Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H11N3O |
| Molecular Weight | 225.2459 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(=O)C1=CC2=C(NC3=CC=CC=C23)C=N1
InChI
InChIKey=QMCOPDWHWYSJSA-UHFFFAOYSA-N
InChI=1S/C13H11N3O/c1-14-13(17)11-6-9-8-4-2-3-5-10(8)16-12(9)7-15-11/h2-7,16H,1H3,(H,14,17)
| Molecular Formula | C13H11N3O |
| Molecular Weight | 225.2459 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27838748 | https://www.ncbi.nlm.nih.gov/pubmed/15655523
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27838748 | https://www.ncbi.nlm.nih.gov/pubmed/15655523
FG-7142 is a partial inverse agonist at the benzodiazepine allosteric site with its highest affinity for the α1 subunit-containing GABAA receptor, although it is not selective. FG-7142 also has its highest efficacy for modulation of GABA-induced chloride flux mediated at the α1 subunit-containing GABAA receptor. FG-7142 activates a recognized anxiety-related neural network and interacts with serotonergic, dopaminergic, cholinergic, and noradrenergic modulatory systems within that network. FG-7142 has been shown to induce anxietyrelated behavioral and physiological responses in a variety of experimental paradigms across numerous mammalian and non-mammalian species, including humans. FG-7142 has proconflict actions across anxiety-related behavioral paradigms, modulates attentional processes, and increases cardioacceleratory sympathetic reactivity and neuroendocrine reactivity. Both acute and chronic FG-7142 treatment are proconvulsive, upregulate cortical adrenoreceptors, decrease subsequent actions of GABA and β-carboline agonists, and increase the effectiveness of subsequent GABAA receptor antagonists and β-carboline inverse agonists. FG-7142, as a partial inverse agonist, can help to elucidate individual components of full agonism of benzodiazepine binding sites and may serve to identify the specific GABAA receptor subtypes involved in specific behavioral and physiological responses.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2093872 |
265.0 nM [Ki] | ||
Target ID: CHEMBL2094121 |
91.0 nM [Ki] | ||
Target ID: CHEMBL2094130 |
330.0 nM [Ki] | ||
Target ID: CHEMBL2094120 |
492.0 nM [Ki] | ||
Target ID: CHEMBL2094122 |
2150.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Modulation of constitutive androstane receptor (CAR) and pregnane X receptor (PXR) by 6-arylpyrrolo[2,1-d][1,5]benzothiazepine derivatives, ligands of peripheral benzodiazepine receptor (PBR). | 2011-04-25 |
|
| Multiple anxiogenic drugs recruit a parvalbumin-containing subpopulation of GABAergic interneurons in the basolateral amygdala. | 2010-10-01 |
|
| The anxiogenic drug FG7142 increases self-injurious behavior in male rhesus monkeys (Macaca mulatta). | 2009-11-18 |
|
| A spectroscopic study of the interaction of the fluorescent beta-carboline-3-carboxylic acid N-methylamide with DNA constituents: nucleobases, nucleosides and nucleotides. | 2008-09 |
|
| Early life programming of hemispheric lateralization and synchronization in the adult medial prefrontal cortex. | 2008-08-26 |
|
| Early life stress causes FG-7142-induced corticolimbic dysfunction in adulthood. | 2008-02-08 |
|
| Effects of the interaction between beta-carboline-3-carboxylic acid N-methylamide and polynucleotides on singlet oxygen quantum yield and DNA oxidative damage. | 2007-11-22 |
|
| Identification of an immune-responsive mesolimbocortical serotonergic system: potential role in regulation of emotional behavior. | 2007-05-11 |
|
| 5-Hydroxytryptamine2C receptor contribution to m-chlorophenylpiperazine and N-methyl-beta-carboline-3-carboxamide-induced anxiety-like behavior and limbic brain activation. | 2007-03 |
|
| Do subtype-selective gamma-aminobutyric acid A receptor modulators have a reduced propensity to induce physical dependence in mice? | 2006-03 |
