Page last updated: 2024-11-07

desmethylastemizole

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

Description

desmethylastemizole: astemizole metabolite in dog plasma; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID155805
CHEMBL ID60796
CHEBI ID175566
SCHEMBL ID1152697
MeSH IDM0120478

Synonyms (28)

Synonym
4-[2-[4-[[1-[(4-luorophenyl)methyl]benzimidazol-2-yl]amino]piperidin-1-yl]ethyl]phenol
CHEBI:175566
demethylastemizole
4-(2-{4-[1-(4-fluoro-benzyl)-1h-benzoimidazol-2-ylamino]-piperidin-1-yl}-ethyl)-phenol
4-(2-(4-(1-(4-fluorobenzyl)-1h-benzo[d]imidazol-2-ylamino)piperidin-1-yl)ethyl)phenol
bdbm50131433
desmethylasteizole
CHEMBL60796 ,
4-[2-[4-[[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]amino]piperidin-1-yl]ethyl]phenol
73736-50-2
r-44-271
desmethylastemizole
r 44 271
phenol, 4-(2-(4-((1-((4-fluorophenyl)methyl)-1h-benzimidazol-2-yl)amino)-1-piperidinyl)ethyl)-
FT-0666079
l460qhm1yn ,
unii-l460qhm1yn
o-demethylastemizole
o-desmethyl astemizole
SCHEMBL1152697
r-44271
DTXSID10224058
4-[2-{4-[1-(4-fluorophenylmethyl)-1h-benzimidazol-2-ylamino]-1-piperidinyl}ethyl]phenol
LAGYWHSFHIMTPE-UHFFFAOYSA-N
o-desmethylastemizole
AKOS030240026
C90313
Q27282678

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
"Matrix-assisted laser desorption/ionization (MALDI)-tandem mass spectrometry (MS)/MS is a proven reliable tool for visualizing the spatial distribution of dosed drugs and their primary metabolites in animal tissue sections."( MALDI-tandem mass spectrometry imaging of astemizole and its primary metabolite in rat brain sections.
Hsieh, Y; Kang, L; Korfmacher, WA; Lachowicz, J; Li, F; Sondey, C, 2009
)
0.35
"The results indicated that the dosed compound alone might be responsible for the CNS side-effects when drug exposures became elevated."( MALDI-tandem mass spectrometry imaging of astemizole and its primary metabolite in rat brain sections.
Hsieh, Y; Kang, L; Korfmacher, WA; Lachowicz, J; Li, F; Sondey, C, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzimidazolesAn organic heterocyclic compound containing a benzene ring fused to an imidazole ring.
[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)
Potassium voltage-gated channel subfamily H member 2Homo sapiens (human)IC50 (µMol)0.00100.00091.901410.0000AID161281; AID392051; AID408340
[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)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (50)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IINuclear receptor subfamily 4 group A member 2Homo sapiens (human)
response to hypoxiaNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
neuron migrationNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
response to amphetamineNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
DNA-templated transcriptionNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
transcription by RNA polymerase IINuclear receptor subfamily 4 group A member 2Homo sapiens (human)
adult locomotory behaviorNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
post-embryonic developmentNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
central nervous system projection neuron axonogenesisNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
habenula developmentNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
intracellular receptor signaling pathwayNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
cellular response to oxidative stressNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
regulation of dopamine metabolic processNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
dopamine biosynthetic processNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
neuron maturationNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
negative regulation of neuron apoptotic processNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
regulation of respiratory gaseous exchangeNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
fat cell differentiationNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
positive regulation of transcription by RNA polymerase IINuclear receptor subfamily 4 group A member 2Homo sapiens (human)
neuron apoptotic processNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
general adaptation syndromeNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
canonical Wnt signaling pathwayNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
cellular response to corticotropin-releasing hormone stimulusNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
dopaminergic neuron differentiationNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
midbrain dopaminergic neuron differentiationNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
negative regulation of apoptotic signaling pathwayNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
regulation of transcription by RNA polymerase IINuclear receptor subfamily 4 group A member 2Homo sapiens (human)
central nervous system neuron differentiationNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
regulation of heart rate by cardiac conductionPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of heart rate by hormonePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of membrane potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
positive regulation of DNA-templated transcriptionPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
potassium ion homeostasisPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
cardiac muscle contractionPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of membrane repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of ventricular cardiac muscle cell membrane repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
cellular response to xenobiotic stimulusPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
potassium ion transmembrane transportPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
ventricular cardiac muscle cell action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane depolarization during action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane repolarization during action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane repolarization during cardiac muscle cell action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of heart rate by cardiac conductionPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
potassium ion export across plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane repolarization during ventricular cardiac muscle cell action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of potassium ion transmembrane transportPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
negative regulation of potassium ion transmembrane transportPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
positive regulation of potassium ion transmembrane transportPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
negative regulation of potassium ion export across plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
potassium ion import across plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
DNA-binding transcription factor activity, RNA polymerase II-specificNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
DNA bindingNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
nuclear receptor activityNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
protein bindingNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
beta-catenin bindingNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
zinc ion bindingNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
nuclear retinoid X receptor bindingNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
protein heterodimerization activityNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
sequence-specific double-stranded DNA bindingNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
nuclear glucocorticoid receptor bindingNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
transcription cis-regulatory region bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
inward rectifier potassium channel activityPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
voltage-gated potassium channel activityPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
delayed rectifier potassium channel activityPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
protein bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
ubiquitin protein ligase bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
identical protein bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
protein homodimerization activityPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
C3HC4-type RING finger domain bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
voltage-gated potassium channel activity involved in cardiac muscle cell action potential repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
scaffold protein bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
nucleusNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
nucleoplasmNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
cytoplasmNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
nuclear speckNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
chromatinNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
protein-containing complexNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
transcription regulator complexNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
nucleusNuclear receptor subfamily 4 group A member 2Homo sapiens (human)
plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
cell surfacePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
perinuclear region of cytoplasmPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
voltage-gated potassium channel complexPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
inward rectifier potassium channel complexPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (25)

