Page last updated: 2024-12-07

8-(4-carboxymethyloxy)phenyl-1,3-dipropylxanthine

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Description

8-(4-carboxymethyloxy)phenyl-1,3-dipropylxanthine: used to localize adenosine receptors in the brain [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID126079
CHEMBL ID27041
SCHEMBL ID7235224
MeSH IDM0153785

Synonyms (29)

Synonym
gtpl451
PDSP1_000315 ,
PDSP2_000313
PDSP2_001238
xcc ,
PDSP1_001254
CHEMBL27041 ,
L000656
2-[4-(2,6-dioxo-1,3-dipropyl-7h-purin-8-yl)phenoxy]acetic acid
[4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1h-purin-8-yl)phenoxy]acetic acid
96865-83-7
[4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1h-purin-8-yl)-phenoxy]-acetic acid
bdbm50008405
[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1h-purin-8-yl)-phenoxy]-acetic acid
2-(4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1h-purin-8-yl)phenoxy)acetic acid
8-(4-carboxymethyloxy)phenyl-1,3-dipropylxanthine
acetic acid, (4-(2,3,6,7-tetrahydro-2,6-dioxo-1,3-dipropyl-1h-purin-8-yl)phenoxy)-
SCHEMBL7235224
1,3-dipropyl-8-(4-carboxymethyloxy)phenylxanthine
8-(4'-carboxymethyloxyphenyl)-1,3-dipropyl xanthine
2-[4-(2,3,6,7-tetrahydro-2,6-dioxo-1,3-dipropyl-1h-purin-8-yl)phenoxy]-acetic acid
xanthine, 1,3-dipropyl-8-[(4-carboxymethoxy)phenyl]-
[4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1h-purin-8-yl)phenoxy]acetic acid #
xanthatin, 1,3-dipropyl-8-[(4-carboxymethoxy)phenyl]-
AKOS024458041
NCGC00370927-01
[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1h-purin-8-yl)phenoxy]acetic acid
DTXSID20914271
Q27089241

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (10)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cytochrome P450 family 3 subfamily A polypeptide 4Homo sapiens (human)Potency21.31740.01237.983543.2770AID1645841
[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 A3Homo sapiens (human)Ki3.94550.00000.930610.0000AID259517; AID34864
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki0.05880.00011.20929.9700AID259522; AID32177; AID32191; AID32500; AID32514
Adenosine receptor A3Rattus norvegicus (Norway rat)Ki75.70000.00030.91969.0000AID33354; AID33486
Adenosine receptor A2aHomo sapiens (human)Ki0.57000.00001.06099.7920AID259511; AID30622; AID30798; AID34250
Adenosine receptor A2bHomo sapiens (human)Ki0.19080.00021.635210.0000AID259510; AID30622; AID30798; AID33176; AID7693
Adenosine receptor A2bRattus norvegicus (Norway rat)Ki2.20000.00061.353610.0000AID33728
Adenosine receptor A1Homo sapiens (human)Ki0.17500.00020.931610.0000AID30463
Adenosine receptor A2aRattus norvegicus (Norway rat)Ki2.21290.00021.494010.0000AID259521; AID33728; AID33940
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A1Bos taurus (cattle)Kd0.01700.01700.02700.0370AID31846
[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)Kb2.40000.00131.08292.7000AID30639
Adenosine receptor A2bHomo sapiens (human)Kb2.40000.00601.08342.7000AID30639
Adenosine receptor A2bRattus norvegicus (Norway rat)Ratio2.20000.00330.82929.6000AID33746
Adenosine receptor A2aRattus norvegicus (Norway rat)Ratio2.20000.00330.82309.6000AID33746
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (105)

