Page last updated: 2024-11-07

bw a1433u

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Description

BW A1433U: adenosine A3 receptor antagonist; attenuates hypoxia-induced AH interval prolongation; derivative of 1,3-dipropyl-8-phenylxanthine [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID122071
CHEMBL ID423239
MeSH IDM0151323

Synonyms (15)

Synonym
bw a1433u
94781-78-9
CHEMBL423239 ,
bdbm50018151
4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1h-purin-8-yl)-benzoic acid
4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1h-purin-8-yl)-benzoic acid
4-(2,6-dioxo-1,3-dipropyl-7h-purin-8-yl)benzoic acid
bw-1433u
bw 1433u
a1433u
benzoic acid, 4-(2,3,6,7-tetrahydro-2,6-dioxo-1,3-dipropyl-1h-purin-8-yl)-
bw-a1433u
bw a-1433u
DTXSID90915311
4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1h-purin-8-yl)benzoic acid

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Treatment with BW A1433U reduced TOIC [8.7(0.2)min] and markedly reduced lactate release."( Adenosine increases lactate release and delays onset of contracture during global low flow ischaemia.
Lasley, RD; Mentzer, RM, 1993
)
0.63
[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)
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki0.18500.00011.20929.9700AID31856; AID32020; AID32491; AID32514
Adenosine receptor A3Rattus norvegicus (Norway rat)Ki45.10000.00030.91969.0000AID33486
Adenosine receptor A2aHomo sapiens (human)Ki0.32000.00001.06099.7920AID30797; AID92373
Adenosine receptor A2bHomo sapiens (human)Ki0.32000.00021.635210.0000AID30797; AID92373
Adenosine receptor A2bRattus norvegicus (Norway rat)Ki0.25000.00061.353610.0000AID30797; AID33568
Adenosine receptor A2aRattus norvegicus (Norway rat)Ki0.34680.00021.494010.0000AID30797; AID33568; AID33940
Adenosine receptor A2aCavia porcellus (domestic guinea pig)Ki0.11000.11002.63858.0000AID30621
[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)
Adenosine receptor A2aHomo sapiens (human)Kb0.11000.00131.08292.7000AID78490
Adenosine receptor A2bHomo sapiens (human)Kb0.11000.00601.08342.7000AID78490
Adenosine receptor A2bRattus norvegicus (Norway rat)Kb0.64000.25002.14755.4000AID156510
Adenosine receptor A2aRattus norvegicus (Norway rat)Kb0.64000.00071.84855.4000AID156510
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (61)

