Page last updated: 2024-12-06

dihydroalprenolol

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

Description

Dihydroalprenolol (DHA) is a synthetic beta-adrenergic receptor antagonist. It is a derivative of alprenolol, with the double bond in the alprenolol molecule reduced. DHA has been used as a research tool to study the role of beta-adrenergic receptors in various physiological processes, including heart rate, blood pressure, and bronchodilation. It has also been investigated for its potential therapeutic use in treating cardiovascular diseases and asthma. DHA's pharmacological properties, including its high affinity for beta-adrenergic receptors and its selectivity for specific subtypes, make it a valuable tool for research. It has been used in studies to elucidate the mechanism of action of beta-blockers and to develop new drugs targeting beta-adrenergic receptors.'

Dihydroalprenolol: Hydrogenated alprenolol derivative where the extra hydrogens are often tritiated. This radiolabeled form of ALPRENOLOL, a beta-adrenergic blocker, is used to label the beta-adrenergic receptor for isolation and study. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID43216
CHEMBL ID1159723
MeSH IDM0006393

Synonyms (25)

Synonym
PDSP2_000152
PDSP1_000153
dihydroalprenolol
2-propanol, 1-((1-methylethyl)amino)-3-(2-propylphenoxy)-
60106-89-0
1-(propan-2-ylamino)-3-(2-propylphenoxy)propan-2-ol
CHEMBL1159723
nsc_43216
cas_43216
bdbm81447
dihydroalprenolol,(+/-)
unii-2zt5710i4t
2zt5710i4t ,
[3h]-dihydroalprenolol
[2-hydroxy-3-(2-propylphenoxy)propyl](propan-2-yl)amine
gtpl5388
[3h]dihydroalprenolol
h-56/56
dihydroalprenolol, (+/-)-
(+/-)-dihydroalprenolol
(2-hydroxy-3-(2-propylphenoxy)propyl)(propan-2-yl)amine
1-((1-methylethyl)amino)-3-(2-propylphenoxy)-2-propanol
Q5276415
1-[(propan-2-yl)amino]-3-(2-propylphenoxy)propan-2-ol
DTXSID40866788

Research Excerpts

Effects

ExcerptReferenceRelevance
"[3H]Dihydroalprenolol ([3H]DHA) has been used extensively in receptor binding studies to measure beta-adrenergic receptors in the central nervous system. "( Comparison of two putatively selective radioligands for labeling central nervous system beta-adrenergic receptors: inadequacy of [3H]dihydroalprenolol.
Creese, I; Riva, MA, 1989
)
1.04

Toxicity

ExcerptReferenceRelevance
"Neurochemical effects of electroconvulsive shock (ECS) in three neurotransmitter-receptor systems were studied in relation to the mechanism of action and adverse effects of ECT."( Electroconvulsive shock and neurotransmitter receptors: implications for mechanism of action and adverse effects of electroconvulsive therapy.
Lerer, B, 1984
)
0.27
" The toxic parameters used were Na(+)-K(+)-adenosine triphosphatase (Na(+)-K(+)-ATPase), a well-known marker enzyme often used as a membrane toxicity model, and 3H-dihydroalprenolol (3H-DHA)-labeled beta-adrenergic receptor binding that has been shown to be vulnerable to solvent-induced changes in membrane fluidity."( Structure-toxicity relationship of monoketones: in vitro effects on beta-adrenergic receptor binding and Na(+)-K(+)-ATPase activity in mouse synaptosomes.
Hashimoto, K; Huang, J; Ohyashiki, T; Tanii, H,
)
0.33

