Page last updated: 2024-11-06

epanolol

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

Description

epanolol: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72014
CHEMBL ID87697
CHEBI ID4800
SCHEMBL ID78863
MeSH IDM0116143

Synonyms (35)

Synonym
chebi:4800 ,
CHEMBL87697
visacor
ici-141292
D06646
epanolol (usan/inn)
epanolol
86880-51-5
ici 141,292
ici 141292
(+-)-n-(2-((3-(o-cyanophenoxy)-2-hydroxypropyl)amino)ethyl)-2-(p-hydroxyphenyl)acetamide
epanololum [latin]
benzeneacetamide, n-(2-((3-(2-cyanophenoxy)-2-hydroxypropyl)amino)ethyl)-4-hydroxy-
n-[2-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]ethyl]-2-(4-hydroxyphenyl)acetamide
FT-0667874
epanolol [usan:inn:ban]
9kgc55kp6a ,
epanololum
unii-9kgc55kp6a
epanolol [usan]
epanolol [who-dd]
epanolol [mi]
epanolol [inn]
(+/-)-n-(2-((3-(o-cyanophenoxy)-2-hydroxypropyl)amino)ethyl)-2-(p-hydroxyphenyl)acetamide
epanolol [mart.]
SCHEMBL78863
n-[2-[[3-(2-cyanophenoxy)-2-hydroxy-propyl]amino]ethyl]-2-(4-hydroxyphenyl)acetamide
ici141292
CS-7257
HY-U00183
Q4859855
DB13757
visacor;ici141292
DTXSID90868959
AKOS040733417

Research Excerpts

Overview

Espanolol is a beta 1-selective partial agonist with minor effects on blood pressure and heart rate at rest. It has been shown useful in angina pectoris, but its value in patients with left ventricular (LV) dysfunction and CHF is unknown.

ExcerptReferenceRelevance
"Epanolol is a selective beta1-blocker with intrinsic sympathomimetic activity, which has been shown useful in angina pectoris, but its value in patients with left ventricular (LV) dysfunction and CHF is unknown."( Effects of epanolol, a selective beta1-blocker with intrinsic sympathomimetic activity, in patients with ischemic left ventricular dysfunction.
Bartels, GL; Kruijssen, DA; Remme, WJ; Van Den Heuvel, AF; van der Ent, M; van Veldhuisen, DJ, 1998
)
1.41
"Epanolol is a beta 1-selective partial agonist with minor effects on blood pressure and heart rate at rest."( The effects of beta blockade with (epanolol) and without (atenolol) intrinsic sympathomimetic activity in stable angina pectoris. The Visacor Study Group.
Boberg, J; Larsen, FF; Pehrsson, SK, 1992
)
1.28
"1. Epanolol is a novel anti-anginal agent which is a beta 1-adrenoceptor partial agonist exhibiting selective beta 1-adrenoceptor antagonist and selective beta 1-adrenoceptor agonist activity. "( Pharmacokinetics of epanolol after acute and chronic oral dosing in elderly patients with stable angina pectoris.
Cockshott, ID; Hosie, J; Petrie, JC; Scott, AK, 1990
)
1.22
"Epanolol is a new once-daily agent for the treatment of angina pectoris. "( Epanolol. A new once-daily antianginal agent: dose finding and long term efficacy.
Akhras, F; Jackson, G, 1989
)
3.16
"Epanolol is a beta-adrenoceptor antagonist with partial agonist activity, a property which could be useful in reducing the fatigue associated with beta blockers. "( The influence of beta-adrenoceptor antagonists with and without partial agonist activity on exercise tolerance and muscle lactate production.
Borland, WW; Curzio, J; Farish, E; Lees, KR; Rubin, PC, 1987
)
1.72

Effects

Ethanol is a selective beta-adrenoceptor partial agonist with agonist activity about 20 to 25% of that of the full agonist isoprenaline. Epanolol has a favourable safety profile, which compares well with those for placebo and for active antianginal therapies.

ExcerptReferenceRelevance
"Epanolol has a favourable safety profile, which compares well with those for placebo and for active antianginal therapies."( An overview of clinical trial experience with epanolol.
Blake, P, 1989
)
1.26
"Epanolol has been shown in animal models to be a selective beta-adrenoceptor partial agonist with agonist activity about 20 to 25% of that of the full agonist isoprenaline. "( Clinical pharmacology of epanolol. Pharmacodynamic aspects.
Harry, JD, 1989
)
2.02
"Epanolol has a favourable safety profile, which compares well with those for placebo and for active antianginal therapies."( An overview of clinical trial experience with epanolol.
Blake, P, 1989
)
1.26

Treatment

ExcerptReferenceRelevance
"3. Epanolol treatment at this dose was not associated with significant reduction in systolic or diastolic 24 h IABP or heart rate."( The effect of epanolol on intra-arterial ambulatory blood pressure and baroreceptor heart rate reflex in essential hypertension.
Littler, WA; Smith, SA, 1988
)
1.15

Toxicity

ExcerptReferenceRelevance
" It improved the side effect profile in some but not all patients."( Effect of partial agonist activity on the side effects of beta-blockade in patients with chronic stable angina.
Adam, G; Akhras, F; Chambers, J; Jackson, G; Ong, ML, 1989
)
0.28

Pharmacokinetics

The possibility of a pharmacokinetic and/or pharmacodynamic interaction between epanolol and digoxin has been investigated in 10 healthy male subjects taking digoxin 0. Epanolol plasma concentrations declined biexponentially with time after an intravenous dose.

