Page last updated: 2024-11-06

bromodeoxyuridylate

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Description

Bromodeoxyuridylate (BrdU) is a synthetic thymidine analog that incorporates into DNA during replication. BrdU is often used as a marker for cell proliferation, as it can be detected using immunofluorescence or other techniques. BrdU is synthesized by reacting deoxyuridine with bromine. BrdU can have cytotoxic effects and can also induce mutations in DNA. It is studied extensively in biological research because it allows researchers to track cell division and proliferation, making it a useful tool for studying development, cancer, and other processes. BrdU has also been used to study DNA repair mechanisms and to investigate the effects of environmental toxins on cell growth.'

bromodeoxyuridylate: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID93036
CHEMBL ID1160593
SCHEMBL ID335865
MeSH IDM0067543

Synonyms (22)

Synonym
5-bromo-2'-deoxyuridine-5'-monophosphate
[(2r,3s,5r)-5-(5-bromo-2,4-dioxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
bromodeoxyuridylate
5-bromo-2'-deoxyuridine 5'-(dihydrogen phosphate)
DB01903
CHEMBL1160593 ,
[(2r,3s,5r)-5-(5-bromo-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
5-bromo-2'-deoxy-5'-uridylic acid disodium salt
51432-32-7
5-bromo-2'-deoxyuridine 5'-monophosphate
6666-38-2
uridine, 5-bromo-2'-deoxy-, 5'-(dihydrogen phosphate)
einecs 229-706-9
5'-uridylic acid, 5-bromo-2'-deoxy-
SCHEMBL335865
bdbm50010238
((2r,3s,5r)-5-(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
5-bromo-2'-deoxyuridine-5'-phosphate
LHLHVDBXXZVYJT-RRKCRQDMSA-N
5-bromo-1-(2-deoxy-5-o-phosphonopentofuranosyl)-4-hydroxypyrimidin-2(1h)-one
DTXSID00985242
PD060223
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidylate synthaseLacticaseibacillus caseiKi1.40000.01001.65509.3900AID1134942; AID1147592
Thymidylate synthaseMus musculus (house mouse)Ki0.98000.00341.73759.3000AID228251; AID228252
Delta-type opioid receptorRattus norvegicus (Norway rat)Ki1.40000.00000.60689.2330AID1134942
Mu-type opioid receptorRattus norvegicus (Norway rat)Ki1.40000.00000.38458.6000AID1134942
Kappa-type opioid receptorRattus norvegicus (Norway rat)Ki1.40000.00000.18683.9500AID1134942
[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)
Thymidylate synthaseLacticaseibacillus caseiKm5.70001.44004.33505.7000AID1147595
Thymidylate kinaseHomo sapiens (human)Km10.00005.00007.725010.0000AID553325
Thymidylate kinaseMycobacterium tuberculosis H37RvKm33.00004.50004.50004.5000AID211051; AID211056
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
dTDP biosynthetic processThymidylate kinaseHomo sapiens (human)
dTTP biosynthetic processThymidylate kinaseHomo sapiens (human)
response to estrogenThymidylate kinaseHomo sapiens (human)
myoblast differentiationThymidylate kinaseHomo sapiens (human)
thymidine biosynthetic processThymidylate kinaseHomo sapiens (human)
response to cadmium ionThymidylate kinaseHomo sapiens (human)
nucleoside monophosphate phosphorylationThymidylate kinaseHomo sapiens (human)
cellular response to growth factor stimulusThymidylate kinaseHomo sapiens (human)
dUDP biosynthetic processThymidylate kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
thymidylate kinase activityThymidylate kinaseHomo sapiens (human)
ATP bindingThymidylate kinaseHomo sapiens (human)
nucleoside diphosphate kinase activityThymidylate kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
mitochondrial matrixThymidylate kinaseHomo sapiens (human)
cytosolThymidylate kinaseHomo sapiens (human)
mitochondrionThymidylate kinaseHomo sapiens (human)
nucleusThymidylate kinaseHomo sapiens (human)
cytoplasmThymidylate kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID87507Evaluation of antiviral activity against Herpes simplex virus type 1 (HSV-1) strain KOS.1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID98532Evaluation of cytostatic activity by using antitumor assays against murine leukemia L1210 cells1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID233942Ratio between Ki of L1210-R enzyme and Michaelis-Menten constant (kM)2000Journal of medicinal chemistry, Nov-30, Volume: 43, Issue:24
5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID553325Activity at human recombinant TMPK by Michaelis-Menten equation analysis2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Novel antiviral C5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates.
AID228251Time-independent inhibition of thymidylate synthase from FdUrd-resistant L1210 cells2000Journal of medicinal chemistry, Nov-30, Volume: 43, Issue:24
