Page last updated: 2024-12-07

bicuculline methochloride

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

Description

Bicuculline methochloride is a synthetic derivative of the natural product bicuculline. It is a potent and selective antagonist of GABA(A) receptors, which are important for inhibitory neurotransmission in the brain. Bicuculline methochloride is used as a research tool to study the role of GABA(A) receptors in various physiological and pathological processes, including anxiety, epilepsy, and sleep. The compound is typically synthesized by reacting bicuculline with methyl iodide. Its effects include inducing seizures, blocking GABAergic inhibition, and enhancing neuronal excitability. It is studied because it provides valuable insights into the mechanisms of GABAergic neurotransmission and the role of GABA(A) receptors in various brain functions and disorders. The compound's importance lies in its ability to dissect the complex interplay of GABAergic signaling in the brain, facilitating the development of new therapeutic strategies for neurological conditions.'

bicuculline methochloride: guaternary analog of bicuculline; specific GABA antagonist in spinal cord; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10047593
MeSH IDM0049471
PubMed CID104872
CHEMBL ID558625
CHEMBL ID515679
MeSH IDM0049471

Synonyms (36)

Synonym
HMS3266A09
bicuculline methochloride
1,3-dioxolo(4,5-g)isoquinolinium, 5-(6,8-dihydro-8-oxofuro(3,4-e)-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-, chloride, (r-(r*,s*))-
n-methylbicuculline
n-me-bicuculline
unii-i3une1k4af
i3une1k4af ,
38641-83-7
bisculline methyl chloride
1(s),9(r)-(-)-bicuculline methchloride
[r-(r*,s*)]-5-(6,8-dihydro-8-oxofuro[3,4-e]-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-1,3-dioxolo[4,5-g]isoquinolinium chloride
AKOS024456521
1(s),9(r)-(-)-bicuculline methchloride, >=97% (hplc), powder
DTXSID90191956
HMS3678D21
(6r)-6-[(5s)-6,6-dimethyl-7,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolin-6-ium-5-yl]-6h-furo[3,4-g][1,3]benzodioxol-8-one;chloride
HMS3414D21
Q27280354
bicuculline (methochloride)
HY-137790
CS-0141957
FS-8036
LOPAC0_000176
NCGC00023413-03
NCGC00023413-04
CHEMBL558625 ,
CHEMBL515679
CCG-204271
J94 ,
(5s)-6,6-dimethyl-5-[(6r)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl]-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-6-ium
bdbm50377980
cid_104871
(6r)-6-[(5s)-6,6-dimethyl-7,8-dihydro-5h-[1,3]dioxol[4,5-g]isoquinolin-6-ium-5-yl]-6h-furo[3,4-g][1,3]benzodioxol-8-one;iodide
bdbm83106
Q27461657
bicuculline-methochloride-(-)

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Bicuculline 1 microM shifted the dose-response curve of GABA to the right and the excitatory effect was also enhanced."( Excitatory and inhibitory action of GABA on synaptic transmission in slices of guinea pig superior colliculus.
Arakawa, T; Okada, Y, 1988
)
0.27
" The dose-response relationship pooled from nine progenitor cells was best fit by a logistic function of EC50=113 microM and Hill coefficient=0."( Properties of GABA(A) receptors in cultured rat oligodendrocyte progenitor cells.
Grant, AL; Mellor, JR; Randall, AD; Williamson, AV, 1998
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
thioredoxin reductaseRattus norvegicus (Norway rat)Potency8.43680.100020.879379.4328AID488773; AID588453
regulator of G-protein signaling 4Homo sapiens (human)Potency0.00530.531815.435837.6858AID504845
arylsulfatase AHomo sapiens (human)Potency0.75691.069113.955137.9330AID720538
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency5.97280.035520.977089.1251AID504332
ATP-dependent phosphofructokinaseTrypanosoma brucei brucei TREU927Potency37.93300.060110.745337.9330AID485368
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Amine oxidase [flavin-containing] A Rattus norvegicus (Norway rat)IC50 (µMol)7.00000.00071.979812.5000AID346946
Small conductance calcium-activated potassium channel protein 3Rattus norvegicus (Norway rat)IC50 (µMol)7.00000.00151.68587.0000AID346946
Small conductance calcium-activated potassium channel protein 3Rattus norvegicus (Norway rat)Ki4.40000.00182.13265.9000AID346945
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID346945Displacement of [I125]apamine from Wistar rat recombinant SK3 channel expressed in HEK293 cells2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Synthesis and structure-activity relationship studies of 2-(N-substituted)-aminobenzimidazoles as potent negative gating modulators ofsmall conductance Ca2+-activated K+ channels.
AID346946Inhibition of Wistar rat recombinant SK3 channel expressed in HEK293 cells by whole cell patch clamp technique2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
Synthesis and structure-activity relationship studies of 2-(N-substituted)-aminobenzimidazoles as potent negative gating modulators ofsmall conductance Ca2+-activated K+ channels.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347410qHTS for inhibitors of adenylyl cyclases using a fission yeast platform: a pilot screen against the NCATS LOPAC library2019Cellular signalling, 08, Volume: 60A fission yeast platform for heterologous expression of mammalian adenylyl cyclases and high throughput screening.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
AID504836Inducers of the Endoplasmic Reticulum Stress Response (ERSR) in human glioma: Validation2002The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.
AID1347050Natriuretic polypeptide receptor (hNpr2) antagonism - Pilot subtype selectivity assay2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347059CD47-SIRPalpha protein protein interaction - Alpha assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347151Optimization of GU AMC qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID588378qHTS for Inhibitors of ATXN expression: Validation
AID1347405qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS LOPAC collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347049Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot screen2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347058CD47-SIRPalpha protein protein interaction - HTRF assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347045Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot counterscreen GloSensor control cell line2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347057CD47-SIRPalpha protein protein interaction - LANCE assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (63)

TimeframeStudies, This Drug (%)All Drugs %
pre-199023 (36.51)18.7374
1990's14 (22.22)18.2507
2000's10 (15.87)29.6817
2010's10 (15.87)24.3611
2020's6 (9.52)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.18

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 Index20.18 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index5.03 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.18)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other53 (100.00%)84.16%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]