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
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/17064080 | http://www.jbc.org/content/283/4/2167.full#T4 | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346640/ | https://www.ncbi.nlm.nih.gov/pubmed/23986582 | https://www.ncbi.nlm.nih.gov/pubmed/27252124 | https://www.ncbi.nlm.nih.gov/pubmed/21709100https://www.ncbi.nlm.nih.gov/pubmed/17328231 | https://www.ncbi.nlm.nih.gov/pubmed/18479202 | https://www.thepharmaletter.com/article/fda-puts-clinical-hold-on-valopicitabine-over-risk-benefit-profile-idenix-plunges-34
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17064080 | http://www.jbc.org/content/283/4/2167.full#T4 | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2346640/ | https://www.ncbi.nlm.nih.gov/pubmed/23986582 | https://www.ncbi.nlm.nih.gov/pubmed/27252124 | https://www.ncbi.nlm.nih.gov/pubmed/21709100https://www.ncbi.nlm.nih.gov/pubmed/17328231 | https://www.ncbi.nlm.nih.gov/pubmed/18479202 | https://www.thepharmaletter.com/article/fda-puts-clinical-hold-on-valopicitabine-over-risk-benefit-profile-idenix-plunges-34
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL5375 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18479202 |
0.5 µM [IC50] | ||
Target ID: CHEMBL5375 Sources: http://www.jbc.org/content/283/4/2167.full#T4 |
1.05 µM [IC50] | ||
Target ID: human norovirus replication |
18.0 µM [EC50] | ||
Target ID: CHEMBL613008 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17055073 |
6.4 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Ribavirin antagonizes the in vitro anti-hepatitis C virus activity of 2'-C-methylcytidine, the active component of valopicitabine. | 2006 Oct |
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Pyrophosphorolytic excision of nonobligate chain terminators by hepatitis C virus NS5B polymerase. | 2007 Aug |
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2'-C-methylcytidine as a potent and selective inhibitor of the replication of foot-and-mouth disease virus. | 2007 Mar |
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Comparative study of the genetic barriers and pathways towards resistance of selective inhibitors of hepatitis C virus replication. | 2011 Sep |
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The viral polymerase inhibitor 2'-C-methylcytidine inhibits Norwalk virus replication and protects against norovirus-induced diarrhea and mortality in a mouse model. | 2013 Nov |
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Biochemical Evaluation of the Inhibition Properties of Favipiravir and 2'-C-Methyl-Cytidine Triphosphates against Human and Mouse Norovirus RNA Polymerases. | 2015 Dec |
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Treatment with a Nucleoside Polymerase Inhibitor Reduces Shedding of Murine Norovirus in Stool to Undetectable Levels without Emergence of Drug-Resistant Variants. | 2015 Dec 28 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23986582
Curator's Comment: Study in AG129 mice (129/Sv mice deficient in both alpha/beta interferon [IFN-α/β] and IFN-γ receptors)
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17055073
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.
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NCI_THESAURUS |
C1557
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DTXSID70214011
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SUB35614
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C66649
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I2T0B5G94M
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CHEMBL393820
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DB13920
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100000128514
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Valopicitabine
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8625
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C506207
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640281-90-9
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD