Page last updated: 2024-12-11
valopicitabine
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
valopicitabine: prodrug of 2'-C-methylcytidine; an anti-hepatitis C virus agent; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
ID Source | ID |
---|---|
PubMed CID | 6918726 |
CHEMBL ID | 393820 |
SCHEMBL ID | 1378167 |
MeSH ID | M0492933 |
Synonyms (21)
Synonym |
---|
valopicitabine |
val-mcyd |
nmc-283 |
nm-283 |
CHEMBL393820 |
[(2r,3r,4r,5r)-5-(4-amino-2-oxo-pyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)-4-methyl-tetrahydrofuran-3-yl] (2s)-2-amino-3-methyl-butanoate |
2'-c-methyl-3'-o-(l-valinyl)-.beta.-d-cytidine |
2'-c-methylcytidine 3'-o-valinyl ester |
2'-c-methylcytidine 3'-o-l-valinyl ester |
i2t0b5g94m , |
l-valine, 3'-ester with 2'-c-methylcytidine |
valopicitabine [inn] |
unii-i2t0b5g94m |
640281-90-9 |
SCHEMBL1378167 |
DTXSID70214011 |
DB13920 |
HY-108060 |
CS-0027252 |
Q27280296 |
AKOS040740517 |
Research Excerpts
Pharmacokinetics
Excerpt | Reference | Relevance |
---|---|---|
" However, pharmacokinetic studies revealed that 2'-C-methylcytidine suffers from a low oral bioavailability." | ( Synthesis and pharmacokinetics of valopicitabine (NM283), an efficient prodrug of the potent anti-HCV agent 2'-C-methylcytidine. Amador, A; Benzaria, S; Bridges, EG; Cretton-Scott, E; D'Amours, M; Gosselin, G; Mao, J; Mathieu, S; Moussa, A; Pierra, C; Sommadossi, JP; Standring, DN; Storer, R, 2006) | 0.61 |
Bioavailability
Excerpt | Reference | Relevance |
---|---|---|
"In order to improve the oral bioavailability of 2-C-methylcytidine, a potent anti-HCV agent, the corresponding 3'-O-L-valinyl ester derivative (NM 283) has been synthesized Based on its ease of synthesis and its physicochemical properties, NM 283 has emerged as a promising antiviral drug for treatment of chronic HCV infection." | ( Nm 283, an efficient prodrug of the potent anti-HCV agent 2'-C-methylcytidine. Amador, A; Benzaria, S; Gosselin, G; Mathieu, S; Moussa, A; Pierra, C; Storer, R, 2005) | 0.33 |
Dosage Studied
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Bioassays (24)
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID431942 | Stability in cryopreserved primary human hepatocytes assessed as increase in intracellular nucleoside triphosphate formation by LC-MS/MS analysis | 2009 | Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17 | Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. |
AID395002 | Metabolic stability in human hepatocyte assessed as nucleoside triphosphate at 10 uM level after 2 hrs | 2009 | Bioorganic & medicinal chemistry letters, Mar-01, Volume: 19, Issue:5 | Synthesis and evaluation of novel phosphoramidate prodrugs of 2'-methyl cytidine as inhibitors of hepatitis C virus NS5B polymerase. |
AID431946 | Drug concentration in hamster liver assessed as nucleoside triphosphate level at 30.2 umol/kg, po after 6 hrs | 2009 | Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17 | Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. |
AID432340 | Cytotoxicity against human HuH7 cells assessed as cell viability | 2009 | European journal of medicinal chemistry, Sep, Volume: 44, Issue:9 | Cyclic phosphoramidates as prodrugs of 2'-C-methylcytidine. |
AID431939 | Stability in cryopreserved primary human hepatocytes assessed as intracellular nucleoside triphosphate AUC (0 to 4 hrs) at 10 uM by LC-MS/MS analysis | 2009 | Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17 | Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. |
AID299924 | Cytotoxicity against Huh7 cells after 24 hrs by MTS assay | 2007 | Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15 | Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2'-C-methyladenosine. |
AID431936 | Selectivity index, ratio of CC50 for human HBI10A cells to EC50 for HCV infected in human HBI10A cells | 2009 | Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17 | Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. |
AID431938 | Stability in human HBI10A cells assessed as intracellular nucleoside triphosphate AUC (0 to 24 hrs) at 100 uM by LC-MS/MS analysis | 2009 | Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17 | Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. |
AID299923 | Antiviral activity against HCV genotype 1b in Huh7 cells assessed as inhibition of viral RNA replication after 72 hrs by ribonuclease protection assay | 2007 | Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15 | Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2'-C-methyladenosine. |
AID431928 | Antiviral activity against HCV assessed as logarithmic reduction in plasma viral RNA at 800 mg, po BID after 14 days | 2009 | Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17 | Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. |
