Page last updated: 2024-11-07

st 587

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Description

St 587: clonidine derivative which is selective alpha(1)-adrenoceptor stimulator with lipophilic properties; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID114697
CHEMBL ID101340
SCHEMBL ID5154887
SCHEMBL ID9725295
MeSH IDM0096784

Synonyms (14)

Synonym
CHEMBL101340 ,
gtpl513
st 587
L001127
(2-chloro-5-trifluoromethyl-phenyl)-imidazolidin-2-ylidene-amine (st-587)
bdbm50027067
(2-chloro-5-trifluoromethyl-phenyl)-(4,5-dihydro-1h-imidazol-2-yl)-amine
n-[2-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-1h-imidazol-2-amine
SCHEMBL5154887
2-(2-chloro-5-trifluoromethylphenylimino) imidazolidine
SCHEMBL9725295
Q27088882
bdbm50225287
wiaicrsvmjhhjl-uhfffaoysa-n

Research Excerpts

Dosage Studied

The absence of a depression of the maximum of the dose-response curve of ST 587 and the very moderate attenuation of the maximal B-HT 920-induced increase in diastolic blood pressure (BP) confirms the lack of major calcium entry blocking properties of R 56865 for alpha-adrenoceptor-activated calcium channels.

ExcerptRelevanceReference
" Treatment with captopril was found to attenuate pressor responses produced by the administration of either alpha 1- or alpha 2-adrenoceptor agonists, resulting in the displacement to the right of the agonist dose-response curves and significantly increasing the calculated ED50 values."( The interrelationship between the effects of captopril and nifedipine on pressor responses elicited by selective alpha-adrenoceptor agonists in the pithed rat preparation.
Tabrizchi, R; Triggle, CR, 1992
)
0.28
" The ED50 value for the dose-response curves to B-HT 920 and St587 were found to be significantly increased after the administration of staurosporine."( Effects of staurosporine on the pressor responses to alpha-adrenoceptor agonists in pithed rats: a comparison with nifedipine.
Tabrizchi, R; Triggle, CR, 1991
)
0.28
" Bay K 8644 (10(-8) M) markedly potentiated B-HT-958-mediated vasoconstrictor responses with a leftward shift and an increase in the maximum response of the logarithmic dose-response curve."( Sensitivity of alpha-adrenoceptor agonists to the calcium channel activator, Bay K 8644, in canine saphenous vein.
Eskinder, H; Gross, GJ, 1987
)
0.27
" The absence of a depression of the maximum of the dose-response curve of ST 587 and the very moderate attenuation of the maximal B-HT 920-induced increase in diastolic blood pressure (BP) confirms the lack of major calcium entry blocking properties of R 56865 for alpha-adrenoceptor-activated calcium channels in vitro."( Interaction between R 56865 and alpha-adrenoceptors in the pithed rat.
Fruh, C; Koch, P; Peters, T; Schneider, J; Wilffert, B; Wilhelm, D,
)
0.13
" Where pA2 values (-log dose antagonist evoking a twofold shift for the agonist dose-response curve) could be calculated, no significantly different pA2 values against either agonist resulted."( Calcium influx-dependent and -independent alpha 1-adrenoceptor-mediated processes of vasoconstriction in vivo do not operate via different alpha 1-adrenoceptor subtypes.
de Jonge, A; Korstanje, C; Thoolen, MJ; Timmermans, PB; van Zwieten, PA; Wilffert, B,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Alpha-2A adrenergic receptorHomo sapiens (human)Ki1.56000.00010.807410.0000AID35944
Alpha-1B adrenergic receptorRattus norvegicus (Norway rat)Ki65.80000.00010.949010.0000AID37466
Alpha-2B adrenergic receptorRattus norvegicus (Norway rat)Ki0.17900.00000.929610.0000AID36372
Alpha-1D adrenergic receptorRattus norvegicus (Norway rat)Ki65.80000.00000.575110.0000AID37466
Alpha-1A adrenergic receptorRattus norvegicus (Norway rat)Ki65.80000.00000.965010.0000AID37466
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (42)

