U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C4H3BrN2O2
Molecular Weight 190.983
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BROMOURACIL

SMILES

BrC1=CNC(=O)NC1=O

InChI

InChIKey=LQLQRFGHAALLLE-UHFFFAOYSA-N
InChI=1S/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)

HIDE SMILES / InChI

Molecular Formula C4H3BrN2O2
Molecular Weight 190.983
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Polymers for improving the in vivo transduction efficiency of AAV2 vectors.
2010-12-28
Determination of eniluracil and 5-fluorouracil in human plasma by LC-MS/MS.
2010-12
Dynamics and efficiency of electron injection and transport in DNA using pyrenecarboxamide as an electron donor and 5-bromouracil as an electron acceptor.
2010-11-18
5-bromodeoxyuridine induces transcription of repressed genes with disruption of nucleosome positioning.
2010-11
Fragmentation patterns of core-ionized thymine and 5-bromouracil.
2010-10-21
The distance between donor and acceptor affects the proportion of C1' and C2' oxidation products of DNA in a BrU-containing excess electron transfer system.
2010-10-20
Effect of the adsorbate (Bromacil) equilibrium concentration in water on its adsorption on powdered activated carbon. Part 3: Competition with natural organic matter.
2010-10-15
Effect of indole-3-acetic acid (IAA) produced by Pseudomonas aeruginosa in suppression of charcoal rot disease of chickpea.
2010-07
Simultaneous quantitation of hydrochlorothiazide and metoprolol in human plasma by liquid chromatography-tandem mass spectrometry.
2010-05-01
Conformation-dependent formation of the G[8-5]U intrastrand cross-link in 5-bromouracil-containing G-quadruplex DNA induced by UVA irradiation.
2010-03-23
Antimicrobial resistance induced by genetic changes.
2010-01-30
Toxicity of the herbicides bromacil and simazine to the aquatic macrophyte, Vallisneria americana Michx.
2010-01
Spatio-temporal radiation biology: new insights and biomedical perspectives.
2010
Toll-like receptors: role in dermatological disease.
2010
Reactive oxygen and nitrogen species induce protein and DNA modifications driving arthrofibrosis following total knee arthroplasty.
2009-11-13
Estimating the integrity of aged DNA samples by CE.
2009-11
Effect of the adsorbate (Bromacil) equilibrium concentration in water on its adsorption on powdered activated carbon. Part 2: Kinetic parameters.
2009-10-30
Effect of the adsorbate (Bromacil) equilibrium concentration in water on its adsorption on powdered activated carbon. Part 1. Equilibrium parameters.
2009-10-30
DNA interstrand cross-links induced by ionizing radiation: an unsung lesion.
2009-09-15
Resolution of joint molecules by RuvABC and RecG following cleavage of the Escherichia coli chromosome by EcoKI.
2009-08-06
Modelling the dissipation kinetics of six commonly used pesticides in two contrasting soils of New Zealand.
2009-08
[Influence of the selected pyrimidine compounds on the activity of thymidine phosphorylase from normal and tumor endometrial cells].
2009-08
Benign decay vs. photolysis in the photophysics and photochemistry of 5-bromouracil. A computational study.
2009-05-14
Combined photobacterium toxicity of herbicide mixtures containing one insecticide.
2009-04
On the mechanism of the mutagenic action of 5-bromouracil: a DFT study of uracil and 5-bromouracil in a water cluster.
2009-03-19
A beginner's guide to radiation damage.
2009-03
Structure-function studies of the RNA polymerase II elongation complex.
2009-02
Proteomics identifies thymidine phosphorylase as a key regulator of the angiogenic potential of colony-forming units and endothelial progenitor cell cultures.
2009-01-02
Quantitation of bergenin in human plasma by liquid chromatography/tandem mass spectrometry.
2009-01-01
The mutagenic properties of BrdUTP in a random mutagenesis process.
2008-12
