SB-699551

Details

Stereochemistry	ACHIRAL
Molecular Formula	C34H45N3O
Molecular Weight	511.7406
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCN(CC1=CC=C(C=C1)C2=CC=C(CNCCC3=CC=CC=C3)C=C2)C(=O)CCC4CCCC4

InChI

InChIKey=SEQAMPXQRKYYQF-UHFFFAOYSA-N

InChI=1S/C34H45N3O/c1-36(2)24-25-37(34(38)21-16-28-10-6-7-11-28)27-31-14-19-33(20-15-31)32-17-12-30(13-18-32)26-35-23-22-29-8-4-3-5-9-29/h3-5,8-9,12-15,17-20,28,35H,6-7,10-11,16,21-27H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C34H45N3O
Molecular Weight	511.7406
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/16002289 | https://www.ncbi.nlm.nih.gov/pubmed/16516972
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23735322 | https://www.ncbi.nlm.nih.gov/pubmed/24517902 | https://www.ncbi.nlm.nih.gov/pubmed/22785385 | https://www.ncbi.nlm.nih.gov/pubmed/26826431

SB-699551 is the first selective serotonin 5A receptor antagonist. SB-699551 showed an anxiolytic-like property in animal model. It demostrated efficacy against schizophrenia-like cognitive deficits and negative symptoms in rats. Blockade of 5-HT5A receptor with SB-699551 appear to be able to impair the consolidation of memory in rodents. In addition, 5-HT-induced spinal antinociception in the capsaicin and acetic acid tests was blocked by SB-699551.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 5a (5-HT5a) receptor 11 Target ID: CHEMBL3426 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16002289 \| https://www.ncbi.nlm.nih.gov/pubmed/16516972	Antagonist 2778		8.5 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22785385	Primary		Preclinical	Unknown Approved Use Unknown
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26826431	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Discovery of a potent and selective 5-ht5A receptor antagonist by high-throughput chemistry.	2005 Sep 15	16002289
5-ht5A receptors as a therapeutic target.	2006 Sep	16516972
SB-699551-A (3-cyclopentyl-N-[2-(dimethylamino)ethyl]-N-[(4'-{[(2-phenylethyl)amino]methyl}-4-biphenylyl)methyl]propanamide dihydrochloride), a novel 5-ht5A receptor-selective antagonist, enhances 5-HT neuronal function: Evidence for an autoreceptor role for the 5-ht5A receptor in guinea pig brain.	2006 Sep	16846620
Serotonergic modulation of extrapyramidal motor disorders in mice and rats: role of striatal 5-HT3 and 5-HT6 receptors.	2011 Feb-Mar	20813116
The native serotonin 5-HT(5A) receptor: electrophysiological characterization in rodent cortex and 5-HT(1A)-mediated compensatory plasticity in the knock-out mouse.	2012 Apr 25	22539842
Effect of 5-HT5A antagonists in animal models of schizophrenia, anxiety and depression.	2012 Aug	22785385
The 5-HT5A receptor regulates excitability in the auditory startle circuit: functional implications for sensorimotor gating.	2013 Jun 12	23761896
Peripheral and spinal 5-HT receptors participate in the pronociceptive and antinociceptive effects of fluoxetine in rats.	2013 Nov 12	23994595
Role of 5-HT5A receptors in the consolidation of memory.	2013 Sep 1	23735322
GR-127935-sensitive mechanism mediating hypotension in anesthetized rats: are 5-HT5B receptors involved?	2015 Apr	25502305
Role of spinal 5-HT5A, and 5-HT1A/1B/1D, receptors in neuropathic pain induced by spinal nerve ligation in rats.	2015 Oct 5	26168890
The effects of a 5-HT5A receptor antagonist in a ketamine-based rat model of cognitive dysfunction and the negative symptoms of schizophrenia.	2016 Jun	26826431
Role of 5-HT5A and 5-HT1B/1D receptors in the antinociception produced by ergotamine and valerenic acid in the rat formalin test.	2016 Jun 15	27068146

Patents

Sample Use Guides

In Vivo Use Guide

guinea pigs: 0.3, 1 or 3 mg/kg s.c. rodents: 1-60 mg/kg, i.p.

Route of Administration: Other

In Vitro Use Guide

In guinea pig dorsal raphe slices, SB-699551-A (1 uM) did not alter neuronal firing per se but attenuated the 5-carboxamidotryptamine-induced depression in serotonergic neuronal firing in a subpopulation of cells insensitive to the 5-HT1A receptor-selective antagonist WAY-100635 (100 nM).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:57:15 GMT 2023` Edited by `admin` on `Sat Dec 16 16:57:15 GMT 2023`
Record UNII	3FN59X9DPR
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SB-699551

Code

English

N-[2-(Dimethylamino)ethyl]-N-[[4′-[[(2-phenylethyl)amino]methyl][1,1′-biphenyl]-4-yl]methyl]cyclopentanepropanamide

Systematic Name

English

Cyclopentanepropanamide, N-[2-(dimethylamino)ethyl]-N-[[4′-[[(2-phenylethyl)amino]methyl][1,1′-biphenyl]-4-yl]methyl]-

Systematic Name

English

SB-699551A Free Base

Common Name

English

Code System Code Type Description

WIKIPEDIA

SB-699551