Compounds > 1-(2-deoxy-2-fluoroarabinofuranosyl)-5-ethyluracil
Page last updated: 2024-11-08

1-(2-deoxy-2-fluoroarabinofuranosyl)-5-ethyluracil

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Description

1-(2-deoxy-2-fluoroarabinofuranosyl)-5-ethyluracil: RN given refers to (beta-D)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID174316
CHEMBL ID1269499
SCHEMBL ID6538026
MeSH IDM0148596

Synonyms (24)

Synonym
5-ethyl-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
2'-fluoro-5-ethyl-.beta.-d-arabinofuranosyluracil
feau
SWFJAJRDLUUIOA-IBCQBUCCSA-N
5-ethyl-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
83546-42-3
CHEMBL1269499 ,
2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-ethyl
2agf6pbm87 ,
1-(2-deoxy-2-fluoroarabinofuranosyl)-5-ethyluracil
unii-2agf6pbm87
1-dfafeu
1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-ethyluracil
bdbm50367489
DTXSID30232433
SCHEMBL6538026
5-ethyl-1-((2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
F12932
mfcd11973639
1-(2-deoxy-2-fluoro-.beta.-d-arabinofuranosyl)-5-ethyl-2,4(1h,3h)-pyrimidinedione
2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-2-fluoro-.beta.-d-arabinofuranosyl)-5-ethyl-
A900442
2'-fluoro-5-ethyl-beta-d-arabinofuranosyluracil; 5-ethyl-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
5-ethyl-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
"2 mg/kg/day when administered in combination with a sub-effective dose of human recombinant interferon-beta."( Inhibition of simian varicella virus infection of monkeys by 1-(2-deoxy-2- fluoro-1-beta-D-arabinofuranosyl)-5-ethyluracil (FEAU) and synergistic effects of combination with human recombinant interferon-beta.
Chou, TC; Fox, JJ; Gloff, CA; Soike, KF; Watanabe, KA, 1990)		0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine kinase, cytosolicHomo sapiens (human)Ki0.26500.09001.52137.0000AID210534; AID210537
[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)
Thymidine kinase, cytosolicHomo sapiens (human)Km3,154.70000.29002.27675.0000AID210540
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (6)

Processvia Protein(s)Taxonomy
nucleobase-containing compound metabolic processThymidine kinase, cytosolicHomo sapiens (human)
deoxyribonucleoside monophosphate biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine metabolic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
protein homotetramerizationThymidine kinase, cytosolicHomo sapiens (human)
DNA synthesis involved in mitotic DNA replicationThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
thymidine kinase activityThymidine kinase, cytosolicHomo sapiens (human)
protein bindingThymidine kinase, cytosolicHomo sapiens (human)
ATP bindingThymidine kinase, cytosolicHomo sapiens (human)
zinc ion bindingThymidine kinase, cytosolicHomo sapiens (human)
identical protein bindingThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
nucleusThymidine kinase, cytosolicHomo sapiens (human)
cytosolThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID116575Compound was evaluated for its effect on HSV -2 induced mortality in mice measured as mean survival time (MST) at the dose of 12.5 mg/kg per day1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID210537Compound was evaluated for Kinetic constant for viral thymidine kinase of Herpes simplex virus (HSV) -21987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID107303Compound was evaluated for its effect ofHSV -2 induced mortality in mice measured as survivors/total (%) at the dose of 25 mg/kg per day; 0/101987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID107304Compound was evaluated for its effect ofHSV -2 induced mortality in mice measured as survivors/total (%) at the dose of 50 mg/kg per day; 3/101987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID116578Compound was evaluated for its effect on HSV -2 induced mortality in mice measured as mean survival time (MST) at the dose of 50 mg/kg per day1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID217756Compound was tested for cytotoxic activity against rapidly dividing Vero cells.1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Nucleosides. 136. Synthesis and antiviral effects of several 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-alkyluracils. Some structure-activity relationships.
AID217573Compound was tested for antiviral activity against Herpes simplex virus-1 (Strain F) in vero cells by plaque reduction assay.1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Nucleosides. 136. Synthesis and antiviral effects of several 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-alkyluracils. Some structure-activity relationships.
AID107302Compound was evaluated for its effect ofHSV -2 induced mortality in mice measured as survivors/total (%) at the dose of 12.5 mg/kg per day; 2/101987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID235255Theuraptic Index: ratio of ID 50 / ED 90 of compound against HSV 11986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Nucleosides. 136. Synthesis and antiviral effects of several 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-alkyluracils. Some structure-activity relationships.
AID116577Compound was evaluated for its effect on HSV -2 induced mortality in mice measured as mean survival time (MST) at the dose of 25 mg/kg per day1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID74000Compound (5%) was evaluated for its effect on (no. of areas = 4)maximum score in HSV-1 cutaneous infection of guinea pig; expressed as maximum score1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID217755Compound was evaluated for antiviral activity against Herpes simplex virus (HSV) -2 (MS) in Vero cell cultures1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID217596Compound was tested for antiviral activity against Herpes simplex virus-2 (Strain G) in vero cells by plaque reduction assay.1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Nucleosides. 136. Synthesis and antiviral effects of several 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-alkyluracils. Some structure-activity relationships.
AID74003Compound (5%) was evaluated for its effect on (no. of areas = 4) mean area under lesion score-day curve in HSV-1 cutaneous infection of guinea pig; expressed as mean area under lesion score-day curve1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID107301Compound was evaluated for its effect ofHSV -2 induced mortality in mice measured as survivors/total (%) at the dose of 100 mg/kg per day; 5/101987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID218067Compound was evaluated for cellular toxicity performed on Vero cells measured as 50% tissue culture inhibitory dose after 120 hr post exposure1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID116576Compound was evaluated for its effect on HSV -2 induced mortality in mice measured as mean survival time (MST) at the dose of 200 mg/kg per day1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID527284Antiviral activity against HBV infected in human 2.2.15 cell2010Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
Antiviral activity of 2,3'-anhydro and related pyrimidine nucleosides against hepatitis B virus.
AID527281Antiviral activity against HBV infected in duck primary hepatocytes at 10 ug/ml2010Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
Antiviral activity of 2,3'-anhydro and related pyrimidine nucleosides against hepatitis B virus.
AID74001Compound (5%) was evaluated for its effect on (no. of areas = 4)mean peak lesion score in HSV-1 cutaneous infection of guinea pig; expressed as mean peak lesion score1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID74004Compound (5%) was evaluated for its effect on (no. of areas = 4) time to start healing in HSV-1 cutaneous infection of guinea pig; expressed as time to start healing1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID235256Theuraptic Index: ratio of ID 50 / ED 90 of compound against HSV 21986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Nucleosides. 136. Synthesis and antiviral effects of several 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-alkyluracils. Some structure-activity relationships.
AID217595Compound was tested for antiviral activity against Herpes simplex virus-1 (Strain F) in vero cells by plaque reduction assay.1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Nucleosides. 136. Synthesis and antiviral effects of several 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-alkyluracils. Some structure-activity relationships.
AID527283Antiviral activity against HBV infected in human 2.2.15 cell at 10 ug/ml2010Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
Antiviral activity of 2,3'-anhydro and related pyrimidine nucleosides against hepatitis B virus.
AID218068Compound was evaluated for cellular toxicity performed on Vero cells measured as 50% tissue culture inhibitory dose after 72 hr post exposure1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID217574Compound was tested for antiviral activity against Herpes simplex virus-2 (Strain G) in vero cells by plaque reduction assay.1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Nucleosides. 136. Synthesis and antiviral effects of several 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-alkyluracils. Some structure-activity relationships.
AID210540Compound was evaluated for Kinetic constant for cellular thymidine kinase in Vero cells1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID527285Cytotoxicity against human HuH7 cells2010Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
Antiviral activity of 2,3'-anhydro and related pyrimidine nucleosides against hepatitis B virus.
AID210534Compound was evaluated for Kinetic constant for viral thymidine kinase of Herpes simplex virus (HSV) -11987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID107305Compound was evaluated for its effect on HSV -2 induced mortality in mice measured as survivors/total (%) at the dose of 200 mg/kg per day; 6/121987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID217754Compound was evaluated for antiviral activity against Herpes simplex virus (HSV) -1 (BW) in Vero cell cultures1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
AID116574Compound was evaluated for its effect on HSV -2 induced mortality in mice measured as mean survival time (MST) at the dose of 100 mg/kg per day1987Journal of medicinal chemistry, May, Volume: 30, Issue:5
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (33.33)18.7374
1990's3 (50.00)18.2507
2000's0 (0.00)29.6817
2010's1 (16.67)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: 12.38

