Page last updated: 2024-11-12

cgs 24012

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Description

CGS 24012: adenosine agonist with both high affinity & selectivity for the adenosine A2 receptor [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10391971
CHEMBL ID2094089
SCHEMBL ID788809
MeSH IDM0158255

Synonyms (16)

Synonym
(2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
cgs24012
gtpl418
cgs 24012
adenosine,n-[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]-
CHEMBL2094089 ,
bdbm50452520
SCHEMBL788809
n6-[2-(3,5-dimethoxyphenyl)-2-(-2-methylphenyl)ethyl]adenosine
n6-[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]adenosine
pd 125944;dpma
AKOS030573756
(2r,3r,4s,5r)-2-(6-((2-(3,5-dimethoxyphenyl)-2-(o-tolyl)ethyl)amino)-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
n-[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]adenosine
(2r,3r,4s,5r)-2-(6-(2-(3,5-dimethoxyphenyl)-2-o-tolylethylamino)-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
Q27075942

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" CGS 15943 (100 nM), a nonselective adenosine antagonist, attenuated the VR activity of DPMA and CPA, causing a 9- and 12-fold rightward shift of the dose-response curves, respectively, whereas 8-cyclopentyl-1,3-dipropylxanthine (20 nM), a highly A1-selective blocker, had no such effect."( Demonstration of vasorelaxant activity with an A1-selective adenosine agonist in porcine coronary artery: involvement of potassium channels.
Cox, BF; Lappe, RW; Merkel, LA; Perrone, MH; Rivera, LM, 1992
)
0.28
" The slopes of the dose-response functions to CPA or DPMA were not significantly altered in the normally perfused circumflex vascular bed."( Ischaemia/reperfusion selectively attenuates coronary vasodilatation to an adenosine A2- but not to an A1-agonist in the dog.
Cox, BF; Greenland, BD; Merkel, LA; Perrone, MH, 1994
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki0.11400.00011.20929.9700AID31708; AID32025; AID32177; AID32503
Adenosine receptor A2aHomo sapiens (human)Ki0.03100.00001.06099.7920AID34237; AID34238; AID34239
Adenosine receptor A2bRattus norvegicus (Norway rat)Ki0.00510.00061.353610.0000AID33425; AID33440; AID33574; AID33733
Adenosine receptor A2aRattus norvegicus (Norway rat)Ki0.00510.00021.494010.0000AID33425; AID33440; AID33574; AID33733
[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 A2aHomo sapiens (human)EC50 (µMol)0.00040.00030.708110.0000AID30507
Adenosine receptor A2bHomo sapiens (human)EC50 (µMol)0.00040.00030.946110.0000AID30507
Adenosine receptor A1Cavia porcellus (domestic guinea pig)EC50 (µMol)5.62340.01261.93385.6234AID32148
[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 A2bRattus norvegicus (Norway rat)Ratio0.00440.00330.82929.6000AID33746
Adenosine receptor A2aRattus norvegicus (Norway rat)Ratio0.00440.00330.82309.6000AID33746
[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 (31)

