influenza A viruses (IAV) for the past century continues to be a burden to humans. IAV binds terminal sialic acids (SA) of sugar molecules present within the upper respiratory tract (URT) in order to successfully infect
Synthetic approaches to the neuraminidase inhibitors zanamivir (Relenza) and oseltamivir phosphate (Tamiflu) for the treatment of influenza.
Javier Magano
Chemical reviews, 109(9), 4398-4438 (2009-06-23)
Carl J Heneghan et al.
BMJ (Clinical research ed.), 348, g2547-g2547 (2014-05-09)
To describe the potential benefits and harms of zanamivir. Systematic review of clinical study reports of randomised placebo controlled trials and regulatory information Clinical study reports, trial registries, electronic databases, regulatory archives, and correspondence with manufacturers. Randomised placebo controlled trials
Celia Jakob et al.
Nucleic acids research, 51(12), 6479-6494 (2023-05-24)
A fundamental step in the influenza A virus (IAV) replication cycle is the coordinated packaging of eight distinct genomic RNA segments (i.e. vRNAs) into a viral particle. Although this process is thought to be controlled by specific vRNA-vRNA interactions between
Erhard van der Vries et al.
PLoS pathogens, 8(9), e1002914-e1002914 (2012-10-03)
Two classes of antiviral drugs, neuraminidase inhibitors and adamantanes, are approved for prophylaxis and therapy against influenza virus infections. A major concern is that antiviral resistant viruses emerge and spread in the human population. The 2009 pandemic H1N1 virus is
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