Compounds > n,n'-dicyclopentyl-2-methylsulfanyl-5-nitro-pyrimidine-4,6-diamine
Page last updated: 2024-12-11

n,n'-dicyclopentyl-2-methylsulfanyl-5-nitro-pyrimidine-4,6-diamine

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Description

N,N'-dicyclopentyl-2-methylsulfanyl-5-nitro-pyrimidine-4,6-diamine: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6604928
CHEMBL ID392394
CHEBI ID93326
SCHEMBL ID3578392
MeSH IDM0455037

Synonyms (43)

Synonym
HMS3268D17
BRD-K75478907-001-01-5
tocris-2001
NCGC00025340-01 ,
PDSP2_000399
PDSP1_000401
NCGC00025340-02
CHEMBL392394
gs-39783
4-n,6-n-dicyclopentyl-2-methylsulfanyl-5-nitropyrimidine-4,6-diamine
gs39783
n,n'-dicyclopentyl-2-methylsulfanyl-5-nitro-pyrimidine-4,6-diamine
cas_39069-52-8
bdbm86283
pseudoephedrine,(+)
cas_345-78-8
gs 39783
n,n'-dicyclopentyl-2-(methylthio)-5- nitro-4,6-pyrimidinediamine
39069-52-8
gtpl5446
4-n,6-n-dicyclopentyl-2-(methylsulfanyl)-5-nitropyrimidine-4,6-diamine
SCHEMBL3578392
n,n'-dicyclopentyl-2-(methylthio)-5-nitro-4,6-pyrimidinediamine
n4,n6-dicyclopentyl-2-(methylthio)-5-nitropyrimidine-4,6-diamine
DTXSID30424992
n4,n6-dicyclopentyl-2-(methylthio)-5-nitro-4,6-pyrimidinediamine
AKOS024456904
hd3t22a5dm ,
unii-hd3t22a5dm
sr-01000597525
SR-01000597525-1
CHEBI:93326
gs39783, >=98% (hplc)
Q5514522
HMS3677A11
HMS3413A11
SB58749
n~4~,n~6~-dicyclopentyl-2-(methylsulfanyl)-5-nitropyrimidine-4,6-diamine
QDA ,
HY-103475
4,6-pyrimidinediamine, n4,n6-dicyclopentyl-2-(methylthio)-5-nitro-
c15h23n5o2s
AKOS040745200

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Overall, the data obtained here suggest that positive modulation of GABAB receptors may serve as a novel therapeutic strategy for the development of anxiolytics, with a superior side effect profile to both baclofen and benzodiazepines."( Behavioral characterization of the novel GABAB receptor-positive modulator GS39783 (N,N'-dicyclopentyl-2-methylsulfanyl-5-nitro-pyrimidine-4,6-diamine): anxiolytic-like activity without side effects associated with baclofen or benzodiazepines.
Bettler, B; Chaperon, F; Cryan, JF; Froestl, W; Gentsch, C; Kaupmann, K; Kelly, PH; Lingenhoehl, K; Mombereau, C; Spooren, WP, 2004)		0.55

Pharmacokinetics

ExcerptReferenceRelevance
" Baclofen is known to produce anticonvulsant effects in the DBA/2J mouse audiogenic seizure test (AGS), suggesting it may be a suitable assay for assessing pharmacodynamic effects."( Anticonvulsant effects of structurally diverse GABA(B) positive allosteric modulators in the DBA/2J audiogenic seizure test: Comparison to baclofen and utility as a pharmacodynamic screening model.
Brown, JW; Ma, J; Moeller, A; Nimmrich, V; Rueter, LE; Schmidt, M; Turner, SC; van der Kam, E; Zhang, M, 2016)		0.43

