Page last updated: 2024-12-04

8-bromo cyclic adenosine monophosphate

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Description

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. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [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 CID32014
CHEMBL ID1626177
CHEBI ID64211
SCHEMBL ID2713659
MeSH IDM0023265

Synonyms (37)

Synonym
23583-48-4
8-bromoadenosine 3',5'-cyclic monophosphate
cyclic 8-bromoadenosine 3',5'-monophosphate
8-bromoadenosine cyclic 3',5'-phosphate
bcamp
8-bromo-cyclic amp
8-bromoadenosine 3',5'-monophosphate
8-bromo-cyclic 3',5'-amp
8-bromoadenosine 3',5'-cyclic monophosphate, >=97% (hplc)
8-br-camp
8-bromo cyclic adenosine monophosphate
(4ar,6r,7r,7as)-6-(6-amino-8-bromo-9h-purin-9-yl)tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide
unii-5qo1uw05q5
8-bromoadenosine cyclic 3',5'-(hydrogen phosphate)
einecs 245-760-6
5qo1uw05q5 ,
nsc 171719
CHEBI:64211 ,
8-bromoadenosine 3',5'-(hydrogen phosphate)
SCHEMBL2713659
W-201990
CHEMBL1626177
8-bromo-3',5'-cyclic amp
mfcd00075580
8-bromoadenosine-3',5'-cyclic monophosphate
8-bromoadenosine 3',5'-cyclic monophosphate, >=98.0% (hplc)
W16909
(4ar,6r,7r,7as)-6-(6-amino-8-bromo-9h-purin-9-yl)-2,7-dihydroxytetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinine 2-oxide
AKOS030573818
DVKQVRZMKBDMDH-UUOKFMHZSA-N
Q4644267
8-bromoadenosine cyclic 3',5'-monophosphate
8-bromoadenosine-camp
8-bromoadenosine3:5-cyclicmonophosphate
adenosine,8-bromo-,cyclic 3',5'-(hydrogen phosphate)
4h-furo[3,2-d]-1,3,2-dioxaphosphorin-7-ol, 6-(6-amino-8-bromo-9h-purin-9-yl)tetrahydro-2-hydroxy-, 2-oxide, (4ar,6r,7r,7as)-
PD017512

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The adverse effects of GAA on the production of ROS, cytoplasmic acidification, GSH content, and [Ca2+]i were also attenuated."( Attenuation of gossypol cytotoxicity by cyclic AMP in a rat liver cell line.
Barhoumi, R; Burghardt, RC; Hutchinson, RW; Miles, JM, 1998
)
0.3

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

Bioavailability

ExcerptReferenceRelevance
"Insulin-like growth factor-binding protein 1 (IGFBP-1) is important in regulating minute-to-minute IGF bioavailability in the circulation and is primarily an inhibitor of IGF action systemically and in most cellular systems."( Regulation of insulin-like growth factor-binding protein 1 by hypoxia and 3',5'-cyclic adenosine monophosphate is additive in HepG2 cells.
Giaccia, AJ; Giudice, LC; Kaper, F; Powell, DR; Suen, LF; Sugawara, J; Tazuke, SI, 2000
)
0.31
" This is in line with the suggested role of follistatin as an activin-binding protein, which limits the bioavailability of activin to its membrane receptors."( Activin-A, but not inhibin, regulates 17beta-hydroxysteroid dehydrogenase type 1 activity and expression in cultured rat granulosa cells.
Akinola, L; Ghersevich, S; Isomaa, V; Kaminski, T; Poutanen, M; Vihko, P; Vihko, R,
)
0.13