Dosage Studied

ExcerptRelevanceReference
" Dose-response curves to the pressor response of noradrenaline (NA) did not show any differences between control and experimental animals."( Prenatal nicotine exposure induces cardiac adrenergic subsensitivity in adult rats.
Britos, SA; Keller, EA; Orsingher, OA, 1992
)
0.28
" Dose-response curves were constructed both for the autonomic agonists and the histamine-releasing agents."( Characterization of purified dog mastocytoma cells. Autonomic membrane receptors and pharmacologic modulation of histamine release.
Barnes, PJ; Gold, WM; Phillips, MJ, 1985
)
0.27
" In dose-response curves, the isoproterenol-sensitive K+ efflux was half-maximally inhibited (IC50) with 2-5 X 10(-10) M of isoproterenol concentration."( Stimulation of beta-adrenoceptors inhibits calcium-dependent potassium-channels in mouse macrophages.
Braquet, P; Dausse, JP; Garay, R; Hannaert, P; Rosati, C, 1986
)
0.27
" Airway responsiveness was measured by the ability of isoproterenol infusions to shift the histamine dose-response curve for airway constriction."( Differential recovery of beta adrenoreceptor antagonist and agonist high affinity binding sites in the guinea-pig lung after irreversible blockade.
Baker, SP; Muther, TF; Nelson, CA; Pitha, J, 1986
)
0.27
" Maternal weight gain was significantly reduced in a dose-response manner, but litter size and pup weight on postnatal day (PND) 1 were unaffected."( Effect of prenatal imipramine exposure on development of the postnatal rat heart and brain.
Delongchamp, RR; Harmon, JR; Kimmel, GL; Webb, PJ, 1986
)
0.27
" In contrast, the (R)-glycol appeared to act as an irreversible antagonist, producing complex dose-response curves."( Comparative studies with the enantiomers of the glycol metabolite of propranolol and their effects on the cardiac beta-adrenoceptor.
Lyles, GA; Neilson, DG; Ogg, GD; Stevenson, IH, 1987
)
0.27
" Analysis of the NE-cAMP dose-response curve indicates that the stress reduces the maximum cAMP response to NE but does not increase the EC50 value of NE."( Reduction of the cyclic adenosine 3',5'-monophosphate response to catecholamines in rat brain slices after repeated restraint stress.
Platt, JE; Slucky, AV; Stone, EA; Trullas, R, 1985
)
0.27
" Dose-response curves with NE indicate a reduction of the maximal response after T4 treatment with no change in ED50."( Chronic thyroxine treatment of rats down-regulates the noradrenergic cyclic AMP generating system in cerebral cortex.
Schmidt, BH; Schultz, JE, 1985
)
0.27
" The animals were sacrificed 20 hrs after the last drug dosage and the lung membrane homogenates were prepared for 3H-dihydroalprenolol (3H-DHA) binding in vitro."( Concomitant glucocorticoid treatment prevents the development of beta-adrenoceptor desensitization in the guinea pig lung.
Salonen, RO, 1985
)
0.48
" Dose-response curves of isoproterenol revealed a progressive increase in the activation constant (Kact) with advancing age."( Age-related reduction of beta-adrenoceptor sensitivity in rat heart occurs by multiple mechanisms.
Banerjee, SP; Fan, TH, 1985
)
0.27
" Dose-response studies of the effect of epinephrine on adenosine-deaminase or isoproterenol-stimulated fat-cells demonstrate an inhibitory effect of epinephrine on lipolysis promoted by stimulation of alpha 2-adrenoceptors which occurs before the commonly described beta 1-adrenergic effect which promotes stimulation of lipolysis."( Fat cell adrenoceptors: inter- and intraspecific differences and hormone regulation.
Berlan, M; Carpene, C; Lafontan, M, 1985
)
0.27
" In vitro perfusion of rat lungs with AA (3 X 10(-5)M for 20 min) reduced the relaxant effect of isoproterenol (ISO) on lung parenchymal strips, shown by a shift to the right of ISO dose-response curve, similar to that obtained using desensitizing concentration of specific beta-agonist."( Arachidonic acid metabolites induce beta-adrenoceptor desensitization in rat lung in vitro.
Abbracchio, MP; Cattabeni, F; Daffonchio, L; Giani, E; Hernandez, A; Omini, C, 1985
)
0.27
" However, there is a discontinuity in dose-response functions, such that the deficit which emerges with a higher, acutely toxic dose, is qualitatively different from the impairment induced after lower doses."( Increased forebrain beta-adrenergic ligand binding induced by trimethyltin.
Messing, RB; Sparber, SB,
)
0.13
" Maternal weight gained during the dosing period was decreased in a dose-related manner, but there were no dose-related differences in offspring body weights."( Early neurobehavioral and neurochemical alterations in rats prenatally exposed to imipramine.
