Page last updated: 2024-09-25

1,3-dipropyl-8-phenylxanthine

Description

1,3-dipropyl-8-phenylxanthine: selective antagonist at adenosine A1 receptors [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID128784
CHEMBL ID158507
CHEBI ID107631
SCHEMBL ID661108
SCHEMBL ID12648449
MeSH IDM0140945

Synonyms (39)

Synonym
8-phenyl-1,3-dipropyl-3,9-dihydro-1h-purine-2,6-dione
HMS3266E16
BRD-K41853443-001-01-1
1h-purine-2,6-dione, 3,7-dihydro-8-phenyl-1,3-dipropyl-
1,3-dipropyl-8-phenylxanthine
3,7-dihydro-1,3-dipropyl-8-phenyl-1h-purine-2,6,dione
1h-purine-2,6,dione, 3,7-dihydro-1,3-dipropyl-8-phenyl-
NCGC00024614-01 ,
tocris-0486
PDSP1_000990
PDSP2_000974
NCGC00024614-02
C16510
CHEBI:107631
85872-53-3
CHEMBL158507 ,
8-phenyl-1,3-dipropyl-7h-purine-2,6-dione
nsc_128784
cas_128784
bdbm82025
8-phenyl-1,3-dipropyl-3,9-dihydro-purine-2,6-dione
FT-0642015
SCHEMBL661108
CLIGSMOZKDCDRZ-UHFFFAOYSA-N
SCHEMBL12648449
AKOS024458381
Q27185956
SR-01000597618-1
sr-01000597618
AKOS027320574
8-phenyl-1,3-dipropyl-3,7-dihydro-1h-purine-2,6-dione
HMS3675O21
8-phenyl-1,3-dipropyl-1h-purine-2,6(3h,7h)-dione
bdbm50227332
HMS3411O21
BRD-K41853443-001-02-9
8-phenyl-1,3-dipropyl-1h-purine-2,6(3h,9h)-dione
DTXSID201006449
pmid28870136-compound-44

Drug Classes (1)

ClassDescription
oxopurine
[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 (33)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.79430.003245.467312,589.2998AID2517
Chain A, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID893
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency2.81840.177814.390939.8107AID2147
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency17.78280.011212.4002100.0000AID1030
cytochrome P450 2C19 precursorHomo sapiens (human)Potency10.00000.00255.840031.6228AID899
cytochrome P450 2C9 precursorHomo sapiens (human)Potency1.58490.00636.904339.8107AID883
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency3.54810.00798.23321,122.0200AID2551
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency2.51190.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency1.58490.00638.235039.8107AID883
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency2.51191.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki0.01070.00011.20929.9700AID30341; AID31856; AID31887; AID32020; AID32039; AID32487; AID32491; AID32500
Adenosine receptor A1Bos taurus (cattle)IC50 (µMol)706,270.00040.00001.09106.7400AID31836; AID31838
Adenosine receptor A2aHomo sapiens (human)Ki1.62750.00001.06099.7920AID30796; AID30797; AID33734; AID92373
Adenosine receptor A2bHomo sapiens (human)Ki0.88960.00021.635210.0000AID30797; AID33176; AID33180; AID33734; AID92373
Adenosine receptor A2bRattus norvegicus (Norway rat)Ki1.06910.00061.353610.0000AID30796; AID30797; AID33568; AID33579; AID33728; AID33734
Adenosine receptor A2aRattus norvegicus (Norway rat)Ki0.99170.00021.494010.0000AID30796; AID30797; AID32862; AID33568; AID33579; AID33728; AID33734
Adenosine receptor A2aCavia porcellus (domestic guinea pig)Ki0.30000.11002.63858.0000AID30621
[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)Kb1.20000.00131.08292.7000AID30635; AID78490
Adenosine receptor A2bHomo sapiens (human)Kb1.20000.00601.08342.7000AID30635; AID78490
Adenosine receptor A2bRattus norvegicus (Norway rat)Kb2.30000.25002.14755.4000AID156510
Adenosine receptor A2aRattus norvegicus (Norway rat)Kb2.30000.00071.84855.4000AID156510
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (61)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A1Bos taurus (cattle)
response to purine-containing compoundAdenosine receptor A1Bos taurus (cattle)
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 membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
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)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (43)

