Zanamivir

Base Information

• Chemical Name: Zanamivir
• CAS No.: 139110-80-8
• Molecular Formula: C12H20N4O7
• Molecular Weight: 332.313
• Hs Code.: 2932999000
• European Community (EC) Number: 691-117-1
• UNII: L6O3XI777I
• DSSTox Substance ID: DTXSID0023749
• Nikkaji Number: J680.760G
• Wikipedia: Zanamivir
• Wikidata: Q146075
• NCI Thesaurus Code: C47786
• RXCUI: 69722
• Pharos Ligand ID: K5XHV8828APZ
• Metabolomics Workbench ID: 42894
• ChEMBL ID: CHEMBL222813
• Mol file: 139110-80-8.mol

Synonyms:2,3-Didehydro-2,4-Dideoxy-4-Guanidino-N-Acetyl-D-Neuraminic Acid;2,3-Didehydro-2,4-Dideoxy-4-Guanidinyl-N-Acetylneuraminic Acid;4 Guanidino 2 Deoxy 2,3 Didehydro N Acetylneuraminic Acid;4 Guanidino Neu5Ac2en;4-Guanidino-2,4-Dideoxy-2,3-Didehydro-N-Acetylneuraminic Acid;4-Guanidino-2-Deoxy-2,3-Didehydro-N-Acetylneuraminic Acid;4-Guanidino-Neu5Ac2en;5-Acetylamino-2,6-Anhydro-4-Guanidino-3,4,5-Trideoxy-D-Galacto-Non-Enoic Acid;Acid, 4-Guanidino-2-Deoxy-2,3-Didehydro-N-Acetylneuraminic;GG 167;GG-167;GG167;Relenza;Zanamivir

Chemical Property of Zanamivir

Chemical Property:

• Appearance/Colour: colorless crystalline solid
• Melting Point: 256 °C (dec.)
• PKA: 3.82±0.70(Predicted)
• PSA: 198.22000
• Density: 1.75 g/cm³
• LogP: -1.99400
• Storage Temp.: -20°C Freezer
• Solubility.: H2O: soluble10mg/mL, clear
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 332.13319899
• Heavy Atom Count: 23
• Complexity: 518

Purity/Quality:

≥99% ^*data from raw suppliers

Zanamivir Hydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: CC(=O)NC1C(C=C(OC1C(C(CO)O)O)C(=O)O)N=C(N)N
• 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
• Recent ClinicalTrials: Zanamivir Treatment of Vascular Permeability in Dengue (ZAP-DENGUE)
• Recent EU Clinical Trials: An open label, single arm study to evaluate single and multiple dose pharmacokinetics, safety and tolerability, and to explore clinical outcomes of treatment with intravenous (IV) zanamivir in neonates and infants under 6 months of age with confirmed complicated influenza infection
• Recent NIPH Clinical Trials: Examination of protective efficacy of influenza by zanamivir among the staff of a medical facility: the 2nd trial
• General Description: Zanamivir hydrate, also known by various names including GG167 and Relenza, is a potent inhibitor of influenza virus sialidase, particularly effective against influenza A. Derived from 2,3-didehydro-2,4-dideoxy-4-amino-N-acetylneuraminic acid, its structure features a 4-guanidino group and lacks the polar glycerol sidechain, which enhances its selectivity and inhibitory activity. Comparative studies with related compounds, such as 4-amino and guanidino-4H-pyran-2-carboxylic acid-6-propylamides, suggest that modifications like the 6-dipropylcarboxamide substituent further improve potency against influenza A sialidase, making zanamivir hydrate a clinically relevant antiviral agent.

Technology Process of Zanamivir

There total 58 articles about Zanamivir which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

5-acetamido-4-guanidino-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (913745-34-3) → zanamivir (139110-80-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 5 - 20 ℃; for 0.5h; Reagent/catalyst; Temperature; Time;

Reference yield: 88.0%

(2R,3R,4S)-3-acetamido-6-carboxy-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-4-aminium hydrochloride + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → zanamivir (139110-80-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 50 ℃; for 72h; Inert atmosphere;

DOI:10.1002/anie.201408138

Reference yield: 74.9%

1H-pyrazolecarboxamidine hydrochloride (166197-22-4) + 5-acetamido-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid (130525-62-1) → zanamivir (139110-80-8)

Guidance literature:

With sodium carbonate; In water; at 35 ℃; for 7h; Temperature; Industrial scale;

upstream raw materials:

aminoiminomethanesulfonic acid

5-acetamido-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid

N³-acetyl-S-methylisothiourea

5-acetylamino-2,6-anhydro-4-cyanoamino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid

Refernces

Novel inhibitors of influenza sialidase related to GG167. Synthesis of 4-amino and guanidino-4H-pyran-2-carboxylic acid-6-propylamides; selective inhibitors of influenza A virus sialidase

10.1016/0960-894X(96)00318-6

The study focuses on the synthesis and evaluation of 4-amino and guanidino-4H-pyran-2-carboxylic acid-6-propylamides as selective inhibitors of influenza A virus sialidase. The researchers synthesized these compounds from 2,3-didehydro-2,4-dideoxy-4-amino-N-acetylneuraminic acid (4) and found that the propylamides, particularly the dipropylamides (3a and 3b), exhibited high potency and selectivity against influenza A sialidase compared to the related inhibitors GG167 and 4. The study demonstrated that the 6-dipropylcarboxamide substituent is preferable to the polar glycerol sidechain found in GG167 for inhibiting influenza A sialidase. The synthesized propylamides showed significant inhibitory activity in both sialidase inhibition and in vitro antiviral assays, highlighting their potential as effective inhibitors for influenza A treatment.