Processvia Protein(s)Taxonomy
synaptic transmission, dopaminergicAdenosine receptor A2aHomo sapiens (human)
response to amphetamineAdenosine receptor A2aHomo sapiens (human)
regulation of DNA-templated transcriptionAdenosine receptor A2aHomo sapiens (human)
phagocytosisAdenosine receptor A2aHomo sapiens (human)
apoptotic processAdenosine receptor A2aHomo sapiens (human)
inflammatory responseAdenosine receptor A2aHomo sapiens (human)
cellular defense responseAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
cell-cell signalingAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, cholinergicAdenosine receptor A2aHomo sapiens (human)
central nervous system developmentAdenosine receptor A2aHomo sapiens (human)
blood coagulationAdenosine receptor A2aHomo sapiens (human)
sensory perceptionAdenosine receptor A2aHomo sapiens (human)
locomotory behaviorAdenosine receptor A2aHomo sapiens (human)
blood circulationAdenosine receptor A2aHomo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A2aHomo sapiens (human)
response to xenobiotic stimulusAdenosine receptor A2aHomo sapiens (human)
response to inorganic substanceAdenosine receptor A2aHomo sapiens (human)
positive regulation of glutamate secretionAdenosine receptor A2aHomo sapiens (human)
positive regulation of acetylcholine secretion, neurotransmissionAdenosine receptor A2aHomo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A2aHomo sapiens (human)
response to purine-containing compoundAdenosine receptor A2aHomo sapiens (human)
response to caffeineAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, GABAergicAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
positive regulation of urine volumeAdenosine receptor A2aHomo sapiens (human)
vasodilationAdenosine receptor A2aHomo sapiens (human)
eating behaviorAdenosine receptor A2aHomo sapiens (human)
negative regulation of vascular permeabilityAdenosine receptor A2aHomo sapiens (human)
negative regulation of neuron apoptotic processAdenosine receptor A2aHomo sapiens (human)
positive regulation of circadian sleep/wake cycle, sleepAdenosine receptor A2aHomo sapiens (human)
negative regulation of alpha-beta T cell activationAdenosine receptor A2aHomo sapiens (human)
astrocyte activationAdenosine receptor A2aHomo sapiens (human)
neuron projection morphogenesisAdenosine receptor A2aHomo sapiens (human)
positive regulation of protein secretionAdenosine receptor A2aHomo sapiens (human)
negative regulation of inflammatory responseAdenosine receptor A2aHomo sapiens (human)
regulation of mitochondrial membrane potentialAdenosine receptor A2aHomo sapiens (human)
membrane depolarizationAdenosine receptor A2aHomo sapiens (human)
regulation of calcium ion transportAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
excitatory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
inhibitory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
prepulse inhibitionAdenosine receptor A2aHomo sapiens (human)
apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2aHomo sapiens (human)
positive regulation of long-term synaptic potentiationAdenosine receptor A2aHomo sapiens (human)
positive regulation of apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
positive regulation of chronic inflammatory response to non-antigenic stimulusAdenosine receptor A2bHomo sapiens (human)
G protein-coupled receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
activation of adenylate cyclase activityAdenosine receptor A2bHomo sapiens (human)
positive regulation of vascular endothelial growth factor productionAdenosine receptor A2bHomo sapiens (human)
positive regulation of cGMP-mediated signalingAdenosine receptor A2bHomo sapiens (human)
cGMP-mediated signalingAdenosine receptor A2bHomo sapiens (human)
positive regulation of chemokine productionAdenosine receptor A2bHomo sapiens (human)
positive regulation of interleukin-6 productionAdenosine receptor A2bHomo sapiens (human)
mast cell degranulationAdenosine receptor A2bHomo sapiens (human)
positive regulation of mast cell degranulationAdenosine receptor A2bHomo sapiens (human)
relaxation of vascular associated smooth muscleAdenosine receptor A2bHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2bHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
vasodilationAdenosine receptor A2bHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A2aHomo sapiens (human)
protein bindingAdenosine receptor A2aHomo sapiens (human)
calmodulin bindingAdenosine receptor A2aHomo sapiens (human)
lipid bindingAdenosine receptor A2aHomo sapiens (human)
enzyme bindingAdenosine receptor A2aHomo sapiens (human)
type 5 metabotropic glutamate receptor bindingAdenosine receptor A2aHomo sapiens (human)
identical protein bindingAdenosine receptor A2aHomo sapiens (human)
protein-containing complex bindingAdenosine receptor A2aHomo sapiens (human)
alpha-actinin bindingAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2bHomo sapiens (human)
protein bindingAdenosine receptor A2bHomo sapiens (human)
G protein-coupled receptor activityAdenosine receptor A2bHomo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
plasma membraneAdenosine receptor A2aHomo sapiens (human)
intermediate filamentAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2aHomo sapiens (human)
membraneAdenosine receptor A2aHomo sapiens (human)
dendriteAdenosine receptor A2aHomo sapiens (human)
axolemmaAdenosine receptor A2aHomo sapiens (human)
asymmetric synapseAdenosine receptor A2aHomo sapiens (human)
presynaptic membraneAdenosine receptor A2aHomo sapiens (human)
neuronal cell bodyAdenosine receptor A2aHomo sapiens (human)
postsynaptic membraneAdenosine receptor A2aHomo sapiens (human)
presynaptic active zoneAdenosine receptor A2aHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2bHomo sapiens (human)
