Page last updated: 2024-12-06

5-benzylacyclouridine

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

Description

5-Benzylacyclouridine is a synthetic nucleoside analog that has been studied for its potential antiviral and antitumor activities. It is an analog of uridine, a naturally occurring nucleoside, and differs from uridine by the presence of a benzyl group at the 5' position. The benzyl group modification enhances the compound's stability and bioavailability, allowing it to penetrate cells more effectively. 5-Benzylacyclouridine has been shown to inhibit the replication of several viruses, including herpes simplex virus and cytomegalovirus. It is believed to exert its antiviral effect by acting as a substrate for viral DNA polymerases, ultimately leading to the termination of viral DNA synthesis. Moreover, 5-Benzylacyclouridine has also been investigated for its anticancer properties. Studies have indicated that it can inhibit the growth of various cancer cell lines, suggesting its potential as a therapeutic agent for cancer treatment. Further research is ongoing to explore its pharmacological profile and potential applications in the treatment of viral infections and cancer.'

5-benzylacyclouridine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5-benzyl-1-(2-hydroxyethoxymethyl)uracil : A pyrimidone that is uracil which is substituted by a 2-hydroxyethoxymethyl group at position 1 and a benzyl group at position 5. [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]

Cross-References

ID SourceID
PubMed CID54929
CHEMBL ID17432
CHEBI ID41037
SCHEMBL ID7558156
MeSH IDM0106894

Synonyms (28)

Synonym
5-benzyl-1-(2-hydroxyethoxymethyl)uracil
5-benzylacyclouridine
82857-69-0
2,4(1h,3h)-pyrimidinedione, 1-[(2-hydroxyethoxy)methyl]-5-(phenylmethyl)-
benzylacyclouridine
5-benzyl-1-(2-hydroxyethoxymethyl)pyrimidine-2,4-dione
1-((2-hydroxyethoxy)methyl)-5-benzylpyrimidine-2,4(1h,3h)-dione
2,4(1h,3h)-pyrimidinedione, 1-((2-hydroxyethoxy)methyl)-5-(phenylmethyl)-
5-benzyl-1-(2'-hydroxyethoxymethyl)uracil
5-bacu
DB07437
CHEMBL17432 ,
chebi:41037 ,
bdbm50026387
5-benzyl-1-(2-hydroxy-ethoxymethyl)-1h-pyrimidine-2,4-dione
0h851i3o9d ,
unii-0h851i3o9d
SCHEMBL7558156
5-benzyl-1-[(2-hydroxyethoxy)methyl]pyrimidine-2,4(1h,3h)-dione
DTXSID30232034
Q27096656
MS-23926
HY-106406
5-benzyl-1-[(2-hydroxyethoxy)methyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
EN300-6739960
CS-0025738
AKOS040758372
Z3212792438

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" administration followed first-order kinetics with a half-life of approximately 36 min."( Benzylacyclouridine. Pharmacokinetics, metabolism and biochemical effects in mice.
Darnowski, JW; Handschumacher, RE, 1988
)
0.27
" In addition, uridine pharmacokinetics were associated with a time-dependent relationship as evidenced by an increased total plasma clearance, renal clearance and volume of distribution, resulting in a substantial decrease in uridine peak concentration with time."( Effects of 5-benzylacyclouridine, an inhibitor of uridine phosphorylase, on the pharmacokinetics of uridine in rhesus monkeys: implications for chemotherapy.
Anderson, DC; Cretton, EM; el Kouni, MH; Kidd, LB; McClure, HM; Sommadossi, JP, 1995
)
0.68

Compound-Compound Interactions

ExcerptReferenceRelevance
" Mice receiving the combination of tubercidin (or nebularine) plus NBMPR-P or dilazep, as well as those that survived the combination with dipyridamole, appeared healthy and were found to have normal size livers and spleens."( Treatment of schistosomiasis by purine nucleoside analogues in combination with nucleoside transport inhibitors.
Cha, S; el Kouni, MH; Messier, NJ, 1987
)
0.27

