Page last updated: 2024-11-13

4-cyclopropyl-7-fluoro-3,4-dihydro-2h-1,2,4-benzothiadiazine 1,1-dioxide

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Description

4-cyclopropyl-7-fluoro-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide: a GluA2 positive allosteric modulator; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID67531324
CHEMBL ID2441067
SCHEMBL ID2779104
MeSH IDM0592437

Synonyms (17)

Synonym
4N07
CHEMBL2441067 ,
4-cyclopropyl-7-fluoro-3,4-dihydro-2h-1,2,4-benzothiadiazine 1,1-dioxide
2j9 ,
SCHEMBL2779104
bdbm50032241
bpam344, >=98% (hplc)
1204572-55-3
bpam344
4-cyclopropyl-7-fluoro-3,4-dihydro-2h-benzo[e][1,2,4]thiadiazine 1,1-dioxide
TQR0610
Q27453039
MS-23426
HY-129086
LCZC1071
CS-0103552
AKOS040759705
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor 2Rattus norvegicus (Norway rat)EC50 (µMol)0.90000.00411.62517.6000AID777168
Glutamate receptor 2Homo sapiens (human)EC50 (µMol)0.81140.15003.05607.6000AID1478393
Glutamate receptor 2Homo sapiens (human)Kd0.35000.35002.97505.6000AID1170667
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor 2Rattus norvegicus (Norway rat)Activity0.27000.10500.18630.2700AID777169
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Processvia Protein(s)Taxonomy
signal transductionGlutamate receptor 2Homo sapiens (human)
chemical synaptic transmissionGlutamate receptor 2Homo sapiens (human)
ionotropic glutamate receptor signaling pathwayGlutamate receptor 2Homo sapiens (human)
synaptic transmission, glutamatergicGlutamate receptor 2Homo sapiens (human)
regulation of postsynaptic membrane potentialGlutamate receptor 2Homo sapiens (human)
monoatomic cation transmembrane transportGlutamate receptor 2Homo sapiens (human)
modulation of chemical synaptic transmissionGlutamate receptor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
AMPA glutamate receptor activityGlutamate receptor 2Homo sapiens (human)
amyloid-beta bindingGlutamate receptor 2Homo sapiens (human)
glutamate-gated receptor activityGlutamate receptor 2Homo sapiens (human)
AMPA glutamate receptor activityGlutamate receptor 2Homo sapiens (human)
protein bindingGlutamate receptor 2Homo sapiens (human)
ligand-gated monoatomic cation channel activityGlutamate receptor 2Homo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potentialGlutamate receptor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor 2Homo sapiens (human)
external side of plasma membraneGlutamate receptor 2Homo sapiens (human)
postsynaptic densityGlutamate receptor 2Homo sapiens (human)
dendriteGlutamate receptor 2Homo sapiens (human)
endocytic vesicle membraneGlutamate receptor 2Homo sapiens (human)
asymmetric synapseGlutamate receptor 2Homo sapiens (human)
neuronal cell bodyGlutamate receptor 2Homo sapiens (human)
dendritic spineGlutamate receptor 2Homo sapiens (human)
excitatory synapseGlutamate receptor 2Homo sapiens (human)
postsynapseGlutamate receptor 2Homo sapiens (human)
postsynaptic endocytic zoneGlutamate receptor 2Homo sapiens (human)
AMPA glutamate receptor complexGlutamate receptor 2Homo sapiens (human)
plasma membraneGlutamate receptor 2Homo sapiens (human)
dendritic spineGlutamate receptor 2Homo sapiens (human)
postsynaptic density membraneGlutamate receptor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID777168Positive allosteric modulation of GluA2 receptor in rat embryonic cortex neuron assessed as increase of AMPA-induced membrane depolarization by fluorescence assay2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Synthesis, pharmacological and structural characterization, and thermodynamic aspects of GluA2-positive allosteric modulators with a 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide scaffold.
AID777167Positive allosteric modulation of GluA2 receptor in rat embryonic cortex neuron assessed as increase of AMPA-induced membrane depolarization by fluorescence assay relative to AMPA2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Synthesis, pharmacological and structural characterization, and thermodynamic aspects of GluA2-positive allosteric modulators with a 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide scaffold.
AID1170667Binding affinity to GluA2-LBD-L483Y-N754S complex (unknown origin) by isothermal titration calorimetry2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Positive allosteric modulators of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors belonging to 4-cyclopropyl-3,4-dihydro-2h-1,2,4-pyridothiadiazine dioxides and diversely chloro-substituted 4-cyclopropyl-3,4-dihydro-2H-1,2,4-benzothiad
