SB-271046

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H22ClN3O3S2
Molecular Weight	451.99
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(C=C(NS(=O)(=O)C2=C(C)C3=C(S2)C=CC(Cl)=C3)C=C1)N4CCNCC4

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	451.99
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/10928964 | https://www.ncbi.nlm.nih.gov/pubmed/11527003
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

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/10928964	Antagonist 2778		8.92 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19302808 http://adisinsight.springer.com/drugs/800011590 https://www.ncbi.nlm.nih.gov/pubmed/11527003	Primary		Phase I 428	Unknown Approved Use Unknown
Schizophrenia 298 Sources: http://adisinsight.springer.com/drugs/800011590 https://www.ncbi.nlm.nih.gov/pubmed/18622410	Primary		Phase I 428	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 CYP2C19 1478 CYP1A2 1524	P-gp 1537

Drug as perpetrator

Target	Modality	Activity
P-gp 1650	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363680155	inconclusive [IC50 20.5962 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9925723/	moderate [IC50 26 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9925723/	moderate [IC50 32 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9925723/	moderate [IC50 40 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9925723/	moderate [IC50 66 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9925723/	no [IC50 >100 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16143522/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY539312	https://www.001chemical.com/chem/209481-20-9
AA Blocks	AA002K6I	https://www.aablocks.com/goods/Goods/detail?id=AA002K6I
AK Scientific, Inc. (AKSCI)	2704AH	http://www.aksci.com/item_detail.php?cat=2704AH
AbMole Bioscience	M2999	http://www.abmole.com/products/sb271046.html
Achemtek	0102-013002	http://www.achemtek.com/209481-20-9
Acorn PharmaTech	ACN-038414	http://www.acornpharmatech.com/
Alichem	139002148	http://www.alichem.com/en/products/209481-20-9.html
Ambinter	Amb21863636	http://www.ambinter.com/reference/21863636
Angel Pharmatech	AG-20173	http://www.angelpharmatech.com/209481-20-9.html
ApexBio Technology	B2255	http://www.apexbt.com/sb271046.html
Aurora Fine Chemicals LLC	A19.960.046	http://online.aurorafinechemicals.com/info?ID=A19.960.046
Aurum Pharmatech LLC	Z-3245	http://www.Aurumpharmatech.com/Product/ProductDetails/Z_3245
BLD Pharm	BD628588	http://www.bldpharm.com/products/209481-20-9.html
BOC Sciences	209481-20-9	https://www.bocsci.com/sb271046-cas-209481-20-9-item-84-194063.html
BioChemPartner	BCP03713	http://www.biochempartner.com/209481-20-9-BCP03713
BioCrick	BCC5057	http://www.biocrick.com/SB271046-BCC5057.html
Boerchem	BC282896	http://www.boerchem.com/?product_42752.html
ChemShuttle	141624	http://www.chemshuttle.com/catalogsearch/result/?q=209481-20-9&cat=
Chemspace	CSSB00020618002	https://chem-space.com/CSSB00020618002
Excenen	EX-A2155	https://www.excenen.com/searchresultlist.php?id=209481-20-9
Lab Network	LN01346385	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01346385
MolPort	MolPort-021-806-425	https://www.molport.com/shop/molecule-link/MolPort-021-806-425
Molcore	MC539312	https://www.molcore.com/product/209481-20-9
Selleck Chemicals	S2856	http://www.selleckchem.com/products/sb-271046.html
Smolecule	S620250	https://www.smolecule.com/products/s620250
Synblock Inc	SB19511	http://www.synblock.com/product/209481-20-9.html
THE BioTek	bt-336300	https://www.thebiotek.com/product/others/bt-336300
eNovation Chemicals	D371003	http://www.enovationchem.com/productDetails.asp?productID=D371003
eNovation Chemicals	D480353	https://www.enovationchem.com/ProductDetails.asp?ProductID=D480353
eNovation Chemicals	Y0973982	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0973982

PubMed

Title	Date	PubMed
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	9925723
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	14571256
5-HT6 antagonism attenuates cue-induced relapse to cocaine seeking without affecting cocaine reinforcement.	2010 Aug	20426879

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 Dec 16 05:35:21 UTC 2023` Edited by `admin` on `Sat Dec 16 05:35:21 UTC 2023`
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