Page last updated: 2024-11-06

centbutindole

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

Description

centbutindole: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID68663
CHEMBL ID136711
CHEBI ID135615
SCHEMBL ID635469
MeSH IDM0119166

Synonyms (32)

Synonym
nsc 143691
biriperonum [latin]
butyrophenone, 4'-fluoro-4-(1,2,3,4,6,7,12,12a-octahydropyrazino(1',2':1,6)pyrido(3,4-b)indol-2-yl)-
biriperone [inn]
biriperona [spanish]
(+-)-4'-fluoro-4-(3,4,6,7,12,12a-hexahydropyrazino(1',2':1,6)pyrido(3,4-b)indol-2(1h)-yl)butyrophenone
einecs 255-629-5
pyrazino(1',2':1,6)pyrido(3,4-b)indole, 1,2,3,4,6,7,12,12a-octahydro-2-(3-(p-fluorobenzoyl)propyl)-, dl-
(1)-1-(4-fluorophenyl)-4-(3,4,6,7,12,12a-hexahydropyrazino(1',2':1,6)pyrido(3,4-b)indol-2(1h)-yl)butan-1-one
biriperone
centbutindole
41510-23-0
nsc143691
nsc-143691
CHEBI:135615
bdbm50133931
1-(4-fluoro-phenyl)-4-(3,4,6,7,12,12a-hexahydro-1h-pyrazino[1'',2'':1,6]pyrido[3,4-b]indol-2-yl)-butan-1-one
CHEMBL136711 ,
biriperona
5776hbv7ud ,
unii-5776hbv7ud
biriperonum
42021-34-1
(+/-)-4'-fluoro-4-(3,4,6,7,12,12a-hexahydropyrazino(1',2':1,6)pyrido(3,4-b)indol-2(1h)-yl)butyrophenone
biriperone [mart.]
SCHEMBL635469
DTXSID60866048
Q27261482
1-(4-fluorophenyl)-4-(3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraen-6-yl)butan-1-one
(+/-)-1-(4-fluorophenyl)-4-(3,4,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indol-2(1h)-yl)-1-butanone
2-[4-(4-fluorophenyl)-4-oxobutyl]-1,2,3,4,6,7,12,12a-octahydropyrazino[2',1':6,1]pyrido[3,4-b]indole
(+/-)-1-(4-fluorophenyl)-4-(3,4,6,7,12,12a-hexahydropyrazino[1',2'

Research Excerpts

Overview

Centbutindole is a new neuroleptic drug having a pharmacological profile similar to haloperidol. It does not cause hypothermia and has a higher separation between doses causing catalepsy and neurolepsy.

ExcerptReferenceRelevance
"Centbutindole is a new neuroleptic drug having a pharmacological profile similar to haloperidol, but it does not cause hypothermia and has a higher separation between doses causing catalepsy and neurolepsy. "( Differential alteration in striatal dopaminergic and cortical serotonergic receptors induced by repeated administration of haloperidol or centbutindole in rats.
Dhawan, BN; Gulati, A; Srimal, RC, 1988
)
1.92

Dosage Studied

ExcerptRelevanceReference
" and oral dosing in rats."( Pharmacokinetics, in-situ absorption and protein binding studies of a new neuroleptic agent centbutindole in rats.
Gupta, RC; Issar, M; Mishra, B; Singh, SK, 2003
)
0.54
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
beta-carbolinesAny pyridoindole containing a beta-carboline skeleton and their hydrogenated 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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
D(3) dopamine receptorHomo sapiens (human)Ki0.01100.00000.602010.0000AID65134
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (40)

