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Details

Stereochemistry ACHIRAL
Molecular Formula C20H22ClN3O3S2
Molecular Weight 451.9928
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SB-271046

SMILES

Cc1c2cc(ccc2sc1S(=O)(=O)Nc3ccc(c(c3)N4CCNCC4)OC)Cl

InChI

InChIKey=LOCQRDBFWSXQQI-UHFFFAOYSA-N
InChI=1S/C20H22ClN3O3S2/c1-13-16-11-14(21)3-6-19(16)28-20(13)29(25,26)23-15-4-5-18(27-2)17(12-15)24-9-7-22-8-10-24/h3-6,11-12,22-23H,7-10H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C20H22ClN3O3S2
Molecular Weight 451.9928
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800011590

SB-271046 is one of the first selective 5-HT6 receptor antagonists to be discovered. SB-271046 is a potent, selective and orally active 5-HT6 receptor antagonist with a pKi value of 8.9. This compound provides a useful tool for further elucidating the physiological function of 5-HT6 receptors in vivo. SB-271046 was found to increase levels of the excitatory amino acid neurotransmitters glutamate and aspartate, as well as dopamine and noradrenaline in the frontal cortex and hippocampus of rats, and 5-HT6 antagonists have been shown to produce nootropic effects in a variety of animal studies. Suggested applications of SB-271046 included treatment of schizophrenia and other psychiatric disorders. A phase I clinical development of SB-271046 by GlaxoSmithKline (GSK) was discontinued due to a poor BBB permeability.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.92 null [pKi]
Conditions
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
5-Chloro-N-(4-methoxy-3-piperazin-1-yl- phenyl)-3-methyl-2-benzothiophenesulfon- amide (SB-271046): a potent, selective, and orally bioavailable 5-HT6 receptor antagonist.
1999 Jan 28
An assessment of the effects of serotonin 6 (5-HT6) receptor antagonists in rodent models of learning.
2003 Nov
The 5-HT(6) receptor antagonist SB-271046 reverses scopolamine-disrupted consolidation of a passive avoidance task and ameliorates spatial task deficits in aged rats.
2004 Jan
5-HT6 antagonism attenuates cue-induced relapse to cocaine seeking without affecting cocaine reinforcement.
2010 Aug
Patents

Sample Use Guides

Rats: systemic administration of SB-399885 (3 and 10 mg/kg, i.p.) produced a significant reduction of immobility time in the rat forced swimming test
Route of Administration: Intraperitoneal
SB-271046 (10, 30, 100 and 300 nM) inhibited the 5-HT stimulation of adenylyl cyclase activity in HeLa cells stably expressing human 5-HT6 receptors
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:49:13 UTC 2021
Edited
by admin
on Sat Jun 26 08:49:13 UTC 2021
Record UNII
L3SK5KX24S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SB-271046
Common Name English
5-CHLORO-N-(4-METHOXY-3-(1-PIPERAZINYL)PHENYL)-3-METHYLBENZO(B)THIOPHENE-2-SULFONAMIDE
Systematic Name English
Code System Code Type Description
FDA UNII
L3SK5KX24S
Created by admin on Sat Jun 26 08:49:13 UTC 2021 , Edited by admin on Sat Jun 26 08:49:13 UTC 2021
PRIMARY
PUBCHEM
5312149
Created by admin on Sat Jun 26 08:49:13 UTC 2021 , Edited by admin on Sat Jun 26 08:49:13 UTC 2021
PRIMARY
CAS
209481-20-9
Created by admin on Sat Jun 26 08:49:13 UTC 2021 , Edited by admin on Sat Jun 26 08:49:13 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
ANTAGONIST
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY