Page last updated: 2024-11-06

5-hydroxyuracil

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

Description

5-Hydroxyuracil, also known as isocytosine, is a pyrimidine derivative that is structurally similar to uracil. It is a potent inhibitor of thymidylate synthase, an enzyme essential for DNA synthesis. This inhibition is thought to be due to its ability to bind to the active site of the enzyme and block the conversion of deoxyuridylate to thymidylate. 5-Hydroxyuracil has also been shown to exhibit antiviral activity against certain viruses, including herpes simplex virus. The mechanism of this antiviral activity is not fully understood but may involve inhibition of viral DNA replication. In addition to its biological effects, 5-Hydroxyuracil has also been studied for its potential therapeutic applications. It has been investigated as a possible anticancer agent due to its ability to inhibit DNA synthesis. However, further research is needed to determine its clinical efficacy and safety. 5-Hydroxyuracil is a naturally occurring compound found in biological systems, including urine and the cerebrospinal fluid. It is also a known metabolite of the pyrimidine nucleoside, cytidine. The study of 5-Hydroxyuracil has provided insights into the mechanisms of DNA synthesis and antiviral activity. It has also raised the possibility of developing novel therapeutic agents based on this compound.
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5-hydroxyuracil: used in treatment of colonic adenocarcinoma [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID73268
CHEMBL ID1561505
CHEBI ID29115
SCHEMBL ID48366
SCHEMBL ID14554721
MeSH IDM0133418

Synonyms (44)

Synonym
nsc90431
mls000736897 ,
2,3h)-pyrimidinedione, 5-hydroxy-
5-hydroxyazouracil
isobarbituric acid
20636-41-3
5-hydroxyuracil
5-hydroxy-1h-pyrimidine-2,4-dione
CHEBI:29115 ,
2,4(1h,3h)-pyrimidinedione, 5-hydroxy-
5-hydroxypyrimidine-2,4(1h,3h)-dione
inchi=1/c4h4n2o3/c7-2-1-5-4(9)6-3(2)8/h1,7h,(h2,5,6,8,9
smr000528414
FT-0692745
I0310
AKOS005254881
NCGC00246899-01
AKOS006228120
HMS2268J20
nsc 90431
einecs 243-932-5
pyrimidine-2,4,5-triol
SCHEMBL48366
5-hydroxyprimidine-2,4(1h,3h)-dione
benzphetaminehydrochloride--dea
CHEMBL1561505
SCHEMBL14554721
2,4,5-pyrimidinetriol #
DTXSID30174667
5-hydroxy-2,4(1h,3h)-pyrimidinedione, aldrichcpr
mfcd00082987
mfcd11615701
SY013845
CS-0205379
Q21099624
FS-5176
A12566
2',3'-o-isopropylidene 5-hydroxyuridine5-hydroxy-1-((3as,4s,6s,6as)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1h,3h)-dione
A848689
fluorouracil impurity b
5-hydroxy-1,2,3,4-tetrahydropyrimidine-2,4-dione
5-hydroxy-2,4(1h,3h)-pyrimidinedion
ODF ,
5-oxidanyl-1~{h}-pyrimidine-2,4-dione

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" All three tumor cell lines were more sensitive to OHUrd than were the FeInt cells, whereas 5-FU was more toxic to the latter."( Selective cytotoxicity of 5-hydroxyuridine for human colon adenocarcinoma cells.
Giovanella, BC; Lockshin, A; Mendoza, JT; Stehlin, JS; Warneke, C,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
hydroxypyrimidine
[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
DNA Repair25547
Base Excision Repair3523
Base-Excision Repair, AP Site Formation1716
Depyrimidination159
Cleavage of the damaged pyrimidine109

Protein Targets (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
IDH1Homo sapiens (human)Potency32.64270.005210.865235.4813AID686970
lysosomal alpha-glucosidase preproproteinHomo sapiens (human)Potency5.01190.036619.637650.1187AID2100
importin subunit beta-1 isoform 1Homo sapiens (human)Potency56.23415.804836.130665.1308AID540263
snurportin-1Homo sapiens (human)Potency56.23415.804836.130665.1308AID540263
gemininHomo sapiens (human)Potency1.03230.004611.374133.4983AID624297
[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)
recombinase AMycobacterium tuberculosis H37RvEC50 (µMol)12.23000.018023.2882287.6000AID434968; AID435010
[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)
replicative DNA helicaseMycobacterium tuberculosis H37RvAC507.67200.057030.7482325.3000AID449749; AID449750
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (53)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (1.89)18.7374
1990's8 (15.09)18.2507
2000's23 (43.40)29.6817
2010's15 (28.30)24.3611
2020's6 (11.32)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.14

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 Index23.14 (24.57)
Research Supply Index4.04 (2.92)
Research Growth Index5.54 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.14)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.82%)5.53%
Reviews2 (3.64%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other52 (94.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]