Identification
- Summary
Zanamivir is a neuraminidase inhibitor used to treat influenza A and B.
- Brand Names
- Relenza
- Generic Name
- Zanamivir
- DrugBank Accession Number
- DB00558
- Background
A guanido-neuraminic acid that is used to inhibit neuraminidase.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Zanamivir (DB00558)
- Weight
- Average: 332.3098
Monoisotopic: 332.133199014 - Chemical Formula
- C12H20N4O7
- Synonyms
- (2R,3R,4S)-3-(acetylamino)-4-carbamimidamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
- 4-guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid
- 4-guanidino-Neu5Ac2en
- 5-(acetylamino)-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid
- 5-acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonic acid
- GANA
- Zanamivir
- External IDs
- GG-167
- GG167
- GR 121167X
- GR-121167
- GR-121167X
Pharmacology
- Indication
For the prevention and treatment of influenza A and B.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prophylaxis of Flu caused by influenza •••••••••••• Treatment of Flu caused by influenza •••••••••••• Prophylaxis of Flu caused by influenza •••••••••••• - Contraindications & Blackbox Warnings
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Zanamivir, an antiviral agent, is a neuraminidase inhibitor indicated for treatment of uncomplicated acute illness due to influenza A and B virus in adults and pediatric patients 7 years and older who have been symptomatic for no more than 2 days. Zanamivir has also been shown to significantly inhibit the human sialidases NEU3 and NEU2 in the micromolar range (Ki 3.7 +/-0.48 and 12.9+/-0.07 microM, respectively), which could account for some of the rare side effects of zanamivir.
- Mechanism of action
The proposed mechanism of action of zanamivir is via inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release. By binding and inhibiting the neuraminidase protein, the drug renders the influenza virus unable to escape its host cell and infect others.
Target Actions Organism ANeuraminidase inhibitorInfluenza A virus (strain A/Bangkok/1/1979 H3N2) ANeuraminidase inhibitorInfluenza B virus (strain B/Beijing/1/1987) USialidase-2 inhibitorHumans - Absorption
Absolute bioavailability is very low following oral administration (2%). Following oral inhalation, bioavailability is 4% to 17%.
- Volume of distribution
Not Available
- Protein binding
Zanamivir has limited plasma protein binding (<10%).
- Metabolism
Not metabolized
- Route of elimination
It is excreted unchanged in the urine with excretion of a single dose completed within 24 hours. Unabsorbed drug is excreted in the feces.Zanamivir is renally excreted as unchanged drug.
- Half-life
2.5-5.1 hours
- Clearance
- 2.5 - 10.9 L/h [Following oral inhalation 10 mg]
- 5.3 L/h [Normal renal function receiving IV single dose of 4 mg or 2 mg]
- 2.7 L/h [Patients with mild and moderate renal impairement receiving IV single dose of 4 mg or 2 mg]
- 0.8 L/h [Patients with severe renal impairement receiving IV single dose of 4 mg or 2 mg]
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Zanamivir may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Zanamivir which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Zanamivir which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Zanamivir which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Zanamivir which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dectova Injection, solution 10 mg/ml Intravenous Glaxo Smith Kline Trading Services 2020-12-16 Not applicable EU 
Relenza Powder 5 mg/1 Respiratory (inhalation) Physicians Total Care, Inc. 2009-01-20 Not applicable US 
Relenza Powder 5 mg / act Respiratory (inhalation) Glaxosmithkline Inc 1999-12-07 Not applicable Canada 
Relenza Powder 5 mg/1 Respiratory (inhalation) Dispensing Solutions, Inc. 2002-12-22 Not applicable US Relenza Powder 5 mg/1 Respiratory (inhalation) GlaxoSmithKline LLC 1999-09-22 Not applicable US
Categories
- ATC Codes
- J05AH01 — Zanamivir
- Drug Categories
- Acids, Acyclic
- Amidines
- Amino Sugars
- Anti-Infective Agents
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- Carbohydrates
- Direct Acting Antivirals
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Guanidines
- Hydroxy Acids
- Neuraminic Acids
- Neuraminidase Inhibitors
- Pyrans
- Sialic Acids
- Sugar Acids
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Carboxylic acid derivatives
- Direct Parent
- Acetamides
- Alternative Parents
- Secondary carboxylic acid amides / Secondary alcohols / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Polyols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Primary alcohols show 4 more
- Substituents
- Acetamide / Alcohol / Aliphatic heteromonocyclic compound / Carbonyl group / Carboximidamide / Carboxylic acid / Guanidine / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic 1,3-dipolar compound show 13 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- guanidines (CHEBI:50663)
- Affected organisms
- Influenza A virus
- Influenza B virus
Chemical Identifiers
- UNII
- L6O3XI777I
- CAS number
- 139110-80-8
- InChI Key
- ARAIBEBZBOPLMB-UFGQHTETSA-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
- IUPAC Name
- (2R,3R,4S)-4-[(diaminomethylidene)amino]-3-acetamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
- SMILES
- [H][C@]1(OC(=C[C@H](N=C(N)N)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO
References
- Synthesis Reference
Manjinder Singh Phull, Rajendra Narayanrao Kankan, Dharmaraj Ramachandra Rao, Ashwini Amol Sawant, Sanoj Thoppil, "Process for Preparing Zanamivir and Intermediates for Use in the Process." U.S. Patent US20110257418, issued October 20, 2011.