Dosage Studied

ExcerptRelevanceReference
" Receptor responses were affected however; the maximum response to N-ethylcarboxamidoadenosine (an A2 receptor agonist) was reduced by 30-40%, there was a small but consistent shift to the right of the dose-response curve for iloprost (a stable analogue of prostacyclin) and [3H]iloprost binding studies revealed a loss of prostacyclin receptors."( Cyclic AMP produces desensitization of prostacyclin and adenosine A2 receptors in hybrid cell lines but does not affect Gs function.
Austin, A; Docherty, K; Keen, M; Kelly, E; Krane, A; MacDermot, J; Taylor, N; Wiltshire, R, 1992
)
0.28
" However, in the presence of ionomycin the dose-response of 8-bromo-cAMP (Br-cAMP) with respect to uPA mRNA accumulation was shifted toward the lower concentrations of Br-cAMP."( Ca2+ potentiates cAMP-dependent expression of urokinase-type plasminogen activator gene through a calmodulin- and protein kinase C-independent mechanism.
Hagmann, J; Kiefer, B; Nagamine, Y; Ziegler, A, 1990
)
0.28
" Dose-response studies reveal that 10(-6) to 10(-4) M concentrations of 8-bromo-cAMP (8-Br-cAMP) elicit a maximal response."( Progesterone receptor regulation in uterine cells: stimulation by estrogen, cyclic adenosine 3',5'-monophosphate, and insulin-like growth factor I and suppression by antiestrogens and protein kinase inhibitors.
Aronica, SM; Katzenellenbogen, BS, 1991
)
0.28
" FSH dose-response studies at 48 h revealed a significant stimulatory effect of 30 ng/ml FSH on P450scc mRNA accumulation and progesterone production, with a maximal effect at 100 ng/ml FSH."( Follicle-stimulating hormone increases concentrations of messenger ribonucleic acid encoding cytochrome P450 cholesterol side-chain cleavage enzyme in primary cultures of porcine granulosa cells.
Garmey, JC; Shupnik, MA; Urban, RJ; Veldhuis, JD, 1991
)
0.28
" The hCG dose-response curve was shifted to the right by the addition of IL-2."( Interleukin-2 is a potent inhibitor of Leydig cell steroidogenesis.
Calkins, JH; Guo, H; Lin, T; Sigel, MM, 1990
)
0.28
" Dose-response curves for MIX potentiation of cAMP-stimulated glycogenolysis and for MIX inhibition of the effects of insulin on cAMP-stimulated glycogenolysis suggested that at higher concentrations (250 microM) MIX may act at a site other than phosphodiesterase inhibition."( Methylisobutylxanthine blocks insulin antagonism of cAMP-stimulated glycogenolysis at a site distinct from phosphodiesterase. Evidence favoring an insulin-insensitive calcium release mechanism.
Gabbay, RA; Lardy, HA, 1986
)
0.27
" The dose-response relationships of this effect were measured by equilibrating cell aliquots with various Ca2+-EGTA buffers, preparing membrane vesicles (in the absence of Ca2+ ions), and assaying them for amiloride-sensitive Na+ permeability."( Ca2+-induced down-regulation of Na+ channels in toad bladder epithelium.
Asher, C; Garty, H, 1986
)
0.27
" Thus, palytoxin exhibited a biphasic dose-response curve for enhanced bone resorption, with stimulation at low concentrations (0."( Palytoxin: an extraordinarily potent stimulator of prostaglandin production and bone resorption in cultured mouse calvariae.
Fujiki, H; Lazzaro, M; Levine, L; Tashjian, AH, 1987
)
0.27
" The dose-response curve for cyclic AMP on ICa was well fitted by the Michaelis equation with a K50 (i."( Cyclic guanosine 3',5'-monophosphate regulates the calcium current in single cells from frog ventricle.
Fischmeister, R; Hartzell, HC, 1987
)
0.27
" ACTH(1-24) and 8-bromocyclic AMP both provoked a dose-related release of putrescine-derived GABA, although the dose-response curve for the latter differed somewhat from that for the release of corticosterone by this secretogogue."( Formation of releasable gamma-aminobutyrate from putrescine by rat adrenal slices in vitro.
Gillham, B; Oon, BB; Scraggs, PR, 1989
)
0.28
" Protein kinase inhibitors block v-Src- and v-Fps-induced 9E3 gene expression with the same dose-response curves seen for PKC agonist-induced 9E3 gene expression."( Evidence that v-src and v-fps gene products use a protein kinase C-mediated pathway to induce expression of a transformation-related gene.
Berg, KL; Foster, DA; Joseph, C; Qureshi, SA; Spangler, R, 1989
)
0.28
" The ACTH dose-response curves for steroidogenic activity and for polyamine uptake were similar."( Hormonal control of polyamine levels in bovine adrenocortical cells.
Chambaz, EM; Feige, JJ; Madani, C, 1986
)
0.27
" Dose-response studies showed that the effect on gonadotropin secretion occurred at concentrations of 8-bromo-cyclic adenosine monophosphate two orders of magnitude lower than those affecting adrenocorticotropic hormone secretion."( Corticotropin-releasing factor can stimulate gonadotropin secretion by human fetal pituitaries in superfusion.