Bioavailability

ExcerptReferenceRelevance
" with BAU at 90 mg/kg, and a comparison of the AUC values showed an oral bioavailability of 70%."( Species-dependent differences in the biochemical effects and metabolism of 5-benzylacyclouridine.
Baccanari, DP; Chandrasurin, P; Davis, ST; Joyner, SS, 1993
)
0.52
"6 h in dogs, with bioavailability levels of 85% (30 mg/kg) and 42."( Phase I clinical and pharmacological studies of benzylacyclouridine, a uridine phosphorylase inhibitor.
Burtness, BA; Calabresi, P; Chu, E; Chu, MY; Chu, SH; Darnowski, JW; Handschumacher, RE; Leffert, JJ; Marsh, JC; Pizzorno, G; Yee, L, 1998
)
0.3

Dosage Studied

ExcerptRelevanceReference
" Low dose and either continuous infusion or repetitive dosing of leucovorin, as well as the effect of treatment sequence and intervals between drugs, require additional investigation."( Preclinical and clinical aspects of biomodulation of 5-fluorouracil.
Allegra, CJ; Grogan, L; Sotos, GA, 1994
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
primary alcoholA primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.
hydroxyetherAny ether carrying a hydroxy group at unspecified position.
pyrimidoneA pyrimidine carrying one or more oxo substituents.
[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]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Uridine phosphorylase 1Mus musculus (house mouse)IC50 (µMol)0.46000.08402.08135.7000AID215632
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Uridine phosphorylase 1Homo sapiens (human)Kd2.60000.02001.49956.6000AID1054084; AID1054085; AID1054086; AID1054087
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Uridine phosphorylase 1Homo sapiens (human)Kii0.22350.13000.77102.5460AID1054090; AID1054092
Uridine phosphorylase 1Homo sapiens (human)Kis0.54700.37501.02422.6100AID1054091
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
nucleobase-containing compound metabolic processUridine phosphorylase 1Homo sapiens (human)
uridine catabolic processUridine phosphorylase 1Homo sapiens (human)
CMP catabolic processUridine phosphorylase 1Homo sapiens (human)
dCMP catabolic processUridine phosphorylase 1Homo sapiens (human)
cellular response to glucose starvationUridine phosphorylase 1Homo sapiens (human)
UMP salvageUridine phosphorylase 1Homo sapiens (human)
UMP catabolic processUridine phosphorylase 1Homo sapiens (human)
dTMP catabolic processUridine phosphorylase 1Homo sapiens (human)
dUMP catabolic processUridine phosphorylase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
uridine phosphorylase activityUridine phosphorylase 1Homo sapiens (human)
thymidine phosphorylase activityUridine phosphorylase 1Homo sapiens (human)
identical protein bindingUridine phosphorylase 1Homo sapiens (human)
deoxyuridine phosphorylase activityUridine phosphorylase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
nucleoplasmUridine phosphorylase 1Homo sapiens (human)
cytosolUridine phosphorylase 1Homo sapiens (human)
cytosolUridine phosphorylase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1054087Binding affinity to human recombinant UP1 expressed in Escherichia coli Rosetta (DE3) by isothermal titration calorimetric analysis2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Design of novel potent inhibitors of human uridine phosphorylase-1: synthesis, inhibition studies, thermodynamics, and in vitro influence on 5-fluorouracil cytotoxicity.
AID1054084Binding affinity to human recombinant UP1-R1P binary complex expressed in Escherichia coli Rosetta (DE3) at 150 uM R1P by isothermal titration calorimetric analysis2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Design of novel potent inhibitors of human uridine phosphorylase-1: synthesis, inhibition studies, thermodynamics, and in vitro influence on 5-fluorouracil cytotoxicity.
AID1054079Effect on 5-FU-induced cytotoxicity against human HaCaT cells at 30 uM after 72 hrs by MTT assay2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Design of novel potent inhibitors of human uridine phosphorylase-1: synthesis, inhibition studies, thermodynamics, and in vitro influence on 5-fluorouracil cytotoxicity.
AID215630Tested for inhibition of Uridine Phosphorylase (UrdPase) in murine liver1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