Bioavailability

ExcerptReferenceRelevance
" Across all schedules, CGP7930 was more effective at decreasing cocaine self-administration than GS39783, a finding that may be due to differences in bioavailability between the two drugs."( Effects of positive allosteric modulators of the GABAB receptor on cocaine self-administration in rats.
Froestl, W; Liu, Y; Morgan, D; Roberts, DC; Smith, MA; Yancey, DL, 2004)		0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aryl sulfideAny organic sulfide in which the sulfur is attached to at least one aromatic group.
[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 (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency0.89130.004023.8416100.0000AID485290
USP1 protein, partialHomo sapiens (human)Potency15.84890.031637.5844354.8130AID504865
cytochrome P450 2C19 precursorHomo sapiens (human)Potency5.01190.00255.840031.6228AID899
cytochrome P450 2C9 precursorHomo sapiens (human)Potency1.99530.00636.904339.8107AID883
lethal factor (plasmid)Bacillus anthracis str. A2012Potency10.00000.020010.786931.6228AID912
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency1.99530.00638.235039.8107AID883
[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)
Gamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)EC50 (µMol)0.74130.53001.87365.3700AID301941
Gamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)EC50 (µMol)0.41040.07941.62765.3700AID1474762; AID301941
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
negative regulation of adenylate cyclase activityGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
gamma-aminobutyric acid signaling pathwayGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
chemical synaptic transmissionGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
synaptic transmission, GABAergicGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
neuron-glial cell signalingGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
osteoblast differentiationGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
gamma-aminobutyric acid signaling pathwayGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
negative regulation of cell population proliferationGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
positive regulation of glutamate secretionGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
negative regulation of gamma-aminobutyric acid secretionGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
negative regulation of epinephrine secretionGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
negative regulation of dopamine secretionGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
response to nicotineGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
response to ethanolGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
negative regulation of synaptic transmissionGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
synaptic transmission, GABAergicGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
regulation of postsynaptic membrane potentialGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
positive regulation of growth hormone secretionGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
regulation of presynaptic membrane potentialGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
neuron-glial cell signalingGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
G protein-coupled GABA receptor activityGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
protein bindingGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
protein heterodimerization activityGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
transmembrane signaling receptor activityGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
G protein-coupled GABA receptor activityGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
G protein-coupled GABA receptor activityGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
protein bindingGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
protein heterodimerization activityGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
G protein-coupled neurotransmitter receptor activity involved in regulation of postsynaptic membrane potentialGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
G protein-coupled neurotransmitter receptor activity involved in regulation of presynaptic membrane potentialGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
extracellular matrix protein bindingGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (19)

Processvia Protein(s)Taxonomy
cytoplasmGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
plasma membraneGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
neuron projectionGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
postsynaptic membraneGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
G protein-coupled GABA receptor complexGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
G protein-coupled receptor heterodimeric complexGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
GABA receptor complexGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
extracellular spaceGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
endoplasmic reticulum membraneGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
plasma membraneGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
synaptic vesicleGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
axolemmaGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
mitochondrial membraneGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
presynaptic membraneGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
neuronal cell bodyGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
dendritic spineGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
dendritic shaftGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
postsynaptic membraneGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
Schaffer collateral - CA1 synapseGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
glutamatergic synapseGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
GABA-ergic synapseGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
G protein-coupled GABA receptor complexGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
G protein-coupled receptor heterodimeric complexGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (33)

