ChemFOnt: Showing chemical card for Zanamivir (CFc000009050)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:04 UTC

Chemfont ID

CFc000009050

Molecule Identification

Common Name

Zanamivir

Definition

Zanamivir 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R,3R,4S)-3-(Acetylamino)-4-carbamimidamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid	ChEBI
4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid	ChEBI
4-Guanidino-neu5ac2En	ChEBI
5-(Acetylamino)-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid	ChEBI
5-Acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonic acid	ChEBI
GANA	ChEBI
Relenza	ChEBI
(2R,3R,4S)-3-(Acetylamino)-4-carbamimidamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate	Generator
4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminate	Generator
5-(Acetylamino)-2,6-anhydro-4-carbamimidamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate	Generator
5-Acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonate	Generator
GNA	HMDB
Modified sialic acid	HMDB
Zanamavir	HMDB
ZMR	HMDB
Biota brand OF zanamivir	HMDB
Zanamivir glaxosmithkline brand	HMDB
2,3-Didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid	HMDB
4 Guanidino neu5ac2En	HMDB
4-Guanidino-2,4-dideoxy-2,3-didehydro-N-acetylneuraminic acid	HMDB
4-Guanidino-2-deoxy-2,3-didehydro-N-acetylneuraminic acid	HMDB
5-Acetylamino-2,6-anhydro-4-guanidino-3,4,5-trideoxy-D-galacto-non-enoic acid	HMDB
Glaxo wellcome brand OF zanamivir	HMDB
4 Guanidino 2 deoxy 2,3 didehydro N acetylneuraminic acid	HMDB
Acid, 4-guanidino-2-deoxy-2,3-didehydro-N-acetylneuraminic	HMDB
Zanamivir biota brand	HMDB
2,3-Didehydro-2,4-dideoxy-4-guanidino-N-acetyl-D-neuraminic acid	HMDB
GlaxoSmithKline brand OF zanamivir	HMDB

Chemical Formula

C₁₂H₂₀N₄O₇

Average Molecular Weight

332.3098

Monoisotopic Molecular Weight

332.133199014

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 Name

zanamivir

CAS Registry Number

139110-80-8

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 Key

ARAIBEBZBOPLMB-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Acetamides

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

guanidines (CHEBI:50663 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014698)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.31 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-5.8	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.25	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	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon