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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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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
Benjamin O Fulton et al.
Journal of virology, 89(23), 12226-12231 (2015-09-25)
Influenza B virus is a human pathogen responsible for significant health and economic burden. Research into this pathogen has been limited by the lack of reporter viruses. Here we describe the development of both a replication-competent fluorescent influenza B reporter
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
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)
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