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Valganciclovir

July 24, 2017
Common Name

Valganciclovir Description

Valganciclovir hydrochloride (Valcyte, manufactured by Roche) is an antiviral medication used to treat cytomegalovirus infections. As the L-valyl ester of ganciclovir, it is actually a prodrug for ganciclovir. After oral administration, it is rapidly converted to ganciclovir by intestinal and hepatic esterases. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source CymevalHMDB L-Valine, ester with ganciclovirHMDB Valganciclovir hydrochlorideMeSH Ganciclovir L-valyl esterMeSH ValcytMeSH ValcyteMeSH

Chemical Formlia

C14H22N6O5 Average Molecliar Weight

354.3617 Monoisotopic Molecliar Weight

354.165167844 IUPAC Name

2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]-3-hydroxypropyl (2S)-2-amino-3-methylbutanoate Traditional Name

valganciclovir CAS Registry Number

175865-60-8 SMILES

CC(C)[C@H](N)C(=O)OCC(CO)OCN1C=NC2=C1NC(N)=NC2=O

InChI Identifier

InChI=1S/C14H22N6O5/c1-7(2)9(15)13(23)24-4-8(3-21)25-6-20-5-17-10-11(20)18-14(16)19-12(10)22/h5,7-9,21H,3-4,6,15H2,1-2H3,(H3,16,18,19,22)/t8?,9-/m0/s1

InChI Key

WPVFJKSGQUFQAP-GKAPJAKFSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Alpha amino acid esters Alternative Parents

  • Valine and derivatives
  • Purines and purine derivatives
  • Fatty acid esters
  • Glycerolipids
  • Hydroxypyrimidines
  • N-substituted imidazoles
  • Heteroaromatic compounds
  • Carboxylic acid esters
  • Azacyclic compounds
  • Monocarboxylic acids and derivatives
  • Hydrocarbon derivatives
  • Monoalkylamines
  • Organic oxides
  • Organopnictogen compounds
  • Carbonyl compounds
  • Primary alcohols

    • Substituents

  • Alpha-amino acid ester
  • Valine or derivatives
  • Imidazopyrimidine
  • Purine
  • Fatty acid ester
  • Hydroxypyrimidine
  • Glycerolipid
  • Fatty acyl
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Primary amine
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • purines (CHEBI:63635 )
  • L-valinyl ester (CHEBI:63635 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antiviral Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility4.79e+00 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility4.79 mg/mLALOGPS logP-0.81ALOGPS logP-1.1ChemAxon logS-1.9ALOGPS pKa (Strongest Acidic)8.1ChemAxon pKa (Strongest Basic)7.36ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count9ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area167.08 Å2ChemAxon Rotatable Bond Count9ChemAxon Refractivity86.6 m3·mol-1ChemAxon Polarizability34.88 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0udi-0239000000-850143c9c0e2faa19d0fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0gbi-0930000000-c4c88d5b9acc354dad95View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0gb9-0900000000-6c74a9e70b949b0b1a00View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0159-0900000000-a71a2b4b1f37329ca7f0View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0159-1900000000-58d3e9baef3c5fcd5255View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0159-4900000000-dc9a9c630ba915c7aec2View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01610

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01610

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01610 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    57721 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Valganciclovir NuGOwiki Link

    HMDB15548 Metagene Link

    HMDB15548 METLIN ID

    Not Available PubChem Compound

    64147 PDB ID

    Not Available ChEBI ID

    63635

    Product: CGP 57381

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Umapathy NS, Ganapathy V, Ganapathy ME: Transport of amino acid esters and the amino-acid-based prodrug valganciclovir by the amino acid transporter ATB(0,+). Pharm Res. 2004 Jul;21(7):1303-10. [PubMed:15290873 ]

    PMID: 15520202

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