Compounds > valopicitabine
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 SourceID
PubMed CID6918726
CHEMBL ID393820
SCHEMBL ID1378167
MeSH IDM0492933

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

ExcerptReferenceRelevance
" 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

ExcerptReferenceRelevance
"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

ExcerptRelevanceReference
" Our SAR studies ultimately led to compounds that gave high levels of NTP in hamster and rat liver after subcutaneous dosing and that were devoid of the toxic phenol moiety usually found in ProTides."( Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.
Attenni, B; Di Marco, A; Donghi, M; Fiore, F; Gardelli, C; Gennari, N; Giuliano, C; Harper, S; Laufer, R; Leone, JF; MacCoss, M; Marcucci, I; Meppen, M; Narjes, F; Olsen, DB; Pacini, B; Pucci, V; Rowley, M, 2009)		0.35
" Screening for 2'-C-methylcytidine triphosphate levels in rat liver after oral dosing identified 1-[3,5-difluorophenyl]-1,3-propandiol as an efficient prodrug modification."( Antiviral efficacy upon administration of a HepDirect prodrug of 2'-C-methylcytidine to hepatitis C virus-infected chimpanzees.
Boyer, SH; Carroll, SS; Erion, MD; Fujitaki, JM; Handt, L; Hecker, SJ; Koeplinger, K; Linemeyer, DL; MacCoss, M; Olsen, DB; Reddy, KR; Sun, Z; van Poelje, PD; Vavrek, M; Zhang, NR, 2011)		0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID431942Stability in cryopreserved primary human hepatocytes assessed as increase in intracellular nucleoside triphosphate formation by LC-MS/MS analysis2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.
AID395002Metabolic stability in human hepatocyte assessed as nucleoside triphosphate at 10 uM level after 2 hrs2009Bioorganic & 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.
AID431946Drug concentration in hamster liver assessed as nucleoside triphosphate level at 30.2 umol/kg, po after 6 hrs2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.
AID432340Cytotoxicity against human HuH7 cells assessed as cell viability2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Cyclic phosphoramidates as prodrugs of 2'-C-methylcytidine.
AID431939Stability in cryopreserved primary human hepatocytes assessed as intracellular nucleoside triphosphate AUC (0 to 4 hrs) at 10 uM by LC-MS/MS analysis2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.
AID299924Cytotoxicity against Huh7 cells after 24 hrs by MTS assay2007Bioorganic & 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.
AID431936Selectivity index, ratio of CC50 for human HBI10A cells to EC50 for HCV infected in human HBI10A cells2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.
AID431938Stability in human HBI10A cells assessed as intracellular nucleoside triphosphate AUC (0 to 24 hrs) at 100 uM by LC-MS/MS analysis2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.
AID299923Antiviral activity against HCV genotype 1b in Huh7 cells assessed as inhibition of viral RNA replication after 72 hrs by ribonuclease protection assay2007Bioorganic & 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.
AID431928Antiviral activity against HCV assessed as logarithmic reduction in plasma viral RNA at 800 mg, po BID after 14 days2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.
AID431943Stability in rat hepatocytes assessed as intracellular nucleoside triphosphate AUC (0 to 4 hrs) at 10 uM by LC-MS/MS analysis2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.
AID520334Antiviral activity against HCV infected in human assessed as log reduction in viral load at 800 mg/kg SID2008Antimicrobial 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.
AID431933Antiviral activity against HCV infected in human HBI10A cells by subgenomic viral replicon assay2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.
AID431945Stability in human hepatocytes assessed as intracellular nucleoside triphosphate AUC (0 to 2 hrs) by LC-MS/MS analysis2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.
AID432331Antiviral activity against HCV infected in human HuH7 cells by cell-based subgenomic replicon assay2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Cyclic phosphoramidates as prodrugs of 2'-C-methylcytidine.
AID395011Metabolic stability in rat liver assessed as nucleoside triphosphate formation at 30 umol/kg, po after 6 hrs2009Bioorganic & 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.
AID431935Cytotoxicity against human HBI10A cells2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.
AID395012Metabolic stability in rat liver assessed as nucleoside triphosphate formation at 1.5 umol/kg, iv after 6 hrs2009Bioorganic & 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.
AID299922Antiviral activity against HCV genotype 1b in Huh7 cells assessed as inhibition of viral RNA replication after 24 hrs by ribonuclease protection assay2007Bioorganic & 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.
AID432332AUC (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 uM2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Cyclic phosphoramidates as prodrugs of 2'-C-methylcytidine.
AID431937Stability in human HBI10A cells assessed as intracellular nucleoside triphosphate AUC (0 to 24 hrs) at 10 uM by LC-MS/MS analysis2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Phosphoramidate prodrugs of 2'-C-methylcytidine for therapy of hepatitis C virus infection.
AID432237Metabolic 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 hrs2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Cyclic phosphoramidates as prodrugs of 2'-C-methylcytidine.
AID395000Antiviral activity against HCV infected in human hepatoma cells by replicon assay2009Bioorganic & 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.
AID395001Metabolic stability in rat hepatocyte assessed as nucleoside triphosphate at 10 uM level after 2 hrs2009Bioorganic & 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)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's16 (88.89)29.6817
2010's2 (11.11)24.3611
2020's0 (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.