Assay IDTitleYearJournalArticle
AID230229Inhibitory selectivity for A2 receptor in rat striatal membranes and A1 receptor in rat cortical membranes1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Sulfur-containing 1,3-dialkylxanthine derivatives as selective antagonists at A1-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.
AID33176Binding affinity at human Adenosine A2B receptor expressed in HEK293 cells, using [125I]ABOPX as radioligand2002Journal of medicinal chemistry, May-23, Volume: 45, Issue:11
Structure-activity relationships at human and rat A2B adenosine receptors of xanthine derivatives substituted at the 1-, 3-, 7-, and 8-positions.
AID32868Binding affinity for adenosine A2A receptor using [3H]-NECA in rat brain striatal membranes2004Journal of medicinal chemistry, Feb-12, Volume: 47, Issue:4
Preparation, properties, reactions, and adenosine receptor affinities of sulfophenylxanthine nitrophenyl esters: toward the development of sulfonic acid prodrugs with peroral bioavailability.
AID30341Evaluated for binding affinity against Adenosine A1 receptor1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
A steric and electrostatic comparison of three models for the agonist/antagonist binding site on the adenosine A1 receptor.
AID33728Inhibition of binding of [3H]5'-(N-ethylcarbamoyl)-adenosine to adenosine A2 receptor in rat striatal membranes1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Sulfur-containing 1,3-dialkylxanthine derivatives as selective antagonists at A1-adenosine receptors.
AID32500Inhibition of binding of 1 nM [3H]N-6-(phenylisopropyl)adenosine to adenosine A1 receptor in rat cortical membranes1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Sulfur-containing 1,3-dialkylxanthine derivatives as selective antagonists at A1-adenosine receptors.
AID54313log(1000/IC50 determined from bovine brain membrane) expressed as potency1985Journal of medicinal chemistry, Aug, Volume: 28, Issue:8
Synthesis of xanthines as adenosine antagonists, a practical quantitative structure-activity relationship application.
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.
AID32495Inhibition of [3H]- PIA binding at adenosine A1 receptor on rat cerebral cortex membranes.1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Xanthine functionalized congeners as potent ligands at A2-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.
AID33441Binding affinity against adenosine A2 receptor in rat striatum by the displacement of [3H]N-ethyladenosine-5''-uronamide(NECA).1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
1,3,8-trisubstituted xanthines. Effects of substitution pattern upon adenosine receptor A1/A2 affinity.
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.
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.
AID33579Binding affinity to A2 adenosine receptor from rat striatal membrane in presence of [3H]5'-(N-ethylcarboximido)-adenosine1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
Synthesis and structure-activity relationships of deazaxanthines: analogs of potent A1- and A2-adenosine receptor antagonists.
AID31887Binding affinity for adenosine A1 receptor from rat brain membranes using [3H]PIA as radioligand1993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Effect of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors.
AID34727Binding affinity for human adenosine A3 receptor using [3H]PBS-11 in CHO cell membranes; ND denotes not determined2004Journal of medicinal chemistry, Feb-12, Volume: 47, Issue:4
Preparation, properties, reactions, and adenosine receptor affinities of sulfophenylxanthine nitrophenyl esters: toward the development of sulfonic acid prodrugs with peroral bioavailability.
AID31838Log IC50 value was determined against adenosine A1 receptor in bovine brain membranes1985Journal of medicinal chemistry, Aug, Volume: 28, Issue:8
Synthesis of xanthines as adenosine antagonists, a practical quantitative structure-activity relationship application.
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.
AID227036A1 selectivity is the ratio between A2 and A1 receptor1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
Synthesis and structure-activity relationships of deazaxanthines: analogs of potent A1- and A2-adenosine receptor antagonists.
AID32487Inhibition of 1 nM [3H]- N6 -(phenylisopropyl) adenosine binding to Adenosine A1 receptor in rat fat cell membrane1989Journal 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.
AID32862Binding affinity for adenosine A2A receptor from rat brain membranes using [3H]CGS-216801993Journal of medicinal chemistry, Sep-03, Volume: 36, Issue:18