Processvia Protein(s)Taxonomy
inflammatory responseAdenosine receptor A3Homo sapiens (human)
signal transductionAdenosine receptor A3Homo sapiens (human)
activation of adenylate cyclase activityAdenosine receptor A3Homo sapiens (human)
regulation of heart contractionAdenosine receptor A3Homo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A3Homo sapiens (human)
response to woundingAdenosine receptor A3Homo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A3Homo sapiens (human)
negative regulation of cell migrationAdenosine receptor A3Homo sapiens (human)
negative regulation of NF-kappaB transcription factor activityAdenosine receptor A3Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A3Homo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A3Homo sapiens (human)
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)
temperature homeostasisAdenosine receptor A1Homo sapiens (human)
response to hypoxiaAdenosine receptor A1Homo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A1Homo sapiens (human)
regulation of respiratory gaseous exchange by nervous system processAdenosine receptor A1Homo sapiens (human)
negative regulation of acute inflammatory responseAdenosine receptor A1Homo sapiens (human)
negative regulation of leukocyte migrationAdenosine receptor A1Homo sapiens (human)
positive regulation of peptide secretionAdenosine receptor A1Homo sapiens (human)
positive regulation of systemic arterial blood pressureAdenosine receptor A1Homo sapiens (human)
negative regulation of systemic arterial blood pressureAdenosine receptor A1Homo sapiens (human)
regulation of glomerular filtrationAdenosine receptor A1Homo sapiens (human)
protein targeting to membraneAdenosine receptor A1Homo sapiens (human)
phagocytosisAdenosine receptor A1Homo sapiens (human)
inflammatory responseAdenosine receptor A1Homo sapiens (human)
signal transductionAdenosine receptor A1Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayAdenosine receptor A1Homo sapiens (human)
cell-cell signalingAdenosine receptor A1Homo sapiens (human)
nervous system developmentAdenosine receptor A1Homo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A1Homo sapiens (human)
response to inorganic substanceAdenosine receptor A1Homo sapiens (human)
negative regulation of glutamate secretionAdenosine receptor A1Homo sapiens (human)
response to purine-containing compoundAdenosine receptor A1Homo sapiens (human)
lipid catabolic processAdenosine receptor A1Homo sapiens (human)
negative regulation of synaptic transmission, GABAergicAdenosine receptor A1Homo sapiens (human)
positive regulation of nucleoside transportAdenosine receptor A1Homo sapiens (human)
negative regulation of neurotrophin productionAdenosine receptor A1Homo sapiens (human)
positive regulation of protein dephosphorylationAdenosine receptor A1Homo sapiens (human)
vasodilationAdenosine receptor A1Homo sapiens (human)
negative regulation of circadian sleep/wake cycle, non-REM sleepAdenosine receptor A1Homo sapiens (human)
negative regulation of apoptotic processAdenosine receptor A1Homo sapiens (human)
positive regulation of potassium ion transportAdenosine receptor A1Homo sapiens (human)
positive regulation of MAPK cascadeAdenosine receptor A1Homo sapiens (human)
negative regulation of hormone secretionAdenosine receptor A1Homo sapiens (human)
cognitionAdenosine receptor A1Homo sapiens (human)
leukocyte migrationAdenosine receptor A1Homo sapiens (human)
detection of temperature stimulus involved in sensory perception of painAdenosine receptor A1Homo sapiens (human)
negative regulation of lipid catabolic processAdenosine receptor A1Homo sapiens (human)
positive regulation of lipid catabolic processAdenosine receptor A1Homo sapiens (human)
regulation of sensory perception of painAdenosine receptor A1Homo sapiens (human)
negative regulation of synaptic transmission, glutamatergicAdenosine receptor A1Homo sapiens (human)
fatty acid homeostasisAdenosine receptor A1Homo sapiens (human)
excitatory postsynaptic potentialAdenosine receptor A1Homo sapiens (human)
long-term synaptic depressionAdenosine receptor A1Homo sapiens (human)
mucus secretionAdenosine receptor A1Homo sapiens (human)
negative regulation of mucus secretionAdenosine receptor A1Homo sapiens (human)
triglyceride homeostasisAdenosine receptor A1Homo sapiens (human)
regulation of cardiac muscle cell contractionAdenosine receptor A1Homo sapiens (human)
apoptotic signaling pathwayAdenosine receptor A1Homo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentrationAdenosine receptor A1Homo sapiens (human)
negative regulation of long-term synaptic potentiationAdenosine receptor A1Homo sapiens (human)
negative regulation of long-term synaptic depressionAdenosine receptor A1Homo sapiens (human)
G protein-coupled receptor signaling pathwayAdenosine receptor A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A3Homo sapiens (human)
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 receptor bindingAdenosine receptor A1Homo sapiens (human)
purine nucleoside bindingAdenosine receptor A1Homo sapiens (human)
protein bindingAdenosine receptor A1Homo sapiens (human)
heat shock protein bindingAdenosine receptor A1Homo sapiens (human)
G-protein beta/gamma-subunit complex bindingAdenosine receptor A1Homo sapiens (human)
heterotrimeric G-protein bindingAdenosine receptor A1Homo sapiens (human)
protein heterodimerization activityAdenosine receptor A1Homo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A1Homo 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 (19)

