6-amino-5-bromouracil profile

6-amino-5-bromouracil is a synthetic analog of uracil that has been extensively studied for its mutagenic properties. It is incorporated into DNA in place of thymine, leading to base pairing errors and mutations. Its synthesis typically involves bromination of uracil followed by amination. The effects of 6-amino-5-bromouracil on DNA replication and repair mechanisms have been studied in various organisms, including bacteria and mammalian cells. This compound is important in understanding the mechanisms of mutagenesis, DNA replication, and DNA repair. It has been used in research to investigate the role of DNA polymerase fidelity, the effects of DNA damage, and the development of anticancer therapies. Its ability to induce mutations and its impact on DNA replication make it a valuable tool in studies of these biological processes. 6-amino-5-bromouracil is also used as a probe in spectroscopic studies of DNA and its interactions with proteins.'

ID Source	ID
PubMed CID	80578
CHEMBL ID	64909
SCHEMBL ID	2894070
MeSH ID	M0119114

Synonym
einecs 228-638-7
nsc 27652
nsc 40394
unii-hcs8t22jqz
hcs8t22jqz ,
nsc-40394
nsc40394
nsc-27652
nsc27652
6312-73-8
6-amino-5-bromopyrimidine-2,4(1h,3h)-dione
AB-323/25048333
SR-01000636616-1
6-amino-5-bromouracil
AKOS000265969
6-amino-5-bromo-1h-pyrimidine-2,4-dione(6a5bu)
bdbm50122770
6-amino-5-bromo-1,2,3,4-tetrahydropyrimidine-2,4-dione
STK832489
CHEMBL64909 ,
F2113-0105
6-amino-5-bromo-1h-pyrimidine-2,4-dione
A834224
5-bromo-6-aminouracil
AKOS024325110
CCG-46953
FT-0620144
SCHEMBL2894070
BBL029044
SS-4601
FSLBEEVCUZFKRL-UHFFFAOYSA-N
6-amino-5-bromo-2,4(1h,3h)-pyrimidinedione
DTXSID60212460
mfcd00830386
CS-0045887
'6-amino-5-bromopyrimidine-2,4(1h,3h)-dione'
JFD ,
Q27461691
SB58264
EN300-235988
PD182823
Z1269134599

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Thymidine phosphorylase	Escherichia coli K-12	IC50 (µMol)	1.6000	0.0027	1.7914	6.5000	AID241246; AID241389; AID363280
Thymidine phosphorylase	Escherichia coli K-12	Ki	1.9500	0.0350	1.3117	3.1000	AID238745; AID465575
Thymidine phosphorylase	Homo sapiens (human)	IC50 (µMol)	12.3544	0.0200	1.5838	6.8000	AID1055580; AID1623806; AID211071; AID213303; AID241061; AID241372; AID241539; AID363289
Thymidine phosphorylase	Homo sapiens (human)	Ki	2.6000	0.0013	0.2704	2.6000	AID211063
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
DNA damage response	Thymidine phosphorylase	Escherichia coli K-12
pyrimidine nucleobase metabolic process	Thymidine phosphorylase	Escherichia coli K-12
pyrimidine nucleoside metabolic process	Thymidine phosphorylase	Escherichia coli K-12
thymidine metabolic process	Thymidine phosphorylase	Escherichia coli K-12
mitochondrial genome maintenance	Thymidine phosphorylase	Homo sapiens (human)
angiogenesis	Thymidine phosphorylase	Homo sapiens (human)
pyrimidine nucleobase metabolic process	Thymidine phosphorylase	Homo sapiens (human)
pyrimidine nucleoside metabolic process	Thymidine phosphorylase	Homo sapiens (human)
chemotaxis	Thymidine phosphorylase	Homo sapiens (human)
signal transduction	Thymidine phosphorylase	Homo sapiens (human)
cell differentiation	Thymidine phosphorylase	Homo sapiens (human)
regulation of myelination	Thymidine phosphorylase	Homo sapiens (human)
dTMP catabolic process	Thymidine phosphorylase	Homo sapiens (human)
regulation of transmission of nerve impulse	Thymidine phosphorylase	Homo sapiens (human)
regulation of gastric motility	Thymidine phosphorylase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
1,4-alpha-oligoglucan phosphorylase activity	Thymidine phosphorylase	Escherichia coli K-12
thymidine phosphorylase activity	Thymidine phosphorylase	Escherichia coli K-12
glycosyltransferase activity	Thymidine phosphorylase	Escherichia coli K-12
pentosyltransferase activity	Thymidine phosphorylase	Escherichia coli K-12
1,4-alpha-oligoglucan phosphorylase activity	Thymidine phosphorylase	Homo sapiens (human)
protein binding	Thymidine phosphorylase	Homo sapiens (human)
growth factor activity	Thymidine phosphorylase	Homo sapiens (human)
thymidine phosphorylase activity	Thymidine phosphorylase	Homo sapiens (human)
protein homodimerization activity	Thymidine phosphorylase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cytosol	Thymidine phosphorylase	Escherichia coli K-12
membrane	Thymidine phosphorylase	Escherichia coli K-12
cytosol	Thymidine phosphorylase	Escherichia coli K-12
cytosol	Thymidine phosphorylase	Homo sapiens (human)
cytosol	Thymidine phosphorylase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (21)

