Zanamivir (CHEM016938)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:48:11 UTC
Update Date2016-11-09 01:15:30 UTC
Accession NumberCHEM016938
Identification
Common NameZanamivir
ClassSmall Molecule
Description
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass332.310 g/mol
Monoisotopic Mass332.133 g/mol
CAS Registry Number139110-80-8
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-c06e9379cf7d274c600aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m4-0094000000-97290cd8e79a4d977d7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4390000000-2420ed6c3d9c972f2424Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-0092000000-284f672e9e6f973e4eafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056s-0390000000-5251af99ef7e14b4f0c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3930000000-a904eb807a510f8f96a0Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00558
HMDB IDHMDB0014698
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkZanamivir
Chemspider ID54842
ChEBI ID50663
PubChem Compound ID60855
Kegg Compound IDC08095
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
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.
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.