Page last updated: 2024-11-07

di-n-desethylamiodarone

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

Description

di-N-desethylamiodarone: amiodarone metabolite in dogs; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID125134
CHEMBL ID1598
SCHEMBL ID7242769
MeSH IDM0128614

Synonyms (15)

Synonym
3-{[4-(2-aminoethoxy)-3,5-diiodophenyl]carbonyl}-2-butyl-1-benzofuran
chembl1598 ,
desdiethylamiodarone
l 33530
bdbm18959
di-n-desethylamiodarone
ddea
[4-(2-aminoethoxy)-3,5-diiodophenyl]-(2-butyl-1-benzofuran-3-yl)methanone
94317-95-0
methanone, (4-(2-aminoethoxy)-3,5-diiodophenyl)(2-butyl-3-benzofuranyl)-
di-n-desethyl amiodarone
SCHEMBL7242769
DTXSID90241425
n,n-di-desethyl amiodarone
(2-butylbenzofuran-3-yl)[4-[2- aminoethoxy]-3,5-diiodophenyl]methanone

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" First, we showed that 50μM amiodarone is more toxic to primary human hepatocytes after CYP induction with rifampicin."( The role of CYP3A4 in amiodarone-associated toxicity on HepG2 cells.
Brecht, K; Krähenbühl, S; Lindinger, PW; Maseneni, S; Morand, R; Török, M; Zahno, A, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Lysine-specific demethylase 4AHomo sapiens (human)IC50 (µMol)49.00000.20002.83194.7600AID1289408; AID1885325
Thyroid hormone receptor betaRattus norvegicus (Norway rat)IC50 (µMol)19.00000.00020.00830.0350AID1797808
Lysine-specific demethylase 5AHomo sapiens (human)IC50 (µMol)26.00000.13002.374710.0000AID1289407; AID1885324
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Trace amine-associated receptor 1Rattus norvegicus (Norway rat)EC50 (µMol)1.00000.01390.42632.0440AID409813
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (40)