Assay ID	Title	Year	Journal	Article
AID241061	Inhibitory concentration against human thymidine phosphorylase	2005	Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2	Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID241246	Inhibition of Thymidine phosphorylase from Escherichia coli	2004	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 14, Issue:21	Synthesis and enzymatic evaluation of xanthine oxidase-activated prodrugs based on inhibitors of thymidine phosphorylase.
AID465575	Inhibition of Escherichia coli thymidine phosphorylase	2010	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5	The role of phosphate in the action of thymidine phosphorylase inhibitors: Implications for the catalytic mechanism.
AID241372	Inhibitory concentration against horse liver thymidine phosphorylase of horse liver	2005	Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2	Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID211071	Inhibitory activity against human thymidine phosphorylase	2003	Bioorganic & medicinal chemistry letters, Nov-03, Volume: 13, Issue:21	Identification of a novel class of inhibitor of human and Escherichia coli thymidine phosphorylase by in silico screening.
AID660984	Inhibition of Escherichia coli thymidine phosphorylase at 100 uM incubated for 20 mins at room temperature followed by 5 mins incubation at 90 degC by HPLC analysis	2012	Journal of medicinal chemistry, Mar-22, Volume: 55, Issue:6	Fluorophosphonylated nucleoside derivatives as new series of thymidine phosphorylase multisubstrate inhibitors.
AID363280	Inhibition of Escherichia coli thymidine phosphorylase	2008	European journal of medicinal chemistry, Jun, Volume: 43, Issue:6	Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors.
AID211063	Inhibitory activity against Escherichia coli thymidine phosphorylase	2003	Bioorganic & medicinal chemistry letters, Nov-03, Volume: 13, Issue:21	Identification of a novel class of inhibitor of human and Escherichia coli thymidine phosphorylase by in silico screening.
AID363295	Inhibition of horse liver recombinant thymidine phosphorylase	2008	European journal of medicinal chemistry, Jun, Volume: 43, Issue:6	Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors.
AID1335971	Inhibition of horse liver thymidine phosphorylase using thymidine as substrate	2016	European journal of medicinal chemistry, Nov-29, Volume: 124	Recent discovery of non-nucleobase thymidine phosphorylase inhibitors targeting cancer.
AID241389	Inhibitory concentration against thymidine phosphorylase of Escherichia coli	2005	Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2	Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID1055580	Inhibition of thymidine phosphorylase (unknown origin)	2013	European journal of medicinal chemistry, , Volume: 70	Fragment-based approach to the design of 5-chlorouracil-linked-pyrazolo[1,5-a][1,3,5]triazines as thymidine phosphorylase inhibitors.
AID213307	Inhibition of Escherichia coli TPase at a concentration of 25 uM after 60 minutes	2000	Journal of medicinal chemistry, Mar-09, Volume: 43, Issue:5	Design, synthesis, and enzymatic evaluation of multisubstrate analogue inhibitors of Escherichia coli thymidine phosphorylase.
AID363289	Inhibition of human recombinant thymidine phosphorylase	2008	European journal of medicinal chemistry, Jun, Volume: 43, Issue:6	Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors.
AID238745	Inhibitory activity against Escherichia coli thymidine phosphorylase	2005	Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2	Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID660983	Inhibition of Escherichia coli thymidine phosphorylase at 1 mM incubated for 20 mins at room temperature followed by 5 mins incubation at 90 degC by HPLC analysis	2012	Journal of medicinal chemistry, Mar-22, Volume: 55, Issue:6	Fluorophosphonylated nucleoside derivatives as new series of thymidine phosphorylase multisubstrate inhibitors.
AID213303	Compound was evaluated for its inhibitory activity against recombinant purified Escherichia coli Thymidine Phosphorylase	2003	Journal of medicinal chemistry, Jan-16, Volume: 46, Issue:2	Potential tumor-selective nitroimidazolylmethyluracil prodrug derivatives: inhibitors of the angiogenic enzyme thymidine phosphorylase.
AID241539	Inhibitory concentration against human thymidine phosphorylase	2005	Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2	Aminoimidazolylmethyluracil analogues as potent inhibitors of thymidine phosphorylase and their bioreductive nitroimidazolyl prodrugs.
AID1623806	Inhibition of thymidine phosphorylase (unknown origin)	2019	Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3	Design of Novel Inhibitors of Human Thymidine Phosphorylase: Synthesis, Enzyme Inhibition, in Vitro Toxicity, and Impact on Human Glioblastoma Cancer.
AID213313	Inhibition of Escherichia coli Thymidine Phosphorylase at a concentration of 100 uM after 60 minutes	2000	Journal of medicinal chemistry, Mar-09, Volume: 43, Issue:5	Design, synthesis, and enzymatic evaluation of multisubstrate analogue inhibitors of Escherichia coli thymidine phosphorylase.
AID1159607	Screen for inhibitors of RMI FANCM (MM2) intereaction	2016	Journal of biomolecular screening, Jul, Volume: 21, Issue:6	A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (6.25)	18.7374