Processvia Protein(s)Taxonomy
positive regulation of cytokine productionAlpha-2A adrenergic receptorHomo sapiens (human)
DNA replicationAlpha-2A adrenergic receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
Ras protein signal transductionAlpha-2A adrenergic receptorHomo sapiens (human)
Rho protein signal transductionAlpha-2A adrenergic receptorHomo sapiens (human)
female pregnancyAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of cell population proliferationAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of norepinephrine secretionAlpha-2A adrenergic receptorHomo sapiens (human)
regulation of vasoconstrictionAlpha-2A adrenergic receptorHomo sapiens (human)
actin cytoskeleton organizationAlpha-2A adrenergic receptorHomo sapiens (human)
platelet activationAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of cell migrationAlpha-2A adrenergic receptorHomo sapiens (human)
activation of protein kinase activityAlpha-2A adrenergic receptorHomo sapiens (human)
activation of protein kinase B activityAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of epinephrine secretionAlpha-2A adrenergic receptorHomo sapiens (human)
cellular response to hormone stimulusAlpha-2A adrenergic receptorHomo sapiens (human)
receptor transactivationAlpha-2A adrenergic receptorHomo sapiens (human)
vasodilationAlpha-2A adrenergic receptorHomo sapiens (human)
glucose homeostasisAlpha-2A adrenergic receptorHomo sapiens (human)
fear responseAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of potassium ion transportAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of MAP kinase activityAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of MAPK cascadeAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of epidermal growth factor receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of calcium ion-dependent exocytosisAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of insulin secretionAlpha-2A adrenergic receptorHomo sapiens (human)
intestinal absorptionAlpha-2A adrenergic receptorHomo sapiens (human)
thermoceptionAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of lipid catabolic processAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of membrane protein ectodomain proteolysisAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of calcium ion transportAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of insulin secretion involved in cellular response to glucose stimulusAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of uterine smooth muscle contractionAlpha-2A adrenergic receptorHomo sapiens (human)
adrenergic receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
adenylate cyclase-inhibiting adrenergic receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
phospholipase C-activating adrenergic receptor signaling pathwayAlpha-2A adrenergic receptorHomo sapiens (human)
positive regulation of wound healingAlpha-2A adrenergic receptorHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAlpha-2A adrenergic receptorHomo sapiens (human)
negative regulation of calcium ion transmembrane transporter activityAlpha-2A adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
alpha2-adrenergic receptor activityAlpha-2A adrenergic receptorHomo sapiens (human)
protein bindingAlpha-2A adrenergic receptorHomo sapiens (human)
protein kinase bindingAlpha-2A adrenergic receptorHomo sapiens (human)
alpha-1B adrenergic receptor bindingAlpha-2A adrenergic receptorHomo sapiens (human)
alpha-2C adrenergic receptor bindingAlpha-2A adrenergic receptorHomo sapiens (human)
thioesterase bindingAlpha-2A adrenergic receptorHomo sapiens (human)
heterotrimeric G-protein bindingAlpha-2A adrenergic receptorHomo sapiens (human)
protein homodimerization activityAlpha-2A adrenergic receptorHomo sapiens (human)
protein heterodimerization activityAlpha-2A adrenergic receptorHomo sapiens (human)
epinephrine bindingAlpha-2A adrenergic receptorHomo sapiens (human)
norepinephrine bindingAlpha-2A adrenergic receptorHomo sapiens (human)
guanyl-nucleotide exchange factor activityAlpha-2A adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
cytoplasmAlpha-2A adrenergic receptorHomo sapiens (human)
plasma membraneAlpha-2A adrenergic receptorHomo sapiens (human)
basolateral plasma membraneAlpha-2A adrenergic receptorHomo sapiens (human)
neuronal cell bodyAlpha-2A adrenergic receptorHomo sapiens (human)
axon terminusAlpha-2A adrenergic receptorHomo sapiens (human)
presynaptic active zone membraneAlpha-2A adrenergic receptorHomo sapiens (human)
dopaminergic synapseAlpha-2A adrenergic receptorHomo sapiens (human)
postsynaptic density membraneAlpha-2A adrenergic receptorHomo sapiens (human)