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 Index12.38 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.38)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
thymidine
[no description available]		2.420pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
floxuridine
Floxuridine: An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection; when administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.. floxuridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.		2.0510nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
uridine
[no description available]		2.3720uridinesdrug metabolite;
fundamental metabolite;
human metabolite
trifluridine
Trifluridine: An antiviral derivative of THYMIDINE used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis due to HERPES SIMPLEX virus. (From Martindale, The Extra Pharmacopoeia, 30th ed, p557). trifluridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-trifluoromethyluracil as the nucleobase. An antiviral drug used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis.		2.0510nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
EC 2.1.1.45 (thymidylate synthase) inhibitor
deoxyuridine
[no description available]		2.0510pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
fialuridine
[no description available]		1.9710
lamivudine
[no description available]		2.0510monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
edoxudin
[no description available]		2.0510pyrimidine 2'-deoxyribonucleoside
clevudine
[no description available]		2.3720
arabinofuranosyluracil
Arabinofuranosyluracil: A pyrimidine nucleoside formed in the body by the deamination of CYTARABINE.		2.8940
acyclovir
Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.		2.38202-aminopurines;
oxopurine		antimetabolite;
antiviral drug
ConditionIndicatedRelationship StrengthStudiesTrials
Brain Inflammation
[description not available]		01.9710
Herpes Simplex Virus Infection
[description not available]		01.9710
Dermatoses
[description not available]		01.9710
Encephalitis
Inflammation of the BRAIN due to infection, autoimmune processes, toxins, and other conditions. Viral infections (see ENCEPHALITIS, VIRAL) are a relatively frequent cause of this condition.		01.9710
Herpes Simplex
A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)		01.9710
Skin Diseases
Diseases involving the DERMIS or EPIDERMIS.		01.9710
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		01.9810
Herpes Simplex Keratitis
[description not available]		01.9810
Keratitis, Herpetic
A superficial, epithelial Herpesvirus hominis infection of the cornea, characterized by the presence of small vesicles which may break down and coalesce to form dendritic ulcers (KERATITIS, DENDRITIC). (Dictionary of Visual Science, 3d ed)		01.9810
Adenovirus Infections
[description not available]		01.9710
Viremia
The presence of viruses in the blood.		01.9710
Adenoviridae Infections
Virus diseases caused by the ADENOVIRIDAE.		01.9710