Assay IDTitleYearJournalArticle
AID392051Inhibition of human ERG channel in HEK293 cells by voltage-clamp method2008European journal of medicinal chemistry, Nov, Volume: 43, Issue:11
Identification of "toxicophoric" features for predicting drug-induced QT interval prolongation.
AID76791In vivo histamine induced lethality after 8 hours of iv administration in guinea pig1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
New antihistaminic N-heterocyclic 4-piperidinamines. 2. Synthesis and antihistaminic activity of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-a mines.
AID513160Antimalarial activity against Plasmodium falciparum 3D7 assessed as inhibition of parasite growth after 48 to 96 hrs by [3H]hypoxanthine incorporation assay2006Nature chemical biology, Aug, Volume: 2, Issue:8
A clinical drug library screen identifies astemizole as an antimalarial agent.
AID176155In vivo antihistaminic activity using compound 48/80 induced lethality test after 1 hr of subcutaneous administration in rat1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
New antihistaminic N-heterocyclic 4-piperidinamines. 2. Synthesis and antihistaminic activity of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-a mines.
AID76790In vivo histamine induced lethality after 48 hours of iv administration in guinea pig1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
New antihistaminic N-heterocyclic 4-piperidinamines. 2. Synthesis and antihistaminic activity of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-a mines.
AID513178Antimalarial activity against chloroquine-sensitive Plasmodium vinckei infected in mice (Mus musculus) assessed as complete cure from parasite infection at 15 mg/m'2, intraperitoneally qd for 4 days administered 2 hrs post infection measured on day 52006Nature chemical biology, Aug, Volume: 2, Issue:8
A clinical drug library screen identifies astemizole as an antimalarial agent.
AID513173Antimalarial activity against chloroquine-sensitive Plasmodium yoelii 17X infected in mice (Mus musculus) assessed as reduction in parasitaemia at 15 mg/m'2, intraperitoneal daily for 5 days administered 2 hrs post infection measured on day 52006Nature chemical biology, Aug, Volume: 2, Issue:8
A clinical drug library screen identifies astemizole as an antimalarial agent.
AID513157Metabolic stability in human plasma assessed as desmethylastemizole half life2006Nature chemical biology, Aug, Volume: 2, Issue:8
A clinical drug library screen identifies astemizole as an antimalarial agent.
AID76788In vivo histamine induced lethality after 24 hours of iv administration in guinea pig1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
New antihistaminic N-heterocyclic 4-piperidinamines. 2. Synthesis and antihistaminic activity of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-a mines.
AID76792In vivo histamine induced lethality after 96 hours of iv administration in guinea pig1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
New antihistaminic N-heterocyclic 4-piperidinamines. 2. Synthesis and antihistaminic activity of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-a mines.
AID76789In vivo histamine induced lethality after 3 hours of iv administration in guinea pig1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
New antihistaminic N-heterocyclic 4-piperidinamines. 2. Synthesis and antihistaminic activity of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-a mines.
AID513158Inhibition of heme crystallization after 16 hrs2006Nature chemical biology, Aug, Volume: 2, Issue:8
A clinical drug library screen identifies astemizole as an antimalarial agent.
AID176161In vivo antihistaminic activity using compound 48/80 induced lethality test in rat after 2 hr of oral administration1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
New antihistaminic N-heterocyclic 4-piperidinamines. 2. Synthesis and antihistaminic activity of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-a mines.