Effect of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors.
AID30796Inhibition of stimulation by 5'-(N-ethylcarbamoyl) adenosine of adenyl cyclase via A2 adenosine receptor in human platelet 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.
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.
AID33753Ratio of the binding affinities of A2 /A1 receptor1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
1,3,8-trisubstituted xanthines. Effects of substitution pattern upon adenosine receptor A1/A2 affinity.
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.
AID33734Inhibition of the stimulation by 5'-(N-ethylcarbamoyl) adenosine of adenyl cyclase via Adenosine A2 receptor in rat PC12 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.
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.
AID32039Binding affinity to A1 adenosine receptor from rat cortical membrane in presence of [3H]R-(phenylisopropyl)-adenosine1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
Synthesis and structure-activity relationships of deazaxanthines: analogs of potent A1- and A2-adenosine receptor antagonists.
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.
AID33180Binding affinity for human HEK293 adenosine A2B receptor using [125I]ABOPX in CHO cell membranes2004Journal of medicinal chemistry, Feb-12, Volume: 47, Issue:4
Preparation, properties, reactions, and adenosine receptor affinities of sulfophenylxanthine nitrophenyl esters: toward the development of sulfonic acid prodrugs with peroral bioavailability.
AID32046Binding affinity for adenosine A1 receptor using [3H]PIA in rat brain cortical membrane2004Journal of medicinal chemistry, Feb-12, Volume: 47, Issue:4
Preparation, properties, reactions, and adenosine receptor affinities of sulfophenylxanthine nitrophenyl esters: toward the development of sulfonic acid prodrugs with peroral bioavailability.
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.
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.
AID30635Antagonism of NECA-induced stimulation of adenylate cyclase activity in human platelet membranes at A2-adenosine receptor1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Xanthine functionalized congeners as potent ligands at A2-adenosine receptors.
AID30335Log IC50 value was determined against adenosine A1 receptor in rat brain membranes1985Journal of medicinal chemistry, Aug, Volume: 28, Issue:8
Synthesis of xanthines as adenosine antagonists, a practical quantitative structure-activity relationship application.
AID31869Binding affinity against adenosine A1 receptor in rat cortex by the displacement of [3H]cyclohexyladenosine (CHA).1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
1,3,8-trisubstituted xanthines. Effects of substitution pattern upon adenosine receptor A1/A2 affinity.
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.
AID31836Binding affinity against bovine brain adenosine A1 receptor by using N6-[3H]- cyclohexyladenosine1985Journal of medicinal chemistry, Aug, Volume: 28, Issue:8
Synthesis of xanthines as adenosine antagonists, a practical quantitative structure-activity relationship application.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID493017Wombat Data for BeliefDocking1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
Synthesis and structure-activity relationships of deazaxanthines: analogs of potent A1- and A2-adenosine receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-199013 (39.39)18.7374
1990's4 (12.12)18.2507
2000's7 (21.21)29.6817
2010's3 (9.09)24.3611
2020's6 (18.18)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies2 (5.71%)4.05%
Observational0 (0.00%)0.25%
Other33 (94.29%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Pharmacokinetics (1)

ArticleYear
Altered intravenous pharmacokinetics of topotecan in rats with acute renal failure (ARF) induced by uranyl nitrate: do adenosine A1 antagonists (selective/non-selective) normalize the altered topotecan kinetics in ARF?
Xenobiotica; the fate of foreign compounds in biological systems, Volume: 36, Issue: 12
2006
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (1)

ArticleYear
Preparation, properties, reactions, and adenosine receptor affinities of sulfophenylxanthine nitrophenyl esters: toward the development of sulfonic acid prodrugs with peroral bioavailability.
Journal of medicinal chemistry, Feb-12, Volume: 47, Issue: 4
2004
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (2)

ArticleYear
Exercise in the heat: effects of an adenosine antagonist.
International journal of sports medicine, Volume: 21, Issue: 4
2000
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]