Processvia Protein(s)Taxonomy
plasma membraneAdenosine receptor A3Homo sapiens (human)
presynaptic membraneAdenosine receptor A3Homo sapiens (human)
Schaffer collateral - CA1 synapseAdenosine receptor A3Homo sapiens (human)
dendriteAdenosine receptor A3Homo sapiens (human)
plasma membraneAdenosine receptor A3Homo sapiens (human)
synapseAdenosine receptor A3Homo sapiens (human)
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)
plasma membraneAdenosine receptor A1Homo sapiens (human)
plasma membraneAdenosine receptor A1Homo sapiens (human)
basolateral plasma membraneAdenosine receptor A1Homo sapiens (human)
axolemmaAdenosine receptor A1Homo sapiens (human)
asymmetric synapseAdenosine receptor A1Homo sapiens (human)
presynaptic membraneAdenosine receptor A1Homo sapiens (human)
neuronal cell bodyAdenosine receptor A1Homo sapiens (human)
terminal boutonAdenosine receptor A1Homo sapiens (human)
dendritic spineAdenosine receptor A1Homo sapiens (human)
calyx of HeldAdenosine receptor A1Homo sapiens (human)
postsynaptic membraneAdenosine receptor A1Homo sapiens (human)
presynaptic active zoneAdenosine receptor A1Homo sapiens (human)
synapseAdenosine receptor A1Homo sapiens (human)
dendriteAdenosine receptor A1Homo sapiens (human)
Golgi membraneAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (41)