|
| Immediate-early gene expression in the central nucleus of the amygdala is not specific for anxiolytic or anxiogenic drugs. | 2006-01 |
|
| TPA023 [7-(1,1-dimethylethyl)-6-(2-ethyl-2H-1,2,4-triazol-3-ylmethoxy)-3-(2-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine], an agonist selective for alpha2- and alpha3-containing GABAA receptors, is a nonsedating anxiolytic in rodents and primates. | 2006-01 |
|
| Dopamine D3 receptor antagonists improve the learning performance in memory-impaired rats. | 2005-05 |
|
| Anxiogenic properties of an inverse agonist selective for alpha3 subunit-containing GABA A receptors. | 2005-02 |
|
| Serotonergic systems associated with arousal and vigilance behaviors following administration of anxiogenic drugs. | 2005 |
|
| Determination of the effectiveness of components of the herbal medicine Toki-Shakuyaku-San and fractions of Angelica acutiloba in improving the scopolamine-induced impairment of rat's spatial cognition in eight-armed radial maze test. | 2004-09 |
|
| Antagonism of the stress-induced increase in cortical norepinephrine output by the selective norepinephrine reuptake inhibitor reboxetine. | 2003-08-22 |
|
| Tail-swing behavior: a novel animal model for anxiety. | 2003-06 |
|
| Cocaine- and amphetamine-regulated transcript peptide produces anxiety-like behavior in rodents. | 2003-03-07 |
|
| Prior exposure to the elevated plus-maze sensitizes mice to the acute behavioral effects of fluoxetine and phenelzine. | 2003-01-17 |
|
| The early acquisition of two-way (shuttle-box) avoidance as an anxiety-mediated behavior: psychopharmacological validation. | 1991-01 |
|
| Nitrendipine decreases benzodiazepine withdrawal seizures but not the development of benzodiazepine tolerance or withdrawal signs. | 1990-11 |
|
| Anticonvulsant action of the beta-carboline abecarnil: studies in rodents and baboon, Papio papio. | 1990-04 |
|
| Enhanced sensitivity to beta-carboline inverse agonists in rats chronically treated with FG 7142. | 1987-09 |
|
| Behavioural and biochemical evidence for a long-lasting decrease in GABAergic function elicited by chronic administration of FG 7142. | 1986-10-01 |
|
| Triazolobenzodiazepines antagonize the effects of anxiogenic drugs mediated at three different central nervous system sites. | 1985-10-24 |
|
| Chlordiazepoxide enhances the anxiogenic action of CGS 8216 in the social interaction test: evidence for benzodiazepine withdrawal? | 1985-07 |
Patents
Sample Use Guides
The affinity of FG 7142 (2nM-10mkM) for various human recombinant GABAA receptors (b3, g2 plus either a1, a2, a3, a4, a5 or a6 subunits) was measuredin mouse fibroblast L(tk-) cells. Membrane preparations from cells expressing a1-, a2-, a3- or a5-containing GABAA receptors were incubatedwith 1.8 nM [ 3 H]Ro 15-1788, whereas the radioligand used for a4- or a6-containing receptors was 8.0 nM [3H]Ro 15-4513. Nonspecific binding (NSB) was defined using 10 mM (final concentration) flunitrazepam for the a1, a2, a3 and a5 subtypes and10 mM Ro 15-4513 for the a4 and a6 subtypes. IC50 values were calculatedusing XLfit (IDBS, Guildford, U.K.) and converted to KI values using the Cheng– Prussof equation (Cheng & Prussof, 1973) assuming respective affinities (KD values) for [3 H]Ro 15-1788 of 0.92, 1.05, 0.58 and 0.45 nM at a1-, a2-, a3- or a5-containing receptors and5.0 and 6.5 nM for [3 H]Ro 15-4513 at a4- and a6-containing receptors
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:55:03 GMT 2025
by
admin
on
Mon Mar 31 18:55:03 GMT 2025
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| Record UNII |
60PO70N1BP
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| Record Status |
Validated (UNII)
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| Record Version |
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