Page last updated: 2024-12-06

carazolol

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

Description

Carazolol is a non-selective beta blocker that is used to treat hypertension. It is synthesized through a multi-step process involving the reaction of 1-indanone with 2-chloro-4-nitroaniline to form a key intermediate. This intermediate is then subjected to various chemical transformations to obtain the final compound. Carazolol exerts its effects by blocking the beta receptors in the heart, which leads to a decrease in heart rate and blood pressure. Its importance lies in its ability to control hypertension, a major risk factor for cardiovascular disease. Carazolol is studied to understand its mechanisms of action, pharmacological properties, and potential therapeutic applications in various cardiovascular conditions. It has been investigated for its potential role in treating angina, heart failure, and arrhythmias.'

carazolol: RN given refers to parent cpd without isomeric designation; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID71739
CHEMBL ID324665
CHEBI ID135261
SCHEMBL ID77901
SCHEMBL ID77902
MeSH IDM0062870

Synonyms (63)

Synonym
LS-14657
gtpl569
conducton
carazololum [inn-latin]
4-(2-hydroxy-3-isopropylamino-propoxy)-carbazole
2-propanol, 1-(9h-carbazol-4-yloxy)-3-((1-methylethyl)amino)-
1-(9h-carbazol-4-yloxy-3-((1-methylethyl)amino)-2-propanol)
suacron
ccris 1047
1-(4-carbazolyloxy)-3-isopropylamino-2-propanol
brn 3620576
carazolol [inn:ban]
einecs 260-945-1
bm 51052
1-(carbazol-4-yloxy)-3-(isopropylamino)-2-propanol
57775-29-8
carazolol (inn)
suacron [veterinary] (tn)
D07608
conducton (tn)
carazolol
CHEBI:135261
L000159
1-(9h-carbazol-4-yloxy)-3-(isopropylamino)propan-2-ol
CHEMBL324665 ,
bm-51052
1-(9h-carbazol-4-yloxy)-3-(propan-2-ylamino)propan-2-ol
1-(9h-carbazol-4-yloxy)-3-isopropylamino-propan-2-ol
1-(9h-carbazol-4-yloxy)-3-isopropylamino-propan-2-ol(carazolol)
bdbm50027663
corazolol
1-((9h-carbazol-4-yl)oxy)-3-(isopropylamino)propan-2-ol
A831600
carazololum
29pw75s82a ,
unii-29pw75s82a
FT-0601602
S6447
SCHEMBL77901
SCHEMBL77902
MLS006010892
smr002529709
C2578
1-(9h-carbazol-4-yloxy)-3-(isopropylamino)-2-propanol
carazolol [inn]
carazolol [mi]
carazolol [who-dd]
carazolol [mart.]
2-propanol, 1-(9h-carbazol-4-yloxy)-3-[(1-methylethyl)amino]-
1-(9h-carbazol-4-yloxy)-3-(isopropylamino)-2-propanol #
BQXQGZPYHWWCEB-UHFFFAOYSA-N
AKOS027320502
carazolol, analytical standard
(isopropylamino)propan-2-ol
Q5037818
nnnn-tetraethylisophthalamide
carazolol 100 microg/ml in acetonitrile
T71087
DTXSID00866648
SB66991
CS-0028150
HY-107327
carazolol 1000 microg/ml in acetonitrile

Research Excerpts

Overview

Carazolol is a beta1/beta2 adrenoceptor antagonist of high potency. Used to improve meat quality by reducing animal stress and skeletal muscle (SM) proteolysis.

ExcerptReferenceRelevance
"Carazolol is a beta1/beta2 adrenoceptor antagonist of high potency used in the treatment of hypertension. "( Carazolol: a potent, selective beta 3-adrenoceptor agonist.
Guillaume, JL; Méjean, A; Strosberg, AD, 1995
)
3.18
"Carazolol (CZL) is a known agonist of β3 and antagonist of β1 and β2 adrenoceptors (AR), used in the animal production industry to improve meat quality by reducing animal stress and skeletal muscle (SM) proteolysis. "( Intracellular effect of β3-adrenoceptor agonist Carazolol on skeletal muscle, a direct interaction with SERCA.
Alvarez, R; Ortega, A; Quiroz, E; Ramirez-Soto, I; Rodriguez, E, 2019
)
2.21
"Carazolol is a promising high-affinity beta-adrenergic receptor ligand for the noninvasive determination of beta receptor status using PET. "( Specific beta-adrenergic receptor binding of carazolol measured with PET.
Berridge, MS; Leisure, GP; Miraldi, F; Nelson, AD; Zheng, L, 1994
)
1.99
"Carazolol is a high affinity beta-adrenergic receptor antagonist which is relatively non-specific for the receptor subtypes. "( Preparation and in vivo binding of [11C]carazolol, a radiotracer for the beta-adrenergic receptor.
Berridge, MS; Cassidy, EH; Terris, AH; Vesselle, JM, 1992
)
1.99
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
carbazoles
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Beta-2 adrenergic receptorHomo sapiens (human)Ki0.00010.00000.66359.5499AID1598554; AID389416
Beta-1 adrenergic receptorMus musculus (house mouse)Ki0.00010.00010.13100.5500AID1598553
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (32)