Inhibition of uridine phosphorylase. Synthesis and structure-activity relationships of aryl-substituted 1-((2-hydroxyethoxy)methyl)-5-(3-phenoxybenzyl)uracil.
AID1054090Non-competitive inhibition of human recombinant UP1 expressed in Escherichia coli Rosetta (DE3) using inorganic phosphate as substrate assessed as equilibrium dissociation constant for enzyme-substrate-inhibitor complex by Lineweaver-Burk plot analysis2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Design of novel potent inhibitors of human uridine phosphorylase-1: synthesis, inhibition studies, thermodynamics, and in vitro influence on 5-fluorouracil cytotoxicity.
AID1054085Binding affinity to human recombinant UP1-R1P binary complex expressed in Escherichia coli Rosetta (DE3) at 50 uM R1P by isothermal titration calorimetric analysis2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Design of novel potent inhibitors of human uridine phosphorylase-1: synthesis, inhibition studies, thermodynamics, and in vitro influence on 5-fluorouracil cytotoxicity.
AID1054078Potentiation of 5-FU-induced cytotoxicity against human HT-29 cells assessed as reduction in compound IC50 at 30 uM after 72 hrs by MTT assay relative to control2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Design of novel potent inhibitors of human uridine phosphorylase-1: synthesis, inhibition studies, thermodynamics, and in vitro influence on 5-fluorouracil cytotoxicity.
AID1054076Inhibition of mouse UPase by Dixon plot analysis2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Design of novel potent inhibitors of human uridine phosphorylase-1: synthesis, inhibition studies, thermodynamics, and in vitro influence on 5-fluorouracil cytotoxicity.
AID1054092Competitive inhibition of human recombinant UP1 expressed in Escherichia coli Rosetta (DE3) using URD as substrate by Lineweaver-Burk plot analysis2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Design of novel potent inhibitors of human uridine phosphorylase-1: synthesis, inhibition studies, thermodynamics, and in vitro influence on 5-fluorouracil cytotoxicity.
AID215631Binding affinity was determined against uridine phosphorylase in Sarcoma 180 cells1985Journal of medicinal chemistry, Jul, Volume: 28, Issue:7
Synthesis of 1-[[2-hydroxy-1-(hydroxymethyl)ethoxy] methyl]-5-benzyluracil and its amino analogue, new potent uridine phosphorylase inhibitors with high water solubility.
AID1054091Non-competitive inhibition of human recombinant UP1 expressed in Escherichia coli Rosetta (DE3) using inorganic phosphate as substrate assessed as equilibrium dissociation constant for enzyme-inhibitor complex by Lineweaver-Burk plot analysis2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Design of novel potent inhibitors of human uridine phosphorylase-1: synthesis, inhibition studies, thermodynamics, and in vitro influence on 5-fluorouracil cytotoxicity.
AID1054086Binding affinity to human recombinant UP1-inorganic phosphate binary complex expressed in Escherichia coli Rosetta (DE3) by isothermal titration calorimetric analysis2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Design of novel potent inhibitors of human uridine phosphorylase-1: synthesis, inhibition studies, thermodynamics, and in vitro influence on 5-fluorouracil cytotoxicity.
AID215632Inhibition of uridine phosphorylase (UrdPase) from murine liver.1995Journal of medicinal chemistry, Sep-15, Volume: 38, Issue:19
Inhibition of uridine phosphorylase: synthesis and structure-activity relationships of aryl-substituted 5-benzyluracils and 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (31)

TimeframeStudies, This Drug (%)All Drugs %
pre-199014 (45.16)18.7374
1990's14 (45.16)18.2507
2000's1 (3.23)29.6817
2010's2 (6.45)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: 11.07

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 Index11.07 (24.57)
Research Supply Index3.53 (2.92)
Research Growth Index4.60 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.07)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (3.13%)5.53%
Reviews2 (6.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other29 (90.63%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]