Ali, SF; Buelke-Sam, J; Newport, GD; Slikker, W, 1986
)
0.27
" The dose-response curves of terbutaline on isolated tracheae of actively sensitized guinea pigs were significantly shifted to the right in comparison with control trachea (ED50 11."( Mechanical and biochemical alterations in guinea-pig tracheae caused by sensitisation.
Beier, W; Feddersen, C; Kaukel, E; Koppermann, G; Schrum, C, 1984
)
0.27
" Dose-response curves revealed that (-)-propranolol was about 100 fold more potent than (+)-propranolol in all tissues examined, and that there was a small (3 fold) degree of selectivity for both isomers towards lung and spleen over heart, cortex and cerebellum."( Disposition and activity of beta-adrenoceptor antagonists in the rat using an ex vivo receptor binding assay.
Nahorski, SR; Sriwatanakul, K, 1980
)
0.26
" The maximum of the dose-response curve to isoprenaline, constructed after incubation with Ro 03-7894 and a 3 hr bath-washout, was depressed by 89."( Comparison of the apparent irreversible beta-adrenoceptor antagonist Ro 03-7894 with propranolol in cardiac ventricular muscle by pharmacological and radioligand binding techniques.
Broadley, KJ; Rankin, A, 1982
)
0.26
" In similarly prepared animals, the dose-response curve for (-)isoprenaline stimulated adenylate cyclase was shifted to the right 3-to-4 fold for mono and disubstituted derivatives but was unaffected by (+/-)alprenolol and the trisubstituted derivative."( Beta-adrenoreceptor antagonists with multiple pharmacophores: persistent inhibition of rat heart adenylate cyclase.
Kusiak, JW; Pitha, J, 1983
)
0.27
" No age differences were seen in the time course of amylase release following (-)-isoproterenol stimulation or in the (-)-isoproterenol dose-response curve."( Beta-adrenergic regulation of rat parotid gland exocrine protein secretion during aging.
Baum, BJ; Ito, H; Roth, GS, 1981
)
0.26
" Dose-response curves for isoproterenol and fluoride in the reconstituted system were similar to those reported for avian erythrocyte and liver membranes, respectively."( Reconstitution of a hormone-sensitive adenylate cyclase with membrane extracts from Neurospora and avian erythrocytes.
FlawiĆ”, MM; Kornblihtt, AR; Reig, JA; Torres, HN; Torruella, M, 1983
)
0.27
"5-1 mg/kg) at a dosage which increased both surfactant synthesis and release did not alter pulmonary receptor concentration."( Glucocorticoids increase pulmonary beta-adrenergic receptors in fetal rabbit.
Ballard, PL; Cheng, JB; Goldfien, A; Roberts, JM, 1980
)
0.26
" The dose-response curves for adrenaline did not correspond to simple mass action kinetics and their computer analysis suggests the presence of both beta 1- and beta 2-adrenergic-sensitive adenylate cyclase (58 plus or minus 17% and 42 plus or minus 17% respectively)."( Characteristics of the beta 1-and beta 2-adrenergic-sensitive adenylate cyclases in glial cell primary cultures and their comparison with beta 2-adrenergic-sensitive adenylate cyclase of meningeal cells.
Bockaert, J; Ebersolt, C; Perez, M; Vassent, G, 1981
)
0.26
" The catecholamine analogue dose-response curves were shifted to the right."( Impaired metabolic response to nerve stimulation in brown adipose tissue of hypothyroid rats.
Giacobino, JP; Girardier, L; Seydoux, J, 1982
)
0.26
" Cyclic AMP accumulation was stimulated by norepinephrine in cells from both groups of animals, although the dose-response curve for cells from cold-acclimated animals was shifted to the right and the maximum value obtained was less than half that found in cells from control animals."( Desensitisation of beta-adrenergic responsiveness in vivo. Decreased coupling between receptors and adenylate cyclase in isolated brown-fat cells.
Cannon, B; Svartengren, J; Svoboda, P, 1982
)
0.26
" For both tissue regions fasting induced a right-ward shift in the dose-response curve for the inhibitory effect of the alpha 2 agonist, clonidine, on theophylline-induced lipolysis, corresponding to a 10-fold decrease in sensitivity."( Influence of fasting on lipolytic response to adrenergic agonists and on adrenergic receptors in subcutaneous adipocytes.
Arner, P; Engfeldt, P; Kimura, H; Ostman, J; Wahrenberg, H, 1984
)
0.27
" The dose-response curve for forskolin was shifted to the right in hypothyroid animals fed the n-3 diet indicating a decrease in sensitivity."( Thyroid status and dietary fatty acids affect beta-adrenoceptor agonist stimulation of tension development in rat myocardium.
Awumey, EM; Paton, DM; Pehowich, DJ, 1995
)
0.29