Assay IDTitleYearJournalArticle
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.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings 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.
AID737346Hypnotic effect in DBA mouse assessed as increase in baclofen-induced duration of loss of righting reflex at 100 to 300 mg/kg, ip incubated for 30 mins prior to baclofen-challenge relative to vehicle-treated control2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID737353Hypnotic effect in DBA mouse assessed as potentiation of baclofen-induced loss of righting reflex at 30 mg/kg, ip incubated for 30 mins prior to baclofen-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID737344Hypnotic effect in DBA mouse assessed as reduction in baclofen-induced onset of loss of righting reflex over 10 mg/kg, ip incubated for 30 mins prior to baclofen-challenge relative to vehicle-treated control2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID301940Activity at GABAB 1b/2 receptor expressed in CHO-K1 cells assessed as effect on glutamate-induced [35S]GTP-gamma-S binding at 25 uM2007Bioorganic & medicinal chemistry letters, Nov-15, Volume: 17, Issue:22
Syntheses and optimization of new GS39783 analogues as positive allosteric modulators of GABA B receptors.
AID741679Hypnotic effect in DBA mouse assessed as increase in pentobarbital-induced duration of loss of righting reflex at 30 mg/kg, ip incubated for 30 mins prior to pentobarbital-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID741682Hypnotic effect in DBA mouse assessed as reduction in pentobarbital-induced onset of loss of righting reflex at 30 mg/kg, ip incubated for 30 mins prior to pentobarbital-challenge (Rvb = 60.0 +/- 0.0 min)2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID301941Activity at GABAB 1b/2 receptor expressed in CHO-K1 cells assessed as effect on glutamate-induced [35S]GTP-gamma-S binding2007Bioorganic & medicinal chemistry letters, Nov-15, Volume: 17, Issue:22
Syntheses and optimization of new GS39783 analogues as positive allosteric modulators of GABA B receptors.
AID737352Hypnotic effect in ip dosed DBA mouse assessed as reduction in baclofen-induced onset of loss of righting reflex incubated 30 mins prior to baclofen-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID301939Activity at GABAB 1b/2 receptor expressed in CHO-K1 cells assessed as effect on glutamate-induced [35S]GTP-gamma-S binding at 2.5 uM2007Bioorganic & medicinal chemistry letters, Nov-15, Volume: 17, Issue:22
Syntheses and optimization of new GS39783 analogues as positive allosteric modulators of GABA B receptors.
AID737349Hypnotic effect in DBA mouse assessed as potentiation of baclofen-induced loss of righting reflex at 100 mg/kg, ip incubated for 30 mins prior to baclofen-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID737354Hypnotic effect in DBA mouse assessed as potentiation of baclofen-induced loss of righting reflex at 10 mg/kg, ip incubated for 30 mins prior to baclofen-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID737367Positive allosteric modulation of GABAB receptor in rat cortical membranes assessed as potentiation of GABA-induced [35S]GTPgammaS binding at 10 uM after 30 mins by liquid scintillation counting analysis relative to GABA2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID741687Hypnotic effect in DBA mouse assessed as reduction in baclofen-induced onset of loss of righting reflex at 300 mg/kg, ig incubated for 30 mins prior to baclofen-challenge relative to vehicle-treated control2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID301942Activity at GABAB 1b/2 receptor expressed in CHO-K1 cells assessed as effect on glutamate-induced [35S]GTP-gamma-S binding in presence of 1 uM GABA2007Bioorganic & medicinal chemistry letters, Nov-15, Volume: 17, Issue:22
Syntheses and optimization of new GS39783 analogues as positive allosteric modulators of GABA B receptors.
AID737363Cytotoxicity against mouse NIH/3T3 cells after 24 hrs by neutral red staining-based UV/visible spectrophotometric analysis2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID1474763Positive allosteric modulation at human GABA-B1 expressed in CHO-K1 cell membranes co-expressing rat GABA-B2 assessed as potentiation of GABA-induced reduction in [3H]-CGP62349 binding to GABA-B1 receptor at 0.3 uM measured after 20 mins in presence of 0.2017Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11
Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective.
AID737350Hypnotic effect in ip dosed DBA mouse assessed as increase in baclofen-induced duration of loss of righting reflex incubated for 30 mins prior to baclofen-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID741686Hypnotic effect in DBA mouse assessed as potentiation of pentobarbital-induced loss of righting reflex at 30 mg/kg, ip incubated for 30 mins prior to pentobarbital-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID741678Hypnotic effect in DBA mouse assessed as increase in pentobarbital-induced duration of loss of righting reflex at 100 mg/kg, ip incubated for 30 mins prior to pentobarbital-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID1237987Positive allosteric modulator activity at GABA-B receptor (unknown origin) assessed as potentiation of GABA-induced [35S]GTPgammaS binding2015Journal of medicinal chemistry, Aug-27, Volume: 58, Issue:16
Activation of the γ-Aminobutyric Acid Type B (GABA(B)) Receptor by Agonists and Positive Allosteric Modulators.
AID741684Hypnotic effect in DBA mouse assessed as potentiation of pentobarbital-induced loss of righting reflex at 300 mg/kg, ip incubated for 30 mins prior to pentobarbital-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID737341Hypnotic effect in DBA mouse assessed as increase in baclofen-induced duration of loss of righting reflex at 300 mg/kg, ig incubated for 30 mins prior to baclofen-challenge relative to vehicle-treated control2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID741681Hypnotic effect in DBA mouse assessed as reduction in pentobarbital-induced onset of loss of righting reflex at 100 mg/kg, ip incubated for 30 mins prior to pentobarbital-challenge (Rvb = 60.0 +/- 0.0 min)2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID741677Hypnotic effect in DBA mouse assessed as increase in pentobarbital-induced duration of loss of righting reflex at 300 mg/kg, ip incubated for 30 mins prior to pentobarbital-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID741680Hypnotic effect in DBA mouse assessed as reduction in pentobarbital-induced onset of loss of righting reflex at 300 mg/kg, ip incubated for 30 mins prior to pentobarbital-challenge (Rvb = 60.0 +/- 0.0 min)2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID737355Hypnotic effect in DBA mouse assessed as potentiation of baclofen-induced loss of righting reflex at 3 mg/kg, ip incubated for 30 mins prior to baclofen-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID1474761Positive allosteric modulation at human GABA-B 1b expressed in CHO cells co-expressing rat GABA-B2 assessed as potentiation of GABA-induced inhibition of 7beta forskolin-stimulated cyclic AMP formation at 10 uM after 2 hrs in presence of 0.3 uM GABA relat2017Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11
Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective.
AID1474762Positive allosteric modulation at human GABA-B 1b expressed in CHO cells co-expressing rat GABA-B2 assessed as potentiation of GABA-induced inhibition of 7beta forskolin-stimulated cyclic AMP formation after 2 hrs in presence of 0.3 uM GABA relative to 102017Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11
Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective.
AID741676Hypnotic effect in DBA mouse assessed as potentiation of baclofen-induced loss of righting reflex at 300 mg/kg, ig incubated for 30 mins prior to baclofen-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID737348Hypnotic effect in DBA mouse assessed as potentiation of baclofen-induced loss of righting reflex at 300 mg/kg, ip incubated for 30 mins prior to baclofen-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
AID741685Hypnotic effect in DBA mouse assessed as potentiation of pentobarbital-induced loss of righting reflex at 100 mg/kg, ip incubated for 30 mins prior to pentobarbital-challenge2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (46)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's18 (39.13)29.6817
2010's25 (54.35)24.3611
2020's3 (6.52)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.77