Blumenfeld, Z; Jaffe, RB; Kuhn, RW, 1986
)
0.27
" Dose-response curves with cAMP and adenosine 3',5'-monophosphorothioate, a nonhydrolyzable analog, revealed that the requirement for high concentrations of exogenous cAMP for regulating gene expression is due to the rapid degradation of cAMP by phosphodiesterase."( Pharmacological characterization of cyclic AMP receptors mediating gene regulation in Dictyostelium discoideum.
Dottin, RP; Haribabu, B, 1986
)
0.27
" The vasopressin analogs [1-(beta-mercapto-beta,beta-cyclopentamethylene propionic acid),2-(O-methyl)tyrosine,8-arginine]vasopressin (SK&F 100273), [1-(beta-mercapto-beta,beta-cyclopentamethylene propionic acid),2-(O-methyl)tyrosine,4-valine,8-arginine]vasopressin (SK&F 100501), [1-(beta-mercapto-beta,beta-cyclopentamethylene propionic acid),2-D-tyrosine,4-valine,8-arginine]vasopressin (SK&F 100885), [1-(beta-mercapto-beta,beta-cyclopentamethylene propionic acid),2-(O-ethyl)tyrosine,4-valine,8-arginine]vasopressin (SK&F 100398), [1-(beta-mercapto-beta,beta-cyclopentamethylene propionic acid),2-D-isoleucine,4-valine,8-arginine]vasopressin (SK&F 101485), [1-(beta-mercapto-beta,beta-cyclopentamethylene propionic acid),2-(O-ethyl)-tyrosine,4-valine,8-arginine]vasopressin (SK&F 101498), [1-(beta-mercapto-beta,beta-cyclopentamethylene propionic acid),2-(O-ethyl)D-tyrosine,4-valine,8-arginine,9-desglycine]vasop ressin (SK&F 101926) and [1-(beta-mercapto-beta-beta-cyclopentamethylene propionic acid),2-D-phenylalanine,4-valine,8-arginine] vasopressin (SK&F 101071) antagonized arginine vasopressin-stimulated water flux and displaced the agonist dose-response relationship to the right in a parallel fashion."( Mechanism of action and structural requirements of vasopressin analog inhibition of transepithelial water flux in toad urinary bladder.
Huffman, W; Kinter, LB; Mann, WA; Stassen, F, 1986
)
0.27
" A dose-response curve for amiloride obtained in the presence of AVT showed that amiloride completely inhibits ISC."( Stimulation of sodium transport by aldosterone and arginine vasotocin in A6 cells.
Bindels, RJ; Reif, MC; Schafer, JA, 1988
)
0.27
" Similar temporal and dose-response relationships were observed for LH-stimulated IP3 and cAMP accumulation."( Luteinizing hormone increases inositol trisphosphate and cytosolic free Ca2+ in isolated bovine luteal cells.
Davis, JS; Farese, RV; Weakland, LL; West, LA, 1987
)
0.27
" Nonetheless, PT treatment caused a rightward shift in the dose-response curve for insulin-stimulated glucose oxidation as well as a small reduction in insulin binding."( Action of insulin modulated by pertussis toxin in rat adipocytes.
Goren, HJ; Hollenberg, MD; Northup, JK, 1985
)
0.27
" The ED50 for TRH stimulation of hormone release was increased 2- to 4-fold in down-regulated cells, but the dose-response curves for other secretagogues were not shifted."( Differential effects of thyrotropin-releasing hormone, vasoactive intestinal peptide, phorbol ester, and depolarization in GH4C1 rat pituitary cells.
Aizawa, T; Hinkle, PM, 1985
)
0.27
" We found that butyrate stimulated fibronectin synthesis in a dose-response fashion, and that butyrate had a greater stimulatory effect than did any of its derivatives examined."( Butyrate stimulates fibronectin synthesis in cultured rabbit cornea.
Nishida, T; Tanaka, H, 1985
)
0.27
" This phosphorylation of the receptor is dose-dependent with respect to isoproterenol and exhibits a dose-response curve coincidental with that for isoproterenol-induced desensitization of adenylate cyclase."( Desensitization of turkey erythrocyte adenylate cyclase. Beta-adrenergic receptor phosphorylation is correlated with attenuation of adenylate cyclase activity.
Caron, MG; Lefkowitz, RJ; Nambi, P; Peters, JR; Sibley, DR, 1984
)
0.27
" The facilitative interaction between E2 and FSH could not be accounted for by mitogenic effects, by a leftward shift in the dose-response curves for FSH or E2, or by catabolism of progesterone to 20 alpha-hydroxypregn-4-en-3-one."( The role of estradiol as a biological amplifier of the actions of follicle-stimulating hormone: in vitro studies in swine granulosa cells.
Hammond, JM; Klase, PA; Strauss, JF; Veldhuis, JD, 1982
)
0.26
" Dose-response curves for glycosylation in response to 8-Br-cAMP and GnRH were parallel."( Differential effects of cyclic nucleotide analogues and GnRH on LH synthesis and release.
Jackson, GL; Liu, TC, 1981
)
0.26
" This stimulation of 32P incorporation was dependent on the concentrations of LH, and this dose-response relationship correlated well with the dose response of LH-induced progesterone production."( Stimulation of phospholipid labeling and steroidogenesis by luteinizing hormone in isolated bovine luteal cells.
Davis, JS; Farese, RV; Marsh, JM, 1981
)
0.26
" It also produced a decrease in 8-Br-cGMP mediated inhibition which was more pronounced when the dosage of LH was increased to 10 microgram/ml."( Inhibitory action of cyclic guanosine 5'-phosphoric acid (GMP) on oocyte maturation: dependence on an intact cumulus.
Hubbard, CJ; Terranova, PF, 1982
)
0.26
" No other hormone altered the FSH dose-response curve."( Proteoglycan production by bovine granulosa cells in vitro occurs in response to fsh.
Ax, RL; Bellin, ME; Lenz, RW; Steadman, LE, 1983
)
0.27
" Dose-response curves for the increase in the content of proenkephalin mRNA and of enkephalin-containing peptides were essentially identical."( Enkephalin biosynthesis in adrenal medulla. Modulation of proenkephalin mRNA content of cultured chromaffin cells by 8-bromo-adenosine 3',5'-monophosphate.
Costa, E; Guidotti, A; Kageyama, H; Meek, JL; Mocchetti, I; Quach, TT; Schwartz, JP; Tang, F, 1984
)
0.27
" The dose-response curves of induction of HGF secretion by cholera toxin and forskolin were nearly parallel with those of the intracellular cAMP levels."( Expression of hepatocyte growth factor is up-regulated through activation of a cAMP-mediated pathway.
Gohda, E; Iwao, M; Kataoka, H; Matsunaga, T; Takebe, T; Wu, YL; Yamamoto, I, 1994
)
0.29
" Caffeine shifted the dose-response curves of the [Ca2+]i rise induced by vasopressin (0."( Caffeine inhibits cytosolic calcium oscillations induced by noradrenaline and vasopressin in rat hepatocytes.
Berthon, B; Claret, M; Combettes, L, 1994
)
0.29
" cAMP shifted the dose-response curve for calcium-induced secretion leftwards and elevated the peak value of secretion."( Inhibition by somatostatin of amylase secretion induced by calcium and cyclic AMP in rat pancreatic acini.
Kojima, I; Mine, T; Ohnishi, H, 1994
)
0.29
" The dose-response relation for the reduction of channel open probability showed that Mg2+o binds to a site (KD = approximately 25 microM at -160 mV) that senses approximately 38% of the potential drop from the external membrane surface."( The role of Mg2+ in the inactivation of inwardly rectifying K+ channels in aortic endothelial cells.
Elam, TR; Lansman, JB, 1995
)
0.29
" Exposure of transfected cells to human chorionic gonadotropin (hCG) resulted in a dose-dependent loss of maximal hCG-stimulable adenylyl cyclase activity without a significant shift to the right of the dose-response curve to hCG."( Homologous desensitization of the murine luteinizing hormone receptor expressed in L cells.
Birnbaumer, L; Birnbaumer, M; Gudermann, T, 1995
)
0.29
" 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
)
0.29
" The only dose-response curves that differed in slope between thermal groups were those produced by the TSH response to TRH (p < ."( Somatotroph, lactotroph and thyrotroph function in three-week-old gilts reared in a hot or cool environment.
Becker, BA; Matteri, RL, 1994
)
0.29
" TPA markedly enhanced both haptotactic response to type-IV collagen and motility on tissue-culture glass substrate of L-10 cells in a dose-response manner quite similar to that of TPA-enhanced invasion of Matrigel."( TPA-enhanced invasion of Matrigel associated with augmentation of cell motility but not metalloproteinase activity in a highly metastatic variant (L-10) of human rectal adenocarcinoma cell line RCM-1.
Hayakawa, T; Inoue, T; Kishi, J; Koita, H; Komada, N; Koono, M; Nabeshima, K, 1993
)
0.29
" In treated TASM, washed free of AP III, acute dose-response curves of cGMP to AP III were not different from that in untreated cells."( Regulation of atrial natriuretic peptide receptors in vascular smooth muscle cells: role of cGMP.
Newman, WH; Tao, H; Zhang, LM, 1993
)
0.29
" In acini prepared from the camostate-treated rats, responsiveness to both CCK-8 and carbamylcholine was greatly decreased with no shift in the dose-response curves compared to control acini prepared from saline-treated rats."( Chronic oral administration of synthetic trypsin inhibitor camostate reduces amylase release from isolated rat pancreatic acini.
Fujii, M; Nakamura, T; Okabayashi, Y; Otsuki, M; Tani, S, 1995
)
0.29
" Dose-response curves show that the potentiation by 17 beta-estradiol was evident at a concentration as low as 10 nM and saturated at 10 microM."( 17 beta-Estradiol potentiates kainate-induced currents via activation of the cAMP cascade.
Gu, Q; Moss, RL, 1996
)
0.29
" 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