Processvia Protein(s)Taxonomy
response to ethanolD(3) dopamine receptorHomo sapiens (human)
synaptic transmission, dopaminergicD(3) dopamine receptorHomo sapiens (human)
G protein-coupled receptor internalizationD(3) dopamine receptorHomo sapiens (human)
intracellular calcium ion homeostasisD(3) dopamine receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayD(3) dopamine receptorHomo sapiens (human)
adenylate cyclase-activating dopamine receptor signaling pathwayD(3) dopamine receptorHomo sapiens (human)
adenylate cyclase-inhibiting dopamine receptor signaling pathwayD(3) dopamine receptorHomo sapiens (human)
learning or memoryD(3) dopamine receptorHomo sapiens (human)
learningD(3) dopamine receptorHomo sapiens (human)
locomotory behaviorD(3) dopamine receptorHomo sapiens (human)
visual learningD(3) dopamine receptorHomo sapiens (human)
response to xenobiotic stimulusD(3) dopamine receptorHomo sapiens (human)
regulation of dopamine secretionD(3) dopamine receptorHomo sapiens (human)
positive regulation of cytokinesisD(3) dopamine receptorHomo sapiens (human)
circadian regulation of gene expressionD(3) dopamine receptorHomo sapiens (human)
response to histamineD(3) dopamine receptorHomo sapiens (human)
social behaviorD(3) dopamine receptorHomo sapiens (human)
response to cocaineD(3) dopamine receptorHomo sapiens (human)
dopamine metabolic processD(3) dopamine receptorHomo sapiens (human)
response to morphineD(3) dopamine receptorHomo sapiens (human)
negative regulation of blood pressureD(3) dopamine receptorHomo sapiens (human)
positive regulation of mitotic nuclear divisionD(3) dopamine receptorHomo sapiens (human)
acid secretionD(3) dopamine receptorHomo sapiens (human)
behavioral response to cocaineD(3) dopamine receptorHomo sapiens (human)
negative regulation of oligodendrocyte differentiationD(3) dopamine receptorHomo sapiens (human)
arachidonic acid secretionD(3) dopamine receptorHomo sapiens (human)
negative regulation of protein secretionD(3) dopamine receptorHomo sapiens (human)
musculoskeletal movement, spinal reflex actionD(3) dopamine receptorHomo sapiens (human)
regulation of dopamine uptake involved in synaptic transmissionD(3) dopamine receptorHomo sapiens (human)
negative regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionD(3) dopamine receptorHomo sapiens (human)
prepulse inhibitionD(3) dopamine receptorHomo sapiens (human)
positive regulation of dopamine receptor signaling pathwayD(3) dopamine receptorHomo sapiens (human)
negative regulation of adenylate cyclase activityD(3) dopamine receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayD(3) dopamine receptorHomo sapiens (human)
negative regulation of voltage-gated calcium channel activityD(3) dopamine receptorHomo sapiens (human)
regulation of potassium ion transportD(3) dopamine receptorHomo sapiens (human)
phospholipase C-activating dopamine receptor signaling pathwayD(3) dopamine receptorHomo sapiens (human)
positive regulation of MAPK cascadeD(3) dopamine receptorHomo sapiens (human)
negative regulation of cytosolic calcium ion concentrationD(3) dopamine receptorHomo sapiens (human)
negative regulation of synaptic transmission, glutamatergicD(3) dopamine receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
dopamine neurotransmitter receptor activity, coupled via Gi/GoD(3) dopamine receptorHomo sapiens (human)
protein bindingD(3) dopamine receptorHomo sapiens (human)
G protein-coupled receptor activityD(3) dopamine receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
plasma membraneD(3) dopamine receptorHomo sapiens (human)
synapseD(3) dopamine receptorHomo sapiens (human)
plasma membraneD(3) dopamine receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID301872Blockade of conditioned avoidance response in ip dosed rat2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Rational design, synthesis and evaluation of (6aR( *),11bS( *))-1-(4-fluorophenyl)-4-{7-[4-(4-fluorophenyl)-4-oxobutyl]1,2,3,4,6,6a,7,11b,12,12a(RS)-decahydropyrazino[2',1':6,1]pyrido[3,4-b]indol-2-yl}-butan-1-one as a potential neuroleptic agent.
AID301868Selectivity ratio of pKi for rat brain 5HT2A receptor to pKi for rat brain dopamine D2 receptor2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Rational design, synthesis and evaluation of (6aR( *),11bS( *))-1-(4-fluorophenyl)-4-{7-[4-(4-fluorophenyl)-4-oxobutyl]1,2,3,4,6,6a,7,11b,12,12a(RS)-decahydropyrazino[2',1':6,1]pyrido[3,4-b]indol-2-yl}-butan-1-one as a potential neuroleptic agent.
