Page last updated: 2024-11-07

8-chloro-cyclic adenosine monophosphate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

8-chloro-cyclic adenosine monophosphate (8-Cl-cAMP) is a synthetic analog of cyclic adenosine monophosphate (cAMP). It is a potent and selective activator of protein kinase A (PKA), a key enzyme involved in signal transduction pathways. 8-Cl-cAMP is often used as a research tool to study the role of cAMP in various cellular processes. It is particularly useful in cell culture experiments where it can mimic the effects of cAMP without the need for external stimulation. 8-Cl-cAMP is also used in the development of new drugs targeting PKA, as it is believed to have therapeutic potential in treating a variety of diseases, including cancer and neurological disorders.'

Cross-References

ID SourceID
PubMed CID100299
CHEMBL ID2107085
SCHEMBL ID125595
MeSH IDM0129416

Synonyms (46)

Synonym
ncs 614491
8-chloroadenosine 3',5'-cyclic phosphate
8-chloroadenosine 3',5'-monophosphate
8-chloro-camp
ccris 846
adenosine, 8-chloro-, cyclic 3',5'-(hydrogen phosphate)
8-chloro-cyclic adenosine monophosphate
tocladesine
8-chloroadenosine 3',5'-cyclic monophosphate
8-chloro-cyclic amp
nsc614491
nsc-614491
41941-56-4
(4ar,6r,7r,7as)-6-(6-amino-8-chloro-purin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
4h-furo[3,2-d]-1,3,2-dioxaphosphorin-7-ol, 6-(6-amino-8-chloro-9h-purin-9-yl)tetrahydro-2-hydroxy-, 2-oxide, (4ar,6r,7r,7as)-
8-cl-camp
nsc-284751
D06173
tocladesine (usan/inn)
8-chloroadenosine-cyclic-3',5'-monophosphate
(4ar,6r,7r,7as)-6-(6-amino-8-chloropurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
6-(6-amino-8-chloropurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
tocladesine [usan:inn:ban]
unii-bq94z7e5or
icn-1256
nsc 614491
bq94z7e5or ,
adenazole
CHEMBL2107085
8-chloro cyclic amp
tocladesine [usan]
(4ar,6r,7r,7as)-6-(6-amino-8-chloro-purin-9-yl)-2-oxo-tetrahydro-2lambda*5*-furo(3,2-d)(1,3,2)dioxaphosphinine-2,7-diol
8-chloro-cyclic adenosine 3',5'-monophosphate
tocladesine [inn]
SCHEMBL125595
8-chloroadenosine-cyclic-3',5'-monophosphate dihydrate
W-202723
DB13046
8-chloroadenosine-3',5'-o-monophosphate
8-chloroadenosine 3',5'-cyclic-monophosphate
Q27274811
cn 1256
cn1256
HY-123396
DTXSID101024678
AKOS040749661

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" We have also evaluated the effects of this anti-CRIPTO antisense oligonucleotide in combination with a chimeric anti-human epidermal growth factor receptor (EGFR) monoclonal antibody (MAb C225) and with 8-Cl-cAMP, a cAMP analog that specifically inhibits type I protein kinase A (PKAI), since a functional EGFR-driven autocrine pathway is operative and PKAI is overexpessed in GEO colon cancer cells."( Synergistic growth inhibition and induction of apoptosis by a novel mixed backbone antisense oligonucleotide targeting CRIPTO in combination with C225 anti-EGFR monoclonal antibody and 8-Cl-cAMP in human GEO colon cancer cells.
Agrawal, S; Bianco, AR; Casamassimi, A; Ciardiello, F; De Luca, A; Mendelsohn, J; Normanno, N; Pomatico, G; Tortora, G,
)
0.13

Dosage Studied

ExcerptRelevanceReference
" Moreover, the dose-response curves and the IC50 values of the latter compound for the various cell lines were compatible with those observed for 8-Cl-cAMP in fresh serum."( Effects of 8-chloro-cyclic adenosine monophosphate on the growth and sensitivity to doxorubicin of multidrug-resistant tumour cell lines.
Borsellino, N; Crescimanno, M; D'Alessandro, N; Leonardi, V, 1994
)
0.68
" The RI alpha antisense, which produces a biochemical imprint for growth control, requires infrequent dosing to restrain neoplastic growth in vivo."( Antisense DNA toward type I protein kinase A produces sustained inhibition of tumor growth.
Cho-Chung, YS, 1997
)
0.3
[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)34.33330.00001.068010.0000AID219834; AID219983
cAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)IC50 (µMol)34.33330.00001.104010.0000AID219834; AID219983
cAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)IC50 (µMol)34.33330.00001.465110.0000AID219834; AID219983
cAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)IC50 (µMol)34.33330.00001.146310.0000AID219834; 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 (4)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (256)

TimeframeStudies, This Drug (%)All Drugs %
pre-199098 (38.28)18.7374
1990's85 (33.20)18.2507
2000's40 (15.63)29.6817
2010's29 (11.33)24.3611
2020's4 (1.56)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.73

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 Index8.73 (24.57)
Research Supply Index5.61 (2.92)
Research Growth Index4.34 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.73)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (1.12%)5.53%
Reviews10 (3.72%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other256 (95.17%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (6)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Phase II Pilot Evaluation of Infusional 8 Cl-cAMP in the Treatment of Relapsed or Refractory Multiple Myeloma [NCT00004902]Phase 20 participants Interventional1998-01-31Completed
Effects of Including 30-s Sprints During Low-intensity Cycling Exercises During a Training Camp on Performance and Muscle/Blood Characterisitcs [NCT04640883]18 participants (Actual)Interventional2017-10-23Completed
MemoTV: Epigenetic, Neural and Cognitive Memories of Traumatic Stress and Violence in Former Offenders of the Townships of South Africa [NCT02012738]45 participants (Actual)Interventional2013-10-31Completed
Phase I Study Of Tocladesine In Patients With Colorectal Carcinoma Following Therapy With 5-FU And Irinotecan [NCT00021268]Phase 10 participants Interventional2001-04-30Active, not recruiting
Testing Bootle Boot Camp - A New Movement Tracking App to Engage Kids in Home Exercise Programs [NCT05998239]16 participants (Anticipated)Interventional2024-01-31Not yet recruiting
HEART (Heart Failure Exercise and Resistance Training) Camp Connect: Promoting Adherence to Exercise in Adults With Heart Failure With Preserved Ejection Fraction [NCT05784753]300 participants (Anticipated)Interventional2023-08-31Not yet recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]