glutamatergic synapseAlpha-2A adrenergic receptorHomo sapiens (human)
GABA-ergic synapseAlpha-2A adrenergic receptorHomo sapiens (human)
receptor complexAlpha-2A adrenergic receptorHomo sapiens (human)
plasma membraneAlpha-2A adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID37466Displacement of [3H]prazosin from rat cortex Alpha-1 adrenergic receptor1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Design, synthesis, and structure-activity relationships of a new series of alpha-adrenergic agonists: spiro[(1,3-diazacyclopent-1-ene)-5,2'-(1',2',3',4'- tetrahydronaphthalene)].
AID185723The maximal pressure response caused by the compound in pithed rat1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
(S)-spiro[(1,3-diazacyclopent-1-ene)-5,2'-(7'-methyl-1',2',3',4'- tetrahydronaphthalene)]: resolution, stereospecific synthesis, and preliminary pharmacological characterization as a partial alpha-adrenergic agonist.
AID232349Ratio of C20 obtained in the absence or presence of [C20 ( 0.1 mg of prazosin ) / C20 (control)]1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Design, synthesis, and structure-activity relationships of a new series of alpha-adrenergic agonists: spiro[(1,3-diazacyclopent-1-ene)-5,2'-(1',2',3',4'- tetrahydronaphthalene)].
AID60507Maximal contractile response obtained with the agonist (expressed as a percentage of the maximal contraction to phenylephrine in the dog saphenous vein)1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Design, synthesis, and structure-activity relationships of a new series of alpha-adrenergic agonists: spiro[(1,3-diazacyclopent-1-ene)-5,2'-(1',2',3',4'- tetrahydronaphthalene)].
AID231664C20 ratio was determined in the presence or absence of 1 mg of yohimbine for the compound which are indicative of the contribution of alpha-2 adnergic mechanisms to the pressor response1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
(S)-spiro[(1,3-diazacyclopent-1-ene)-5,2'-(7'-methyl-1',2',3',4'- tetrahydronaphthalene)]: resolution, stereospecific synthesis, and preliminary pharmacological characterization as a partial alpha-adrenergic agonist.
AID60506Maximal contractile response obtained with the agonist (expressed as a percentage of the maximal contraction to phenylephrine in the dog femoral artery)1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Design, synthesis, and structure-activity relationships of a new series of alpha-adrenergic agonists: spiro[(1,3-diazacyclopent-1-ene)-5,2'-(1',2',3',4'- tetrahydronaphthalene)].
AID171336Concentration which increases the arterial blood pressure by 20 mmHg in the pithed rat in vivo by intravenous administration1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
(S)-spiro[(1,3-diazacyclopent-1-ene)-5,2'-(7'-methyl-1',2',3',4'- tetrahydronaphthalene)]: resolution, stereospecific synthesis, and preliminary pharmacological characterization as a partial alpha-adrenergic agonist.
AID59112Effective concentration for the agonist in the isolated blood vessel using in vitro saphenous vein1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Design, synthesis, and structure-activity relationships of a new series of alpha-adrenergic agonists: spiro[(1,3-diazacyclopent-1-ene)-5,2'-(1',2',3',4'- tetrahydronaphthalene)].
AID36715Binding affinity against alpha-1 adrenergic receptor is the ability to inhibit the specific [3H]prazosin binding (0.4 nM) to rat isolated brain membranes by 50% was reported.1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Quantitative relationships between alpha-adrenergic activity and binding affinity of alpha-adrenoceptor agonists and antagonists.
AID185553Alpha adrenergic activity was evaluated as maximal pressure response caused by agonist, expressed in mmHg (the maximum obtained with phenylephrine is 150 mmHg).1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Design, synthesis, and structure-activity relationships of a new series of alpha-adrenergic agonists: spiro[(1,3-diazacyclopent-1-ene)-5,2'-(1',2',3',4'- tetrahydronaphthalene)].
AID60967Effective concentration of compound in isolated canine saphenous vein1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
(S)-spiro[(1,3-diazacyclopent-1-ene)-5,2'-(7'-methyl-1',2',3',4'- tetrahydronaphthalene)]: resolution, stereospecific synthesis, and preliminary pharmacological characterization as a partial alpha-adrenergic agonist.
AID60979Maximum contractile response expressed as percentage (mean) of the maximal contraction to KCl (100 nM) in the isolated femoral artery1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