" We used primary cerebrocortical cell cultures from fetal mice to examine the dose-response and time-course of ppSom gene expression in response to the cyclic-AMP analogs, dibutyrl-cAMP (dbcAMP), and 8-bromo-cAMP (8-BrcAMP)."( Regulation of the preprosomatostatin gene by cyclic-AMP in cerebrocortical neurons.
Capone, G; Choi, C; Vertifuille, J, 1998
)
0.3
" The present study examined whether inactivation of alpha1-adrenoceptors in the BLA would alter the dose-response effects on memory storage of intra-BLA infusions of a beta-adrenoceptor agonist, as well as that of a synthetic cAMP analog."( Basolateral amygdala noradrenergic influences on memory storage are mediated by an interaction between beta- and alpha1-adrenoceptors.
Ferry, B; McGaugh, JL; Roozendaal, B, 1999
)
0.3
" The dose-response profile of V(1) receptor agonist-induced neurotrophism exhibited a biphasic function, with lower concentrations inducing a significant increase while higher concentrations generally induced no significant effect."( Vasopressin-induced neurotrophism in cultured neurons of the cerebral cortex: dependency on calcium signaling and protein kinase C activity.
Brinton, RD; Chen, Q; Kim, J; Monreal, AW; Oji, G; Patel, R; Sales, A, 2000
)
0.31
" 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
" The levels of activin betaA and ActRIIA receptor mRNA elevated with increasing dose of hCG; however, the effect significantly decreased at dosage higher than 15 IU/ml."( Gonadotropin regulation of activin betaA and activin type IIA receptor expression in the ovarian follicle cells of the zebrafish, Danio rerio.
Ge, W; Pang, Y, 2002
)
0.31
" Moreover, ACh and Ca(2+) dose-response studies showed that accumulation of cAMP shifted the dose-response curves to the low concentration side, suggesting that it increases Ca(2+) sensitivity in the fusion of the exocytotic cycle."( cAMP modulation of Ca(2+)-regulated exocytosis in ACh-stimulated antral mucous cells of guinea pig.
Fujiwara, S; Imai, Y; Katsu, K; Kojima, K; Nakahari, T; Shimamoto, C, 2002
)
0.31
" Dose-response curves were constructed for the chorion cell cultures with CRH or 8-bromo-cAMP."( Regulation of 15-hydroxy prostaglandin dehydrogenase by corticotrophin-releasing hormone through a calcium-dependent pathway in human chorion trophoblast cells.
Challis, JR; McKeown, KJ, 2003
)
0.32
" In the present study, comparison of dose-response relations for hyperalgesia produced by PGE2, forskolin, 8-Br-cAMP, or the protein kinase A (PKA) catalytic subunit, in primed versus normal animals, demonstrated that priming-induced enhancement of the PGE2-activated second messenger cascade occurs downstream to adenylate cyclase and upstream to PKA."( Chronic hyperalgesic priming in the rat involves a novel interaction between cAMP and PKCepsilon second messenger pathways.
Levine, JD; Parada, CA; Reichling, DB, 2005
)
0.33
" The cumulative dose-response curve of SMA to NE and Ca2+ after shock was shifted to the right."( The role of calcium desensitization in vascular hyporeactivity and its regulation after hemorrhagic shock in the rat.
Liu, L; Xu, J, 2005
)
0.33
" Both 8-Br-cAMP (100 microM) and forskolin (10 microM) right-shifted the dose-response curves for the TRPM8-mediated effect of icilin and menthol on intracellular Ca(2+)."( Regulation of transient receptor potential channels of melastatin type 8 (TRPM8): effect of cAMP, cannabinoid CB(1) receptors and endovanilloids.
De Petrocellis, L; Di Marzo, V; Moriello, AS; Orlando, P; Starowicz, K; Vivese, M, 2007
)
0.34
"5-10 microg) microinjected into the VTA induces penile erection with an inverted U-shaped dose-response curve; the maximal effective dose being 3 microg."( Oxytocin induces penile erection when injected into the ventral tegmental area of male rats: role of nitric oxide and cyclic GMP.
Argiolas, A; Boi, A; Cocco, C; Ferri, GL; Melis, MR; Melis, T; Sanna, F; Succu, S, 2008
)
0.35
" The model of HCO(3)(-) inhibiting osteoclast via sAC was further supported by the fact that the HCO(3)(-) dose-response on osteoclasts is flat when cells were saturated with 8-bromo-cAMP, a permeant cAMP analog downstream from sAC thus simulating sAC activation."( Inhibition of osteoclast formation and function by bicarbonate: role of soluble adenylyl cyclase.
Geng, W; Hill, K; Kohler, T; Moe, OW; Müller, R; Zerwekh, JE, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
protein kinase agonistAn agonist that selectively binds to and activates a protein kinase receptor.
antidepressantAntidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
[role 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]

