NAV

Des(carbamimidoyl) zanamivir

Identification

Generic Name
Des(carbamimidoyl) zanamivir
DrugBank Accession Number
DB03321
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 290.2698
Monoisotopic: 290.11140094
Chemical Formula
C11H18N2O7
Synonyms
  • 4-AM-DANA
  • 4-Amino-2-deoxy-2,3-dehydro-N-neuraminic acid
  • 4-amino-4-deoxy-Neu5Ac2en
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNeuraminidaseNot AvailableInfluenza A virus (strain A/Tern/Australia/G70C/1975 H11N9)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
Secondary carboxylic acid amides / Secondary alcohols / Amino acids / Polyols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Primary alcohols / Organopnictogen compounds / Organic oxides
show 3 more
Substituents
Acetamide / Alcohol / Aliphatic heteromonocyclic compound / Amine / Amino acid / Amino acid or derivatives / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / Monocarboxylic acid or derivatives
show 14 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
OE4L5BBV9M
CAS number
130525-62-1
InChI Key
NKENBBIXEGPQLS-UFGQHTETSA-N
InChI
InChI=1S/C11H18N2O7/c1-4(15)13-8-5(12)2-7(11(18)19)20-10(8)9(17)6(16)3-14/h2,5-6,8-10,14,16-17H,3,12H2,1H3,(H,13,15)(H,18,19)/t5-,6+,8+,9+,10+/m0/s1
IUPAC Name
(2R,3R,4S)-4-amino-3-acetamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
SMILES
[H][C@]1(OC(=C[C@H](N)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO

References

General References
Not Available
PubChem Compound
445533
PubChem Substance
46508941
ChemSpider
393148
BindingDB
50063303
ChEMBL
CHEMBL52270
ZINC
ZINC000005884083
PDBe Ligand
4AM
PDB Entries
1f8c / 2qwd / 8gfm

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility58.0 mg/mLALOGPS
logP-3ALOGPS
logP-6.1Chemaxon
logS-0.7ALOGPS
pKa (Strongest Acidic)3.11Chemaxon
pKa (Strongest Basic)8.44Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area162.34 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity65.77 m3·mol-1Chemaxon
Polarizability27.17 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8169
Blood Brain Barrier-0.9035
Caco-2 permeable-0.7674
P-glycoprotein substrateNon-substrate0.5518
P-glycoprotein inhibitor INon-inhibitor0.8512
P-glycoprotein inhibitor IINon-inhibitor0.989
Renal organic cation transporterNon-inhibitor0.9757
CYP450 2C9 substrateNon-substrate0.8508
CYP450 2D6 substrateNon-substrate0.8483
CYP450 3A4 substrateNon-substrate0.6839
CYP450 1A2 substrateNon-inhibitor0.9419
CYP450 2C9 inhibitorNon-inhibitor0.9119
CYP450 2D6 inhibitorNon-inhibitor0.9488
CYP450 2C19 inhibitorNon-inhibitor0.9018
CYP450 3A4 inhibitorNon-inhibitor0.9632
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9758
Ames testNon AMES toxic0.6328
CarcinogenicityNon-carcinogens0.931
BiodegradationReady biodegradable0.7489
Rat acute toxicity1.7943 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9916
hERG inhibition (predictor II)Non-inhibitor0.9638
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-03kc-9240000000-c7b2728b522fc8f1efe1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-006y-0090000000-869d4058374fb5fff53b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1790000000-dd2f91afaf624f589eb1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052b-0490000000-279f8dfe51cd38441a72
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03e9-0960000000-9685aea219c734de97db
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1930000000-6f8f77a478310c27c6b8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ue9-1910000000-14a9819bd89d1ccde73a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-169.24245
predicted
DeepCCS 1.0 (2019)
[M+H]+171.15019
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.06331
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Neuraminidase
Kind
Protein
Organism
Influenza A virus (strain A/Tern/Australia/G70C/1975 H11N9)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the removal of terminal sialic acid residues from viral and cellular glycoconjugates. Cleaves off the terminal sialic acids on the glycosylated HA during virus budding to facilitate virus...
Gene Name
NA
Uniprot ID
P03472
Uniprot Name
Neuraminidase
Molecular Weight
52468.405 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52