Schaffer collateral - CA1 synapseAdenosine receptor A2bHomo sapiens (human)
presynapseAdenosine receptor A2bHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2bHomo sapiens (human)
plasma membraneAdenosine receptor A2bHomo sapiens (human)
Golgi membraneAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID33940Displacement of [3H]-CGS- 21680 from adenosine A2a receptors of rat striatal membrane1994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Structure-activity relationships of 1,3-dialkylxanthine derivatives at rat A3 adenosine receptors.
AID33907Selectivity ratio was expressed as the ratio of binding affinity towards Adenosine A2 receptor to that of Adenosine A1 receptor in rat1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Analogues of 1,3-dipropyl-8-phenylxanthine: enhancement of selectivity at A1-adenosine receptors by aryl substituents.
AID31692Antagonistic activity on N6-([3H]-phenylisopropyl)adenosine binding to rat brain membrane (Adenosine A1 receptor)1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
8-Aryl-and 8-cycloalkyl-1,3-dipropylxanthines: further potent and selective antagonists for A1-adenosine receptors.
AID31856Antagonism of binding of 1 nM [3H]cyclohexyladenosine to adenosine A1 receptors on rat cortical membranes1985Journal of medicinal chemistry, Apr, Volume: 28, Issue:4
1,3-Dialkyl-8-(p-sulfophenyl)xanthines: potent water-soluble antagonists for A1- and A2-adenosine receptors.
AID230535Ratio of selectivity for A3 and A2a receptors at rat brain1994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Structure-activity relationships of 1,3-dialkylxanthine derivatives at rat A3 adenosine receptors.
AID78490Inhibition of stimulation of adenylate cyclase in guinea pig brain slices at A2 receptor (2-chloroadenosine-elicited accumulations of cyclic AMP)1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
8-Aryl-and 8-cycloalkyl-1,3-dipropylxanthines: further potent and selective antagonists for A1-adenosine receptors.
AID156510Inhibition of 5'-(N-ethylcarbamoyl)adenosine-elicited stimulation of adenylate cyclase in rat PC12 cell membranes1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
8-Aryl-and 8-cycloalkyl-1,3-dipropylxanthines: further potent and selective antagonists for A1-adenosine receptors.
AID229822Ratio of antagonism at A2 versus A1 receptors (Ki values)1985Journal of medicinal chemistry, Apr, Volume: 28, Issue:4
1,3-Dialkyl-8-(p-sulfophenyl)xanthines: potent water-soluble antagonists for A1- and A2-adenosine receptors.
AID92373Inhibition of 5'-(N-ethylcarbamoyl)adenosine-elicited stimulation of adenylate cyclase in human platelet membranes1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
8-Aryl-and 8-cycloalkyl-1,3-dipropylxanthines: further potent and selective antagonists for A1-adenosine receptors.
AID32514Displacement of [3H]PIA from adenosine A1 receptors of rat brain membrane1994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Structure-activity relationships of 1,3-dialkylxanthine derivatives at rat A3 adenosine receptors.
AID32491Inhibition of 1 nM [3H]- N6-(phenylisopropyl) adenosine binding to Adenosine A1 receptor in rat cerebral cortical membranes1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions.
AID21139Solubility in water at PH 7.4 in the presence of Tris.HCl buffer1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
8-Aryl-and 8-cycloalkyl-1,3-dipropylxanthines: further potent and selective antagonists for A1-adenosine receptors.
AID230534Ratio of selectivity for A3 and A1 receptors at rat brain1994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Structure-activity relationships of 1,3-dialkylxanthine derivatives at rat A3 adenosine receptors.
AID32020Binding affinity against A1 adenosine receptors of the central nervous system1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Analogues of 1,3-dipropyl-8-phenylxanthine: enhancement of selectivity at A1-adenosine receptors by aryl substituents.
AID33568Binding affinity against A2 adenosine receptors of the central nervous system1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Analogues of 1,3-dipropyl-8-phenylxanthine: enhancement of selectivity at A1-adenosine receptors by aryl substituents.
AID30621Antagonism of cyclic [3H]AMP accumulation in guinea pig cerebral cortical slices (elicited by 15 uM 2-chloroadenosine at adenosine A2 receptor)1985Journal of medicinal chemistry, Apr, Volume: 28, Issue:4
1,3-Dialkyl-8-(p-sulfophenyl)xanthines: potent water-soluble antagonists for A1- and A2-adenosine receptors.
AID33486Displacement of [125I]AB-MECA from membranes of CHO cells stably transfected with the rat adenosine A3 receptor cDNA1994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Structure-activity relationships of 1,3-dialkylxanthine derivatives at rat A3 adenosine receptors.
AID30797Inhibition of the stimulation by 5'-(N-ethylcarbamoyl) adenosine of adenyl cyclase via adenosine A2 receptor in human platelet membranes.1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions.
AID230900Ratio of antagonist activity at A1 and A2 receptors1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
8-Aryl-and 8-cycloalkyl-1,3-dipropylxanthines: further potent and selective antagonists for A1-adenosine receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (32.00)18.7374
1990's16 (64.00)18.2507
2000's0 (0.00)29.6817
2010's1 (4.00)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: 11.07

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 Index11.07 (24.57)
Research Supply Index3.30 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.07)

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%
Other26 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]