(S)-spiro[(1,3-diazacyclopent-1-ene)-5,2'-(7'-methyl-1',2',3',4'- tetrahydronaphthalene)]: resolution, stereospecific synthesis, and preliminary pharmacological characterization as a partial alpha-adrenergic agonist.
AID171335Alpha adrenergic activity was evaluated as concentration (iv) which increases the arterial pressure by 20 mmHg in the pithed rat1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Design, synthesis, and structure-activity relationships of a new series of alpha-adrenergic agonists: spiro[(1,3-diazacyclopent-1-ene)-5,2'-(1',2',3',4'- tetrahydronaphthalene)].
AID197169Hypertensive activity (increase in arterial pressure to 60 mmHg)) after i.v. administration to pithed rats.1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Quantitative relationships between alpha-adrenergic activity and binding affinity of alpha-adrenoceptor agonists and antagonists.
AID36372Binding affinity towards Alpha-2B adrenergic receptor in neonatal rat lung using [3H]-RX-821002 as radioligand1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Design, synthesis, and structure-activity relationships of a new series of alpha-adrenergic agonists: spiro[(1,3-diazacyclopent-1-ene)-5,2'-(1',2',3',4'- tetrahydronaphthalene)].
AID24217Apparent partion coefficient of compound was evaluated in octanol/buffer at pH of 7.4 at 37 degree Centigrade1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Quantitative relationships between alpha-adrenergic activity and binding affinity of alpha-adrenoceptor agonists and antagonists.
AID60966Effective Concentration compound in isolated canine femoral artery1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
(S)-spiro[(1,3-diazacyclopent-1-ene)-5,2'-(7'-methyl-1',2',3',4'- tetrahydronaphthalene)]: resolution, stereospecific synthesis, and preliminary pharmacological characterization as a partial alpha-adrenergic agonist.
AID60980Maximum contractile response expressed as percentage (mean) of the maximal contraction to KCl (100 nM) in the isolated saphenous vein1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
(S)-spiro[(1,3-diazacyclopent-1-ene)-5,2'-(7'-methyl-1',2',3',4'- tetrahydronaphthalene)]: resolution, stereospecific synthesis, and preliminary pharmacological characterization as a partial alpha-adrenergic agonist.
AID231663C20 ratio was determined in the presence or absence of 0.1 mg of prazosin for the compound which are indicative of the contribution of alpha-1 adnergic mechanisms to the pressor response1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
(S)-spiro[(1,3-diazacyclopent-1-ene)-5,2'-(7'-methyl-1',2',3',4'- tetrahydronaphthalene)]: resolution, stereospecific synthesis, and preliminary pharmacological characterization as a partial alpha-adrenergic agonist.
AID35944Binding affinity towards Alpha-2A adrenergic receptor in human platelets using [3H]RX-821002 as radioligand1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Design, synthesis, and structure-activity relationships of a new series of alpha-adrenergic agonists: spiro[(1,3-diazacyclopent-1-ene)-5,2'-(1',2',3',4'- tetrahydronaphthalene)].
AID36795Binding affinity against alpha-2 adrenergic receptor is the ability to inhibit the specific [3H]clonidine binding (0.4 nM) to rat isolated brain membranes by 50% was reported.1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Quantitative relationships between alpha-adrenergic activity and binding affinity of alpha-adrenoceptor agonists and antagonists.
AID232350Ratio of C20 obtained in the absence or presence of [C20 (1 mg of yohimbine.) / C20 (control)]1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Design, synthesis, and structure-activity relationships of a new series of alpha-adrenergic agonists: spiro[(1,3-diazacyclopent-1-ene)-5,2'-(1',2',3',4'- tetrahydronaphthalene)].
AID59111Effective concentration for the agonist in the isolated blood vessel using in vitro femoral artery1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Design, synthesis, and structure-activity relationships of a new series of alpha-adrenergic agonists: spiro[(1,3-diazacyclopent-1-ene)-5,2'-(1',2',3',4'- tetrahydronaphthalene)].
AID1345920Rat alpha1D-adrenoceptor (Adrenoceptors)1994Molecular pharmacology, Nov, Volume: 46, Issue:5
Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (65)

TimeframeStudies, This Drug (%)All Drugs %
pre-199038 (58.46)18.7374
1990's26 (40.00)18.2507
2000's1 (1.54)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]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.49%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other66 (98.51%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]