5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID98529Evaluation of antitumor activity against mutant murine leukemia L1210 cells1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID218132Evaluation of antiviral activity against Vaccinia virus1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID212663Compound was evaluated for the inhibition of L1210 Thymidylate synthase1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID211056Compound was tested for binding affinity against Mycobacterium tuberculosis thymidine monophosphate kinase2002Bioorganic & medicinal chemistry letters, Oct-07, Volume: 12, Issue:19
Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID221339Evaluation for antitumor activity against human lymphoblast Raji cells1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID211054Kinetic parameter Vm of thymidine monophosphate kinase (TMPKmt) in Mycobacterium tuberculosis was determined2003Bioorganic & medicinal chemistry letters, Sep-15, Volume: 13, Issue:18
Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID1147595Activity at amethopterin-resistant Lactobacillus casei thymidylate synthetase assessed as dTMP formation by absorbance analysis in presence of CH2-H4-folate1977Journal of medicinal chemistry, Nov, Volume: 20, Issue:11
Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
AID220992Evaluation of antitumor activity against thymidine kinase deficient Raji cell line1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID211051Affinity towards thymidine monophosphate kinase (TMPKmt) in Mycobacterium tuberculosis2003Bioorganic & medicinal chemistry letters, Sep-15, Volume: 13, Issue:18
Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID1134942Competitive inhibition of thymidylate synthase purified from methotrexate-resistant Lactobacillus casei using 2'-deoxy[5-3H]uridine 5'-phosphate by radioisotope assay1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
5-Cyano-2'-deoxyuridine 5'-phosphate: a potent competitive inhibitor of thymidylate synthetase.
AID553326Ratio of kcat/km for human recombinant TMPK by Michaelis-Menten equation analysis2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Novel antiviral C5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates.
AID87828Evaluation of antiviral activity against Herpes simplex virus type 2 (HSV-2) strain Lyons1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID1147596Activity at amethopterin-resistant Lactobacillus casei thymidylate synthetase assessed as rate of dTMP formation by absorbance analysis in presence of CH2-H4-folate1977Journal of medicinal chemistry, Nov, Volume: 20, Issue:11
Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
AID87506Evaluation of antiviral activity against Herpes simplex virus type 1 (HSV-1) strain F1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID87508Evaluation of antiviral activity against Herpes simplex virus type 1 (HSV-1) strain McIntyre1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID233940Ratio between Ki of L1210-P enzyme and Michaelis-Menten constant (kM)2000Journal of medicinal chemistry, Nov-30, Volume: 43, Issue:24
5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID211057Enzyme Kinetic constant was determined in the presence of Mycobacterium tuberculosis thymidine monophosphate kinase2002Bioorganic & medicinal chemistry letters, Oct-07, Volume: 12, Issue:19
Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID228252Time-independent inhibition of thymidylate synthase from parenteral L1210 cells2000Journal of medicinal chemistry, Nov-30, Volume: 43, Issue:24
5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID87827Evaluation of antiviral activity against Herpes simplex virus type 2 (HSV-2) strain G1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID1147592Inhibition of amethopterin-resistant Lactobacillus casei thymidylate synthetase-catalyzed dTMP formation using dUMP as substrate by spectrophotometric analysis in presence of CH2-H4-folate1977Journal of medicinal chemistry, Nov, Volume: 20, Issue:11
Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
AID216539Evaluation of antiviral activity against Vesicular stomatitis virus.1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID87826Evaluation of antiviral activity against Herpes simplex virus type 2 (HSV-2) strain 196.1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (60.00)18.7374
1990's2 (13.33)18.2507
2000's3 (20.00)29.6817
2010's1 (6.67)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: 11.38

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 Index11.38 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index4.16 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.38)

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%
Other15 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]