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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H24N4O6
Molecular Weight 356.3743
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALOPICITABINE

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

InChI

InChIKey=TVRCRTJYMVTEFS-ICGCPXGVSA-N
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

HIDE SMILES / InChI

Molecular Formula C15H24N4O6
Molecular Weight 356.3743
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Valopicitabine is a nucleoside analog and the orally bioavailable prodrug of NM107 that competitively inhibits HCV NS5B polymerase, causing chain termination. Valopicitabine had been in phase II clinical trial for once-daily oral treatment of Hepatitis C virus infection. However, because of the overall risk/benefit profile of subjects undergoing clinical trials, further development of the drug has been temporarily placed on hold by the Swiss drug major Novartis and USA-based Idenix Pharmaceuticals company and the FDA.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.5 µM [IC50]
1.05 µM [IC50]
18.0 µM [EC50]
6.4 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Treatment with 2CMC (2'-C-methylcytidine ) was initiated 1 h before human norovirus infection with a dose of 100 mg/kg/day divided into two daily treatments (2 × 50 mg/kg) for 7 consecutive days by the subcutaneous route (n = 15).
Route of Administration: Other
In Vitro Use Guide
The 50% and 90% effective concentrations (EC50 and EC90) for inhibition of the foot-and-mouth disease virus (FMDV) - induced cytopathic effect (CPE) formation were 6.4+/-3.8 and 10.8+/-5.4 uM. Comparable EC50 values for inhibition of viral RNA synthesis were observed. Treatment of FMDV-infected BHK-21 cells with 77 uM 2'-C-MetCyt resulted in a (1.6-3.2)x10(3)-fold reduction of infectious virus yield.
Substance Class Chemical
Record UNII
I2T0B5G94M
Record Status Validated (UNII)
Record Version