Page last updated: 2024-12-07

5-bromouridine

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

Description

5-bromouridine is a synthetic nucleoside analog that is a structural analog of uridine. It is incorporated into DNA and RNA, causing a variety of effects. It is used as a research tool to study DNA replication, transcription, and translation. 5-bromouridine is synthesized by bromination of uridine. It inhibits DNA polymerase and RNA polymerase. 5-bromouridine also has mutagenic and cytotoxic effects. It is important for studying DNA replication, transcription, and translation because it can be used to label DNA and RNA. 5-bromouridine is also used to study the effects of DNA damage on cellular processes.'

5-bromouridine : A uridine having a bromo substituent at the 5-position. [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 CID236183
SCHEMBL ID654693
MeSH IDM0049610
PubMed CID91494
CHEMBL ID2206658
CHEBI ID20553
SCHEMBL ID41201
MeSH IDM0049610

Synonyms (86)

Synonym
HMS1753D03
5-bromouracil ribonucleoside
nsc38296
nsc-38296
CMAP_000053
nsc-82222
uracil, 1-.beta.-d-arabinofuranosyl-5-bromo-
3370-69-2
2,3h)-pyrimidinedione, 1-.beta.-d-arabinofuranosyl-5-bromo-
nsc82222
MLS001166624
smr000595447
STK366961
5-bromo-1-pentofuranosylpyrimidine-2,4(1h,3h)-dione
KBIO2_007577
KBIO3_002919
KBIOSS_002447
KBIOGR_002441
KBIO2_002441
KBIO2_005009
NCIOPEN2_009259
5-bromo-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
AKOS001010424
HMS2895E08
FT-0620180
SCHEMBL654693
5-bro-mouridine
AKOS016876670
(-)-(5)-bromouridine
AGFIRQJZCNVMCW-UHFFFAOYSA-N
1-.beta.-ribofuranosyl-5-bromo-uracil
SY057067
5-bromo-1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
82950-04-7
A900446
2,4 (1h, 3h)-pyrimidinedione, 1-.beta.-d-arabinofuranosyl-5-bromo-
DTXSID10870817
PD131204
Z56786795
AKOS015834419
5-bromouridine
957-75-5
uridine, 5-bromo-
5-bromo-1-((2r,3r,4s,5r)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1h-pyrimidine-2,4-dione
5-bromo-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
TIMTEC1_003895
CHEBI:20553 ,
5-bromo-1-beta-d-ribofuranosylpyrimidine-2,4(1h,3h)-dione
BRU ,
5-bromouridine, 98%
NCGC00142488-01
nsc 38296
einecs 213-486-6
1-beta-ribofuranosyl-5-bromo-uracil
c9h11brn2o6
bromouridine
brn 0033664
HMS1545B01
B0666
5-bromo-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
cyclohexen-1-yl-(4-phenylphenyl)methanone
A845464
1-[(4s,2r,3r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-bromo-1,3-dihyd ropyrimidine-2,4-dione
unii-key8pg1brc
key8pg1brc ,
5-24-06-00337 (beilstein handbook reference)
CHEMBL2206658
5-bromo-1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
EPITOPE ID:138106
AKOS015907263
(-)-5-bromouridine
HG1067
5-bromo-uridine
AM83946
SCHEMBL41201
J-700087
AC-32307
mfcd00006528
AGFIRQJZCNVMCW-UAKXSSHOSA-N
Q4639573
DS-18294
5-bromo-1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione
DTXSID401317210
5-bromouracil-1-beta-d-ribofuranoside
PD131203
BP-58645

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" This procedure provides the following advantages: 1) it uses common, affordable mammalian cells (HeLa cells, WI38VA13 cells, human dermal fibroblasts, or Chinese hamster ovary cells) rather than genetically modified microorganisms; 2) it can be completed within approximately 8 hr after the cells are prepared because RNA polymerase responses during TC-NER are faster than other DNA damage responses (replication, recombination, and apoptosis); and 3) it is safe because it uses non-radioactive bromouridine and antibodies to detect RNA synthesis on undamaged transcribed DNA strands."( A method for detecting genetic toxicity using the RNA synthesis response to DNA damage.
Iwai, S; Kuraoka, I; Morita, Y, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mutagenAn agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
[role 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]

Drug Classes (1)

ClassDescription
uridines
[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 (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency19.47630.000811.382244.6684AID686978; AID686979
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency50.11870.354828.065989.1251AID504847
DNA polymerase eta isoform 1Homo sapiens (human)Potency89.12510.100028.9256213.3130AID588591
gemininHomo sapiens (human)Potency0.00410.004611.374133.4983AID624297
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.35480.003245.467312,589.2998AID2517
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (21)

Assay IDTitleYearJournalArticle
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.
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
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
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.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID718193Competitive inhibition of bovine pancreatic RNase A type 12-A assessed as degradation of yeast tRNA preincubated for 10 mins before addition of the enzyme by double reciprocal plot analysis2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Triazole pyrimidine nucleosides as inhibitors of Ribonuclease A. Synthesis, biochemical, and structural evaluation.
AID1135723Growth inhibition of human MGL8 cells at 5 uM after 48 hrs1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Synthesis of branched-chain apiosylpyrimidines and their inhibition of lymphocyte proliferation.
AID1135724Growth inhibition of human MGL8 cells at 50 uM after 48 hrs relative to control1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Synthesis of branched-chain apiosylpyrimidines and their inhibition of lymphocyte proliferation.
AID1135725Growth inhibition of human MGL8 cells at 500 uM after 48 hrs relative to control1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Synthesis of branched-chain apiosylpyrimidines and their inhibition of lymphocyte proliferation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (77)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (11.69)18.7374
1990's13 (16.88)18.2507
2000's19 (24.68)29.6817
2010's30 (38.96)24.3611
2020's6 (7.79)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.42

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

MetricThis Compound (vs All)
Research Demand Index29.42 (24.57)
Research Supply Index4.41 (2.92)
Research Growth Index4.76 (4.65)
Search Engine Demand Index34.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.42)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews5 (6.17%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
Other76 (93.83%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (2)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Cell Kinetic Study of Bromodeoxyuridine (BrdU) in Prostate Cancer [NCT00003832]Phase 275 participants (Actual)Interventional1999-07-31Completed
Treatment Protocol for Patients With Standard Risk Acute Myelogenous Leukemia and Its Variants: Induction Using High-Dose Cytarabine, Mitoxantrone and Ethyol; Consolidation With Cytarabine and Idarubicin and Maintenance With 13 Cis Retinoic Acid and Alpha [NCT00003405]Phase 20 participants (Actual)Interventional1998-04-30Withdrawn(stopped due to No enrollment)
[information is prepared from clinicaltrials.gov, extracted Sep-2024]