Page last updated: 2024-12-10

denopamine

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

Description

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

Cross-References

ID SourceID
PubMed CID5311064
CHEMBL ID493682
CHEBI ID135359
SCHEMBL ID218640
MeSH IDM0112982

Synonyms (51)

Synonym
gtpl534
ta-064 ,
kalgut
kalgut (tn)
denopamine (jan/inn)
D02614
71771-90-9
r(-)-denopamine, >=98% (hplc), powder
4-[(1r)-2-[2-(3,4-dimethoxyphenyl)ethylamino]-1-hydroxy-ethyl]phenol
denopamina [spanish]
benzenemethanol, alpha-(((2-(3,4-dimethoxyphenyl)ethyl)amino)methyl)-4-hydroxy-, (r)-
denopamine [inn:jan]
(-)-(r)-alpha-(((3,4-dimethoxyphenethyl)amino)methyl)-p-hydroxybenzyl alcohol
ta 064
denopaminum [latin]
(-)-(r)-1-(p-hydroxyphenyl)-2-((3,4-dimethoxyphenethyl)amino)ethanol
lopac-d-7815
NCGC00015367-01
denopamine
NCGC00094384-01
r(-)-denopamine
CHEBI:135359
bdbm50252956
CHEMBL493682 ,
4-[(1r)-2-[2-(3,4-dimethoxyphenyl)ethylamino]-1-hydroxyethyl]phenol
tox21_111272
dtxsid8045800 ,
cas-71771-90-9
dtxcid6025800
v5f60upd8p ,
denopamina
unii-v5f60upd8p
denopaminum
(-)-(r)-.alpha.-(((3,4-dimethoxyphenethyl)amino)methyl)-p-hydroxybenzyl alcohol
denopamine [mart.]
denopamine [jan]
denopamine [inn]
denopamine [mi]
denopamine [who-dd]
benzenemethanol, a-[[[2-(3,4-dimethoxyphenyl)ethyl]amino]methyl]-4-hydroxy-,(ar)-
SCHEMBL218640
4-[(1r)-2-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-1-hydroxyethyl]phenol
AKOS030574096
(r)-4-(2-(3,4-dimethoxyphenethylamino)-1-hydroxyethyl)phenol
BCP17423
(r)-(-)-denopamine
MS-24686
HY-119515
dimethoxyphenyl)ethylamino]-1-hydroxyethyl]phenol
4-[(1r)-2-[2-(3,4-
CS-0068617

Research Excerpts

Overview

Denopamine is an orally active beta 1 agonist whose cardiovascular action in the newborn is unknown. Denopamine may prove to be an additional therapeutic agent in the management of severe variant angina.

ExcerptReferenceRelevance
"Denopamine is a new, orally active, positive inotropic agent. "( [Clinical effects of denopamine in patients with cardiac operations].
Itoh, T; Kikuchi, S; Mohri, H; Sekino, Y; Suzuki, Y; Tabayashi, K, 1989
)
2.04
"Denopamine is an orally active beta 1 agonist whose cardiovascular action in the newborn is unknown. "( Circulatory effects of denopamine in newborn piglets.
Coe, JY; Olley, PM; Tomita, H, 1992
)
2.04
"Denopamine may prove to be an additional therapeutic agent in the management of severe variant angina."( Refractory variant angina relieved by denopamine--a case report.
Hara, A; Lee, JD; Nakamura, T; Ogawa, KB; Shimizu, H; Sugiyama, T; Yamamoto, M, 1991
)
1.27
"Denopamine (DP) is a new, orally active, selectively positive inotropic agent and used for the treatment of chronic cardiac insufficiency. "( [Development of a simple analytical method to determine the serum concentration of denopamine by high performance liquid chromatography with electrochemical detection and its clinical application].
Higuchi, K; Morikawa, N; Nakano, M; Terada, H; Tsukamoto, T, 1989
)
1.94
"Denopamine is a new orally active cardiotonic agent. "( Studies on the affinity and selectivity of denopamine (TA-064), a new cardiotonic agent, for beta-adrenergic receptors.
Harigaya, S; Nagao, T; Naito, K; Nakajima, H; Otsuka, M, 1985
)
1.97

Effects

ExcerptReferenceRelevance
"Denopamine has been regarded as a selective beta 1-adrenergic agonist."( [Denopamine responsive pulmonary hypertension in a patient with collagen disease].
Hanawa, N; Inokuma, S; Kashiwado, T; Yamada, H, 1989
)
1.91

Actions

Denopamine did not inhibit c-AMP phosphodiesterase of guinea-pig cardiac muscle. Denopamine produced an increase in LV dp/dtmax by 90% at a rate of 4 micrograms/kg/min.