AID431943 | Stability in rat hepatocytes assessed as intracellular nucleoside triphosphate AUC (0 to 4 hrs) at 10 uM by LC-MS/MS analysis | 2009 | Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17 | Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. |
AID520334 | Antiviral activity against HCV infected in human assessed as log reduction in viral load at 800 mg/kg SID | 2008 | Antimicrobial agents and chemotherapy, May, Volume: 52, Issue:5 | The hepatitis C virus replicon presents a higher barrier to resistance to nucleoside analogs than to nonnucleoside polymerase or protease inhibitors. |
AID431933 | Antiviral activity against HCV infected in human HBI10A cells by subgenomic viral replicon assay | 2009 | Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17 | Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. |
AID431945 | Stability in human hepatocytes assessed as intracellular nucleoside triphosphate AUC (0 to 2 hrs) by LC-MS/MS analysis | 2009 | Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17 | Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. |
AID432331 | Antiviral activity against HCV infected in human HuH7 cells by cell-based subgenomic replicon assay | 2009 | European journal of medicinal chemistry, Sep, Volume: 44, Issue:9 | Cyclic phosphoramidates as prodrugs of 2'-C-methylcytidine. |
AID395011 | Metabolic stability in rat liver assessed as nucleoside triphosphate formation at 30 umol/kg, po after 6 hrs | 2009 | Bioorganic & medicinal chemistry letters, Mar-01, Volume: 19, Issue:5 | Synthesis and evaluation of novel phosphoramidate prodrugs of 2'-methyl cytidine as inhibitors of hepatitis C virus NS5B polymerase. |
AID431935 | Cytotoxicity against human HBI10A cells | 2009 | Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17 | Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. |
AID395012 | Metabolic stability in rat liver assessed as nucleoside triphosphate formation at 1.5 umol/kg, iv after 6 hrs | 2009 | Bioorganic & medicinal chemistry letters, Mar-01, Volume: 19, Issue:5 | Synthesis and evaluation of novel phosphoramidate prodrugs of 2'-methyl cytidine as inhibitors of hepatitis C virus NS5B polymerase. |
AID299922 | Antiviral activity against HCV genotype 1b in Huh7 cells assessed as inhibition of viral RNA replication after 24 hrs by ribonuclease protection assay | 2007 | Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15 | Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2'-C-methyladenosine. |
AID432332 | AUC (0 to 2 hrs) in human hepatocytes assessed as conversion to 2'-C-methylcytidine triphosphate ((2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate at 10 uM | 2009 | European journal of medicinal chemistry, Sep, Volume: 44, Issue:9 | Cyclic phosphoramidates as prodrugs of 2'-C-methylcytidine. |
AID431937 | Stability in human HBI10A cells assessed as intracellular nucleoside triphosphate AUC (0 to 24 hrs) at 10 uM by LC-MS/MS analysis | 2009 | Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17 | Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection. |
AID432237 | Metabolic stability in sc dosed hamster liver assessed as formation of 2'-C-methylcytidine triphosphate ((2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate at 1.5 umol after 6 hrs | 2009 | European journal of medicinal chemistry, Sep, Volume: 44, Issue:9 | Cyclic phosphoramidates as prodrugs of 2'-C-methylcytidine. |
AID395000 | Antiviral activity against HCV infected in human hepatoma cells by replicon assay | 2009 | Bioorganic & medicinal chemistry letters, Mar-01, Volume: 19, Issue:5 | Synthesis and evaluation of novel phosphoramidate prodrugs of 2'-methyl cytidine as inhibitors of hepatitis C virus NS5B polymerase. |
AID395001 | Metabolic stability in rat hepatocyte assessed as nucleoside triphosphate at 10 uM level after 2 hrs | 2009 | Bioorganic & medicinal chemistry letters, Mar-01, Volume: 19, Issue:5 | Synthesis and evaluation of novel phosphoramidate prodrugs of 2'-methyl cytidine as inhibitors of hepatitis C virus NS5B polymerase. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (18)
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 16 (88.89) | 29.6817 |
2010's | 2 (11.11) | 24.3611 |
2020's | 0 (0.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Market Indicators
Research Demand Index: 18.92
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (18.92) All Compounds (24.57) |
Study Types
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 7 (38.89%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 11 (61.11%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |