Page last updated: 2024-12-07

pyrimidin-2-one beta-ribofuranoside

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

pyrimidin-2-one beta-ribofuranoside: RN given refers to (D)-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID100016
CHEMBL ID504567
CHEBI ID46938
SCHEMBL ID13032
MeSH IDM0053562

Synonyms (55)

Synonym
3690-10-6
nsc-309132
zebularine
NCGC00159549-02
DB03068
dhz ,
CHEBI:46938 ,
2-pyrimidone-1-beta-d-riboside
pyrimidin-2-one beta-d-ribofuranoside
1-beta-d-ribofuranosylpyrimidin-2(1h)-one
1-beta-d-ribofuranosyl-2(1h)-pyrimidinone
pyrimidin-2-one beta-ribofuranoside
pyrimidin-2-one ribonucleoside
c9h12n2o5
2(1h)-pyrimidinone, 1-beta-d-ribofuranosyl-
nsc 309132
pyrimidin-2-one-ribonucleoside
1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
CHEMBL504567
nsc 309132; pyrimidin-2-one beta-d-ribofuranoside; zebularine;1-beta-d-ribofuranosyl-2(1h)-pyrimidinone;1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1h)-one;zebularine
A823445
unii-7a9y5sx0gy
7a9y5sx0gy ,
BRD-K87714311-001-01-9
1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
gtpl4729
SCHEMBL13032
ze8 ,
J-700277
CS-3403
1-((2r,3r,4s,5r)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1h-pyrimidin-2-one
1-?-d-ribofuranosyl-2(1h)-pyrimidinone
HY-13420
AKOS024457033
1-.beta.-d-ribofuranosyl-2(1h)-pyrimidinone
pyrimidin-2-one .beta.-d-ribofuranoside
uridine, 4-deoxy-
1-(.beta.-d-ribofuranosyl)-2-pyrimidone
mfcd04973699
4PD7
RPQZTTQVRYEKCR-WCTZXXKLSA-N
1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1h)-one
zebularine, >=98% (hplc), solid
1-(beta-d-ribofuranosyl)pyrimidin-2(1h)-one
nsc309132;4-deoxyuridine
HB1378
1-beta-d-ribofuranosyl-2(1h)-pyrimidino ne
HMS3677C14
DS-11855
bdbm50226311
HMS3413C14
Q8068322
DTXSID20958099
1-pentofuranosylpyrimidin-2(1h)-one
BP-58607

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The fluorescence properties of dZeb were used to quantify the amount of this analog incorporated into cellular DNA of mismatch repair-deficient cells expressing Dm-dNK and the results showed that in a mismatch correction-defective strain a high percentage of DNA bases may be replaced with the analog without long term toxic effects."( Use of Drosophila deoxynucleoside kinase to study mechanism of toxicity and mutagenicity of deoxycytidine analogs in Escherichia coli.
Betham, B; Bhagwat, AS; Marquez, VE; Shalhout, S, 2010
)
0.36

Pharmacokinetics

ExcerptReferenceRelevance
" When co-delivered with pSL, zebularine increased cellular gemcitabine concentration by 4-fold, and extended the half-life of gemcitabine in plasma by 22-fold in rats."( Zebularine suppressed gemcitabine-induced senescence and improved the cellular and plasma pharmacokinetics of gemcitabine, augmented by liposomal co-delivery.
Leung, E; Lozano Hernandez, L; Reginald-Opara, JN; Svirskis, D; Tang, M; Wang, H; Wu, Z, 2021
)
0.62

Compound-Compound Interactions

ExcerptReferenceRelevance
" The current study was designed to evaluate the effect of zebularine in comparison to and in combination with trichostatin A (TSA) on p21Cip1/Waf1/Sdi1, p27Kip1, p57Kip2, DNA methyltransferases (DNMT1, 3a and 3b) and histone deacetylases (HDAC1, 2, and 3) genes expression, cell growth inhibition and apoptosis induction in colon cancer LS 180 cell line."( Investigation of the Effect of Zebularine in Comparison to and in Combination with Trichostatin A on p21Cip1/Waf1/ Sdi1, p27Kip1, p57Kip2, DNA Methyltransferases and Histone Deacetylases in Colon Cancer LS 180 Cell Line.
Kavoosi, F; Sanaei, M, 2020
)
0.56
" The present study was designed to investigate the effect of zebularine in comparison to and in combination with trichostatin A on p21Cip1/Waf1/Sdi1, p27Kip1, p57Kip2, DNMT1, DNMT3a and DNMT3b, Class I HDACs (HDACs 1, 2, 3) and Class II HDACs (HDACs 4, 5, 6) gene expression, cell growth inhibition and apoptosis induction in colon cancer LS 174T cell line."( Effect of Zebularine in Comparison to and in Combination with Trichostatin A on CIP/KIP Family (p21Cip1/Waf1/Sdi1, p27Kip1, and p57Kip2), DNMTs (DNMT1, DNMT3a, and DNMT3b), Class I HDACs (HDACs 1, 2, 3) and Class II HDACs (HDACs 4, 5, 6) Gene Expression,
Kavoosi, F; Sanaei, M, 2020
)
0.56

Bioavailability

ExcerptReferenceRelevance
"Zebularine is a second-generation, highly stable hydrophilic inhibitor of DNA methylation with oral bioavailability that preferentially target cancer cells."( Zebularine induces replication-dependent double-strand breaks which are preferentially repaired by homologous recombination.
Burgos-Morón, E; Calderón-Montaño, JM; Domínguez, I; Helleday, T; Huertas Castaño, C; López-Lázaro, M; Mateos, S; Orta, ML; Pastor, N, 2017
)
0.46

Dosage Studied

ExcerptRelevanceReference
"Differential progression of global DNA hypomethylation was studied by comparatively dosing zebularine (ZEB) and 5-azacytidine (AZA)."( 3-D DNA methylation phenotypes correlate with cytotoxicity levels in prostate and liver cancer cell models.
Gertych, A; Oh, JH; Tajbakhsh, J; Wawrowsky, KA; Weisenberger, DJ, 2013
)
0.39
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pyrimidine ribonucleosides
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (5)

PathwayProteinsCompounds
pyrimidine ribonucleosides degradation513
superpathway of pyrimidine ribonucleosides salvage2237
pyrimidine ribonucleosides salvage I613
pyrimidine ribonucleosides salvage II812
salvage pathways of pyrimidine ribonucleotides936

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine deaminaseMus musculus (house mouse)Ki1.00001.00005.45009.9000AID33972
Cytidine deaminaseHomo sapiens (human)Ki14.10000.00001.43332.3000AID238723; AID55388; AID55389
Cytidine deaminaseMus musculus (house mouse)Ki2.00002.00006.000010.0000AID55384
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
cell surface receptor signaling pathwayCytidine deaminaseHomo sapiens (human)
pyrimidine-containing compound salvageCytidine deaminaseHomo sapiens (human)
cytidine deaminationCytidine deaminaseHomo sapiens (human)
cytosine metabolic processCytidine deaminaseHomo sapiens (human)
negative regulation of cell growthCytidine deaminaseHomo sapiens (human)
UMP salvageCytidine deaminaseHomo sapiens (human)
negative regulation of nucleotide metabolic processCytidine deaminaseHomo sapiens (human)
response to cycloheximideCytidine deaminaseHomo sapiens (human)
cellular response to external biotic stimulusCytidine deaminaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
nucleoside bindingCytidine deaminaseHomo sapiens (human)
cytidine deaminase activityCytidine deaminaseHomo sapiens (human)
protein bindingCytidine deaminaseHomo sapiens (human)
zinc ion bindingCytidine deaminaseHomo sapiens (human)
identical protein bindingCytidine deaminaseHomo sapiens (human)
protein homodimerization activityCytidine deaminaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
extracellular regionCytidine deaminaseHomo sapiens (human)
cytosolCytidine deaminaseHomo sapiens (human)
secretory granule lumenCytidine deaminaseHomo sapiens (human)
tertiary granule lumenCytidine deaminaseHomo sapiens (human)
ficolin-1-rich granule lumenCytidine deaminaseHomo sapiens (human)
cytosolCytidine deaminaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (57)

