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:

99.9% ^*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
• Description: Zanamivir was launched as Relenza in Australia for treatment of human influenza A and B virus infections. Zanamivir (4-guanidino-Neu5Ac2en) can be obtained by several similar ways, for instance in seven step synthesis starting from N-acetyI-D-neuraminic acid. Mechanistically, Zanamivir is a potent and specific inhibitor of neuraminidase (or sialidase), a key viral surface glycohydrolase essential for viral replication and disease progression by catalyzing the cleavage of terminal sialic acid residues from the glycoprotein. The in vitro activity of Zanamivir against a wide variety of influenza A and B strains was demonstrated in different model systems; its activity against clinically relevant isolates of influenza virus, with IC50 values ranging from 0.005 to 15 pM was superior to those of amantadine and rimantadine.
• Uses: Influenza viral neuraminidase inhibitor; structural analog of the sialic acid. Antiviral antineoplastic, anti-metabolite ZANAMIVIR HYDRATE is a sialic acid analog that inhibits neuraminidase release of newly replicated influenza virus particles. It has been shown to selectively inhibit the growth of influenza A and B viruses in plaque reduction assays with IC50 values ranging from 5 to 14 nM and to directly inhibit influenza A and B virus neuraminidases with IC50 values ranging from 0.6 to 7.9 nM in vitro. The efficacy and tolerabilbity of zanamivir has also been established in clinical trial.[Cayman Chemical]
• Indications: Zanamivir (Relenza) is a neuraminidase inhibitor with activity against influenza A and B strains. Like oseltamivir, zanamivir is a reversible competitive antagonist of viral neuraminidase. It inhibits the release of progeny virus, causes viral aggregation at the cell surface, and impairs viral movement through respiratory secretions. Resistant variants with hemagglutinin and/or neuraminidase mutations have been produced in vivo; however, clinical resistance to zanamivir is quite rare at present.
• Therapeutic Function: Antiviral
• Clinical Use: Treatment of influenza A and B infections in patients over 7 years of age, and prophylaxis of patients ??5 years of age Zanamivir is indicated for treatment of uncomplicated acute influenza A and B virus in patients aged 7 and older.Treatment should be initiated no later than 2 days after the onset of symptoms. Zanamivir shortens the duration of illness by 1 to 1.5 days. It is also an effective prophylaxis against influenza; however, the FDA has not approved this indication at the time of publication.
• Drug interactions: Potentially hazardous interactions with other drugs None known

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

• 1、 Hsu, Peng-Hao,Chiu, Din-Chi,Wu, Kuan-Lin,Lee, Pei-Shan,Jan, Jia-Tsrong,Cheng, Yih-Shyun E.,Tsai, Keng-Chang,Cheng, Ting-Jen,Fang, Jim-Min. "Acylguanidine derivatives of zanamivir and oseltamivir: Potential orally available prodrugs against influenza viruses". . p. 314 - 323. Retrieved 2018/05/29.
• 2、 -. "PROCESS FOR THE PREPARATION OF ZANAMIVIR". Paragraph 0053; 0054. . Retrieved 2014/03/25.