Processvia Protein(s)Taxonomy
negative regulation of autophagyLysine-specific demethylase 4AHomo sapiens (human)
positive regulation of gene expressionLysine-specific demethylase 4AHomo sapiens (human)
negative regulation of gene expressionLysine-specific demethylase 4AHomo sapiens (human)
cardiac muscle hypertrophy in response to stressLysine-specific demethylase 4AHomo sapiens (human)
apoptotic chromosome condensationLysine-specific demethylase 4AHomo sapiens (human)
response to nutrient levelsLysine-specific demethylase 4AHomo sapiens (human)
positive regulation of neuron differentiationLysine-specific demethylase 4AHomo sapiens (human)
negative regulation of DNA-templated transcriptionLysine-specific demethylase 4AHomo sapiens (human)
negative regulation of astrocyte differentiationLysine-specific demethylase 4AHomo sapiens (human)
chromatin remodelingLysine-specific demethylase 4AHomo sapiens (human)
regulation of gene expressionLysine-specific demethylase 4AHomo sapiens (human)
positive regulation of thyroid hormone mediated signaling pathwayThyroid hormone receptor alphaGallus gallus (chicken)
negative regulation of RNA polymerase II transcription preinitiation complex assemblyThyroid hormone receptor alphaGallus gallus (chicken)
mRNA transcription by RNA polymerase IIThyroid hormone receptor alphaGallus gallus (chicken)
positive regulation of transcription by RNA polymerase IIThyroid hormone receptor alphaGallus gallus (chicken)
cell differentiationThyroid hormone receptor alphaGallus gallus (chicken)
retinoic acid receptor signaling pathwayThyroid hormone receptor alphaGallus gallus (chicken)
negative regulation of transcription by RNA polymerase IIThyroid hormone receptor alphaGallus gallus (chicken)
thyroid hormone mediated signaling pathwayThyroid hormone receptor alphaGallus gallus (chicken)
negative regulation of transcription by RNA polymerase IILysine-specific demethylase 5AHomo sapiens (human)
circadian regulation of gene expressionLysine-specific demethylase 5AHomo sapiens (human)
positive regulation of DNA-templated transcriptionLysine-specific demethylase 5AHomo sapiens (human)
regulation of DNA-binding transcription factor activityLysine-specific demethylase 5AHomo sapiens (human)
facultative heterochromatin formationLysine-specific demethylase 5AHomo sapiens (human)
regulation of DNA-templated transcriptionLysine-specific demethylase 5AHomo sapiens (human)
chromatin remodelingLysine-specific demethylase 5AHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIInhibitor of growth protein 2Homo sapiens (human)
regulation of DNA-templated transcriptionInhibitor of growth protein 2Homo sapiens (human)
DNA damage responseInhibitor of growth protein 2Homo sapiens (human)
male meiosis IInhibitor of growth protein 2Homo sapiens (human)
signal transductionInhibitor of growth protein 2Homo sapiens (human)
spermatogenesisInhibitor of growth protein 2Homo sapiens (human)
spermatid developmentInhibitor of growth protein 2Homo sapiens (human)
flagellated sperm motilityInhibitor of growth protein 2Homo sapiens (human)
negative regulation of cell migrationInhibitor of growth protein 2Homo sapiens (human)
positive regulation of transforming growth factor beta receptor signaling pathwayInhibitor of growth protein 2Homo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathwayInhibitor of growth protein 2Homo sapiens (human)
negative regulation of gene expression, epigeneticInhibitor of growth protein 2Homo sapiens (human)
positive regulation of DNA-templated transcriptionInhibitor of growth protein 2Homo sapiens (human)
male germ-line stem cell asymmetric divisionInhibitor of growth protein 2Homo sapiens (human)
seminiferous tubule developmentInhibitor of growth protein 2Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorInhibitor of growth protein 2Homo sapiens (human)
negative regulation of stem cell population maintenanceInhibitor of growth protein 2Homo sapiens (human)
positive regulation of stem cell population maintenanceInhibitor of growth protein 2Homo sapiens (human)
regulation of cellular senescenceInhibitor of growth protein 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (28)