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 Index10.77 (24.57)
Research Supply Index3.87 (2.92)
Research Growth Index4.64 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.77)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (8.51%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other43 (91.49%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
gamma-aminobutyric acid
gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.		8.360amino acid zwitterion;
gamma-amino acid;
monocarboxylic acid		human metabolite;
neurotransmitter;
Saccharomyces cerevisiae metabolite;
signalling molecule
2-hydroxysaclofen
2-hydroxysaclofen: structure given in first source		2.0510organochlorine compound
baclofen
[no description available]		10.92180amino acid zwitterion;
gamma-amino acid;
monocarboxylic acid;
monochlorobenzenes;
primary amino compound		central nervous system depressant;
GABA agonist;
muscle relaxant
desipramine
Desipramine: A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.. desipramine : A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.		2.0210dibenzoazepine;
secondary amino compound		adrenergic uptake inhibitor;
alpha-adrenergic antagonist;
antidepressant;
cholinergic antagonist;
drug allergen;
EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
H1-receptor antagonist;
serotonin uptake inhibitor
amphetamine
Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.		2.4920primary amine
fluoxetine
Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.		2.0210(trifluoromethyl)benzenes;
aromatic ether;
secondary amino compound
fenclonine
Fenclonine: A selective and irreversible inhibitor of tryptophan hydroxylase, a rate-limiting enzyme in the biosynthesis of serotonin (5-HYDROXYTRYPTAMINE). Fenclonine acts pharmacologically to deplete endogenous levels of serotonin.		2.0210phenylalanine derivative
cyclohexanol
Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.		2.0710cyclohexanols;
secondary alcohol		solvent
thiophenes
Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.		2.2110mancude organic heteromonocyclic parent;
monocyclic heteroarene;
thiophenes;
volatile organic compound		non-polar solvent
cyclopentane
Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.		6.71410cycloalkane;
cyclopentanes;
volatile organic compound		non-polar solvent
oleanolic acid
[no description available]		2.1310hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
methamphetamine
Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.		2.0610amphetamines;
secondary amine		central nervous system stimulant;
environmental contaminant;
neurotoxin;
psychotropic drug;
xenobiotic
4-amino-3-phenylbutyric acid
4-amino-3-phenylbutyric acid: phenyl deriv of GABA; RN given refers to cpd without isomeric designation; structure		3.2110organonitrogen compound;
organooxygen compound
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		2.0710glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
Arbaclofen
[no description available]		3.2110organonitrogen compound;
organooxygen compound
colforsin
Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.		2.0310acetate ester;
cyclic ketone;
labdane diterpenoid;
organic heterotricyclic compound;
tertiary alpha-hydroxy ketone;
triol		adenylate cyclase agonist;
anti-HIV agent;
antihypertensive agent;
plant metabolite;
platelet aggregation inhibitor;
protein kinase A agonist
aripiprazole
Aripiprazole: A piperazine and quinolone derivative that is used primarily as an antipsychotic agent. It is a partial agonist of SEROTONIN RECEPTOR, 5-HT1A and DOPAMINE D2 RECEPTORS, where it also functions as a post-synaptic antagonist, and an antagonist of SEROTONIN RECEPTOR, 5-HT2A. It is used for the treatment of SCHIZOPHRENIA and BIPOLAR DISORDER, and as an adjunct therapy for the treatment of depression.. aripiprazole : An N-arylpiperazine that is piperazine substituted by a 4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]butyl group at position 1 and by a 2,3-dichlorophenyl group at position 4. It is an antipsychotic drug used for the treatment of Schizophrenia, and other mood disorders.		3.2510aromatic ether;
delta-lactam;
dichlorobenzene;
N-alkylpiperazine;
N-arylpiperazine;
quinolone		drug metabolite;
H1-receptor antagonist;
second generation antipsychotic;
serotonergic agonist
nicotine
(S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.		2.03103-(1-methylpyrrolidin-2-yl)pyridineanxiolytic drug;
biomarker;
immunomodulator;
mitogen;
neurotoxin;
