NAV

Valopicitabine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Valopicitabine
DrugBank Accession Number
DB13920
Background

The 3-O-valine ester prodrug of the nucleoside analog 2'-C-methylcytidine with anti-hepatitis C virus (HCV) activity. Upon administration, valopicitabine is converted into 2'-C-methylcytidine; upon phosphorylation into its 5-triphosphate form, this metabolite inhibits viral RNA chain elongation and viral RNA-dependent RNA polymerase activity. This blocks viral production of HCV RNA and thus viral replication. [from NCI]

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 356.379
Monoisotopic: 356.169584509
Chemical Formula
C15H24N4O6
Synonyms
  • 2'-C-methylcytidine 3'-O-L-valinyl ester
  • Valopicitabina
  • Valopicitabine
External IDs
  • NM-283
  • NM283
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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
Not Available
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

Products

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Product Ingredients
IngredientUNIICASInChI Key
Valopicitabine dihydrochloride7KNU786IT4640725-71-9XENHXZMAOSTXGD-DSMKLBDQSA-N

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
I2T0B5G94M
CAS number
640281-90-9
InChI Key
TVRCRTJYMVTEFS-ICGCPXGVSA-N
InChI
InChI=1S/C15H24N4O6/c1-7(2)10(17)12(21)25-11-8(6-20)24-13(15(11,3)23)19-5-4-9(16)18-14(19)22/h4-5,7-8,10-11,13,20,23H,6,17H2,1-3H3,(H2,16,18,22)/t8-,10+,11-,13-,15-/m1/s1
IUPAC Name
(2R,3R,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)-4-methyloxolan-3-yl (2S)-2-amino-3-methylbutanoate
SMILES
CC(C)[C@H](N)C(=O)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CC(N)=NC2=O)[C@]1(C)O

References

General References
  1. Krecmerova M: Amino Acid Ester Prodrugs of Nucleoside and Nucleotide Antivirals. Mini Rev Med Chem. 2017;17(10):818-833. doi: 10.2174/1389557517666170216151601. [Article]
  2. Toniutto P, Fabris C, Bitetto D, Fornasiere E, Rapetti R, Pirisi M: Valopicitabine dihydrochloride:a specific polymerase inhibitor of hepatitis C virus. Curr Opin Investig Drugs. 2007 Feb;8(2):150-8. [Article]
PubChem Compound
6918726
PubChem Substance
347829335
ChemSpider
5293918
ChEMBL
CHEMBL393820
ZINC
ZINC000053188593

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection3
1, 2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1

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 Solubility7.77 mg/mLALOGPS
logP-0.8ALOGPS
logP-1.5Chemaxon
logS-1.7ALOGPS
pKa (Strongest Acidic)12.59Chemaxon
pKa (Strongest Basic)7.48Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area160.7 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity85.18 m3·mol-1Chemaxon
Polarizability35.02 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1009000000-ba7b92a67399e4693fdd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-0797000000-46487e1b89ca4e26f274
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9203000000-f994672840cb36979f8b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-08mu-4591000000-53ea1befbab38559da38
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bt9-7931000000-c84ca3fda409401a2563
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01xx-8691000000-a900d1baff148dd87723
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]-199.1498294
predicted
DarkChem Lite v0.1.0
[M+H]+199.2998294
predicted
DarkChem Lite v0.1.0
[M+Na]+198.5112294
predicted
DarkChem Lite v0.1.0

Drug created at October 23, 2017 13:43 / Updated at February 21, 2021 18:54