Drug Classes (3)

ClassDescription
3',5'-cyclic purine nucleotide
organobromine compoundA compound containing at least one carbon-bromine bond.
adenyl ribonucleotideA purine riboncleotide where adenine is the purine.
[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]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)IC50 (µMol)18.46670.00001.068010.0000AID219834; AID219983
cAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)IC50 (µMol)18.46670.00001.104010.0000AID219834; AID219983
cAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)IC50 (µMol)18.46670.00001.465110.0000AID219834; AID219983
cAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)IC50 (µMol)18.46670.00001.146310.0000AID219834; 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 (8)

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.
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.
AID1145763Inhibition of rabbit lung PDE assessed as inhibition 8-[3H]-cAMP substrate hydrolysis1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis of some 1, 8- and 2, 8-disubstituted derivatives of adenosine cyclic 3', 5'-phosphate and their interaction with some enzymes of cAMP metabolism.
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.
AID1145764Inhibition of bovine heart PDE assessed as inhibition 8-[3H]-cAMP substrate hydrolysis1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis of some 1, 8- and 2, 8-disubstituted derivatives of adenosine cyclic 3', 5'-phosphate and their interaction with some enzymes of cAMP metabolism.
AID1145761Ratio of Ka for cAMP to Ka for compound for bovine brain protein kinase in presence of 0.5 nmol [32P]ATP-gamma by liquid scintillation spectrometer1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis of some 1, 8- and 2, 8-disubstituted derivatives of adenosine cyclic 3', 5'-phosphate and their interaction with some enzymes of cAMP metabolism.
AID1145762Activity of rabbit kidney PDE assessed as enzyme-mediated compound hydrolysis after 10 to 60 mins by colorimetric assay relative to cAMP1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis of some 1, 8- and 2, 8-disubstituted derivatives of adenosine cyclic 3', 5'-phosphate and their interaction with some enzymes of cAMP metabolism.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (3,619)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990903 (24.95)18.7374
1990's1615 (44.63)18.2507
2000's860 (23.76)29.6817
2010's232 (6.41)24.3611
2020's9 (0.25)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (0.13%)5.53%
Reviews29 (0.78%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other3,673 (99.08%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]