Processvia Protein(s)Taxonomy
protein bindingLysine-specific demethylase 4AHomo sapiens (human)
zinc ion bindingLysine-specific demethylase 4AHomo sapiens (human)
ubiquitin protein ligase bindingLysine-specific demethylase 4AHomo sapiens (human)
histone demethylase activityLysine-specific demethylase 4AHomo sapiens (human)
methylated histone bindingLysine-specific demethylase 4AHomo sapiens (human)
histone H3K36 demethylase activityLysine-specific demethylase 4AHomo sapiens (human)
histone H3K36me2/H3K36me3 demethylase activityLysine-specific demethylase 4AHomo sapiens (human)
histone H3K9me2/H3K9me3 demethylase activityLysine-specific demethylase 4AHomo sapiens (human)
histone H3K9 demethylase activityLysine-specific demethylase 4AHomo sapiens (human)
nuclear receptor activityThyroid hormone receptor alphaGallus gallus (chicken)
protein bindingThyroid hormone receptor alphaGallus gallus (chicken)
zinc ion bindingThyroid hormone receptor alphaGallus gallus (chicken)
TBP-class protein bindingThyroid hormone receptor alphaGallus gallus (chicken)
protein domain specific bindingThyroid hormone receptor alphaGallus gallus (chicken)
thyroid hormone bindingThyroid hormone receptor alphaGallus gallus (chicken)
sequence-specific double-stranded DNA bindingThyroid hormone receptor alphaGallus gallus (chicken)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingThyroid hormone receptor alphaGallus gallus (chicken)
transcription cis-regulatory region bindingLysine-specific demethylase 5AHomo sapiens (human)
DNA bindingLysine-specific demethylase 5AHomo sapiens (human)
transcription coactivator activityLysine-specific demethylase 5AHomo sapiens (human)
enzyme inhibitor activityLysine-specific demethylase 5AHomo sapiens (human)
protein bindingLysine-specific demethylase 5AHomo sapiens (human)
zinc ion bindingLysine-specific demethylase 5AHomo sapiens (human)
chromatin DNA bindingLysine-specific demethylase 5AHomo sapiens (human)
histone demethylase activityLysine-specific demethylase 5AHomo sapiens (human)
histone H3K4me/H3K4me2/H3K4me3 demethylase activityLysine-specific demethylase 5AHomo sapiens (human)
methylated histone bindingLysine-specific demethylase 5AHomo sapiens (human)
histone bindingLysine-specific demethylase 5AHomo sapiens (human)
DNA bindingInhibitor of growth protein 2Homo sapiens (human)
chromatin bindingInhibitor of growth protein 2Homo sapiens (human)
protein bindingInhibitor of growth protein 2Homo sapiens (human)
histone deacetylase regulator activityInhibitor of growth protein 2Homo sapiens (human)
methylated histone bindingInhibitor of growth protein 2Homo sapiens (human)
phosphatidylinositol bindingInhibitor of growth protein 2Homo sapiens (human)
protein-containing complex bindingInhibitor of growth protein 2Homo sapiens (human)
metal ion bindingInhibitor of growth protein 2Homo sapiens (human)
histone reader activityInhibitor of growth protein 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
fibrillar centerLysine-specific demethylase 4AHomo sapiens (human)
nucleusLysine-specific demethylase 4AHomo sapiens (human)
nucleoplasmLysine-specific demethylase 4AHomo sapiens (human)
cytosolLysine-specific demethylase 4AHomo sapiens (human)
pericentric heterochromatinLysine-specific demethylase 4AHomo sapiens (human)
nucleusLysine-specific demethylase 4AHomo sapiens (human)
chromatinLysine-specific demethylase 4AHomo sapiens (human)
nucleusThyroid hormone receptor alphaGallus gallus (chicken)
cytosolThyroid hormone receptor alphaGallus gallus (chicken)
RNA polymerase II transcription regulator complexThyroid hormone receptor alphaGallus gallus (chicken)
nucleusThyroid hormone receptor alphaGallus gallus (chicken)
nucleusLysine-specific demethylase 5AHomo sapiens (human)
nucleoplasmLysine-specific demethylase 5AHomo sapiens (human)
nucleolusLysine-specific demethylase 5AHomo sapiens (human)
nucleusLysine-specific demethylase 5AHomo sapiens (human)
chromatinLysine-specific demethylase 5AHomo sapiens (human)
nucleusInhibitor of growth protein 2Homo sapiens (human)
nucleoplasmInhibitor of growth protein 2Homo sapiens (human)
plasma membraneInhibitor of growth protein 2Homo sapiens (human)
Sin3-type complexInhibitor of growth protein 2Homo sapiens (human)
CCAAT-binding factor complexInhibitor of growth protein 2Homo sapiens (human)