nicotinic acetylcholine receptor agonist;
peripheral nervous system drug;
phytogenic insecticide;
plant metabolite;
psychotropic drug;
teratogenic agent;
xenobiotic
3-aminopropylphosphonic acid
3-aminopropylphosphonic acid: RN given refers to parent cpd; structure. (3-aminopropyl)phosphonic acid : A phosphonic acid in which the hydrogen attached to the phosphorus of phosphonic acid is substituted by a 3-aminopropyl group. It is a partial agonist of GABAB receptors.		3.2110phosphonic acids;
primary amino compound;
zwitterion		GABAB receptor agonist
cgp 35348
CGP 35348: antagonizes both GABA-A and GABA-B receptors		2.1310
saikosaponin d
[no description available]		2.1310
4-amino-3-(5-chloro-2-thienyl)butyric acid
4-amino-3-(5-chloro-2-thienyl)butyric acid: binds GABA receptors; RN & structure given in first source		3.2110
cgp 52432
[no description available]		2.0810dichlorobenzene
(3-(1-((3-(cyclohexylmethyl)hydroxyphosphinyl)-2-hydroxypropyl)amino)ethyl)benzoic acid
(3-(1-((3-(cyclohexylmethyl)hydroxyphosphinyl)-2-hydroxypropyl)amino)ethyl)benzoic acid: RN given for (mono-Li salt,(S-(R*,S*)))-isomer		2.4220
bifeprunox
bifeprunox: an antipsychotic agent		3.2510biphenyls
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		2.8130
cocaine
Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.		2.9540benzoate ester;
methyl ester;
tertiary amino compound;
tropane alkaloid		adrenergic uptake inhibitor;
central nervous system stimulant;
dopamine uptake inhibitor;
environmental contaminant;
local anaesthetic;
mouse metabolite;
plant metabolite;
serotonin uptake inhibitor;
sodium channel blocker;
sympathomimetic agent;
vasoconstrictor agent;
xenobiotic
3-amino-n-(4-methoxybenzyl)-4,6-dimethylthieno(2,3-b)pyridine-2-carboxamide
3-amino-N-(4-methoxybenzyl)-4,6-dimethylthieno(2,3-b)pyridine-2-carboxamide: structure in first source		2.2110
1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid: has been shown to exhibit unprecedented positive allosteric activity for ACh binding as well as inherent agonist activity at the M1 muscarinic receptor; structure in first source		3.2510
6-methyl-2-(phenylethynyl)pyridine
6-methyl-2-(phenylethynyl)pyridine: an mGlu5 antagonist. 2-methyl-6-(phenylethynyl)pyridine : A methylpyridine that coinsists of 2-methylp[yridine bearing an additional phenylethynyl group at position 6. Potent and highly selective non-competitive antagonist at the mGlu5 receptor subtype (IC50 = 36 nM) and a positive allosteric modulator at mGlu4 receptors. Centrally active following systemic administration in vivo. Reverses mechanical hyperalgesia in the inflamed rat hind paw.		2.0610acetylenic compound;
methylpyridines		anxiolytic drug;
metabotropic glutamate receptor antagonist
(r,s)-5,7-di-tert-butyl-3-hydroxy-3-trifluoromethyl-3h-benzofuran-2-one
(R,S)-5,7-di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one: a positive allosteric modulator of GABAB receptors; structure in first source		4.1340
3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol
3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol: (-)-CP-55,940 and (+)-CP-56,667 are enantiomers; RN refers to CP-55,940		2.0710alkylbenzene;
ring assembly
cgp 7930
2,6-di-tert-butyl-4-(3-hydroxy-2,2-dimethylpropyl)phenol: structure in first source		4.2450alkylbenzene
naloxone
Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.		2.2110morphinane alkaloid;
organic heteropentacyclic compound;
tertiary alcohol		antidote to opioid poisoning;
central nervous system depressant;
mu-opioid receptor antagonist
cgp 62349
[no description available]		2.0410
sch 50911
[no description available]		3.2110
dizocilpine maleate
Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.		2.1310maleate salt;
tetracyclic antidepressant		anaesthetic;
anticonvulsant;
neuroprotective agent;
nicotinic antagonist;
NMDA receptor antagonist
beta-escin
[no description available]		2.1310
cgp 56999a
CGP 56999A: structure given in first source		2.0310
ucb 34714
brivaracetam: A pyrrolidinone compound that is used to treat partial onset seizures in adult patients; structure in first source.. brivaracetam : A non-proteinogenic amino acid derivative that is butanamide in which the pro-S hydrogen at position 2 is replaced by a (4R)-2-oxo-4-propylpyrrolidin-1-yl. Used for treatment of partial onset seizures related to epilepsy.		3.3110gamma-lactam;
non-proteinogenic amino acid derivative		anticonvulsant
perampanel
