Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H21Cl2N3O4S |
| Molecular Weight | 446.348 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(C=C(C=C1)S(=O)(=O)NC2=CC(Cl)=CC(Cl)=C2OC)N3CCNCC3
InChI
InChIKey=ATKZKAYWARYLBW-UHFFFAOYSA-N
InChI=1S/C18H21Cl2N3O4S/c1-26-17-4-3-13(11-16(17)23-7-5-21-6-8-23)28(24,25)22-15-10-12(19)9-14(20)18(15)27-2/h3-4,9-11,21-22H,5-8H2,1-2H3
| Molecular Formula | C18H21Cl2N3O4S |
| Molecular Weight | 446.348 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20732355 | https://www.ncbi.nlm.nih.gov/pubmed/17320917 | https://www.ncbi.nlm.nih.gov/pubmed/19422883 | https://www.ncbi.nlm.nih.gov/pubmed/25034463
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20732355 | https://www.ncbi.nlm.nih.gov/pubmed/17320917 | https://www.ncbi.nlm.nih.gov/pubmed/19422883 | https://www.ncbi.nlm.nih.gov/pubmed/25034463
is a potent, selective, brain penetrant, orally active serotonin 5-HT(6) receptor antagonist with cognitive enhancing, anxiolytic and antidepressant properties. It is able to regulate sleep and wakefulness in rodents. In addition it demostrates antinociceptive and antiepileptic potentials.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3371 |
9.11 null [pKi] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 5-HT6 Receptor Agonist and Antagonist Against β-Amyloid-Peptide-Induced Neurotoxicity in PC-12 Cells. | 2017-05 |
|
| Therapeutic Potential of 5-HT6 Antagonist SB399885 in Traumatic Stress Disorder. | 2015-08 |
|
| Olanzapine augments the effect of selective serotonin reuptake inhibitors by suppressing GABAergic inhibition via antagonism of 5-HT₆ receptors in the dorsal raphe nucleus. | 2015-08 |
|
| Pharmacological Evidence for 5-HT6 Receptor Modulation of 5-HT Neuron Firing in Vivo. | 2015-07-15 |
|
| GR-127935-sensitive mechanism mediating hypotension in anesthetized rats: are 5-HT5B receptors involved? | 2015-04 |
|
| 5-HT6 Receptor Recruitment of mTOR Modulates Seizure Activity in Epilepsy. | 2015 |
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| Distribution of cells responsive to 5-HT₆ receptor antagonist-induced hypophagia. | 2014-06-01 |
|
| Role of glutamate and advantages of combining memantine with a 5HT6 ligand in a model of depression. | 2014-06 |
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| Co-administration of 5-HT6 receptor antagonists with clozapine, risperidone, and a 5-HT2A receptor antagonist: effects on prepulse inhibition in rats. | 2014-01 |
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| The 5-HT6 receptor agonist EMD 386088 produces antidepressant and anxiolytic effects in rats after intrahippocampal administration. | 2011-10 |
|
| Synthesis and in vivo evaluation of [O-methyl-11C] N-[3,5-dichloro-2-(methoxy)phenyl]-4-(methoxy)-3-(1-piperazinyl)benzenesulfonamide as an imaging probe for 5-HT6 receptors. | 2011-09-01 |
|
| Effects of the 5-HT₆ receptor antagonists SB-399885 and RO-4368554 and of the 5-HT(2A) receptor antagonist EMD 281014 on sleep and wakefulness in the rat during both phases of the light-dark cycle. | 2011-01-01 |
|
| Time-course of 5-HT(6) receptor mRNA expression during memory consolidation and amnesia. | 2010-01 |
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| Activation of 5-HT(6) receptors facilitates attentional set shifting. | 2010-01 |
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| Activation of the 5-HT(6) receptor attenuates long-term potentiation and facilitates GABAergic neurotransmission in rat hippocampus. | 2009-12-01 |
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| Dimebolin is a 5-HT6 antagonist with acute cognition enhancing activities. | 2009-10-15 |
|
| Role of peripheral and spinal 5-HT6 receptors according to the rat formalin test. | 2009-08-18 |
|
| Procognitive 5-HT6 antagonists in the rat forced swimming test: potential therapeutic utility in mood disorders associated with Alzheimer's disease. | 2009-04-10 |
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| The effects of the 5-HT(6) receptor agonist EMD and the 5-HT(7) receptor agonist AS19 on memory formation. | 2008-12-16 |
|
| The selective 5-HT6 receptor antagonists SB-271046 and SB-399885 potentiate NCAM PSA immunolabeling of dentate granule cells, but not neurogenesis, in the hippocampal formation of mature Wistar rats. | 2008-06 |
|
| The selective 5-HT(6) receptor antagonist SB-399885 enhances anti-immobility action of antidepressants in rats. | 2008-03-17 |
|
| The anxiolytic-like effect of the selective 5-HT6 receptor antagonist SB-399885: the impact of benzodiazepine receptors. | 2008-02-12 |
|
| Effects of 5-HT drugs in prefrontal cortex during memory formation and the ketamine amnesia-model. | 2008 |
|
| Study into a possible mechanism responsible for the antidepressant-like activity of the selective 5-HT6 receptor antagonist SB-399885 in rats. | 2007-09-09 |
|
| Role of 5-HT1-7 receptors in short- and long-term memory for an autoshaping task: intrahippocampal manipulations. | 2007-05-25 |
|
| Effects of the brain-penetrant and selective 5-HT6 receptor antagonist SB-399885 in animal models of anxiety and depression. | 2007-04 |
|
| Memory consolidation and amnesia modify 5-HT6 receptors expression in rat brain: an autoradiographic study. | 2007-03-12 |
|
| 5-HT6 receptor antagonist SB-399885 potentiates haloperidol and risperidone-induced dopamine efflux in the medial prefrontal cortex or hippocampus. | 2007-02-23 |
|
| SB-399885 is a potent, selective 5-HT6 receptor antagonist with cognitive enhancing properties in aged rat water maze and novel object recognition models. | 2006-12-28 |
|
| Oral administration of the 5-HT6 receptor antagonists SB-357134 and SB-399885 improves memory formation in an autoshaping learning task. | 2005-07 |
Patents
Sample Use Guides
rats: 10 mg/kg p.o., b.i.d. for 7 days
rats: 1 and 3 mg/kg, i.p.
Route of Administration:
Other
As assessed by measuring and evaluating spontaneous inhibitory postsynaptic currents (sIPSCs) in the rat brain slices containing area CA1 of the hippocampus, 200 nM WAY-181187, the selective 5-HT(6) agonist, increased sIPSC frequency, this increase in GABA sIPSCs was prevented by the selective 5-HT(6) antagonist SB-399885 (300 nM).
| Substance Class |
Chemical
Created
by
admin
on
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Wed Apr 02 11:58:17 GMT 2025
by
admin
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Wed Apr 02 11:58:17 GMT 2025
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| Record UNII |
5BH7TN3FWY
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Validated (UNII)
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DTXSID60437717
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5BH7TN3FWY
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SB-399885
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402713-80-8
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| Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
ANTAGONIST
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