Assay IDTitleYearJournalArticle
AID231269Ratio of binding affinity against A2 and A1 receptors1988Journal of medicinal chemistry, Jul, Volume: 31, Issue:7
N6-[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]adenosine and its uronamide derivatives. Novel adenosine agonists with both high affinity and high selectivity for the adenosine A2 receptor.
AID33575Binding affinity against adenosine A2 receptor in rat striatal membranes using [3H]NECA as radioligand1992Journal of medicinal chemistry, Jan-24, Volume: 35, Issue:2
Nucleosides and nucleotides. 103. 2-Alkynyladenosines: a novel class of selective adenosine A2 receptor agonists with potent antihypertensive effects.
AID234758Selectivity determined as Ratio of Ki(nM) of A1 adenosine receptor to the Ki(nM) of A2 adenosine receptor1992Journal of medicinal chemistry, Jul-24, Volume: 35, Issue:15
Nucleosides and nucleotides. 112. 2-(1-Hexyn-1-yl)adenosine-5'-uronamides: a new entry of selective A2 adenosine receptor agonists with potent antihypertensive activity.
AID177036Dose producing 30% decrease in blood pressure of anesthetized spontaneous hypertensive male rat(SHR)1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Nucleosides and nucleotides. 107. 2-(cycloalkylalkynyl)adenosines: adenosine A2 receptor agonists with potent antihypertensive effects.
AID31866Binding affinity at adenosine A1 receptor from rat brain membranes by [3H]N6-cyclohexyladenosine displacement.1988Journal of medicinal chemistry, Jul, Volume: 31, Issue:7
N6-[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]adenosine and its uronamide derivatives. Novel adenosine agonists with both high affinity and high selectivity for the adenosine A2 receptor.
AID31708Inhibition of [3H]CHA binding to adenosine A1 receptor from rat brain membranes1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Nucleosides and nucleotides. 107. 2-(cycloalkylalkynyl)adenosines: adenosine A2 receptor agonists with potent antihypertensive effects.
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.
AID173595Dose producing 10% decrease in heart rate of anaesthetized spontaneous hypertensive male rat(SHR)1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Nucleosides and nucleotides. 107. 2-(cycloalkylalkynyl)adenosines: adenosine A2 receptor agonists with potent antihypertensive effects.
AID32026Binding affinity against adenosine A1 receptor in rat brain membranes using [3H]CHA as radioligand1992Journal of medicinal chemistry, Jan-24, Volume: 35, Issue:2
Nucleosides and nucleotides. 103. 2-Alkynyladenosines: a novel class of selective adenosine A2 receptor agonists with potent antihypertensive effects.
AID32645Selectivity against adenosine A1 to A2 receptors1992Journal of medicinal chemistry, Jan-24, Volume: 35, Issue:2
Nucleosides and nucleotides. 103. 2-Alkynyladenosines: a novel class of selective adenosine A2 receptor agonists with potent antihypertensive effects.
AID232472Selectivity ratio for A1 receptor to that of A2 receptor in vitro in rat tissues1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
C2,N6-disubstituted adenosines: synthesis and structure-activity relationships.
AID33440Binding affinity at adenosine A2 receptor from rat striatal membranes by [3H]NECA displacement.1988Journal of medicinal chemistry, Jul, Volume: 31, Issue:7
N6-[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]adenosine and its uronamide derivatives. Novel adenosine agonists with both high affinity and high selectivity for the adenosine A2 receptor.
AID228183Dose producing 30% decrease in blood pressure of anesthetized spontaneously hypertensive rats (SHR's)1992Journal of medicinal chemistry, Jul-24, Volume: 35, Issue:15
Nucleosides and nucleotides. 112. 2-(1-Hexyn-1-yl)adenosine-5'-uronamides: a new entry of selective A2 adenosine receptor agonists with potent antihypertensive activity.
AID32025Binding affinity against adenosine A1 receptor from rat brain membranes using [3H]cyclohexyladenosine as radioligand.1992Journal of medicinal chemistry, Jul-24, Volume: 35, Issue:15
Nucleosides and nucleotides. 112. 2-(1-Hexyn-1-yl)adenosine-5'-uronamides: a new entry of selective A2 adenosine receptor agonists with potent antihypertensive activity.
AID232382Ratio of EC50 stim-QRS (conduction block) and EC50 for vasodilation of coronary arteries1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
2-Alkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor.
AID34239Binding affinity for HA-tagged wild type human Adenosine A2A receptor (WT) using [3H]CGS-21680 as radioligand expressed in COS-7 cells1997Journal of medicinal chemistry, Aug-01, Volume: 40, Issue:16