Processvia Protein(s)Taxonomy
diet induced thermogenesisBeta-2 adrenergic receptorHomo sapiens (human)
regulation of sodium ion transportBeta-2 adrenergic receptorHomo sapiens (human)
transcription by RNA polymerase IIBeta-2 adrenergic receptorHomo sapiens (human)
receptor-mediated endocytosisBeta-2 adrenergic receptorHomo sapiens (human)
smooth muscle contractionBeta-2 adrenergic receptorHomo sapiens (human)
cell surface receptor signaling pathwayBeta-2 adrenergic receptorHomo sapiens (human)
activation of transmembrane receptor protein tyrosine kinase activityBeta-2 adrenergic receptorHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayBeta-2 adrenergic receptorHomo sapiens (human)
endosome to lysosome transportBeta-2 adrenergic receptorHomo sapiens (human)
response to coldBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of protein kinase A signalingBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of bone mineralizationBeta-2 adrenergic receptorHomo sapiens (human)
heat generationBeta-2 adrenergic receptorHomo sapiens (human)
negative regulation of multicellular organism growthBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of MAPK cascadeBeta-2 adrenergic receptorHomo sapiens (human)
bone resorptionBeta-2 adrenergic receptorHomo sapiens (human)
negative regulation of G protein-coupled receptor signaling pathwayBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIBeta-2 adrenergic receptorHomo sapiens (human)
negative regulation of smooth muscle contractionBeta-2 adrenergic receptorHomo sapiens (human)
brown fat cell differentiationBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of mini excitatory postsynaptic potentialBeta-2 adrenergic receptorHomo sapiens (human)
adrenergic receptor signaling pathwayBeta-2 adrenergic receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of protein serine/threonine kinase activityBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of cold-induced thermogenesisBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of autophagosome maturationBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of lipophagyBeta-2 adrenergic receptorHomo sapiens (human)
cellular response to amyloid-betaBeta-2 adrenergic receptorHomo sapiens (human)
response to psychosocial stressBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of cAMP-dependent protein kinase activityBeta-2 adrenergic receptorHomo sapiens (human)
positive regulation of AMPA receptor activityBeta-2 adrenergic receptorHomo sapiens (human)
norepinephrine-epinephrine-mediated vasodilation involved in regulation of systemic arterial blood pressureBeta-2 adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
amyloid-beta bindingBeta-2 adrenergic receptorHomo sapiens (human)
beta2-adrenergic receptor activityBeta-2 adrenergic receptorHomo sapiens (human)
protein bindingBeta-2 adrenergic receptorHomo sapiens (human)
adenylate cyclase bindingBeta-2 adrenergic receptorHomo sapiens (human)
potassium channel regulator activityBeta-2 adrenergic receptorHomo sapiens (human)
identical protein bindingBeta-2 adrenergic receptorHomo sapiens (human)
protein homodimerization activityBeta-2 adrenergic receptorHomo sapiens (human)
protein-containing complex bindingBeta-2 adrenergic receptorHomo sapiens (human)
norepinephrine bindingBeta-2 adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
nucleusBeta-2 adrenergic receptorHomo sapiens (human)
lysosomeBeta-2 adrenergic receptorHomo sapiens (human)
endosomeBeta-2 adrenergic receptorHomo sapiens (human)
early endosomeBeta-2 adrenergic receptorHomo sapiens (human)
Golgi apparatusBeta-2 adrenergic receptorHomo sapiens (human)
plasma membraneBeta-2 adrenergic receptorHomo sapiens (human)
endosome membraneBeta-2 adrenergic receptorHomo sapiens (human)
membraneBeta-2 adrenergic receptorHomo sapiens (human)
apical plasma membraneBeta-2 adrenergic receptorHomo sapiens (human)
clathrin-coated endocytic vesicle membraneBeta-2 adrenergic receptorHomo sapiens (human)
neuronal dense core vesicleBeta-2 adrenergic receptorHomo sapiens (human)
receptor complexBeta-2 adrenergic receptorHomo sapiens (human)
plasma membraneBeta-2 adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID19680The octanol-water partition coefficient at pH 5.81994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Synthesis, binding properties, and 18F labeling of fluorocarazolol, a high-affinity beta-adrenergic receptor antagonist.