AID301866Displacement of [3H]spiperone from dopamine D2 receptor in rat brain2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Rational design, synthesis and evaluation of (6aR( *),11bS( *))-1-(4-fluorophenyl)-4-{7-[4-(4-fluorophenyl)-4-oxobutyl]1,2,3,4,6,6a,7,11b,12,12a(RS)-decahydropyrazino[2',1':6,1]pyrido[3,4-b]indol-2-yl}-butan-1-one as a potential neuroleptic agent.
AID301870Antagonism of amphetamine-induced toxicity in ip dosed mouse2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Rational design, synthesis and evaluation of (6aR( *),11bS( *))-1-(4-fluorophenyl)-4-{7-[4-(4-fluorophenyl)-4-oxobutyl]1,2,3,4,6,6a,7,11b,12,12a(RS)-decahydropyrazino[2',1':6,1]pyrido[3,4-b]indol-2-yl}-butan-1-one as a potential neuroleptic agent.
AID301876Ratio of ED50 for cataleptic activity in rat to ED50 for conditioned avoidance response in rat2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Rational design, synthesis and evaluation of (6aR( *),11bS( *))-1-(4-fluorophenyl)-4-{7-[4-(4-fluorophenyl)-4-oxobutyl]1,2,3,4,6,6a,7,11b,12,12a(RS)-decahydropyrazino[2',1':6,1]pyrido[3,4-b]indol-2-yl}-butan-1-one as a potential neuroleptic agent.
AID301867Displacement of [3H]ketanserin from 5HT2A receptor in rat brain2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Rational design, synthesis and evaluation of (6aR( *),11bS( *))-1-(4-fluorophenyl)-4-{7-[4-(4-fluorophenyl)-4-oxobutyl]1,2,3,4,6,6a,7,11b,12,12a(RS)-decahydropyrazino[2',1':6,1]pyrido[3,4-b]indol-2-yl}-butan-1-one as a potential neuroleptic agent.
AID301874Effect on locomotor activity in ip dosed mouse assessed as motor deficit by rota rod test2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Rational design, synthesis and evaluation of (6aR( *),11bS( *))-1-(4-fluorophenyl)-4-{7-[4-(4-fluorophenyl)-4-oxobutyl]1,2,3,4,6,6a,7,11b,12,12a(RS)-decahydropyrazino[2',1':6,1]pyrido[3,4-b]indol-2-yl}-butan-1-one as a potential neuroleptic agent.
AID301875Cataleptic activity in ip dosed rat2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Rational design, synthesis and evaluation of (6aR( *),11bS( *))-1-(4-fluorophenyl)-4-{7-[4-(4-fluorophenyl)-4-oxobutyl]1,2,3,4,6,6a,7,11b,12,12a(RS)-decahydropyrazino[2',1':6,1]pyrido[3,4-b]indol-2-yl}-butan-1-one as a potential neuroleptic agent.
AID301869Reduction of amphetamine-induced hyperactivity in ip dosed mouse2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Rational design, synthesis and evaluation of (6aR( *),11bS( *))-1-(4-fluorophenyl)-4-{7-[4-(4-fluorophenyl)-4-oxobutyl]1,2,3,4,6,6a,7,11b,12,12a(RS)-decahydropyrazino[2',1':6,1]pyrido[3,4-b]indol-2-yl}-butan-1-one as a potential neuroleptic agent.
AID301865Displacement of [3H]SCH-23390 from dopamine D1 receptor in rat brain2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Rational design, synthesis and evaluation of (6aR( *),11bS( *))-1-(4-fluorophenyl)-4-{7-[4-(4-fluorophenyl)-4-oxobutyl]1,2,3,4,6,6a,7,11b,12,12a(RS)-decahydropyrazino[2',1':6,1]pyrido[3,4-b]indol-2-yl}-butan-1-one as a potential neuroleptic agent.
AID301871Blockade of secondary conditioned avoidance response in ip dosed rat2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Rational design, synthesis and evaluation of (6aR( *),11bS( *))-1-(4-fluorophenyl)-4-{7-[4-(4-fluorophenyl)-4-oxobutyl]1,2,3,4,6,6a,7,11b,12,12a(RS)-decahydropyrazino[2',1':6,1]pyrido[3,4-b]indol-2-yl}-butan-1-one as a potential neuroleptic agent.
AID301873Blockade of unconditioned avoidance response in ip dosed rat2007Bioorganic & medicinal chemistry, Dec-01, Volume: 15, Issue:23
Rational design, synthesis and evaluation of (6aR( *),11bS( *))-1-(4-fluorophenyl)-4-{7-[4-(4-fluorophenyl)-4-oxobutyl]1,2,3,4,6,6a,7,11b,12,12a(RS)-decahydropyrazino[2',1':6,1]pyrido[3,4-b]indol-2-yl}-butan-1-one as a potential neuroleptic agent.
AID65134Ability to compete with [3H]YM-09151-2 binding to the human dopamine receptor D3 transfected in CHO cells2003Journal of medicinal chemistry, Oct-09, Volume: 46, Issue:21
Molecular modeling of the three-dimensional structure of dopamine 3 (D3) subtype receptor: discovery of novel and potent D3 ligands through a hybrid pharmacophore- and structure-based database searching approach.
[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-19903 (27.27)18.7374
1990's2 (18.18)18.2507
2000's6 (54.55)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (9.09%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]