Assay IDTitleYearJournalArticle
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings 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.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347160Primary screen NINDS Rhodamine 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.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
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.
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.
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.
AID259521Binding affinity to rat adenosine A2A receptor2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Design, synthesis, and structure-activity relationships of 1-,3-,8-, and 9-substituted-9-deazaxanthines at the human A2B adenosine receptor.
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.
AID259511Binding affinity to recombinant human adenosine A2A receptor2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Design, synthesis, and structure-activity relationships of 1-,3-,8-, and 9-substituted-9-deazaxanthines at the human A2B adenosine receptor.
AID32191Binding affinity towards adenosine A1 receptor in rat cerebral cortical membranes by [3H]cyclohexyladenosine displacement.1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Functionalized congeners of 1,3-dialkylxanthines: preparation of analogues with high affinity for adenosine receptors.
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.
AID30622Binding affinity against A2 adenosine receptor in guinea pig cerebral cortical slices by [3H]-adenine displacement.1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Functionalized congeners of 1,3-dialkylxanthines: preparation of analogues with high affinity for adenosine receptors.
AID30798Inhibition of NECA binding to adenosine A2 receptor mediates reduced adenylate cyclase activity in human platelets1988Journal of medicinal chemistry, Apr, Volume: 31, Issue:4
125I-labeled 8-phenylxanthine derivatives: antagonist radioligands for adenosine A1 receptors.
AID32177Binding affinity against adenosine A1 receptor using [3H]-CHA or [3H]PIA as radioligand1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential.
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.
AID259510Binding affinity to recombinant human adenosine A2B receptor2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Design, synthesis, and structure-activity relationships of 1-,3-,8-, and 9-substituted-9-deazaxanthines at the human A2B adenosine receptor.
AID259512Selectivity for human adenosine A2B over human adenosine A2A receptor2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Design, synthesis, and structure-activity relationships of 1-,3-,8-, and 9-substituted-9-deazaxanthines at the human A2B adenosine receptor.
AID34250Antagonist activity against recombinant human adenosine A2A receptor expressed in HEK293 cells in presence of [125I]iodo-ZM-241385 radioligand.2000Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6
Anilide derivatives of an 8-phenylxanthine carboxylic congener are highly potent and selective antagonists at human A(2B) adenosine receptors.
AID234381Selectivity ratio of hA1 to hA2B2000Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6
Anilide derivatives of an 8-phenylxanthine carboxylic congener are highly potent and selective antagonists at human A(2B) adenosine receptors.
AID234382Selectivity ratio of hA2A to hA2B2000Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6
Anilide derivatives of an 8-phenylxanthine carboxylic congener are highly potent and selective antagonists at human A(2B) adenosine receptors.
AID30463Antagonist activity against recombinant human adenosine A1 receptor expressed in HEK293 cells in presence of [125I]IABA radioligand.2000Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6
Anilide derivatives of an 8-phenylxanthine carboxylic congener are highly potent and selective antagonists at human A(2B) adenosine receptors.
AID30639Antagonism of NECA-induced stimulation of adenylate cyclase activity in human platelet membranes at A2-adenosine receptor; value ranges from 1500-39001987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Xanthine functionalized congeners as potent ligands at A2-adenosine receptors.
AID230003Ratio of Ki for A1 and A2 receptors1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Functionalized congeners of 1,3-dialkylxanthines: preparation of analogues with high affinity for adenosine receptors.
AID33752Ratio of A2 to A1.1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential.
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.
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.
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.
AID33354Antagonist activity against rat adenosine A3 receptor using [125I]I-AB-MECA or [125 I]IABA2000Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6
Anilide derivatives of an 8-phenylxanthine carboxylic congener are highly potent and selective antagonists at human A(2B) adenosine receptors.
AID34864Antagonist activity against human adenosine A3 receptor expressed in HEK cells in presence of [125]IAB-MECA or [125I]IABA radioligand.2000Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6
Anilide derivatives of an 8-phenylxanthine carboxylic congener are highly potent and selective antagonists at human A(2B) adenosine receptors.
AID259517Binding affinity to recombinant human adenosine A3 receptor2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Design, synthesis, and structure-activity relationships of 1-,3-,8-, and 9-substituted-9-deazaxanthines at the human A2B adenosine receptor.
AID32886Antagonist activity against adenosine A2A receptor in rat striatal membrane in presence of [3H]CGS-21680 radioligand.2000Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6
Anilide derivatives of an 8-phenylxanthine carboxylic congener are highly potent and selective antagonists at human A(2B) adenosine receptors.
AID259522Binding affinity to rat adenosine A1 receptor2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
Design, synthesis, and structure-activity relationships of 1-,3-,8-, and 9-substituted-9-deazaxanthines at the human A2B adenosine receptor.
AID31846Binding affinity for adenosine A1 receptor as inhibition of [125-I]-labeled aminobenzyl adenosine binding to bovine brain membranes1988Journal of medicinal chemistry, Apr, Volume: 31, Issue:4
125I-labeled 8-phenylxanthine derivatives: antagonist radioligands for adenosine A1 receptors.
AID32335Antagonist activity against adenosine A1 receptor in rat brain membrane in presence of [3H]R-PIA radioligand.2000Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6
Anilide derivatives of an 8-phenylxanthine carboxylic congener are highly potent and selective antagonists at human A(2B) 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.
AID234383Selectivity ratio of hA3 to hA2B2000Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6
Anilide derivatives of an 8-phenylxanthine carboxylic congener are highly potent and selective antagonists at human A(2B) adenosine receptors.
AID7693Antagonist activity against human A2B adenosine receptor expressed in HEK293 cells uisng [3H]ZM-241385 or [125I]-IABOPX2000Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6
Anilide derivatives of an 8-phenylxanthine carboxylic congener are highly potent and selective antagonists at human A(2B) adenosine receptors.
AID33746Binding affinity against adenosine A2 receptor using [3H]- NECA as radioligand1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential.
AID1345721Human A2B receptor (Adenosine receptors)2001Biochemical pharmacology, Mar-15, Volume: 61, Issue:6
[3H]MRS 1754, a selective antagonist radioligand for A(2B) adenosine receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (31.25)18.7374
1990's2 (12.50)18.2507
2000's6 (37.50)29.6817
2010's1 (6.25)24.3611
2020's2 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.57

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 Index11.57 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.41 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.57)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (6.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (93.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]