Page last updated: 2024-12-11

3-bromocytisine

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

Description

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

Cross-References

ID SourceID
PubMed CID15519735
CHEMBL ID365956
SCHEMBL ID20164035
MeSH IDM0404190

Synonyms (22)

Synonym
CHEMBL365956 ,
(-)-9-bromocytisine
3-bromocytisine
(1r,5s)-9-bromo-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one
bdbm50329578
(1r,5s)-9-bromo-1,2,3,4,5,6-hexahydro-1,5-methano-8h-pyrido[1,2-a][1,5]diazocin-8-one
207390-14-5
AKOS024457677
(1r,5s)-9-bromo-1,2,3,4,5,6-hexahydro-8h-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one
Q15405282
PL64C996QA ,
(-)-3-bromocytisine
(1r,5s)-9-bromo-1,2,3,4,5,6-hexahydro-1,5-methano-8h-pyrido(1,2-a)(1,5)diazocin-8-one
1,5-methano-8h-pyrido(1,2-a)(1,5)diazocin-8-one, 9-bromo-1,2,3,4,5,6-hexahydro-, (1r,5s)-
1,5-methano-8h-pyrido(1,2-a)(1,5)diazocin-8-one, 9-bromo-1,2,3,4,5,6-hexahydro-, (1r-cis)-
unii-pl64c996qa
SCHEMBL20164035
HY-107684
CS-0029172
(1r,9s)-5-bromo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
(1r,9s)-5-bromo-7,11-diazatricyclo[7.3.1.0?,?]trideca-2,4-dien-6-one
PD069997

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" In rodent, the compound displays high oral bioavailability and excellent brain penetration affording high levels of receptor occupancy and in vivo efficacy in auditory sensory gating and novel object recognition."( Discovery of 4-(5-methyloxazolo[4,5-b]pyridin-2-yl)-1,4-diazabicyclo[3.2.2]nonane (CP-810,123), a novel alpha 7 nicotinic acetylcholine receptor agonist for the treatment of cognitive disorders in schizophrenia: synthesis, SAR development, and in vivo eff
Bronk, BS; Bryce, DK; Coe, JW; Cook, KK; Duplantier, AJ; Evrard, E; Hajós, M; Hoffmann, WE; Hurst, RS; Maklad, N; Mather, RJ; McLean, S; Nedza, FM; O'Donnell, CJ; O'Neill, BT; Peng, L; Qian, W; Rogers, BN; Rottas, MM; Sands, SB; Schmidt, AW; Shrikhande, AV; Spracklin, DK; Wong, DF; Zhang, A; Zhang, L, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Neuronal acetylcholine receptor subunit alpha-4Rattus norvegicus (Norway rat)IC50 (µMol)0.00030.00030.30952.3000AID484912
Neuronal acetylcholine receptor subunit beta-2Rattus norvegicus (Norway rat)IC50 (µMol)0.00030.00030.32092.3000AID484912
Neuronal acetylcholine receptor subunit beta-4Homo sapiens (human)IC50 (µMol)0.01560.00181.67796.5000AID460748
Neuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)IC50 (µMol)0.01560.00181.31326.5000AID431144; AID460748
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (23)

Processvia Protein(s)Taxonomy
monoatomic ion transportNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
smooth muscle contractionNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
regulation of smooth muscle contractionNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
signal transductionNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
synaptic transmission, cholinergicNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
locomotory behaviorNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
neuronal action potentialNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
monoatomic ion transmembrane transportNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
behavioral response to nicotineNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
regulation of neurotransmitter secretionNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
positive regulation of transmission of nerve impulseNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
synaptic transmission involved in micturitionNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
chemical synaptic transmissionNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
acetylcholine receptor signaling pathwayNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
membrane depolarizationNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
monoatomic ion transportNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
regulation of smooth muscle contractionNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
signal transductionNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
activation of transmembrane receptor protein tyrosine kinase activityNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
synaptic transmission, cholinergicNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
nervous system developmentNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
locomotory behaviorNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
regulation of acetylcholine secretion, neurotransmissionNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
monoatomic ion transmembrane transportNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
behavioral response to nicotineNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
regulation of membrane potentialNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
regulation of dendrite morphogenesisNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
synaptic transmission involved in micturitionNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
acetylcholine receptor signaling pathwayNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
response to acetylcholineNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
response to nicotineNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
membrane depolarizationNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
protein bindingNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
ligand-gated monoatomic ion channel activityNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
acetylcholine receptor activityNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
acetylcholine-gated monoatomic cation-selective channel activityNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
protein bindingNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
ligand-gated monoatomic ion channel activityNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
acetylcholine receptor activityNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
acetylcholine-gated monoatomic cation-selective channel activityNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
acetylcholine bindingNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
plasma membraneNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
membraneNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
specific granule membraneNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
postsynaptic membraneNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
tertiary granule membraneNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
cholinergic synapseNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
acetylcholine-gated channel complexNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
plasma membraneNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
neuron projectionNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
synapseNeuronal acetylcholine receptor subunit beta-4Homo sapiens (human)
endoplasmic reticulumNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
Golgi apparatusNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
plasma membraneNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
postsynaptic densityNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
membraneNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
nuclear speckNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
dendriteNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
neuronal cell bodyNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
plasma membrane raftNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
postsynaptic membraneNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
acetylcholine-gated channel complexNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
neuron projectionNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
synapseNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
plasma membraneNeuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID527075Displacement of [125I]alpha-Bungarotoxin from alpha7 nAchR in rat brain cell membrane2010Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
Identification of 9-fluoro substituted (-)-cytisine derivatives as ligands with high affinity for nicotinic receptors.
AID242877Maximal response against Nicotinic acetylcholine receptor alpha4-beta22005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Neuronal nicotinic acetylcholine receptors: structural revelations, target identifications, and therapeutic inspirations.
AID484912Displacement of [3H]epibatidine from rat alpha4beta2 nAChR2010Bioorganic & medicinal chemistry letters, Jun-15, Volume: 20, Issue:12
In silico characterization of cytisinoids docked into an acetylcholine binding protein.
AID431144Displacement of [3H]epibatidine from alpha3 nAChR in human IMR32 cells2009Bioorganic & medicinal chemistry letters, Aug-15, Volume: 19, Issue:16
Synthesis and SAR studies of 1,4-diazabicyclo[3.2.2]nonane phenyl carbamates--subtype selective, high affinity alpha7 nicotinic acetylcholine receptor agonists.
AID242872Maximal response against Nicotinic acetylcholine receptor alpha 72005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Neuronal nicotinic acetylcholine receptors: structural revelations, target identifications, and therapeutic inspirations.
AID242878Maximal response against Nicotinic acetylcholine receptor alpha4-beta42005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
Neuronal nicotinic acetylcholine receptors: structural revelations, target identifications, and therapeutic inspirations.
AID460748Displacement of [3H]epibatidine from alpha3beta4 nAChR expressed in IMR32 cells2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Discovery of 4-(5-methyloxazolo[4,5-b]pyridin-2-yl)-1,4-diazabicyclo[3.2.2]nonane (CP-810,123), a novel alpha 7 nicotinic acetylcholine receptor agonist for the treatment of cognitive disorders in schizophrenia: synthesis, SAR development, and in vivo eff
AID527074Displacement of [3H]cytisine from rat alpha4beta2 nAChR in rat brain cell membrane2010Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
Identification of 9-fluoro substituted (-)-cytisine derivatives as ligands with high affinity for nicotinic receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (50.00)29.6817
2010's4 (40.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (10.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]