AID1668033Antiproliferative activity against human SK-MEL-5 cells assessed as cell growth inhibition incubated for 48 hrs by MTT assay2020Bioorganic & medicinal chemistry, 05-01, Volume: 28, Issue:9
Drug repurposing and rediscovery: Design, synthesis and preliminary biological evaluation of 1-arylamino-3-aryloxypropan-2-ols as anti-melanoma agents.
AID350218Octanol-water partition coefficient, log PC of the compound2009Journal of medicinal chemistry, May-28, Volume: 52, Issue:10
Lipophilicity of basic drugs measured by hydrophilic interaction chromatography.
AID1722507Antibacterial activity against Staphylococcus aureus ATCC 29213 measured after 24 hrs by microplate reader analysis
AID19682The octanol-water partition coefficient at pH 7.01994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Synthesis, binding properties, and 18F labeling of fluorocarazolol, a high-affinity beta-adrenergic receptor antagonist.
AID19685The octanol-water partition coefficient at pH 9.41994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Synthesis, binding properties, and 18F labeling of fluorocarazolol, a high-affinity beta-adrenergic receptor antagonist.
AID781326pKa (acid-base dissociation constant) as determined by Avdeef ref: DOI: 10.1002/047145026X2014Pharmaceutical research, Apr, Volume: 31, Issue:4
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.
AID350220Lipophilicity, log K at pH 2 by by hydrophilic interaction chromatography using 100% water as mobile phase2009Journal of medicinal chemistry, May-28, Volume: 52, Issue:10
Lipophilicity of basic drugs measured by hydrophilic interaction chromatography.
AID19678The octanol-water partition coefficient at pH 3.31994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Synthesis, binding properties, and 18F labeling of fluorocarazolol, a high-affinity beta-adrenergic receptor antagonist.
AID312895Partition coefficient, log P of the compound2008Journal of medicinal chemistry, Feb-14, Volume: 51, Issue:3
High-throughput log P determination by ultraperformance liquid chromatography: a convenient tool for medicinal chemists.
AID19679The octanol-water partition coefficient at pH 4.51994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Synthesis, binding properties, and 18F labeling of fluorocarazolol, a high-affinity beta-adrenergic receptor antagonist.
AID41147Dissociation constant against beta adrenergic receptor1983Journal of medicinal chemistry, Jun, Volume: 26, Issue:6
Synthesis of iodine-125 labeled (+/-)-15-(4-azidobenzyl)carazolol: a potent beta-adrenergic photoaffinity probe.
AID1668035Antiproliferative activity against human A375 cells assessed as cell growth inhibition incubated for 48 hrs by MTT assay2020Bioorganic & medicinal chemistry, 05-01, Volume: 28, Issue:9
Drug repurposing and rediscovery: Design, synthesis and preliminary biological evaluation of 1-arylamino-3-aryloxypropan-2-ols as anti-melanoma agents.
AID1722509Antibacterial activity against methicillin-resistant Staphylococcus aureus NCTC 10442 measured after 24 hrs by microplate reader analysis
AID19684The octanol-water partition coefficient at pH 8.31994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Synthesis, binding properties, and 18F labeling of fluorocarazolol, a high-affinity beta-adrenergic receptor antagonist.
AID19677The octanol-water partition coefficient at pH 10.81994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Synthesis, binding properties, and 18F labeling of fluorocarazolol, a high-affinity beta-adrenergic receptor antagonist.
AID1598554Displacement of [3H]-CGP-12177 from human beta2-adrenergic receptor expressed in CHO cells after 60 mins by radioligand competition binding assay2019Journal of medicinal chemistry, 05-23, Volume: 62, Issue:10
Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias.
AID366095Lipophilicity, log P at pH 7.42008Journal of medicinal chemistry, Aug-28, Volume: 51, Issue:16
Facile radiosynthesis of fluorine-18 labeled beta-blockers. Synthesis, radiolabeling, and ex vivo biodistribution of [18F]-(2S and 2R)-1-(1-fluoropropan-2-ylamino)-3-(m-tolyloxy)propan-2-ol.