Mutagenesis reveals structure-activity parallels between human A2A adenosine receptors and biogenic amine G protein-coupled receptors.
AID33733Inhibition of binding of [3H]NECA to adenosine A2 receptor of rat striatal membranes.1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
C2,N6-disubstituted adenosines: synthesis and structure-activity relationships.
AID33425Inhibition of [3H]NECA binding to adenosine A2 receptor from rat striatal membranes1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Nucleosides and nucleotides. 107. 2-(cycloalkylalkynyl)adenosines: adenosine A2 receptor agonists with potent antihypertensive effects.
AID235149Selectivity for adenosine receptor subtype, ratio of Ki(nM) at A1 receptor to Ki(nM) at A2 receptor1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Nucleosides and nucleotides. 107. 2-(cycloalkylalkynyl)adenosines: adenosine A2 receptor agonists with potent antihypertensive effects.
AID34238Binding affinity for HA-tagged mutant human Adenosine A2A receptor (V84L), using [3H]CGS-21680 as radioligand expressed in COS-7 cells1997Journal of medicinal chemistry, Aug-01, Volume: 40, Issue:16
Mutagenesis reveals structure-activity parallels between human A2A adenosine receptors and biogenic amine G protein-coupled receptors.
AID32503Inhibition of binding of [3H]N6-cyclohexyladenosine to adenosine A1 receptor of rat whole brain membranes.1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
C2,N6-disubstituted adenosines: synthesis and structure-activity relationships.
AID34237Binding affinity for HA-tagged mutant human Adenosine A2A receptor (H250N) using [3H]-CGS-21,680 as radioligand expressed in COS-7 cells1997Journal of medicinal chemistry, Aug-01, Volume: 40, Issue:16
Mutagenesis reveals structure-activity parallels between human A2A adenosine receptors and biogenic amine G protein-coupled receptors.
AID33574Binding affinity against adenosine A2 receptor from rat striatum using [3H]NECA as radioligand.1992Journal of medicinal chemistry, Jul-24, Volume: 35, Issue:15
Nucleosides and nucleotides. 112. 2-(1-Hexyn-1-yl)adenosine-5'-uronamides: a new entry of selective A2 adenosine receptor agonists with potent antihypertensive activity.
AID30507Coronary arteries vasodilation at the adenosine A2 receptor in langendorff guinea pig heart preparation1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
2-Alkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor.
AID228181Dose producing 10% decrease in heart rate of anesthetized spontaneously hypertensive rats (SHR's)1992Journal of medicinal chemistry, Jul-24, Volume: 35, Issue:15
Nucleosides and nucleotides. 112. 2-(1-Hexyn-1-yl)adenosine-5'-uronamides: a new entry of selective A2 adenosine receptor agonists with potent antihypertensive activity.
AID32148Prolongation of the stimulus-QRS interval by 50% of the maximum response at the adenosine A1 receptor in langendorff guinea pig heart preparation1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
2-Alkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor.
AID33752Ratio of A2 to A1.1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential.
AID224981Dose producing 10% decrease of heart rate in anesthetized rats (SHR)1992Journal of medicinal chemistry, Jan-24, Volume: 35, Issue:2
Nucleosides and nucleotides. 103. 2-Alkynyladenosines: a novel class of selective adenosine A2 receptor agonists with potent antihypertensive effects.
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.
AID224988Dose producing 30% decrease of blood pressure in anesthetized rats (SHR)1992Journal of medicinal chemistry, Jan-24, Volume: 35, Issue:2
Nucleosides and nucleotides. 103. 2-Alkynyladenosines: a novel class of selective adenosine A2 receptor agonists with potent antihypertensive effects.
AID1345618Human A2A receptor (Adenosine receptors)1995The Journal of biological chemistry, Jun-09, Volume: 270, Issue:23
Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (51)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (3.92)18.7374
1990's32 (62.75)18.2507
2000's13 (25.49)29.6817
2010's3 (5.88)24.3611
2020's1 (1.96)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.85

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 Index11.85 (24.57)
Research Supply Index3.95 (2.92)
Research Growth Index5.80 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.85)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.96%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other50 (98.04%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]