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 |
|---|---|---|
| Oral administration of the 5-HT6 receptor antagonists SB-357134 and SB-399885 improves memory formation in an autoshaping learning task. | 2005 Jul |
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| 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 Dec 28 |
|
| Effects of the brain-penetrant and selective 5-HT6 receptor antagonist SB-399885 in animal models of anxiety and depression. | 2007 Apr |
|
| 5-HT6 receptor antagonist SB-399885 potentiates haloperidol and risperidone-induced dopamine efflux in the medial prefrontal cortex or hippocampus. | 2007 Feb 23 |
|
| Memory consolidation and amnesia modify 5-HT6 receptors expression in rat brain: an autoradiographic study. | 2007 Mar 12 |
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| Role of 5-HT1-7 receptors in short- and long-term memory for an autoshaping task: intrahippocampal manipulations. | 2007 May 25 |
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| Study into a possible mechanism responsible for the antidepressant-like activity of the selective 5-HT6 receptor antagonist SB-399885 in rats. | 2007 Nov-Dec |
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| Effects of 5-HT drugs in prefrontal cortex during memory formation and the ketamine amnesia-model. | 2008 |
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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 Dec 16 |
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| The anxiolytic-like effect of the selective 5-HT6 receptor antagonist SB-399885: the impact of benzodiazepine receptors. | 2008 Feb 12 |
|
| 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 Jun |
|
| The selective 5-HT(6) receptor antagonist SB-399885 enhances anti-immobility action of antidepressants in rats. | 2008 Mar 17 |
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| Procognitive 5-HT6 antagonists in the rat forced swimming test: potential therapeutic utility in mood disorders associated with Alzheimer's disease. | 2009 Apr 10 |
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| Role of peripheral and spinal 5-HT6 receptors according to the rat formalin test. | 2009 Aug 18 |
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| Activation of the 5-HT(6) receptor attenuates long-term potentiation and facilitates GABAergic neurotransmission in rat hippocampus. | 2009 Dec 1 |
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| Dimebolin is a 5-HT6 antagonist with acute cognition enhancing activities. | 2009 Oct 15 |
|
| Time-course of 5-HT(6) receptor mRNA expression during memory consolidation and amnesia. | 2010 Jan |
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| Activation of 5-HT(6) receptors facilitates attentional set shifting. | 2010 Jan |
|
| 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 Jan 1 |
|
| The 5-HT6 receptor agonist EMD 386088 produces antidepressant and anxiolytic effects in rats after intrahippocampal administration. | 2011 Oct |
|
| 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 Sep 1 |
|
| Co-administration of 5-HT6 receptor antagonists with clozapine, risperidone, and a 5-HT2A receptor antagonist: effects on prepulse inhibition in rats. | 2014 Jan |
|
| Role of glutamate and advantages of combining memantine with a 5HT6 ligand in a model of depression. | 2014 Jun |
|
| Distribution of cells responsive to 5-HT₆ receptor antagonist-induced hypophagia. | 2014 Jun 1 |
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| 5-HT6 Receptor Recruitment of mTOR Modulates Seizure Activity in Epilepsy. | 2015 |
|
| GR-127935-sensitive mechanism mediating hypotension in anesthetized rats: are 5-HT5B receptors involved? | 2015 Apr |
|
| Therapeutic Potential of 5-HT6 Antagonist SB399885 in Traumatic Stress Disorder. | 2015 Aug |
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| 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 Aug |
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| Pharmacological Evidence for 5-HT6 Receptor Modulation of 5-HT Neuron Firing in Vivo. | 2015 Jul 15 |
|
| 5-HT6 Receptor Agonist and Antagonist Against β-Amyloid-Peptide-Induced Neurotoxicity in PC-12 Cells. | 2017 May |
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
Edited
Sat Dec 16 18:39:51 UTC 2023
by
admin
on
Sat Dec 16 18:39:51 UTC 2023
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| Record UNII |
5BH7TN3FWY
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| Record Status |
Validated (UNII)
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| Record Version |
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6918649
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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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