Valopicitabine

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

Identification

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Name
Valopicitabine
Accession Number
DB13920
Type
Small Molecule
Groups
Experimental
Description

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]

Structure
Thumb
Synonyms
  • 2'-C-methylcytidine 3'-O-L-valinyl ester
External IDs
NM-283 / NM283
Product Ingredients
IngredientUNIICASInChI Key
Valopicitabine dihydrochloride7KNU786IT4640725-71-9XENHXZMAOSTXGD-DSMKLBDQSA-N
Categories
UNII
I2T0B5G94M
CAS number
640281-90-9
Weight
Average: 356.379
Monoisotopic: 356.169584509
Chemical Formula
C15H24N4O6
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)-4-hydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)-2-(hydroxymethyl)-4-methyloxolan-3-yl (2S)-2-amino-3-methylbutanoate
SMILES
[H][C@](N)(C(C)C)C(=O)O[C@]1([H])[C@@]([H])(CO)O[C@@]([H])(N2C=CC(=N)N=C2O)[C@]1(C)O

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:28215138]
  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. [PubMed:17328231]
External Links
PubChem Compound
6918726
PubChem Substance
347829335
ChemSpider
5293918
ChEMBL
CHEMBL393820

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.723 mg/mLALOGPS
logP-0.88ALOGPS
logP-2.3ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)5.79ChemAxon
pKa (Strongest Basic)7.49ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area161.69 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.6 m3·mol-1ChemAxon
Polarizability35.82 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
Not Available

Taxonomy

Classification
Not classified

Drug created on October 23, 2017 07:43 / Updated on May 01, 2019 13:30