AID350216Dissociation constant, pKa of the compound2009Journal of medicinal chemistry, May-28, Volume: 52, Issue:10
Lipophilicity of basic drugs measured by hydrophilic interaction chromatography.
AID1722510Hemolytic activity in rabbit erythrocytes measured after 1 hr by microplate reader analysis
AID312896Partition coefficient, log P by UPLC method2008Journal of medicinal chemistry, Feb-14, Volume: 51, Issue:3
High-throughput log P determination by ultraperformance liquid chromatography: a convenient tool for medicinal chemists.
AID1598553Displacement of [3H]-CGP-12177 from murine beta1-adrenergic receptor expressed in HEK293T cells after 60 mins by radioligand competition binding assay2019Journal of medicinal chemistry, 05-23, Volume: 62, Issue:10
Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias.
AID1722508Antibacterial activity against methicillin-resistant Staphylococcus aureus N315 measured after 24 hrs by microplate reader analysis
AID19676The octanol-water partition coefficient at pH 10.01994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Synthesis, binding properties, and 18F labeling of fluorocarazolol, a high-affinity beta-adrenergic receptor antagonist.
AID19683The octanol-water partition coefficient at pH 7.51994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Synthesis, binding properties, and 18F labeling of fluorocarazolol, a high-affinity beta-adrenergic receptor antagonist.
AID19681The octanol-water partition coefficient at pH 6.41994Journal of medicinal chemistry, Sep-30, Volume: 37, Issue:20
Synthesis, binding properties, and 18F labeling of fluorocarazolol, a high-affinity beta-adrenergic receptor antagonist.
AID350217Octanol-water partition coefficient, log P of the cationic form of the compound2009Journal of medicinal chemistry, May-28, Volume: 52, Issue:10
Lipophilicity of basic drugs measured by hydrophilic interaction chromatography.
AID1668034Antiproliferative activity against human SK-MEL-28 cells assessed as cell growth inhibition incubated for 48 hrs by MTT assay2020Bioorganic & medicinal chemistry, 05-01, Volume: 28, Issue:9
Drug repurposing and rediscovery: Design, synthesis and preliminary biological evaluation of 1-arylamino-3-aryloxypropan-2-ols as anti-melanoma agents.
AID389416Displacement of [3H]DHA from human beta2 adrenoceptor by liquid scintillation counter2008Bioorganic & medicinal chemistry letters, Oct-15, Volume: 18, Issue:20
Use of the X-ray structure of the beta2-adrenergic receptor for drug discovery. Part 2: Identification of active compounds.
AID350219Lipophilicity, log K at pH 2 by by hydrophilic interaction chromatography using 95% acetonitrile as mobile phase2009Journal of medicinal chemistry, May-28, Volume: 52, Issue:10
Lipophilicity of basic drugs measured by hydrophilic interaction chromatography.
AID1346312Mouse beta3-adrenoceptor (Adrenoceptors)1995European journal of pharmacology, Nov-30, Volume: 291, Issue:3
Carazolol: a potent, selective beta 3-adrenoceptor agonist.
AID1346250Human beta2-adrenoceptor (Adrenoceptors)2008Bioorganic & medicinal chemistry letters, Oct-15, Volume: 18, Issue:20
Use of the X-ray structure of the beta2-adrenergic receptor for drug discovery. Part 2: Identification of active compounds.
AID1346297Human beta3-adrenoceptor (Adrenoceptors)1995European journal of pharmacology, Nov-30, Volume: 291, Issue:3
Carazolol: a potent, selective beta 3-adrenoceptor agonist.
AID1347018Rat beta3-adrenoceptor (Adrenoceptors)1995European journal of pharmacology, Nov-30, Volume: 291, Issue:3
Carazolol: a potent, selective beta 3-adrenoceptor agonist.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (107)

TimeframeStudies, This Drug (%)All Drugs %
pre-199029 (27.10)18.7374
1990's25 (23.36)18.2507
2000's26 (24.30)29.6817
2010's24 (22.43)24.3611
2020's3 (2.80)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.32

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

MetricThis Compound (vs All)
Research Demand Index35.32 (24.57)
Research Supply Index4.74 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index48.73 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (35.32)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (3.64%)5.53%
Reviews4 (3.64%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other102 (92.73%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]