ExcerptReferenceRelevance
" Plasma concentrations declined biphasically with a mean terminal phase half-life of 17 h and 5 fold inter-individual variation."( Pharmacokinetics of epanolol after acute and chronic oral dosing in elderly patients with stable angina pectoris.
Cockshott, ID; Hosie, J; Petrie, JC; Scott, AK, 1990
)
0.6
"The pharmacokinetic profile of a single dose of 100 mg of (+/-)-N-[2-[[3-(o-cyanophenoxy)-2-hydroxypropyl]amino]ethyl]- 2-(p-hydroxyphenyl) acetamide (epanolol, Visacor), has been determined in an open study of 15 elderly patients with stable angina pectoris."( Pharmacokinetics of epanolol in elderly patients with stable angina pectoris.
Cockshott, ID; Marlier, R; McAinsh, J, 1990
)
0.8
" There was wide inter-individual variability in peak plasma ICI 141,292 concentrations (Cmax) but no significant difference was found between mean Cmax after a single dose (44."( ICI 141,292 (epanolol)--pharmacokinetics after single and repeated oral administration in the elderly with moderate renal impairment.
Ankier, SI; Cockshott, ID; Crome, P; Laher, MS; Rakhra, GS, 1990
)
0.65
" Epanolol plasma concentrations declined biexponentially with time after an intravenous dose, with a half-life of 7 minutes for the first phase and about 3 hours for the second."( Pharmacokinetics of epanolol (ICI 141,292) in healthy young volunteers and comparative data in elderly patients with angina and subjects with renal or hepatic impairment.
Cockshott, ID, 1989
)
1.51
" The pharmacodynamic consequences in man of the degree of agonist activity possessed by the beta 1-selective partial agonist epanolol include little reductions at rest in heart rate, blood pressure, various measures of cardiac haemodynamic parameters, peripheral blood flow and renal function."( Clinical pharmacology of epanolol. Pharmacodynamic aspects.
Harry, JD, 1989
)
0.79

Bioavailability

ExcerptReferenceRelevance
" The bioavailability of epanolol for the tablet and solution administered to fasted volunteers was similar (7-8%), but it was about 25% lower when administered as a tablet with food."( Pharmacokinetics of epanolol (ICI 141,292) in healthy young volunteers and comparative data in elderly patients with angina and subjects with renal or hepatic impairment.
Cockshott, ID, 1989
)
0.91
" The systemic bioavailability of ICI 141,292 was only about 40%."( Absolute bioavailability study in the dog with Visacor, a new cardioselective beta blocking drug with intrinsic sympathomimetic activity.
Ferguson, RA; McAinsh, J; Smith, RP,
)
0.13
"The quantitative structure-bioavailability relationship of 232 structurally diverse drugs was studied to evaluate the feasibility of constructing a predictive model for the human oral bioavailability of prospective new medicinal agents."( QSAR model for drug human oral bioavailability.
Topliss, JG; Yoshida, F, 2000
)
0.31

Dosage Studied

ExcerptRelevanceReference
"A single oral dosage of 100, 200 or 300 mg Epanolol or placebo was administered in a randomized double-blind, cross-over fashion to 12 patients with stable effort angina."( Effects of a single oral administration of Epanolol on exercise tolerance in patients with stable effort angina pectoris.
De Geest, H; Piessens, J; Vandenbosch, H, 1991
)
0.81
"2 h on acute and chronic dosing respectively."( Pharmacokinetics of epanolol after acute and chronic oral dosing in elderly patients with stable angina pectoris.
Cockshott, ID; Hosie, J; Petrie, JC; Scott, AK, 1990
)
0.6
" Venous blood samples were collected pre-dose and at various times after dosing and the concentrations of ICI 141,292 in the plasma were determined by radioimmunoassay."( Pharmacokinetic and pharmacodynamic studies in man with an antianginal agent 'Visacor'.
Cockshott, ID; McAinsh, J; Norris, S, 1990
)
0.28
" Dose-response curves were constructed for the changes in heart rate, finger tremor, blood pressure and forearm blood flow produced by each infusion."( Effects of ICI 141,292 on exercise tachycardia and isoprenaline-induced beta-adrenoceptor responses in man.
Finch, MB; McNeill, AJ; O'Connor, PC; Pringle, TH; Riddell, JG; Shanks, RG, 1986
)
0.27
"The cardioselective beta-adrenergic blocking drug Visacor (ICI 141,292) was dosed to six beagle dogs in a randomized cross-over manner."( Absolute bioavailability study in the dog with Visacor, a new cardioselective beta blocking drug with intrinsic sympathomimetic activity.
Ferguson, RA; McAinsh, J; Smith, RP,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
acetamidesCompounds with the general formula RNHC(=O)CH3.
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)244.40000.11007.190310.0000AID1449628
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID27167Delta logD (logD6.5 - logD7.4)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID28681Partition coefficient (logD6.5)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID29359Ionization constant (pKa)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID29811Oral bioavailability in human2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (58)

TimeframeStudies, This Drug (%)All Drugs %
pre-199034 (58.62)18.7374
1990's22 (37.93)18.2507
2000's1 (1.72)29.6817
2010's1 (1.72)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: 23.01

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index23.01 (24.57)
Research Supply Index4.57 (2.92)
Research Growth Index4.25 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.01)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials37 (62.71%)5.53%
Reviews2 (3.39%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (33.90%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]