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zanamivir   Click here for help

GtoPdb Ligand ID: 12307

Synonyms: Dectova® | GG-167 | GG167 | GR-121167 | GR-121167X | ZMR
Approved drug PDB Ligand
zanamivir is an approved drug (FDA (1999), EMA (2019))
Compound class: Synthetic organic
Comment: Zanamivir (GG167) is a sialic acid-analogue that is used as an antiviral drug. Mechanistcally it inhibits the neuraminidases of both influenza A and B, enzymes that cleave sialic acid residues from host membrane-bound glycoproteins to increase both infection and release of new virus particles from the infected respiratory epithelium. Oseltamivir also belongs to this class of anti-influenza drugs.
A combination of zanamivir and oseltamivir is reported to inhibit mammalian neuraminidase 1 (NEU1) which has the effect of reducing neutrophil overactivation in response to severe viral infection [1]. It is proposed that pharmacological modulation of human NEU1 may represent a novel intervention to dampen neutrophil dysfunction (and the associated tissue damage) during severe infections, as observed in COVID-19.

zanamivir is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 11
Hydrogen bond donors 7
Rotatable bonds 7
Topological polar surface area 200.72
Molecular weight 332.13
XLogP -3.01
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OC[C@H]([C@H]([C@@H]1OC(=C[C@@H]([C@H]1NC(=O)C)N=C(N)N)C(=O)O)O)O
Isomeric SMILES CC(=O)N[C@@H]1[C@H](C=C(O[C@H]1[C@@H]([C@@H](CO)O)O)C(=O)O)N=C(N)N
InChI 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. EU EMA (2019)  |  US FDA (1999)
IUPAC Name Click here for help
(2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
7272 zanamivir
Synonyms Click here for help
Dectova® | GG-167 | GG167 | GR-121167 | GR-121167X | ZMR
Database Links Click here for help
BindingDB Ligand 4934
CAS Registry No. 139110-80-8 (source: WHO INN record)
ChEMBL Ligand CHEMBL222813
DrugBank Ligand DB00558
GtoPdb PubChem SID 479821098
PubChem CID 60855
RCSB PDB Ligand ZMR
Search Google for chemical match using the InChIKey ARAIBEBZBOPLMB-UFGQHTETSA-N
Search Google for chemicals with the same backbone ARAIBEBZBOPLMB
Search PubMed clinical trials zanamivir
Search PubMed titles zanamivir
Search PubMed titles/abstracts zanamivir
UniChem Compound Search for chemical match using the InChIKey ARAIBEBZBOPLMB-UFGQHTETSA-N
UniChem Connectivity Search for chemical match using the InChIKey ARAIBEBZBOPLMB-UFGQHTETSA-N

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

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MedChemExpress
Zanamivir (links to external site)
Cat. No. HY-13210