nucleusInhibitor of growth protein 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID409813Agonist activity at rat TAAR1 expressed in HEK293 cells assessed as intracellular cAMP level2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Trace amine-associated receptor 1 (TAAR1) is activated by amiodarone metabolites.
AID1885324Inhibition of recombinant HQ5-Halo-tagged KDM5A PHD3 domain (unknown origin) measured by fluorescence polarization assay2022Journal of medicinal chemistry, 07-28, Volume: 65, Issue:14
Recent Advances with KDM4 Inhibitors and Potential Applications.
AID1289409Inhibition of recombinant GST-tagged ING2 PHD (201 to 281 residues) (unknown origin) using biotin-H3K4me3 ( 1 to 14 residues) peptide substrate by fluorescence polarization assay2016Journal of medicinal chemistry, Feb-25, Volume: 59, Issue:4
Recent Progress in Histone Demethylase Inhibitors.
AID1885325Inhibition of recombinant HQ5-Halo-tagged KDM4A tudor domain (unknown origin) measured by fluorescence polarization assay2022Journal of medicinal chemistry, 07-28, Volume: 65, Issue:14
Recent Advances with KDM4 Inhibitors and Potential Applications.
AID1289407Inhibition of recombinant GST-tagged KDM5A PHD3 (1601 to 1660 residues) (unknown origin) using biotin-H3K4me3 ( 1 to 14 residues) peptide substrate by fluorescence polarization assay2016Journal of medicinal chemistry, Feb-25, Volume: 59, Issue:4
Recent Progress in Histone Demethylase Inhibitors.
AID445744Activation of human TAAR1 expressed in CHOK1 cells coexpressing Galpha16 assessed as calcium accumulation at 10 uM relative to beta-phenethylamine2009Bioorganic & medicinal chemistry letters, Oct-15, Volume: 19, Issue:20
Amiodarone and its putative metabolites fail to activate wild type hTAAR1.
AID445740Activation of human TAAR1 expressed in CHOK1 cells assessed as cAMP accumulation at 0.1 to 1 uM2009Bioorganic & medicinal chemistry letters, Oct-15, Volume: 19, Issue:20
Amiodarone and its putative metabolites fail to activate wild type hTAAR1.
AID409812Agonist activity at rat TAAR1 expressed in HEK293 cells assessed as intracellular cAMP level at <=10 uM after 1 hr2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Trace amine-associated receptor 1 (TAAR1) is activated by amiodarone metabolites.
AID445743Activation of human TAAR1 expressed in CHOK1 cells assessed as cAMP accumulation at 10 uM relative to beta-phenethylamine2009Bioorganic & medicinal chemistry letters, Oct-15, Volume: 19, Issue:20
Amiodarone and its putative metabolites fail to activate wild type hTAAR1.
AID445741Activation of human TAAR1 expressed in CHOK1 cells coexpressing Galpha16 assessed as calcium accumulation at 0.1 to 1 uM relative to beta-phenethylamine2009Bioorganic & medicinal chemistry letters, Oct-15, Volume: 19, Issue:20
Amiodarone and its putative metabolites fail to activate wild type hTAAR1.
AID1289408Inhibition of recombinant GST-tagged KDM4A double tudor domain (895 to 1011 residues) (unknown origin) using biotin-H3K4me3 ( 1 to 14 residues) peptide substrate by fluorescence polarization assay2016Journal of medicinal chemistry, Feb-25, Volume: 59, Issue:4
Recent Progress in Histone Demethylase Inhibitors.
AID1797807TRalpha-Binding Assay. from Article 10.1210/endo.137.7.8770901: \\Structure-function relationship of the inhibition of the 3,5,3'-triiodothyronine binding to the alpha1- and beta1-thyroid hormone receptor by amiodarone analogs.\\1996Endocrinology, Jul, Volume: 137, Issue:7
Structure-function relationship of the inhibition of the 3,5,3'-triiodothyronine binding to the alpha1- and beta1-thyroid hormone receptor by amiodarone analogs.
AID1797808TRbeta-Binding Assay from Article 10.1210/endo.137.7.8770901: \\Structure-function relationship of the inhibition of the 3,5,3'-triiodothyronine binding to the alpha1- and beta1-thyroid hormone receptor by amiodarone analogs.\\1996Endocrinology, Jul, Volume: 137, Issue:7
Structure-function relationship of the inhibition of the 3,5,3'-triiodothyronine binding to the alpha1- and beta1-thyroid hormone receptor by amiodarone analogs.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (14.29)18.7374
1990's1 (14.29)18.2507
2000's2 (28.57)29.6817
2010's2 (28.57)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.72

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 Index12.72 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.80 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (28.57%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (71.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]