" Dose-response curves to isoproterenol (10(-9)-10(-8) M) and phenylephrine (10(-9)-10(-6) M) were also obtained."( Ricin depresses cardiac function in the rabbit heart.
Hsu, CH; Ma, L; Patterson, E; Robinson, CP; Thadani, U, 1996
)
0.29
" The dose-response curves of ternary complex formation revealed maximal assembly for ligands previously classified as full agonists and reduced assembly for ligands previously classified as partial agonists."( Real-time analysis of ternary complex on particles: direct evidence for partial agonism at the agonist-receptor-G protein complex assembly step of signal transduction.
Biggs, SM; Cimino, DF; Foutz, T; Guo, Q; Neubig, RR; Prossnitz, ER; Simons, PC; Sklar, LA; Tang, WJ; Waller, A, 2004
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Beta-2 adrenergic receptor Bos taurus (cattle)Kd0.00060.00061.47759.1200AID40694
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Processvia Protein(s)Taxonomy
receptor-mediated endocytosisBeta-2 adrenergic receptor Bos taurus (cattle)
regulation of smooth muscle contractionBeta-2 adrenergic receptor Bos taurus (cattle)
positive regulation of MAPK cascadeBeta-2 adrenergic receptor Bos taurus (cattle)
negative regulation of G protein-coupled receptor signaling pathwayBeta-2 adrenergic receptor Bos taurus (cattle)
adenylate cyclase-activating adrenergic receptor signaling pathwayBeta-2 adrenergic receptor Bos taurus (cattle)
positive regulation of autophagosome maturationBeta-2 adrenergic receptor Bos taurus (cattle)
positive regulation of lipophagyBeta-2 adrenergic receptor Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
beta2-adrenergic receptor activityBeta-2 adrenergic receptor Bos taurus (cattle)
protein homodimerization activityBeta-2 adrenergic receptor Bos taurus (cattle)
norepinephrine bindingBeta-2 adrenergic receptor Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
early endosomeBeta-2 adrenergic receptor Bos taurus (cattle)
Golgi apparatusBeta-2 adrenergic receptor Bos taurus (cattle)
receptor complexBeta-2 adrenergic receptor Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID218848Change in Gibb's free energy at Low affinity beta-2-adrenoceptor in the Chang living cells1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Mapping of the beta 2-adrenoceptor on Chang liver cells. Differences between high- and low-affinity receptor states.
AID1135590Antagonist activity at beta adrenergic receptor in frog erythrocyte membrane assessed as inhibition of (-)-isoproterenol-stimulated adenylate cyclase activity measured as [32P]-cAMP level1977Journal of medicinal chemistry, Aug, Volume: 20, Issue:8
Structure and biological activity of (-)-[3H]dihydroalprenolol, a radioligand for studies of beta-adrenergic receptors.
AID218845Change in Gibb's free energy at Low affinity beta-2-adrenoceptor in the membranes of bovine skeletal muscle preparation1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Mapping of the beta 2-adrenoceptor on Chang liver cells. Differences between high- and low-affinity receptor states.
AID40694Affinity for cow beta-2 adrenergic receptor by measuring displacement (-)-[3H]dihydroalprenolol (DHA)1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Quantitative evaluation of the beta 2-adrenoceptor affinity of phenoxypropanolamines and phenylethanolamines.
AID40686Affinity for cow beta-2 adrenergic receptor by measuring displacement (-)-[3H]dihydroalprenolol (DHA)1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
Quantitative evaluation of the beta 2-adrenoceptor affinity of phenoxypropanolamines and phenylethanolamines.
AID1135589Displacement of (-)-[3H]dihydroalprenolol from beta adrenergic receptor in frog erythrocyte membrane after 10 mins by liquid scintillation counting analysis1977Journal of medicinal chemistry, Aug, Volume: 20, Issue:8
Structure and biological activity of (-)-[3H]dihydroalprenolol, a radioligand for studies of beta-adrenergic receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,181)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990956 (80.95)18.7374
1990's180 (15.24)18.2507
2000's37 (3.13)29.6817
2010's7 (0.59)24.3611
2020's1 (0.08)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.94

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 Index11.94 (24.57)
Research Supply Index7.13 (2.92)
Research Growth Index3.88 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (11.94)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (0.16%)5.53%
Reviews18 (1.45%)6.00%
Case Studies1 (0.08%)4.05%
Observational0 (0.00%)0.25%
Other1,219 (98.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]