AID1170671Positive allosteric modulation of AMPA receptor in rat hippocampal slice assessed as increase in AMPA-mediated presynaptic noradrenaline release2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Positive allosteric modulators of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors belonging to 4-cyclopropyl-3,4-dihydro-2h-1,2,4-pyridothiadiazine dioxides and diversely chloro-substituted 4-cyclopropyl-3,4-dihydro-2H-1,2,4-benzothiad
AID1478393Positive allosteric modulation of GluA2 (Q) flop isoform (unknown origin) expressed in HEK293 cells assessed as potentiation of glutamate-evoked calcium flux by fluo-4/AM dye-based fluorescence assay2018Journal of medicinal chemistry, 01-11, Volume: 61, Issue:1
7-Phenoxy-Substituted 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides as Positive Allosteric Modulators of α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptors with Nanomolar Potency.
AID1478394Induction of dimerization of rat N-terminal His-tagged GluA2-LBD-N775S mutant expressed in Escherichia coli Origami B (DE3) assessed as intrinsic binding constant by small-angle X-ray scattering method2018Journal of medicinal chemistry, 01-11, Volume: 61, Issue:1
7-Phenoxy-Substituted 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides as Positive Allosteric Modulators of α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptors with Nanomolar Potency.
AID1170670Positive allosteric modulation of AMPA receptor in rat embryonic cortex primary neuronal culture assessed as increase in AMPA-induced membrane depolarization by microplate reader2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Positive allosteric modulators of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors belonging to 4-cyclopropyl-3,4-dihydro-2h-1,2,4-pyridothiadiazine dioxides and diversely chloro-substituted 4-cyclopropyl-3,4-dihydro-2H-1,2,4-benzothiad
AID1170668Potentiation of AMPA receptor in rat embryonic cortex primary neuronal culture assessed as concentration required to 2-fold increase in AMPA-induced membrane depolarization by microplate reader2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Positive allosteric modulators of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors belonging to 4-cyclopropyl-3,4-dihydro-2h-1,2,4-pyridothiadiazine dioxides and diversely chloro-substituted 4-cyclopropyl-3,4-dihydro-2H-1,2,4-benzothiad
AID777169Positive allosteric modulation of GluA2 receptor in rat embryonic cortex neuron assessed as concentration required to 2 fold increase of AMPA-induced membrane depolarization by fluorescence assay2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Synthesis, pharmacological and structural characterization, and thermodynamic aspects of GluA2-positive allosteric modulators with a 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide scaffold.
AID1170669Positive allosteric modulation of AMPA receptor in rat embryonic cortex primary neuronal culture assessed as maximal increase in AMPA-induced membrane depolarization normalized to AMPA-evoked response by microplate reader2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Positive allosteric modulators of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors belonging to 4-cyclopropyl-3,4-dihydro-2h-1,2,4-pyridothiadiazine dioxides and diversely chloro-substituted 4-cyclopropyl-3,4-dihydro-2H-1,2,4-benzothiad
AID777162Binding affinity to rat LBD of GluA2 receptor L483Y and N754S mutant at 243 uM by isothermal titration calorimetry analysis2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Synthesis, pharmacological and structural characterization, and thermodynamic aspects of GluA2-positive allosteric modulators with a 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide scaffold.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Synthesis, pharmacological and structural characterization, and thermodynamic aspects of GluA2-positive allosteric modulators with a 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide scaffold.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's4 (80.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.80

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 Index12.80 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.80)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]