Page last updated: 2024-12-05

ethaverine

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

Description

Ethaverine is a synthetic alkaloid that is structurally related to papaverine. It is a potent vasodilator that acts by inhibiting the activity of the enzyme phosphodiesterase, which leads to an increase in the levels of cyclic adenosine monophosphate (cAMP) in smooth muscle cells. This increase in cAMP causes smooth muscle relaxation, leading to vasodilation. Ethaverine has been used to treat various conditions, including peripheral vascular disease, angina pectoris, and migraine headaches. However, its use has declined in recent years due to the availability of safer and more effective alternative treatments. Despite this, ethaverine remains an important research tool for studying the role of phosphodiesterase in smooth muscle function and vascular disease. '

ethaverine: tetraethyl homolog of papaverine; smooth muscle relaxant; RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3280
CHEMBL ID1555736
CHEBI ID94592
SCHEMBL ID25606
MeSH IDM0050961

Synonyms (78)

Synonym
BRD-K36756879-003-05-3
isoquinoline, 1-(3,4-diethoxybenzyl)-6,7-diethoxy-
isoquinoline, 1-[(3,4-diethoxyphenyl)methyl]-6,7-diethoxy-
DIVK1C_000199
KBIO1_000199
1-{[3,4-bis(ethyloxy)phenyl]methyl}-6,7-bis(ethyloxy)isoquinoline
486-47-5
brn 0342349
dyscural
6,7-diethoxy-1-(3,4-diethoxybenzyl)isoquinoline
etaverina [inn-spanish]
einecs 207-633-3
isoquinoline, 6,7-diethoxy-1-(3,4-diethoxybenzyl)-
ethaverine [inn]
barbonin
ethylpapaverine
isoquinoline, 1-((3,4-diethoxyphenyl)methyl)-6,7-diethoxy-
1-(3,4-diethoxybenzyl)-6,7-diethoxyisoquinoline
barbonine
ethaverinum [inn-latin]
6,7-diaethoxy-1-(3,4-diaethoxybenzyl)isochinolin [german]
SPECTRUM_001218
BSPBIO_000759
NCGC00016557-01
cas-985-13-7
BSPBIO_003130
perparine
perperine
PRESTWICK2_000830
PRESTWICK3_000830
SPECTRUM5_001524
1-[(3,4-diethoxyphenyl)methyl]-6,7-diethoxy-isoquinoline
ethaverine
isoquinolinium, 1-[(3,4-diethoxyphenyl)methyl]-6,7-diethoxy-
AB00053589
IDI1_000199
KBIO3_002350
KBIO2_001698
KBIOGR_000672
KBIOSS_001698
KBIO2_004266
KBIO2_006834
PRESTWICK1_000830
PRESTWICK0_000830
SPECTRUM2_001385
SPBIO_001370
SPECTRUM3_001425
SPECTRUM4_000406
SPBIO_002680
NINDS_000199
BPBIO1_000835
NCGC00016557-02
NCGC00016557-03
ethaverine (inn)
D07926
ethquinol (tn)
1-[(3,4-diethoxyphenyl)methyl]-6,7-diethoxyisoquinoline
ethquinol
CHEMBL1555736
etaverina
2h2hc19dyz ,
unii-2h2hc19dyz
5-21-06-00183 (beilstein handbook reference)
6,7-diaethoxy-1-(3,4-diaethoxybenzyl)isochinolin
ethaverinum
ethaverine [vandf]
ethaverine [who-dd]
ethaverine [mi]
SCHEMBL25606
AKOS024366261
ZOWYFYXTIWQBEP-UHFFFAOYSA-N
AB00053589_04
DTXSID3023009
CHEBI:94592
SBI-0051627.P002
Q27166421
BRD-K36756879-003-06-1
EX-A5513

Research Excerpts

Overview

Ethaverine is a derivative of papaverine used in the treatment of peripheral vascular disease. It is thought to cause vasodilation by reducing intracellular Ca2+ concentrations in vascular smooth muscle cells.

ExcerptReferenceRelevance
"Ethaverine is a derivative of papaverine used in the treatment of peripheral vascular disease and is thought to cause vasodilation by reducing intracellular Ca2+ concentrations in vascular smooth muscle cells. "( Ethaverine, a derivative of papaverine, inhibits cardiac L-type calcium channels.
Rosenberg, RL; Wang, Y, 1991
)
3.17

Treatment

Ethaverine pretreatment for 1 min prior to stimulation by 70 mM K+ also decreased the level of intracellular Ca2+ in a concentration-dependent manner, as measured by fura-2 fluorescence. Treatment with ethaverine reduced catecholamine secretion in a concentration- dependent manner.

ExcerptReferenceRelevance
"Ethaverine pretreatment for 1 min prior to stimulation by 70 mM K+ also decreased the level of intracellular Ca2+ in a concentration-dependent manner, as measured by fura-2 fluorescence."( Inhibition by ethaverine of catecholamine secretion through blocking L-type Ca2+ channels in PC12 cells.
Kim, KT; Suh, BC, 1994
)
1.37
"Treatment with ethaverine reduced catecholamine secretion in a concentration-dependent manner."( Inhibition by ethaverine of catecholamine secretion through blocking L-type Ca2+ channels in PC12 cells.
Kim, KT; Suh, BC, 1994
)
0.99
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
isoquinolinesA class of organic heteropolycyclic compound consisting of isoquinoline and its substitution 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 (28)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency0.00180.004023.8416100.0000AID485290
glp-1 receptor, partialHomo sapiens (human)Potency10.00000.01846.806014.1254AID624172
USP1 protein, partialHomo sapiens (human)Potency25.11890.031637.5844354.8130AID504865
thyroid stimulating hormone receptorHomo sapiens (human)Potency12.58930.001318.074339.8107AID926; AID938
cytochrome P450 2C9 precursorHomo sapiens (human)Potency3.98110.00636.904339.8107AID883
mitogen-activated protein kinase 1Homo sapiens (human)Potency3.98110.039816.784239.8107AID995
peripheral myelin protein 22Rattus norvegicus (Norway rat)Potency2.45210.005612.367736.1254AID624032
survival motor neuron protein isoform dHomo sapiens (human)Potency5.01190.125912.234435.4813AID1458
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency5.01190.031610.279239.8107AID884; AID885
lethal factor (plasmid)Bacillus anthracis str. A2012Potency5.01190.020010.786931.6228AID912
lamin isoform A-delta10Homo sapiens (human)Potency0.00200.891312.067628.1838AID1487
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency3.98110.00638.235039.8107AID883
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
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 (3)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID628752Inhibition of bovine aortic PDE4 using cAMP as substrate in presence of cGMP2011Bioorganic & medicinal chemistry letters, Nov-01, Volume: 21, Issue:21
New PDE4 inhibitors based on pharmacophoric similarity between papaverine and tofisopam.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-199013 (56.52)18.7374
1990's3 (13.04)18.2507
2000's3 (13.04)29.6817
2010's3 (13.04)24.3611
2020's1 (4.35)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.89

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 Index27.89 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index28.85 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.89)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (4.17%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other23 (95.83%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]