US20110257418- General References
- Meindl P, Bodo G, Palese P, Schulman J, Tuppy H: Inhibition of neuraminidase activity by derivatives of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid. Virology. 1974 Apr;58(2):457-63. [Article]
- von Itzstein M, Wu WY, Kok GB, Pegg MS, Dyason JC, Jin B, Van Phan T, Smythe ML, White HF, Oliver SW, et al.: Rational design of potent sialidase-based inhibitors of influenza virus replication. Nature. 1993 Jun 3;363(6428):418-23. [Article]
- Hata K, Koseki K, Yamaguchi K, Moriya S, Suzuki Y, Yingsakmongkon S, Hirai G, Sodeoka M, von Itzstein M, Miyagi T: Limited inhibitory effects of oseltamivir and zanamivir on human sialidases. Antimicrob Agents Chemother. 2008 Oct;52(10):3484-91. doi: 10.1128/AAC.00344-08. Epub 2008 Aug 11. [Article]
- Sugaya N, Tamura D, Yamazaki M, Ichikawa M, Kawakami C, Kawaoka Y, Mitamura K: Comparison of the clinical effectiveness of oseltamivir and zanamivir against influenza virus infection in children. Clin Infect Dis. 2008 Aug 1;47(3):339-45. doi: 10.1086/589748. [Article]
- External Links
- Human Metabolome Database
- HMDB0014698
- KEGG Drug
- D00902
- KEGG Compound
- C08095
- PubChem Compound
- 60855
- PubChem Substance
- 46508581
- ChemSpider
- 54842
- BindingDB
- 50330326
- 69722
- ChEBI
- 50663
- ChEMBL
- CHEMBL222813
- ZINC
- ZINC000003918138
- Therapeutic Targets Database
- DAP000715
- PharmGKB
- PA164740891
- PDBe Ligand
- ZMR
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Zanamivir
- PDB Entries
- 1a4g / 1nnc / 1v3e / 2cml / 2f0z / 2htq / 2qwe / 2ya7 / 3b7e / 3ckz … show 17 more
- FDA label
- Download (36.7 KB)
- MSDS
- Download (53.6 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Prevention Flu caused by Influenza 1 3 Completed Prevention Flu caused by Influenza 1 3 Completed Treatment Influenza A Virus Infection / Influenza B Virus Infection 1 3 Completed Treatment Influenza, Human 2 3 Terminated Treatment Flu caused by Influenza / Upper Respiratory Tract Infection 1
Pharmacoeconomics
- Manufacturers
- Glaxosmithkline
- Packagers
- Dispensing Solutions
- GlaxoSmithKline Inc.
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Tablet, coated Oral 500 mg Injection, solution Intravenous 10 MG/ML Drug delivery system Buccal 5.000 mg Powder Respiratory (inhalation) 5 mg Powder Respiratory (inhalation) 5 mg / act Powder Respiratory (inhalation) 5 mg/1 Powder Respiratory (inhalation) 5 mg/1blister Powder, metered Respiratory (inhalation) Powder, metered Respiratory (inhalation) 5 mg Aerosol, powder Respiratory (inhalation) 5 mg Powder Respiratory (inhalation) - Prices
Unit description Cost Unit Relenza Diskhaler 20 5 mg/blister Aerosol Inhaler 75.73USD inhaler Relenza 5 mg diskhaler 3.54USD each DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6294572 No 2001-09-25 2014-12-15 US US5360817 No 1994-11-01 2013-07-26 US CA2291994 No 2003-10-14 2011-04-24 Canada CA2081356 No 2000-02-22 2011-04-24 Canada
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP -3 Not Available - Predicted Properties
Property Value Source Water Solubility 7.31 mg/mL ALOGPS logP -2.3 ALOGPS logP -5.8 Chemaxon logS -1.7 ALOGPS pKa (Strongest Acidic) 3.06 Chemaxon pKa (Strongest Basic) 11.93 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 7 Chemaxon Polar Surface Area 200.72 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 76.19 m3·mol-1 Chemaxon Polarizability 31.24 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8406 Blood Brain Barrier - 0.8899 Caco-2 permeable - 0.7094 P-glycoprotein substrate Substrate 0.5497 P-glycoprotein inhibitor I Non-inhibitor 0.8288 P-glycoprotein inhibitor II Non-inhibitor 0.9701 Renal organic cation transporter Non-inhibitor 0.9405 CYP450 2C9 substrate Non-substrate 0.7868 CYP450 2D6 substrate Non-substrate 0.8139 CYP450 3A4 substrate Non-substrate 0.6779 CYP450 1A2 substrate Non-inhibitor 0.8684 CYP450 2C9 inhibitor Non-inhibitor 0.8942 CYP450 2D6 inhibitor Non-inhibitor 0.9262 CYP450 2C19 inhibitor Non-inhibitor 0.8727 CYP450 3A4 inhibitor Non-inhibitor 0.9647 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9903 Ames test Non AMES toxic 0.5316 Carcinogenicity Non-carcinogens 0.9226 Biodegradation Ready biodegradable 0.6996 Rat acute toxicity 2.1565 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9827 hERG inhibition (predictor II) Non-inhibitor 0.9528