Assay IDTitleYearJournalArticle
AID124814Antitumor activity against P388 tumor in mice, at a dose of 400 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID124819Antitumor activity against ara-c resistance L1210 tumor in mice, at a dose of 400 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID431237Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as PSI-6130 nucleotide diphosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in presence of 50 uM DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID124820Antitumor activity against ara-c resistance L1210 tumor in mice, at a dose of 800 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID431236Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as PSI-6130 nucleotide diphosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in absence of DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID116797Percent increase in life span of drug-treated mice relative to tumored, vehicle treated controls at a dose of 800 mg/kg ip.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID124803Antitumor activity against L1210 tumor in mice, at a dose of 800 mg/kg per sc administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID116787Percent increase in life span of drug-treated mice relative to tumored, vehicle treated controls at a dose of 200 mg/kg ip.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID116796Percent increase in life span of drug-treated mice relative to tumored, vehicle treated controls at a dose of 800 mg/kg, sc administration1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID116790Percent increase in life span of drug-treated mice relative to tumored, vehicle treated controls at a dose of 400 mg/kg ip.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID431240Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as PSI-6130 nucleotide triphosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in presence of 50 uM DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID124806Antitumor activity against L1210 tumor in mice, at a dose of 800 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID431239Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as PSI-6130 nucleotide triphosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in absence of DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID238723Binding affinity for human cytidine deaminase2005Journal of medicinal chemistry, Feb-10, Volume: 48, Issue:3
Structure of human cytidine deaminase bound to a potent inhibitor.
AID124811Antitumor activity against P388 tumor in mice, at a dose of 200 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID124788Antitumor activity against B16 tumor in mice, at a dose of 200 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID124816Antitumor activity against P388 tumor in mice, at a dose of 600 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID431233Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as PSI-6130 nucleotide monophosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in absence of DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID431235Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as PSI-6130 nucleotide monophosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in presence of 100 uM DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID124789Antitumor activity against B16 tumor in mice, at a dose of 400 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID124796Antitumor activity against L1210 tumor in mice, at a dose of 400 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID431256Antiviral activity against wild type HCV infected in human HuH7 cells assessed as inhibition of viral RNA replication after 4 days by replicon assay2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID431234Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as PSI-6130 nucleotide monophosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in presence of 50 uM DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID431258Cytotoxicity against HCV subgenomic replicon RNA-containing human HuH7 cells at > 400 uM2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID116791Percent increase in life span of drug-treated mice relative to tumored, vehicle treated controls at a dose of 400 mg/kg sc administration1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID431257Antiviral activity against HCV harboring NS5B polymerase S282T mutant infected in human HuH7 cells assessed as inhibition of viral RNA replication after 4 days by replicon assay2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID124797Antitumor activity against L1210 tumor in mice, at a dose of 400 mg/kg per sc administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID33972Compound was tested for the inhibitory constant for adenosine deaminase (ADA)1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis of pyrimidin-2-one nucleosides as acid-stable inhibitors of cytidine deaminase.
AID431244Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as RO2433 nucleotide monophosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in presence of 100 uM DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID124805Antitumor activity against L1210 tumor in mice, at a dose of 1600 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID620532Reactivation of MeCp2 mutant expression in human GM11272 cells at 1 to 100 nM by PCR method2011Bioorganic & medicinal chemistry letters, Sep-15, Volume: 21, Issue:18
Clonal Rett Syndrome cell lines to test compounds for activation of wild-type MeCP2 expression.
AID124817Antitumor activity against P388 tumor in mice, at a dose of 400 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID431247Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as RO2433 nucleotide diphosphate level at 5 uM after 48 hrs by HPLC analysis in presence of 100 uM DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID55388Apparent Ki (binding affinity) was calculated for the compound against cytidine deaminase.1998Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14