MetricThis Compound (vs All)
Research Demand Index18.92 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index4.23 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.92)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews7 (38.89%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (61.11%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbostyril
Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.		3.1410monohydroxyquinoline;
quinolone		bacterial xenobiotic metabolite
cytidine monophosphate
Cytidine Monophosphate: Cytidine (dihydrogen phosphate). A cytosine nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.. cytidine 5'-monophosphate : A pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase.		2.0610cytidine 5'-phosphate;
pyrimidine ribonucleoside 5'-monophosphate		Escherichia coli metabolite;
human metabolite;
mouse metabolite
cytidine
[no description available]		9.0640cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
cytidine triphosphate
Cytidine Triphosphate: Cytidine 5'-(tetrahydrogen triphosphate). A cytosine nucleotide containing three phosphate groups esterified to the sugar moiety.		2.0510cytidine 5'-phosphate;
pyrimidine ribonucleoside 5'-triphosphate		Escherichia coli metabolite;
mouse metabolite
thiazoles
[no description available]		3.15101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
deoxycytidine
[no description available]		2.0210pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
ribavirin
Rebetron: Rebetron is tradename		4.9401-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
nitazoxanide
nitazoxanide: a 5-nitrothiazolyl derivative used for a broad range of intestinal parasitic infections including CRYPTOSPORIDIUM and GIARDIA; it is a redox-active nitrothiazolyl-salicylamide prodrug		3.1510benzamides;
carboxylic ester
proline
Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.		4.0520amino acid zwitterion;
glutamine family amino acid;
L-alpha-amino acid;
proline;
proteinogenic amino acid		algal metabolite;
compatible osmolytes;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
taribavirin
[no description available]		3.5320nucleobase-containing molecular entity
4'-azidocytidine
4'-azidocytidine: antiviral; structure in first source		3.8330N-glycosyl compound
2'-c-methyladenosine
2'-C-methyladenosine: antiviral		2.0310
2'-c-methylcytidine
2'-C-methylcytidine: structure in first source		7.9640
telaprevir
[no description available]		5.4960cyclopentapyrrole;
cyclopropanes;
oligopeptide;
pyrazines		antiviral drug;
hepatitis C protease inhibitor;
peptidomimetic
mk 0608
7-deaza-2'-C-methyladenosine: an antiviral agent		2.0310
jtk-303
[no description available]		3.1410aromatic ether;
monochlorobenzenes;
organofluorine compound;
quinolinemonocarboxylic acid;
quinolone		HIV-1 integrase inhibitor
psi 6130
2'-deoxy-2'-fluoro-2'-C-methylcytidine: PSI-6130 is the (beta-D)-isomer; has antiviral activity against hepatitis C virus; structure in first source		2.0410
hcv 796
HCV 796: inhibits HCV RdRp; structure in first source		2.0410
balapiravir
balapiravir: a prodrug of R1479; structure in first source		3.8330
losartan potassium
Erythropoietin: Glycoprotein hormone, secreted chiefly by the KIDNEY in the adult and the LIVER in the FETUS, that acts on erythroid stem cells of the BONE MARROW to stimulate proliferation and differentiation.		3.1310
rg 7128
2'-fluoro-2'-methyl-3',5'-diisobutyryldeoxycytidine: inhibits HCV polymerase; structure in first source		2.0510
raltegravir potassium
Raltegravir Potassium: A pyrrolidinone derivative and HIV INTEGRASE INHIBITOR that is used in combination with other ANTI-HIV AGENTS for the treatment of HIV INFECTION.		3.1410
ConditionIndicatedRelationship StrengthStudiesTrials
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted
[description not available]		04.8170
Hepatitis C
INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.		09.8170
Chronic Hepatitis C
[description not available]		05.4360
HIV Coinfection
[description not available]		03.8320
Drug Abuse, Intravenous
[description not available]		02.9610
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		03.8320
Hepatitis C, Chronic
INFLAMMATION of the LIVER in humans that is caused by HEPATITIS C VIRUS lasting six months or more. Chronic hepatitis C can lead to LIVER CIRRHOSIS.		17.4360
Cirrhosis, Liver
[description not available]		02.9410
Liver Cirrhosis
Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.		02.9410