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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:10 UTC
HMDB IDHMDB0014698
Secondary Accession Numbers
  • HMDB14698
Metabolite Identification
Common NameZanamivir
DescriptionZanamivir is only found in individuals that have used or taken this drug. It is a guanido-neuraminic acid that is used to inhibit neuraminidase. [PubChem]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.
Structure
Data?1582753210
Synonyms
ValueSource
(2R,3R,4S)-3-(Acetylamino)-4-carbamimidamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acidChEBI
4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acidChEBI
4-Guanidino-neu5ac2EnChEBI
5-(Acetylamino)-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acidChEBI
5-Acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonic acidChEBI
GANAChEBI
RelenzaChEBI
(2R,3R,4S)-3-(Acetylamino)-4-carbamimidamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylateGenerator
4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminateGenerator
5-(Acetylamino)-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonateGenerator
5-Acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonateGenerator
GNAHMDB
Modified sialic acidHMDB
ZanamavirHMDB
ZMRHMDB
Biota brand OF zanamivirHMDB
Zanamivir glaxosmithkline brandHMDB
2,3-Didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acidHMDB
4 Guanidino neu5ac2EnHMDB
4-Guanidino-2,4-dideoxy-2,3-didehydro-N-acetylneuraminic acidHMDB
4-Guanidino-2-deoxy-2,3-didehydro-N-acetylneuraminic acidHMDB
5-Acetylamino-2,6-anhydro-4-guanidino-3,4,5-trideoxy-D-galacto-non-enoic acidHMDB
Glaxo wellcome brand OF zanamivirHMDB
4 Guanidino 2 deoxy 2,3 didehydro N acetylneuraminic acidHMDB
Acid, 4-guanidino-2-deoxy-2,3-didehydro-N-acetylneuraminicHMDB
Zanamivir biota brandHMDB
2,3-Didehydro-2,4-dideoxy-4-guanidino-N-acetyl-D-neuraminic acidHMDB
GlaxoSmithKline brand OF zanamivirHMDB
Chemical FormulaC12H20N4O7
Average Molecular Weight332.3098
Monoisotopic Molecular Weight332.133199014
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
Traditional Namezanamivir
CAS Registry Number139110-80-8
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
InChI Identifier
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 KeyARAIBEBZBOPLMB-UFGQHTETSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentAcetamides
Alternative Parents
Substituents
  • Acetamide
  • Guanidine
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Polyol
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.31 g/LNot Available
LogP-3Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.31 g/LALOGPS
logP-2.3ALOGPS
logP-5.8ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.25ChemAxon
pKa (Strongest Basic)11.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area200.72 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity76.19 m³·mol⁻¹ChemAxon
Polarizability31.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08gi-9333000000-192a3fb0a765cc76272aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0a4i-9120247000-a1f231eacdbcd584b683Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01c9-2089000000-4b363928c7080b58eaf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-8091000000-e955bc5727f97f64f636Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9310000000-1499e6041e5831b4268fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02pr-4092000000-e0a953096602bf725d43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fv-7190000000-e7e50811b55c4d55c4d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9110000000-23c8a48c94cc1cdcc136Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00558 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00558 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00558
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54842
KEGG Compound IDC08095
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkZanamivir
METLIN IDNot Available
PubChem Compound60855
PDB IDNot Available
ChEBI ID50663
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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:4362431 ]
  2. 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:8502295 ]
  3. 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. [PubMed:18582202 ]
  4. 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. [PubMed:18694948 ]

Enzymes

General function:
Involved in exo-alpha-sialidase activity
Specific function:
Hydrolyzes sialylated compounds.
Gene Name:
NEU2
Uniprot ID:
Q9Y3R4
Molecular weight:
Not Available
References
  1. 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. [PubMed:20222714 ]