Carbocyclic analogues of the potent cytidine deaminase inhibitor 1-(beta-D-ribofuranosyl)-1,2-dihydropyrimidin-2-one (zebularine).
AID347364Induction of p16 gene expression in human HCT15 cells at 100 uM after 8 days by real time PCR in presence of 100 mM thymidine2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Activation of p16 gene silenced by DNA methylation in cancer cells by phosphoramidate derivatives of 2'-deoxyzebularine.
AID431243Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as RO2433 nucleotide monophosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in presence of 50 uM DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID431246Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as RO2433 nucleotide diphosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in presence of 50 uM DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID347368Cytotoxicity against human Cf-Pac-1 cells assessed as increase in cell population doubling time at 100 uM after 8 days in presence of 100 uM thymidine2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Activation of p16 gene silenced by DNA methylation in cancer cells by phosphoramidate derivatives of 2'-deoxyzebularine.
AID124802Antitumor activity against L1210 tumor in mice, at a dose of 800 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID347365Induction of p16 gene expression in human T24 cells at 100 uM after 8 days by real time PCR in presence of 100 mM thymidine2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Activation of p16 gene silenced by DNA methylation in cancer cells by phosphoramidate derivatives of 2'-deoxyzebularine.
AID124790Antitumor activity against B16 tumor in mice, at a dose of 800 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID124818Antitumor activity against ara-c resistance L1210 tumor in mice, at a dose of 200 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID431245Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as RO2433 nucleotide diphosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in absence of DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID55384Compound was tested for the inhibitory constant for mouse kidney cytidine deaminase1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis of pyrimidin-2-one nucleosides as acid-stable inhibitors of cytidine deaminase.
AID431249Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as RO2433 nucleotide triphosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in presence of 50 uM DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID431242Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as RO2433 nucleotide monophosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in absence of DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID431248Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as RO2433 nucleotide triphosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in absence of DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID124807Antitumor activity against L7210 tumor in mice, at a dose of 400 mg/kg per ip administration.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID116795Percent increase in life span of drug-treated mice relative to tumored, vehicle treated controls at a dose of 600 mg/kg ip.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID55389Compound was tested for its binding affinity against cytidine deaminase.1998Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14
Carbocyclic analogues of the potent cytidine deaminase inhibitor 1-(beta-D-ribofuranosyl)-1,2-dihydropyrimidin-2-one (zebularine).
AID431241Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as PSI-6130 nucleotide triphosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in presence of 100 uM DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID116785Percent increase in life span of drug-treated mice relative to tumored, vehicle treated controls at a dose of 1600 mg/kg ip.1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID431250Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as RO2433 nucleotide triphosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in presence of 100 uM DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID116798Percent increase in life span of drug-treated mice relative to tumored, vehicle treated controls at a dose of 800 mg/kg sc administration1991Journal of medicinal chemistry, Nov, Volume: 34, Issue:11
Antitumor properties of 2(1H)-pyrimidinone riboside (zebularine) and its fluorinated analogues.
AID431238Drug metabolism in HCV subgenomic replicon RNA-containing human HuH7 cells assessed as PSI-6130 nucleotide diphosphate level per 10 '6 cells at 5 uM after 48 hrs by HPLC analysis in presence of 100 uM DCTD inhibitor zedularine2008Antimicrobial agents and chemotherapy, Feb, Volume: 52, Issue:2
The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.
AID1347411qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Mechanism Interrogation Plate v5.0 (MIPE) Libary2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2014eLife, Jul-31, Volume: 3Structural basis of nucleoside and nucleoside drug selectivity by concentrative nucleoside transporters.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (205)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (1.95)18.7374
1990's5 (2.44)18.2507
2000's62 (30.24)29.6817
2010's107 (52.20)24.3611
2020's27 (13.17)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.42

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.42 (24.57)
Research Supply Index5.34 (2.92)
Research Growth Index5.76 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.42)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews6 (2.90%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other201 (97.10%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]