ExcerptReferenceRelevance
"Denopamine did not inhibit c-AMP phosphodiesterase of both particulate and supernatant fractions of guinea-pig cardiac muscle."( Beta 1-adrenergic selectivity of the new cardiotonic agent denopamine in its stimulating effects on adenylate cyclase.
Ikeo, T; Inamasu, M; Nagao, T; Takeyama, S; Totsuka, T, 1987
)
1.24
"Denopamine produced an increase in LV dp/dtmax by 90% at a rate of 4 micrograms/kg/min with slightly increasing systemic blood pressure and heart rate."( Cardiovascular effects and plasma levels of denopamine (TA-064), a new positive inotropic agent, in chronically instrumented dogs.
Ikeo, T; Nagao, T; Nakajima, H; Suzuki, T; Yabana, H, 1985
)
1.25

Treatment

ExcerptReferenceRelevance
"Denopamine treatment lowered plasma levels of noradrenaline and dopamine (P < 0.05), but affected neither the cardiac contractility nor the beta-adrenoceptor density."( Prolongation of the life span of cardiomyopathic hamster by the adrenergic beta 1-selective partial agonist denopamine.
Doi, H; Itogawa, E; Kaburaki, M; Kurosawa, H; Narita, H; Okamoto, M; Yabana, H, 1996
)
1.23

Pharmacokinetics

ExcerptReferenceRelevance
" Tmax was the only pharmacokinetical parameter that differed significantly between healthy volunteers and hemodialysis patients."( Pharmacokinetics of denopamine in hemodialysis patients.
Fujita, Y; Izumi, M; Kamada, T; Nakahama, H; Orita, Y; Shirai, D; Tanaka, Y; Wada, A, 1991
)
0.6

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Moreover, these agonists caused a shift of the dose-response curve for phenylephrine to the right in a parallel fashion in non-preconstricted preparations."( Vascular alpha-1 antagonistic and agonistic effects of beta adrenoceptor agonists in rabbit common carotid arteries.
Chiba, S; Fujiwara, T, 1992
)
0.28
" It is suggested that denopamine can be administered to hemodialysis both on hemodialysis days and on interdialysis days without dosage adjustments."( Pharmacokinetics of denopamine in hemodialysis patients.
Fujita, Y; Izumi, M; Kamada, T; Nakahama, H; Orita, Y; Shirai, D; Tanaka, Y; Wada, A, 1991
)
0.92
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
dimethoxybenzeneAny methoxybenzene that consists of a benzene skeleton substituted with two methoxy groups and its derivatives.
[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 (27)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
NFKB1 protein, partialHomo sapiens (human)Potency0.17780.02827.055915.8489AID895; AID928
TDP1 proteinHomo sapiens (human)Potency33.49830.000811.382244.6684AID686978
hypoxia-inducible factor 1, alpha subunit (basic helix-loop-helix transcription factor)Homo sapiens (human)Potency2.51190.00137.762544.6684AID914; AID915
thyroid stimulating hormone receptorHomo sapiens (human)Potency31.62280.001318.074339.8107AID926; AID938
aryl hydrocarbon receptorHomo sapiens (human)Potency23.71010.000723.06741,258.9301AID743085
nuclear receptor subfamily 1, group I, member 2Rattus norvegicus (Norway rat)Potency35.48130.10009.191631.6228AID1346983
potassium voltage-gated channel subfamily H member 2 isoform dHomo sapiens (human)Potency1.41250.01789.637444.6684AID588834
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency25.11890.031610.279239.8107AID884; AID885
muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)Potency7.99600.00106.000935.4813AID943; AID944
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier family 22 member 1 Homo sapiens (human)IC50 (µMol)46.90000.21005.553710.0000AID386625
5-hydroxytryptamine receptor 7Cavia porcellus (domestic guinea pig)IC50 (µMol)46.90002.03005.53139.9000AID386625
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (29)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processSolute carrier family 22 member 1 Homo sapiens (human)
neurotransmitter transportSolute carrier family 22 member 1 Homo sapiens (human)
serotonin transportSolute carrier family 22 member 1 Homo sapiens (human)
establishment or maintenance of transmembrane electrochemical gradientSolute carrier family 22 member 1 Homo sapiens (human)
organic cation transportSolute carrier family 22 member 1 Homo sapiens (human)
quaternary ammonium group transportSolute carrier family 22 member 1 Homo sapiens (human)
prostaglandin transportSolute carrier family 22 member 1 Homo sapiens (human)
monoamine transportSolute carrier family 22 member 1 Homo sapiens (human)
putrescine transportSolute carrier family 22 member 1 Homo sapiens (human)
spermidine transportSolute carrier family 22 member 1 Homo sapiens (human)
acetylcholine transportSolute carrier family 22 member 1 Homo sapiens (human)
dopamine transportSolute carrier family 22 member 1 Homo sapiens (human)
norepinephrine transportSolute carrier family 22 member 1 Homo sapiens (human)
thiamine transportSolute carrier family 22 member 1 Homo sapiens (human)
xenobiotic transportSolute carrier family 22 member 1 Homo sapiens (human)
epinephrine transportSolute carrier family 22 member 1 Homo sapiens (human)
serotonin uptakeSolute carrier family 22 member 1 Homo sapiens (human)
norepinephrine uptakeSolute carrier family 22 member 1 Homo sapiens (human)
thiamine transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
metanephric proximal tubule developmentSolute carrier family 22 member 1 Homo sapiens (human)
purine-containing compound transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
dopamine uptakeSolute carrier family 22 member 1 Homo sapiens (human)
monoatomic cation transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
transport across blood-brain barrierSolute carrier family 22 member 1 Homo sapiens (human)
(R)-carnitine transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
acyl carnitine transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
spermidine transmembrane transportSolute carrier family 22 member 1 Homo sapiens (human)
cellular detoxificationSolute carrier family 22 member 1 Homo sapiens (human)
xenobiotic transport across blood-brain barrierSolute carrier family 22 member 1 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (19)

