SB-399885

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17069795
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 6 (5-HT6) receptor 45 Target ID: CHEMBL3371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17069795	Antagonist 2778		9.11 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24905514 https://www.ncbi.nlm.nih.gov/pubmed/25863120 https://www.ncbi.nlm.nih.gov/pubmed/18195455 https://www.ncbi.nlm.nih.gov/pubmed/18234190 https://www.ncbi.nlm.nih.gov/pubmed/19302808 https://www.ncbi.nlm.nih.gov/pubmed/17320917	Primary	Preclinical	Unknown Approved Use Unknown
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18096153 https://www.ncbi.nlm.nih.gov/pubmed/17320917	Primary	Preclinical	Unknown Approved Use Unknown
Cognition disorders 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19733250 https://www.ncbi.nlm.nih.gov/pubmed/15964617 https://www.ncbi.nlm.nih.gov/pubmed/15846482 https://www.ncbi.nlm.nih.gov/pubmed/17069795	Primary	Preclinical	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422883	Primary	Preclinical	Unknown Approved Use Unknown
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25034463	Primary	Preclinical	Unknown Approved Use Unknown
Traumatic stress disorder 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25310249	Primary	Preclinical	Unknown Approved Use Unknown

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	15964617
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	17069795
Memory consolidation and amnesia modify 5-HT6 receptors expression in rat brain: an autoradiographic study.	2007 Mar 12	17267053
Role of 5-HT1-7 receptors in short- and long-term memory for an autoshaping task: intrahippocampal manipulations.	2007 May 25	17368430
Procognitive 5-HT6 antagonists in the rat forced swimming test: potential therapeutic utility in mood disorders associated with Alzheimer's disease.	2009 Apr 10	19302808
Role of peripheral and spinal 5-HT6 receptors according to the rat formalin test.	2009 Aug 18	19422883
Time-course of 5-HT(6) receptor mRNA expression during memory consolidation and amnesia.	2010 Jan	19733250
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	20732355
Co-administration of 5-HT6 receptor antagonists with clozapine, risperidone, and a 5-HT2A receptor antagonist: effects on prepulse inhibition in rats.	2014 Jan	23954911
5-HT6 Receptor Agonist and Antagonist Against β-Amyloid-Peptide-Induced Neurotoxicity in PC-12 Cells.	2017 May	28271324

Patents

Sample Use Guides

In Vivo Use Guide

rats: 10 mg/kg p.o., b.i.d. for 7 days rats: 1 and 3 mg/kg, i.p.

Route of Administration: Other

In Vitro Use Guide

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 `Sat Dec 16 18:39:51 GMT 2023` Edited by `admin` on `Sat Dec 16 18:39:51 GMT 2023`
Record UNII	5BH7TN3FWY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SB-399885

Common Name

English

N-(3,5-DICHLORO-2-METHOXYPHENYL)-4-METHOXY-3-(1-PIPERAZINYL)BENZENESULFONAMIDE

Systematic Name

English

BENZENESULFONAMIDE, N-(3,5-DICHLORO-2-METHOXYPHENYL)-4-METHOXY-3-(1-PIPERAZINYL)-

Systematic Name

English

SB399885

Code

English

Code System Code Type Description

PUBCHEM

6918649