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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00558
rdf:type
n3:Drug
n3:description
A guanido-neuraminic acid that is used to inhibit neuraminidase. [PubChem]
n3:dosage
n31:271B4767-363D-11E5-9242-09173F13E4C5 n31:271B4768-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/4362431 # 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8502295 # 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 Aug 11. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18694948 # 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18582202
n3:group
investigational approved
n3:halfLife
2.5-5.1 hours
n3:indication
For the prevention and treatment of influenza A and B.
n3:manufacturer
n7:271B4764-363D-11E5-9242-09173F13E4C5
owl:sameAs
n13:DB00558 n14:DB00558
dcterms:title
Zanamivir
adms:identifier
n5:PA164740891 n6:Zanamivir n17:50663 n18:54842 n19:4934 n21:C08095 n22:D00902 n23:DB00558 n25:60855 n26:0173-0681-01 n27:ZMR n32:46508581
n3:mechanismOfAction
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.
n3:packager
n7:271B4761-363D-11E5-9242-09173F13E4C5 n7:271B4762-363D-11E5-9242-09173F13E4C5 n7:271B4763-363D-11E5-9242-09173F13E4C5
n3:patent
n24:2291994 n24:5360817 n24:2081356 n24:6294572
n3:routeOfElimination
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.
n3:synonym
5-acetamido-2,6-Anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonic acid 5-(acetylamino)-2,6-Anhydro-4-carbamimidamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid ZANAMIVIR GNA GANA (2R,3R,4S)-3-(acetylamino)-4-Carbamimidamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Zanamavir ZMR Relenza 4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid 4-Guanidino-neu5ac2en Modified sialic acid
n10:hasAHFSCode
n33:08-18-28
n3:proteinBinding
Zanamivir has limited plasma protein binding (<10%).
n3:synthesisReference
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.
n28:hasConcept
n29:M0217195
foaf:page
n16:zanamivir.html n20:zanam.htm
n3:IUPAC-Name
n9:271B476D-363D-11E5-9242-09173F13E4C5
n3:InChI
n9:271B4773-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n9:271B4772-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n9:271B476F-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n9:271B4770-363D-11E5-9242-09173F13E4C5
n3:SMILES
n9:271B4771-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n9:271B476B-363D-11E5-9242-09173F13E4C5
n3:logP
n9:271B4769-363D-11E5-9242-09173F13E4C5 n9:271B476C-363D-11E5-9242-09173F13E4C5 n9:271B4783-363D-11E5-9242-09173F13E4C5
n3:logS
n9:271B476A-363D-11E5-9242-09173F13E4C5
n10:hasATCCode
n11:J05AH01
n3:H-Bond-Acceptor-Count
n9:271B4779-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n9:271B477A-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n9:271B4774-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n9:271B4775-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n9:271B4777-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n9:271B4776-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n9:271B4778-363D-11E5-9242-09173F13E4C5
n3:absorption
Absolute bioavailability is very low following oral administration (2%). Following oral inhalation, bioavailability is 4% to 17%.
n3:affectedOrganism
Influenza A virus Influenza B virus
n3:casRegistryNumber
139110-80-8
n3:category
n3: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]
n3:containedIn
n8:271B4766-363D-11E5-9242-09173F13E4C5 n8:271B4765-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n9:271B477F-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n9:271B4781-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n9:271B4782-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n9:271B477E-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n9:271B477D-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n9:271B4780-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n9:271B476E-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n9:271B477B-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n9:271B477C-363D-11E5-9242-09173F13E4C5