Page last updated: 2024-12-11

adenosine-3',5'-cyclic phosphorothioate

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

Description

adenosine-3',5'-cyclic phosphorothioate: RP-cAMP-S is a protein kinase A inhibitor; SP-cAMP-S is a protein kinase A agonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

(Sp)-cAMPS : A nucleoside 3',5'-cyclic phosphorothioate having adenine as the nucleobase (the Sp-stereoisomer). [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

(Rp)-cAMPS : A nucleoside 3',5'-cyclic phosphorothioate having adenine as the nucleobase (the Rp-stereoisomer). [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID6858240
CHEMBL ID1235719
CHEMBL ID1236010
CHEBI ID84622
CHEBI ID84615
CHEBI ID191063
SCHEMBL ID4159569
SCHEMBL ID22370431
MeSH IDM0067365

Synonyms (59)

Synonym
rp-camps
CHEMBL1235719
chebi:84622 ,
CHEMBL1236010
chebi:84615 ,
RP1 ,
6-(6-amino-purin-9-yl)-2-thioxo-tetrahydro-2-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol
sp-adenosine-3',5'-cyclic-monophosphorothioate
rp-adenosine-3',5'-cyclic-monophosphorothioate
DB01790
sp-camp-s
sp-camps
adenosine 3',5'-monothionophosphate
(r)-p-camps
adenosine 3',5'-cyclic monophosphorothioate
(rp)-camps
adenosine, cyclic 3',5'-(hydrogen phosphorothioate)
rp-camp-s
adenosine-3',5'-cyclic phosphorothioate
r(p)-camps
cyclic apt
3,5'-camps
p-adenosine 3',5'-cyclic phosphorothiate
cyclic adenosine 3,'5'-phosphorothioate
adenosine-3',5'-monophosphorothioate
73208-40-9
71774-13-5
23645-17-2
(4ar,6r,7r,7as)-6-(6-aminopurin-9-yl)-2-hydroxy-2-sulanylidene-4a,6,7,7a-tetrahydro-4h-uro[3,2-d][1,3,2]dioxaphosphinin-7-ol
adenosine, cyclic 3',5'-[hydrogen [p(s)]-phosphorothioate]
CHEBI:191063
NCGC00182722-01
(4ar,6r,7r,7as)-6-(6-aminopurin-9-yl)-2-hydroxy-2-sulfanylidene-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
rp-adenosine 3',5'-cyclic monophosphorothioate, sodium salt
adenosine- 3', 5'- cyclic monophosphorothioate, rp- isomer
gtpl5262
SCHEMBL4159569
adenosine-3',5'-cyclic monophosphorothioate, rp-isomer
(sp)-camps
(sp)-adenosine-3',5'-cyclic monophosphorothioate
(rp)-adenosine-3',5'-cyclic monophosphorothioate
(2r,4ar,6r,7r,7as)-6-(6-amino-9h-purin-9-yl)-7-hydroxy-2-sulfanyltetrahydro-2h,4h-2lambda(5)-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
(2s,4ar,6r,7r,7as)-6-(6-amino-9h-purin-9-yl)-7-hydroxy-2-sulfanyltetrahydro-2h,4h-2lambda(5)-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
adenosine-3',5'-cyclic monophosphorothioate, sp-isomer
SCHEMBL22370431
DTXSID20178316
HY-100530A
CS-0019676
sp-camps (sodium salt)
HY-100530B
CS-0107084
NCGC00485585-01
(2r,4ar,6r,7r,7as)-6-(6-amino-9h-purin-9-yl)tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-sulfide
(2s,4ar,6r,7r,7as)-6-(6-amino-9h-purin-9-yl)tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-sulfide
Q27157921
adenosine-3',5'-cyclic -monophosphorothioate
Q27088619
AKOS040749365
AKOS040745140

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

Dosage Studied

ExcerptRelevanceReference
" (R)-p-cAMPS inhibited VIP-induced relaxation, with a rightward shift in the VIP dose-response curve, suggesting competitive antagonism."( A primary role for protein kinase A in smooth muscle relaxation induced by adrenergic agonists and neuropeptides.
Gu, ZF; Jensen, RT; Maton, PN, 1992
)
0.28
" Dose-response relationships of the shift of the i(f) activation curve showed that both Rp-cAMPs and Sp-cAMPs act as agonists in the cAMP-dependent direct f-channel activation."( Activation of f-channels by cAMP analogues in macropatches from rabbit sino-atrial node myocytes.
Baruscotti, M; Bois, P; DiFrancesco, D; Lenfant, J; Renaudon, B, 1997
)
0.3
" Bilateral intra-NAc infusions of the PKA inhibitor Rp-cAMPS reduced baseline cocaine self-administration, shifted the dose-response curve for cocaine self-administration to the left, and induced relapse of cocaine-seeking behavior after extinction from cocaine self-administration, consistent with an enhancement of cocaine effects in each paradigm."( Involvement of cAMP-dependent protein kinase in the nucleus accumbens in cocaine self-administration and relapse of cocaine-seeking behavior.
Barnhart, WJ; Genova, LM; Hope, BT; Nestler, EJ; Self, DW; Spencer, JJ, 1998
)
0.3
" The Ca(2+) response occurred in all-or-none fashion and the half-maximal dosage of U50488H (812."( Cyclic AMP regulates the calcium transients released from IP(3)-sensitive stores by activation of rat kappa-opioid receptors expressed in CHO cells.
Allen, CN; Grandy, DK; Ikeda, M; Nelson, CS; Shinagawa, H; Shinoe, T; Sugiyama, T; Yoshioka, T, 2001
)
0.31
" Phorbol dibutyrate (PDB), an activator of protein kinase C, stimulated basal phospholipid methylation and also shifted the dose-response curve for dopamine-stimulated phospholipid methylation to the right by more than an order of magnitude."( Protein kinase C regulates dopamine D4 receptor-mediated phospholipid methylation.
Deth, RC; Sharma, A; Waly, M, 2001
)
0.31
" In the present work, the actions of 8-OH-DPAT in SCN slices were confirmed and expanded to include additional dose-response and antagonist treatments."( 8-OH-DPAT as a 5-HT7 agonist: phase shifts of the circadian biological clock through increases in cAMP production.
Braselton, J; Li, X; Reynolds, L; Schmidt, A; Sprouse, J, 2004
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
nucleoside 3',5'-cyclic phosphorothioateAny nucleoside monophosphate analogue that consists of a nucleoside 3',5'-cyclic phosphate in which the phosphate OH group is replaced by SH.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (6)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
AID1649098Binding affinity to GST-tagged human EPAC1 CNBD (149 to 318 residues)expressed in Escherichia coli BL21 (DE3) assessed as binding to R279 Guanidinium residue by guanidinium HSQC NMR spectroscopy2020Journal of medicinal chemistry, 05-14, Volume: 63, Issue:9
Mechanism of Action of an EPAC1-Selective Competitive Partial Agonist.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (493)

TimeframeStudies, This Drug (%)All Drugs %
pre-199031 (6.29)18.7374
1990's218 (44.22)18.2507
2000's187 (37.93)29.6817
2010's52 (10.55)24.3611
2020's5 (1.01)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.97

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 Index8.97 (24.57)
Research Supply Index6.23 (2.92)
Research Growth Index5.20 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.97)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (0.39%)6.00%
Case Studies1 (0.20%)4.05%
Observational0 (0.00%)0.25%
Other504 (99.41%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]