Compounds > 8-benzylthio-n(6)-n-butyladenosine cyclic-3,5'-monophosphate
Page last updated: 2024-11-12

8-benzylthio-n(6)-n-butyladenosine cyclic-3,5'-monophosphate

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Description

8-benzylthio-N(6)-n-butyladenosine cyclic-3,5'-monophosphate: may be useful as myocardial stimulant; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID13388130
CHEMBL ID3142439
SCHEMBL ID9507382
MeSH IDM0121662

Synonyms (9)

Synonym
8-benzylthio-n(6)-n-butyladenosine cyclic-3,5'-monophosphate
8-btbca
8-benzylthio-n-butyl cyclic amp
adenosine, n-butyl-8-((phenylmethyl)thio)-, cyclic 3',5'-(hydrogen phosphate)
n(6)-n-butyl-8-btcamp
56583-64-3
SCHEMBL9507382
CHEMBL3142439
(4ar,6r,7r,7as)-6-[8-benzylsulfanyl-6-(butylamino)purin-9-yl]-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)IC50 (µMol)40.00000.00001.068010.0000AID219834; AID219983
cAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)IC50 (µMol)40.00000.00001.104010.0000AID219834; AID219983
cAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)IC50 (µMol)40.00000.00001.465110.0000AID219834; AID219983
cAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)IC50 (µMol)40.00000.00001.146310.0000AID219834; AID219983
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
cAMP catabolic processcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
signal transductioncAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
G protein-coupled receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
sensory perception of smellcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
regulation of protein kinase A signalingcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
cellular response to xenobiotic stimuluscAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
regulation of adenylate cyclase-activating G protein-coupled receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
cAMP-mediated signalingcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
neutrophil homeostasiscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cAMP catabolic processcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
neutrophil chemotaxiscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
positive regulation of type II interferon productioncAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
positive regulation of interleukin-2 productioncAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
T cell receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
leukocyte migrationcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cellular response to lipopolysaccharidecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cellular response to xenobiotic stimuluscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cellular response to epinephrine stimuluscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
negative regulation of adenylate cyclase-activating adrenergic receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
regulation of cardiac muscle cell contractioncAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
negative regulation of relaxation of cardiac musclecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
regulation of calcium ion transmembrane transport via high voltage-gated calcium channelcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cAMP-mediated signalingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cAMP catabolic processcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
cAMP-mediated signalingcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
regulation of heart ratecAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
cAMP catabolic processcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
positive regulation of heart ratecAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
regulation of release of sequestered calcium ion into cytosol by sarcoplasmic reticulumcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
positive regulation of type II interferon productioncAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
positive regulation of interleukin-2 productioncAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
positive regulation of interleukin-5 productioncAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
negative regulation of peptidyl-serine phosphorylationcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
negative regulation of heart contractioncAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
T cell receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
establishment of endothelial barriercAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
adrenergic receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
regulation of cardiac muscle cell contractioncAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
negative regulation of adenylate cyclase-activating G protein-coupled receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
regulation of cell communication by electrical coupling involved in cardiac conductioncAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
negative regulation of relaxation of cardiac musclecAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
regulation of calcium ion transmembrane transport via high voltage-gated calcium channelcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
cAMP-mediated signalingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
3',5'-cyclic-AMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
protein bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
cAMP bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
metal ion bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
calcium channel regulator activitycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
protein bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cAMP bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
gamma-tubulin bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
transmembrane transporter bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
metal ion bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
metal ion bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
3',5'-cyclic-nucleotide phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
calcium channel regulator activitycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
protein bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
enzyme bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
signaling receptor regulator activitycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
cAMP bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
beta-2 adrenergic receptor bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
transmembrane transporter bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
metal ion bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
ATPase bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
scaffold protein bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
heterocyclic compound bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (19)