Chemistry. Halogen versus hydrogen.
2008-08-15
[18F]FBAU 3',5'-dibenzoate, a lipophilic prodrug, enhances brain uptake of the cell proliferation tracer [18F]FBAU.
2008-07
A general method for phasing novel complex RNA crystal structures without heavy-atom derivatives.
2008-07
Movement of bromacil in a Hawaii soil under pineapple cultivation - a field study.
2008-05
5-Bromouracil disrupts nucleosome positioning by inducing A-form-like DNA conformation in yeast cells.
2008-04-11
Starvation suppresses cell proliferation that rebounds after refeeding in the midgut of the American cockroach, Periplaneta americana.
2008-02
Mechanism of charge separation in DNA by hole transfer through consecutive adenines.
2008
Mitochondrial thymidine kinase and the enzymatic network regulating thymidine triphosphate pools in cultured human cells.
2007-11-30
Evaluation of sources and loading of pesticides to the Sacramento River, California, USA, during a storm event of winter 2005.
2007-11
Tautomerism of uracil and 5-bromouracil in a microcosmic environment with water and metal ions. What roles do metal ions play?
2007-08-09
Determination of bromacil transport as a function of water and carbon content in soils.
2007-06-15
Heterogeneous photocatalyzed degradation of uracil and 5-bromouracil in aqueous suspensions of titanium dioxide.
2007-04-02
Genetic variations in rice in vitro cultures at the EPSPs-RPS20 region.
2007-02
Rapid and random turnover of mitochondrial DNA in rat hepatocytes of primary culture.
2006-12
Reaction mechanism of uracil bromination by HBrO: a new way to generate the enol-keto form of 5-bromouracil.
2006-09-28
Detection of photoinduced electron transfer from Sso7d to DNA.
2006
Evaluation of novel one-electron reduction with metal in DNA.
2006
Reaction of substituted pyrimidines with photochemically generated t-BuO* radicals.
2005-12
Structure-activity relationship of ligands of uracil phosphoribosyltransferase from Toxoplasma gondii.
1994-08-17
Interaction of monoclonal antibodies directed against bromodeoxyuridine with pyrimidine bases, nucleosides, and DNA.
1986-03-01
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:20:43 GMT 2025
Edited
by admin
on Mon Mar 31 21:20:43 GMT 2025
Record UNII
4HK400G5UO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BROMOURACIL
Systematic Name English
5-BROMOURACIL
MI  
Preferred Name English
5-BROMOURACIL [MI]
Common Name English
NSC-19940
Code English
5-BROMO-2,4(1H,3H)-PYRIMIDINEDIONE
Systematic Name English
2,4(1H,3H)-PYRIMIDINEDIONE, 5-BROMO-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID2058758
Created by admin on Mon Mar 31 21:20:43 GMT 2025 , Edited by admin on Mon Mar 31 21:20:43 GMT 2025
PRIMARY
CHEBI
20552
Created by admin on Mon Mar 31 21:20:43 GMT 2025 , Edited by admin on Mon Mar 31 21:20:43 GMT 2025
PRIMARY
NSC
19940
Created by admin on Mon Mar 31 21:20:43 GMT 2025 , Edited by admin on Mon Mar 31 21:20:43 GMT 2025
PRIMARY
PUBCHEM
5802
Created by admin on Mon Mar 31 21:20:43 GMT 2025 , Edited by admin on Mon Mar 31 21:20:43 GMT 2025
PRIMARY
HSDB
7495
Created by admin on Mon Mar 31 21:20:43 GMT 2025 , Edited by admin on Mon Mar 31 21:20:43 GMT 2025
PRIMARY
CAS
51-20-7
Created by admin on Mon Mar 31 21:20:43 GMT 2025 , Edited by admin on Mon Mar 31 21:20:43 GMT 2025
PRIMARY
FDA UNII
4HK400G5UO
Created by admin on Mon Mar 31 21:20:43 GMT 2025 , Edited by admin on Mon Mar 31 21:20:43 GMT 2025
PRIMARY
MERCK INDEX
m2720
Created by admin on Mon Mar 31 21:20:43 GMT 2025 , Edited by admin on Mon Mar 31 21:20:43 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
5-BROMOURACIL
Created by admin on Mon Mar 31 21:20:43 GMT 2025 , Edited by admin on Mon Mar 31 21:20:43 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-084-0
Created by admin on Mon Mar 31 21:20:43 GMT 2025 , Edited by admin on Mon Mar 31 21:20:43 GMT 2025
PRIMARY