Chemical Component Summary

NameZANAMIVIR
Synonyms4-GUANIDINO-2-DEOXY-2,3-DEHYDRO-N-ACETYL-NEURAMINIC ACID; 4-guanidino-Neu5Ac2en; MODIFIED SIALIC ACID
Identifiers(2~{R},3~{R},4~{S})-3-acetamido-4-carbamimidamido-2-[(1~{R},2~{R})-1,2,3-tris(oxidanyl)propyl]-3,4-dihydro-2~{H}-pyran- 6-carboxylic acid
FormulaC12 H20 N4 O7
Molecular Weight332.31
TypeD-SACCHARIDE
Isomeric SMILES[H]/N=C(\N)/N[C@H]1C=C(O[C@H]([C@@H]1NC(=O)C)[C@@H]([C@@H](CO)O)O)C(=O)O
InChIInChI=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
InChIKeyARAIBEBZBOPLMB-UFGQHTETSA-N

Chemical Details

Formal Charge0
Atom Count43
Chiral Atom Count5
Bond Count43
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB00558 
NameZanamivir
Groups
  • approved
  • investigational
DescriptionA guanido-neuraminic acid that is used to inhibit neuraminidase.
Synonyms
  • 5-acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonic acid
  • GANA
  • 4-guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid
  • (2R,3R,4S)-3-(acetylamino)-4-carbamimidamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
  • 4-guanidino-Neu5Ac2en
Brand Names
  • Dectova
  • Relenza
IndicationFor the prevention and treatment of influenza A and B.
Categories
  • Acids, Acyclic
  • Amidines
  • Amino Sugars
  • Anti-Infective Agents
  • Antiinfectives for Systemic Use
ATC-CodeJ05AH01
CAS number139110-80-8

Drug Targets

NameTarget SequencePharmacological ActionActions
NeuraminidaseMNPNQKIITIGSVSLTIATICFLMQIAILVTTVTLHFKQYECSSPPNNQV...unknowninhibitor
NeuraminidaseMLPSTIQTLTLFLTSGGVLLSLYVSASLSYLLYSDILLKFSSKITAPTMT...unknowninhibitor
Sialidase-2MASLPVLQKESVFQSGAHAYRIPALLYLPGQQSLLAFAEQRASKKDEHAE...unknowninhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL222813
PubChem 40469135, 60855
ChEMBL CHEMBL222813
ChEBI CHEBI:50663