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-08gi-9333000000-192a3fb0a765cc76272a Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00lr-0049000000-4d9292e9d35b6be23506 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0fha-0292000000-1d7e6c085fd622cb5a11 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00ke-0294000000-97ab9f84ac64089252c5 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-1690000000-11ba7d2f1987935716f5 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-056r-0291000000-b53986d1fd5539143ca4 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0005-1930000000-cb95c31e27910401cac2 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 188.7101165 predictedDarkChem Lite v0.1.0 [M-H]- 188.9100165 predictedDarkChem Lite v0.1.0 [M-H]- 176.97067 predictedDeepCCS 1.0 (2019) [M+H]+ 190.9492165 predictedDarkChem Lite v0.1.0 [M+H]+ 191.1767165 predictedDarkChem Lite v0.1.0 [M+H]+ 179.36624 predictedDeepCCS 1.0 (2019) [M+Na]+ 190.1458165 predictedDarkChem Lite v0.1.0 [M+Na]+ 189.7429165 predictedDarkChem Lite v0.1.0 [M+Na]+ 185.7863 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Influenza A virus (strain A/Bangkok/1/1979 H3N2)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Catalyzes the removal of terminal sialic acid residues from viral and cellular glycoconjugates. Cleaves off the terminal sialic acids on the glycosylated HA during virus budding to facilitate virus...
- Gene Name
- NA
- Uniprot ID
- P06818
- Uniprot Name
- Neuraminidase
- Molecular Weight
- 52140.54 Da
References
- Macdonald SJ, Cameron R, Demaine DA, Fenton RJ, Foster G, Gower D, Hamblin JN, Hamilton S, Hart GJ, Hill AP, Inglis GG, Jin B, Jones HT, McConnell DB, McKimm-Breschkin J, Mills G, Nguyen V, Owens IJ, Parry N, Shanahan SE, Smith D, Watson KG, Wu WY, Tucker SP: Dimeric zanamivir conjugates with various linking groups are potent, long-lasting inhibitors of influenza neuraminidase including H5N1 avian influenza. J Med Chem. 2005 Apr 21;48(8):2964-71. [Article]
- Murrell MT, Porotto M, Greengard O, Poltoratskaia N, Moscona A: A single amino acid alteration in the human parainfluenza virus type 3 hemagglutinin-neuraminidase glycoprotein confers resistance to the inhibitory effects of zanamivir on receptor binding and neuraminidase activity. J Virol. 2001 Jul;75(14):6310-20. [Article]
- Mungall BA, Xu X, Klimov A: Assaying susceptibility of avian and other influenza A viruses to zanamivir: comparison of fluorescent and chemiluminescent neuraminidase assays. Avian Dis. 2003;47(3 Suppl):1141-4. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Influenza B virus (strain B/Beijing/1/1987)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Catalyzes the removal of terminal sialic acid residues from viral and cellular glycoconjugates. Cleaves off the terminal sialic acids on the glycosylated HA during virus budding to facilitate virus...
- Gene Name
- NA
- Uniprot ID
- P27907
- Uniprot Name
- Neuraminidase
- Molecular Weight
- 51429.21 Da
References
- Eiland LS, Eiland EH: Zanamivir for the prevention of influenza in adults and children age 5 years and older. Ther Clin Risk Manag. 2007 Jun;3(3):461-5. [Article]
- Oakley AJ, Barrett S, Peat TS, Newman J, Streltsov VA, Waddington L, Saito T, Tashiro M, McKimm-Breschkin JL: Structural and functional basis of resistance to neuraminidase inhibitors of influenza B viruses. J Med Chem. 2010 Sep 9;53(17):6421-31. doi: 10.1021/jm100621s. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Exo-alpha-(2->8)-sialidase activity
- Specific Function
- Catalyzes the removal of sialic acid (N-acetylneuraminic acid) moities from glycoproteins, oligosaccharides and gangliosides.
- Gene Name
- NEU2
- Uniprot ID
- Q9Y3R4
- Uniprot Name
- Sialidase-2
- Molecular Weight
- 42253.345 Da
References
- Chavas LM, Kato R, Suzuki N, von Itzstein M, Mann MC, Thomson RJ, Dyason JC, McKimm-Breschkin J, Fusi P, Tringali C, Venerando B, Tettamanti G, Monti E, Wakatsuki S: Complexity in influenza virus targeted drug design: interaction with human sialidases. J Med Chem. 2010 Apr 8;53(7):2998-3002. doi: 10.1021/jm100078r. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54