perampanel : A member of the class of bipyridines that is 2,3'-bipyridin-6'-one substituted at positions 1' and 5' by phenyl and 2-cyanophenyl groups respectively. Used as an adjunctive therapy for the treatment of partial-onset seizures in patients with epilepsy.		3.3110bipyridines;
nitrile;
pyridone		AMPA receptor antagonist;
anticonvulsant
cgp 55845a
CGP 55845A: GABA-B receptor antagonist; RN refers to cpd with no isomeric designation; CGP 55845 is the (1S,2S)-isomer		2.0210
cariprazine
cariprazine: Structure in first source. cariprazine : An N-alkylpiperazine that is N,N-dimethyl-N'-{trans-4-[2-(piperazin-1-yl)ethyl]cyclohexyl}urea substituted at position 4 on the piperazine ring by a 2,3-dichlorophenyl group. Used (as the hydrochloride salt) for treatment of schizophrenia and bipolar disorder.		3.2510
3-cyano-n-(1,3-diphenyl-1h-pyrazol-5-yl)benzamide
3-cyano-N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamide: affects mGluR5 receptors; structure in first source		2.0610
ly2033298
[no description available]		3.2510
vu0357017
[no description available]		2.2110
1-(4-methoxybenzyl)-5-(trifluoromethoxy)indoline-2,3-dione
[no description available]		2.2110
lsp4-2022
LSP4-2022: structure in first source		2.1310
guanosine 5'-o-(3-thiotriphosphate)
Guanosine 5'-O-(3-Thiotriphosphate): Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes.		2.7830nucleoside triphosphate analogue
ConditionIndicatedRelationship StrengthStudiesTrials
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		03.4670
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510
Anxiety
Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.		03.1750
Dementia Praecox
[description not available]		02.5720
Schizophrenia
A severe emotional disorder of psychotic depth characteristically marked by a retreat from reality with delusion formation, HALLUCINATIONS, emotional disharmony, and regressive behavior.		02.5720
Convulsive Generalized Seizure Disorder
[description not available]		03.1210
Absence Seizure
[description not available]		03.4820
Seizures
Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.		03.4820
Alcohol Drinking
Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.		04.4980
Binge Alcohol Consumption
[description not available]		02.110
Alcohol Abuse
[description not available]		03.8840
Alcoholism
A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)		03.8840
Dyskinesia, Medication-Induced
[description not available]		02.1310
Dyskinesia, Drug-Induced
Abnormal movements, including HYPERKINESIS; HYPOKINESIA; TREMOR; and DYSTONIA, associated with the use of certain medications or drugs. Muscles of the face, trunk, neck, and extremities are most commonly affected. Tardive dyskinesia refers to abnormal hyperkinetic movements of the muscles of the face, tongue, and neck associated with the use of neuroleptic agents (see ANTIPSYCHOTIC AGENTS). (Adams et al., Principles of Neurology, 6th ed, p1199)		02.1310
Cocaine Abuse
[description not available]		02.7330
Cocaine-Related Disorders
Disorders related or resulting from use of cocaine.		02.7330
Anochlesia
[description not available]		02.0610
Hyperactivity, Motor
[description not available]		02.4520
Psychoses, Drug
[description not available]		02.0610
Symptom Cluster
[description not available]		02.0610
Syndrome
A characteristic symptom complex.		02.0610
Fra(X) Syndrome
[description not available]		02.0610
Audiogenic Epilepsy
[description not available]		02.0610
Fragile X Syndrome
A condition characterized genotypically by mutation of the distal end of the long arm of the X chromosome (at gene loci FRAXA or FRAXE) and phenotypically by cognitive impairment, hyperactivity, SEIZURES, language delay, and enlargement of the ears, head, and testes. INTELLECTUAL DISABILITY occurs in nearly all males and roughly 50% of females with the full mutation of FRAXA. (From Menkes, Textbook of Child Neurology, 5th ed, p226)		02.0610
Epilepsy, Reflex
A subtype of epilepsy characterized by seizures that are consistently provoked by a certain specific stimulus. Auditory, visual, and somatosensory stimuli as well as the acts of writing, reading, eating, and decision making are examples of events or activities that may induce seizure activity in affected individuals. (From Neurol Clin 1994 Feb;12(1):57-8)		02.0610
Inadequate Sleep
[description not available]		02.0610
Depression
Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.		02.0210
Pyrexia
[description not available]		02.0210
Fever
An abnormal elevation of body temperature, usually as a result of a pathologic process.		02.0210