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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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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
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
Zanamivir
Waghorn S L and Goa K L
Drugs, 55(5), 721-725 (1998)
Emi Takashita et al.
Antimicrobial agents and chemotherapy, 59(5), 2607-2617 (2015-02-19)
Between September 2013 and July 2014, 2,482 influenza 2009 pandemic A(H1N1) [A(H1N1)pdm09] viruses were screened in Japan for the H275Y substitution in their neuraminidase (NA) protein, which confers cross-resistance to oseltamivir and peramivir. We found that a large cluster of
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
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