Processvia Protein(s)Taxonomy
acetylcholine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
neurotransmitter transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
dopamine:sodium symporter activitySolute carrier family 22 member 1 Homo sapiens (human)
norepinephrine:sodium symporter activitySolute carrier family 22 member 1 Homo sapiens (human)
protein bindingSolute carrier family 22 member 1 Homo sapiens (human)
monoamine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
secondary active organic cation transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
organic anion transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
organic cation transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
prostaglandin transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
pyrimidine nucleoside transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
thiamine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
putrescine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
spermidine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
quaternary ammonium group transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
toxin transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
identical protein bindingSolute carrier family 22 member 1 Homo sapiens (human)
xenobiotic transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
(R)-carnitine transmembrane transporter activitySolute carrier family 22 member 1 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
basal plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
membraneSolute carrier family 22 member 1 Homo sapiens (human)
basolateral plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
apical plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
lateral plasma membraneSolute carrier family 22 member 1 Homo sapiens (human)
presynapseSolute carrier family 22 member 1 Homo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID386623Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1.
AID521208Antiproliferative activity against mouse neural precursor cells by MTT assay2007Nature chemical biology, May, Volume: 3, Issue:5
Chemical genetics reveals a complex functional ground state of neural stem cells.
AID521220Inhibition of neurosphere proliferation of mouse neural precursor cells by MTT assay2007Nature chemical biology, May, Volume: 3, Issue:5
Chemical genetics reveals a complex functional ground state of neural stem cells.
AID386625Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells by confocal microscopy2008Journal of medicinal chemistry, Oct-09, Volume: 51, Issue:19
Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1.
AID521209Antiproliferative activity against mouse astrocyte cells by MTT assay2007Nature chemical biology, May, Volume: 3, Issue:5
Chemical genetics reveals a complex functional ground state of neural stem cells.
AID1346260Human beta1-adrenoceptor (Adrenoceptors)1999Molecular pharmacology, Nov, Volume: 56, Issue:5
Binding pockets of the beta(1)- and beta(2)-adrenergic receptors for subtype-selective agonists.
AID1346260Human beta1-adrenoceptor (Adrenoceptors)1993The Journal of pharmacology and experimental therapeutics, Nov, Volume: 267, Issue:2
Cellular characterization of the pharmacological selectivity and tachyphylactic properties of denopamine for the human beta adrenergic receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (112)

TimeframeStudies, This Drug (%)All Drugs %
pre-199043 (38.39)18.7374
1990's47 (41.96)18.2507
2000's13 (11.61)29.6817
2010's7 (6.25)24.3611
2020's2 (1.79)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.29

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 Index25.29 (24.57)
Research Supply Index4.84 (2.92)
Research Growth Index4.35 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.29)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (5.88%)5.53%
Reviews2 (1.68%)6.00%
Case Studies5 (4.20%)4.05%
Observational0 (0.00%)0.25%
Other105 (88.24%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]