Page last updated: 2024-11-12

lecozotan

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

Description

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

Cross-References

ID SourceID
PubMed CID10116877
CHEMBL ID372205
SCHEMBL ID2881511
MeSH IDM0485418

Synonyms (22)

Synonym
4-cyano-n-{(r)-2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-propyl}-n-pyridin-2-yl-benzamide
bdbm50166903
CHEMBL372205 ,
lecozotan
lecozotan [inn]
48854otz5e ,
4-cyano-n-(2r-(4-(2,3-dihydrobenzo(1,4)-dioxin-5-yl)-piperazin-1-yl)-propyl)-n-pyridin-2-yl-benzamide hydrochloride
unii-48854otz5e
(r)-4-cyano-n-{2-[4-(2,3-di hydro-benzo[1,4]dioxin-5-yl]piperazin-1-yl]-propyl}-n-pyridin-2-yl-benzamide
(r)-4-cyano-n-{2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-propyl}-n-pyridin-2-yl-benzamide
(r)-4-cyano-n-{2-[4(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-propyl}-n-pyridin-2-yl-benzamide
(r)-4-cyano-n-{2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl]piperazin-1-yl]-propyl}-n-pyridin-2-yl-benzamide
(r)-4-cyano-n-{2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1yl]-propyl}-n-pyridin-2-yl-benzamide
NRPQELCNMADTOZ-OAQYLSRUSA-N
SCHEMBL2881511
benzamide, 4-cyano-n-((2r)-2-(4-(2,3-dihydro-1,4-benzodioxin-5-yl)-1-piperazinyl)propyl)-n-2-pyridinyl-
4-cyano-n-((2r)-2-(4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl)propyl)-n-(pyridin-2-yl)benzamide
DB12540
4-cyano-n-[(2r)-2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]propyl]-n-pyridin-2-ylbenzamide
Q27259118
DTXSID30870354
4-cyano-n-{(2r)-2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)-1-piperazinyl]propyl}-n-(2-pyridinyl)benzamide

Research Excerpts

Overview

Lecozotan is a selective serotonergic 5-HT(1A) receptor antagonist. It has been shown to enhance task performance efficiency in aged rhesus monkeys.

ExcerptReferenceRelevance
"Lecozotan is a selective serotonergic 5-HT(1A) receptor antagonist previously shown to enhance task performance efficiency in aged rhesus monkeys. "( Acute lecozotan administration increases learning and memory in rats without affecting anxiety or behavioral depression.
Hernandez, L; Rada, P; Schechter, LE; Skirzewski, M, 2010
)
2.28

Toxicity

Lecozotan IR was safe and well tolerated after administration of multiple oral doses up to 5 mg q12h in young and elderly subjects.

ExcerptReferenceRelevance
"Lecozotan was safe and well tolerated at steady state up to 5 mg q12."( Safety, tolerability, pharmacokinetics and pharmacodynamics of ascending single and multiple doses of lecozotan in healthy young and elderly subjects.
Chassard, D; Le Coz, F; Parks, V; Patat, A; Plotka, A; Raje, S, 2009
)
2.01
"Lecozotan IR was safe and well tolerated after administration of multiple oral doses up to 5 mg q12h in young and elderly subjects."( Safety, tolerability, pharmacokinetics and pharmacodynamics of ascending single and multiple doses of lecozotan in healthy young and elderly subjects.
Chassard, D; Le Coz, F; Parks, V; Patat, A; Plotka, A; Raje, S, 2009
)
2.01
"There is a potential risk that 5-HT(1A) receptor blockade combined with blockade of the 5-HT transporter by an SSRI may cause a toxic increase in 5-HT within the synapse, sparking concern for 'serotonin syndrome', a rare but potentially life threatening condition."( Concomitant blockade of 5-HT(1A) receptor and 5-HT transporter: use of the Hunter Serotonin toxicity criteria in a clinical pharmacology study.
Chalon, S; Connell, J; Parks, V; Philipp, AW; Plotka, A; Raje, S; Schechter, LE, 2012
)
0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)10.00000.11007.190310.0000AID1449628
5-hydroxytryptamine receptor 1AHomo sapiens (human)IC50 (µMol)0.03350.00010.666410.0000AID242572; AID248875
5-hydroxytryptamine receptor 1AHomo sapiens (human)Ki0.00160.00010.532610.0000AID239577
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (37)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
behavioral fear response5-hydroxytryptamine receptor 1AHomo sapiens (human)
G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
adenylate cyclase-inhibiting serotonin receptor signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
gamma-aminobutyric acid signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
positive regulation of cell population proliferation5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of serotonin secretion5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of vasoconstriction5-hydroxytryptamine receptor 1AHomo sapiens (human)
exploration behavior5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of dopamine metabolic process5-hydroxytryptamine receptor 1AHomo sapiens (human)
serotonin metabolic process5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of hormone secretion5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of behavior5-hydroxytryptamine receptor 1AHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 1AHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 1AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 1AHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 1AHomo sapiens (human)
receptor-receptor interaction5-hydroxytryptamine receptor 1AHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 1AHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 1AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 1AHomo sapiens (human)
synapse5-hydroxytryptamine receptor 1AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 1AHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 1AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID240454Percent maximal response of 8-OH-DPAT-induced [35S]GTP-gamma-S, binding to 5-HT1A receptor/G protein complex 2005Journal of medicinal chemistry, May-19, Volume: 48, Issue:10
Synthesis and biological evaluation of benzodioxanylpiperazine derivatives as potent serotonin 5-HT(1A) antagonists: the discovery of Lecozotan.
AID248875In vitro antagonism of 8-OH-DPAT inhibition of forskolin-induced cAMP production in CHO cells expressing 5-HT1A receptor2005Journal of medicinal chemistry, May-19, Volume: 48, Issue:10
Synthesis and biological evaluation of benzodioxanylpiperazine derivatives as potent serotonin 5-HT(1A) antagonists: the discovery of Lecozotan.
AID239577Displacement of 8-OH-DPAT from human 5-hydroxytryptamine 1A receptor expressed in chinese hamster ovary cells2005Journal of medicinal chemistry, May-19, Volume: 48, Issue:10
Synthesis and biological evaluation of benzodioxanylpiperazine derivatives as potent serotonin 5-HT(1A) antagonists: the discovery of Lecozotan.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID247122Agonist activity in forskolin-induced cAMP production in CHO cells expressing 5-HT1A receptor compared to 8-OH-DPAT2005Journal of medicinal chemistry, May-19, Volume: 48, Issue:10
Synthesis and biological evaluation of benzodioxanylpiperazine derivatives as potent serotonin 5-HT(1A) antagonists: the discovery of Lecozotan.
AID247049Effective dose on the 8-OH-DPAT induced response at 3 mg/kg sc in presence of 8-OH-DPAT (Effective dose value for 8-OH-DPAT = 0.18)2005Journal of medicinal chemistry, May-19, Volume: 48, Issue:10
Synthesis and biological evaluation of benzodioxanylpiperazine derivatives as potent serotonin 5-HT(1A) antagonists: the discovery of Lecozotan.
AID242572In vitro inhibition of 8-OH-DPAT-induced [35S]GTP-gamma-S, binding to 5-HT1A receptor/G protein complex in CHO cells2005Journal of medicinal chemistry, May-19, Volume: 48, Issue:10
Synthesis and biological evaluation of benzodioxanylpiperazine derivatives as potent serotonin 5-HT(1A) antagonists: the discovery of Lecozotan.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (50.00)29.6817
2010's4 (50.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.56

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 Index23.56 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.40 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (37.50%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (62.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]