AID513179Antimalarial activity against chloroquine-sensitive Plasmodium yoelii 17X infected in mice (Mus musculus) assessed as complete cure from parasite infection at 15 mg/m'2, intraperitoneal daily for 4 days administered 2 hrs post infection measured on day 52006Nature chemical biology, Aug, Volume: 2, Issue:8
A clinical drug library screen identifies astemizole as an antimalarial agent.
AID178527Inhibition of mydriatic activity in rat after 2 hr of intraperitoneal administration.1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
New antihistaminic N-heterocyclic 4-piperidinamines. 2. Synthesis and antihistaminic activity of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-a mines.
AID161281Inhibition of human Potassium channel HERG expressed in mammalian cells2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Prediction of hERG potassium channel affinity by traditional and hologram qSAR methods.
AID178523Inhibition of histamine skin reaction in rat after 2 hr of subcutaneous administration.1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
New antihistaminic N-heterocyclic 4-piperidinamines. 2. Synthesis and antihistaminic activity of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-a mines.
AID408340Inhibition of human ERG expressed in CHO cells by whole cell patch clamp technique2008Bioorganic & medicinal chemistry, Jun-01, Volume: 16, Issue:11
Support vector machines classification of hERG liabilities based on atom types.
AID513172Antimalarial activity against chloroquine-sensitive Plasmodium vinckei infected in mice (Mus musculus) assessed as reduction in parasitemia at 15 mg/m'2, intraperitoneally qd for 5 days administered 2 hrs post infection measured on day 52006Nature chemical biology, Aug, Volume: 2, Issue:8
A clinical drug library screen identifies astemizole as an antimalarial agent.
AID1846886Inhibition of FITC-labeled EZH2 (40 to 63 residues) (unknown origin)-recombinant N-terminal 6His-SUMO tagged human EED (81 to 441 residues) expressed in Escherichia coli BL21 (DE3) cells protein-protein interaction incubated for 2 hrs by fluorescence pola2021Journal of medicinal chemistry, 06-24, Volume: 64, Issue:12
Structure-Guided Development of Small-Molecule PRC2 Inhibitors Targeting EZH2-EED Interaction.
AID178535Inhibition of serotonin skin reaction in rat after 2 hr of subcutaneous administration.1985Journal of medicinal chemistry, Dec, Volume: 28, Issue:12
New antihistaminic N-heterocyclic 4-piperidinamines. 2. Synthesis and antihistaminic activity of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-a mines.
AID1571766Binding affinity to Nurr1 (unknown origin) by 1H-STD-NMR spectroscopy2019Journal of medicinal chemistry, Mar-14, Volume: 62, Issue:5
Ligand-Based Fluorine NMR Screening: Principles and Applications in Drug Discovery Projects.
AID513155Antimalarial activity against Plasmodium falciparum Dd2 assessed as inhibition of parasite growth after 48 to 96 hrs by [3H]hypoxanthine incorporation assay2006Nature chemical biology, Aug, Volume: 2, Issue:8
A clinical drug library screen identifies astemizole as an antimalarial agent.
AID513170Oral bioavailability in human2006Nature chemical biology, Aug, Volume: 2, Issue:8
A clinical drug library screen identifies astemizole as an antimalarial agent.
AID513156Antimalarial activity against Plasmodium falciparum ItG assessed as inhibition of parasite growth after 48 to 96 hrs by [3H]hypoxanthine incorporation assay2006Nature chemical biology, Aug, Volume: 2, Issue:8
A clinical drug library screen identifies astemizole as an antimalarial agent.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (18.18)18.7374
1990's2 (18.18)18.2507
2000's5 (45.45)29.6817
2010's1 (9.09)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.20

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 Index12.20 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.84 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (8.33%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (8.33%)4.05%
Observational0 (0.00%)0.25%
Other10 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]