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Details

Stereochemistry ACHIRAL
Molecular Formula C34H45N3O.2ClH
Molecular Weight 584.662
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SB-699551dihydrochloride

SMILES

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

InChI

InChIKey=QJMKBIHLMPTYTI-UHFFFAOYSA-N
InChI=1S/C34H45N3O.2ClH/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;2*1H

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
Molecular Formula ClH
Molecular Weight 36.461
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 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

CNS Active
3913
Curator's Comment: SB-699551 is CNS active in animals. No human data available.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 8.5 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Discovery of a potent and selective 5-ht5A receptor antagonist by high-throughput chemistry.
2005 Sep 15
5-ht5A receptors as a therapeutic target.
2006 Sep
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
Serotonergic modulation of extrapyramidal motor disorders in mice and rats: role of striatal 5-HT3 and 5-HT6 receptors.
2011 Feb-Mar
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
Effect of 5-HT5A antagonists in animal models of schizophrenia, anxiety and depression.
2012 Aug
The 5-HT5A receptor regulates excitability in the auditory startle circuit: functional implications for sensorimotor gating.
2013 Jun 12
Peripheral and spinal 5-HT receptors participate in the pronociceptive and antinociceptive effects of fluoxetine in rats.
2013 Nov 12
Role of 5-HT5A receptors in the consolidation of memory.
2013 Sep 1
GR-127935-sensitive mechanism mediating hypotension in anesthetized rats: are 5-HT5B receptors involved?
2015 Apr
Role of spinal 5-HT5A, and 5-HT1A/1B/1D, receptors in neuropathic pain induced by spinal nerve ligation in rats.
2015 Oct 5
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
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
Patents

Patents

8686002
2
WO2016146455A1
2

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 19:17:37 GMT 2023
Edited
by admin
on Sat Dec 16 19:17:37 GMT 2023
Record UNII
XDC9VEX4CH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SB-699551dihydrochloride
Common Name English
Cyclopentanepropanamide, N-[2-(dimethylamino)ethyl]-N-[[4′-[[(2-phenylethyl)amino]methyl][1,1′-biphenyl]-4-yl]methyl]-, hydrochloride (1:2)
Systematic Name English
Cyclopentanepropanamide, N-[2-(dimethylamino)ethyl]-N-[[4′-[[(2-phenylethyl)amino]methyl][1,1′-biphenyl]-4-yl]methyl]-, dihydrochloride
Systematic Name English
N-[2-(DIMETHYLAMINO)ETHYL]-N-[[4'-[[(2-PHENYLETHYL)AMINO]METHYL][1,1'-BIPHENYL]-4-YL]METHYL]CYCLOPENTANEPROPANAMIDE DIHYDROCHLORIDE
Systematic Name English
SB699551dihydrochloride
Common Name English
Code System Code Type Description
CAS
864741-95-7
Created by admin on Sat Dec 16 19:17:37 GMT 2023 , Edited by admin on Sat Dec 16 19:17:37 GMT 2023
PRIMARY
PUBCHEM
11983346
Created by admin on Sat Dec 16 19:17:37 GMT 2023 , Edited by admin on Sat Dec 16 19:17:37 GMT 2023
PRIMARY
FDA UNII
XDC9VEX4CH
Created by admin on Sat Dec 16 19:17:37 GMT 2023 , Edited by admin on Sat Dec 16 19:17:37 GMT 2023
PRIMARY
Related Record Type Details
Structure of SB-699551
PARENT -> SALT/SOLVATE
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