1990's	1 (6.25)	18.2507
2000's	8 (50.00)	29.6817
2010's	6 (37.50)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (6.25%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	15 (93.75%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
thymine [no description available]	2.9	4	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
xanthine 7H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-7 is protonated.. 9H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated.	2.04	1	xanthine	Saccharomyces cerevisiae metabolite
temozolomide [no description available]	2.21	1	imidazotetrazine; monocarboxylic acid amide; triazene derivative	alkylating agent; antineoplastic agent; prodrug
thymidine [no description available]	2.93	4	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
bromouracil Bromouracil: 5-Bromo-2,4(1H,3H)-pyrimidinedione. Brominated derivative of uracil that acts as an antimetabolite, substituting for thymine in DNA. It is used mainly as an experimental mutagen, but its deoxyriboside (BROMODEOXYURIDINE) is used to treat neoplasms.. 5-bromouracil : A pyrimidine having keto groups at the 2- and 4-positions and a bromo group at the 5-position. Used mainly as an experimental mutagen.	2.91	4	nucleobase analogue; pyrimidines	mutagen
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	1.96	1	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
deoxyuridine [no description available]	1.96	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
6-aminothymine 6-aminothymine: inhibits degradation of nucleosides (idoxuridine, thymidine) & pyrimidine bases	3.81	3
5-bromocytosine [no description available]	2.43	2
5-nitro-2'-deoxyuridine [no description available]	2.44	2
o-(chloroacetylcarbamoyl)fumagillol O-(Chloroacetylcarbamoyl)fumagillol: Semisynthetic analog of fumagillin (a cyclohexane-sesquiterpene antibiotic isolated from ASPERGILLUS FUMIGATUS) that inhibits angiogenesis.. O-(chloroacetylcarbamoyl)fumagillol : A carbamate ester that is fumagillol in which the hydroxy group has been converted to the corresponding N-(chloroacetyl)carbamate derivative.	1.99	1	carbamate ester; organochlorine compound; semisynthetic derivative; sesquiterpenoid; spiro-epoxide	angiogenesis inhibitor; antineoplastic agent; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; methionine aminopeptidase 2 inhibitor; retinoic acid receptor alpha antagonist
brivudine brivudine: anti-herpes agent	1.96	1
sesquiterpenes [no description available]	1.99	1
5-phenyl-1,3,4-oxadiazole-2-thiol 5-phenyl-1,3,4-oxadiazole-2-thiol: structure in first source	3.23	1
diethyl maleate diethyl maleate : A maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10degreeC) with boiling point 220degreeC at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis.	2.05	1	ethyl ester; maleate ester	glutathione depleting agent
deoxyribose [no description available]	2.05	1	deoxypentose	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
ma-1 tipiracil: inhibits thymidine phosphorylase. tipiracil : A member of the class of pyrimidones that is uracil substituted by chloro and (2-iminopyrrolidin-1-yl)methyl groups at positions 5 and 6 respectively. Used (as the hydrochloride salt) in combination with trifluridine, a nucleoside metabolic inhibitor, for treatment of advanced/relapsed unresectable colorectal cancer.	2.98	4	carboxamidine; organochlorine compound; pyrimidone; pyrrolidines	antineoplastic agent; EC 2.4.2.4 (thymidine phosphorylase) inhibitor
5-chloro-6-(1-(2-iminopyrrolidinyl) methyl)uracil hydrochloride tipiracil hydrochloride : A hydrochloride obtained by combining tipiracil with one equivalent of hydrochloric acid. Used in combination with trifluridine, a nucleoside metabolic inhibitor, for treatment of advanced/relapsed unresectable colorectal cancer.	4.39	6	hydrochloride; iminium salt	antineoplastic agent; EC 2.4.2.4 (thymidine phosphorylase) inhibitor
sesone 7-deazaxanthine: structure in first source	4.83	10
3,n(4)-ethanocytosine [no description available]	2.04	1	organic heterobicyclic compound	mutagen
5'-o-tritylinosine 5'-O-tritylinosine: structure in first source	2.08	1

Condition	Relationship Strength	Studies
Anemia, Fanconi [description not available]	2.13	1
Fanconi Anemia Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)	2.13	1
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	3.04	1
Benign Neoplasms [description not available]	3.04	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.04	1
Benign Neoplasms, Brain [description not available]	2.21	1
Astrocytoma, Grade IV [description not available]	2.21	1
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	2.21	1
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	2.21	1

6-amino-5-bromouracil

Cross-References

Synonyms (42)

Protein Targets (2)

Inhibition Measurements

Biological Processes (13)

Molecular Functions (7)

Ceullar Components (2)

Bioassays (21)

Research

Studies (16)

Market Indicators

Research Demand Index: 12.08

Study Types

6-amino-5-bromouracil

Cross-References

Synonyms (42)

Protein Targets (2)

Inhibition Measurements

Biological Processes (13)

Molecular Functions (7)

Ceullar Components (2)

Bioassays (21)

Research

Studies (16)

Market Indicators

Research Demand Index: 12.08

Study Types

Related Drugs (21)

Related Conditions (9)