Processvia Protein(s)Taxonomy
nucleoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
plasma membranecAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
membranecAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
ruffle membranecAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
perinuclear region of cytoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
perinuclear region of cytoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
nucleuscAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
centrosomecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
synaptic vesiclecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
postsynaptic densitycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
Z disccAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
dendritic spinecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
excitatory synapsecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
gamma-tubulin complexcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
voltage-gated calcium channel complexcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
nucleuscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
perinuclear region of cytoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
extracellular spacecAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
ciliumcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
nucleuscAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
perinuclear region of cytoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
centrosomecAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
plasma membranecAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
apical plasma membranecAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
voltage-gated calcium channel complexcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
calcium channel complexcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
nucleuscAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
perinuclear region of cytoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID219982Susceptibility to be hydrolysed by a partially purified cAMP phosphodiesterase from rabbit kidney1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Synthesis and enzymatic and inotropic activity of some new 8-substituted and 6,8-disubstituted derivatives of adenosine cyclic 3',5'-monophosphate.
AID219983Inhibition of cAMP phosphodiesterase preparation from rabbit lung at a substrate concentration of 0.14 uM1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Synthesis and enzymatic and inotropic activity of some new 8-substituted and 6,8-disubstituted derivatives of adenosine cyclic 3',5'-monophosphate.
AID61103Inotropic change in blood pressure (systolic/diastolic mmHg) in anesthetized dog; 2/-51980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Synthesis and enzymatic and inotropic activity of some new 8-substituted and 6,8-disubstituted derivatives of adenosine cyclic 3',5'-monophosphate.
AID219834Inhibition of cAMP phosphodiesterase preparation from bovine heart at a substrate concentration of 0.14 uM1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Synthesis and enzymatic and inotropic activity of some new 8-substituted and 6,8-disubstituted derivatives of adenosine cyclic 3',5'-monophosphate.
AID61098Change in heart rate (beats/min) in anesthetized dog1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Synthesis and enzymatic and inotropic activity of some new 8-substituted and 6,8-disubstituted derivatives of adenosine cyclic 3',5'-monophosphate.
AID61120Evaluated for dP/dt max in anesthetized dogs1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Synthesis and enzymatic and inotropic activity of some new 8-substituted and 6,8-disubstituted derivatives of adenosine cyclic 3',5'-monophosphate.
AID219827Activate a partially purified type II cAMP-dependent protein kinase from bovine brain1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Synthesis and enzymatic and inotropic activity of some new 8-substituted and 6,8-disubstituted derivatives of adenosine cyclic 3',5'-monophosphate.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (4)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (100.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)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: 12.66

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 Index12.66 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.66)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
tetraethylammonium
Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)		1.9610quaternary ammonium ion
8-bromo cyclic adenosine monophosphate
8-Bromo Cyclic Adenosine Monophosphate: A long-acting derivative of cyclic AMP. It is an activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.. 8-Br-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP bearing an additional bromo substituent at position 8 on the adenine ring. An activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.		1.95103',5'-cyclic purine nucleotide;
adenyl ribonucleotide;
organobromine compound		antidepressant;
protein kinase agonist
8-((4-chlorophenyl)thio)cyclic-3',5'-amp
8-((4-chlorophenyl)thio)cyclic-3',5'-AMP: lowers cAMP in heart & fat cells; cAMP-dependent kinase inhibitor. 8-(4-chlorophenylthio)-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP in which the hydrogen at position 2 on the purine fragment is replaced by a 4-chlorophenylthio group.		1.95103',5'-cyclic purine nucleotide;
adenyl ribonucleotide;
aryl sulfide;
organochlorine compound		protein kinase agonist
8-thio-benzyl cyclic amp
8-thio-benzyl cyclic AMP: RN given refers to parent cpd		2.3620
8-chloro-cyclic adenosine monophosphate
[no description available]		1.9510
n(6)-benzyl-cyclic adenosine 5'-monophosphate
[no description available]		1.9510
8-(methylthio)cyclic 3',5'-adenosine monophosphate
8-(methylthio)cyclic 3',5'-adenosine monophosphate: structure		1.9510
bucladesine
Bucladesine: A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed). bucladesine : A 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP.		1.96103',5'-cyclic purine nucleotide
ConditionIndicatedRelationship StrengthStudiesTrials
Cardiac Failure
[description not available]		01.9610
Shock, Cardiogenic
Shock resulting from diminution of cardiac output in heart disease.		01.9610
Heart Failure
A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.		01.9610