S-14506

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H26FN3O2
Molecular Weight	407.4805
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(C=CC=C2N3CCN(CCNC(=O)C4=CC=C(F)C=C4)CC3)C=C1

InChI

InChIKey=IFMQODYDAUKKEN-UHFFFAOYSA-N

InChI=1S/C24H26FN3O2/c1-30-21-10-7-18-3-2-4-23(22(18)17-21)28-15-13-27(14-16-28)12-11-26-24(29)19-5-8-20(25)9-6-19/h2-10,17H,11-16H2,1H3,(H,26,29)

HIDE SMILES / InChI

Molecular Formula	C24H26FN3O2
Molecular Weight	407.4805
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/8450471 | https://www.ncbi.nlm.nih.gov/pubmed/8905325 | https://www.ncbi.nlm.nih.gov/pubmed/7705455

S-14506 was originally identified and developed in France by Scientists at the Institut de Recherches Servier. S-14506 showed potent binding and antagonistic activity against the 5HT1-A receptor. It was found to work synergistically with D2 receptor antagonists and was therefore studied in animal models for depression, psychosis, and anxiety. A tritium labeled version was also studied as a potential 5HT1-A receptor PET imaging agent.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
5-hydroxytryptamine receptor 1A 54 Target ID: Q64264 Gene ID: 15550.0 Gene Symbol: Htr1a Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9503258 \| https://www.ncbi.nlm.nih.gov/pubmed/11166326	Agonist 2678		0.15 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7667330 http://adisinsight.springer.com/drugs/800001368	Primary	Basic research	Unknown Approved Use Unknown
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7705455 http://adisinsight.springer.com/drugs/800001368	Primary	Preclinical	Unknown Approved Use Unknown
Psychotic disorder 26 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8905325 http://adisinsight.springer.com/drugs/800001368	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.	1998 Aug 21	9760039
S 14506: novel receptor coupling at 5-HT(1A) receptors.	2001 Mar	11166326

Patents

Sample Use Guides

In Vivo Use Guide

In an in vivo radiolabeling study, [3H]-labeled S-14506 was delivered to mice by caudal vein injection (5 seconds) in a solution of 0.9% NaCl supplemented with 0.05% bovine serum albumin (36-40 ~microCi/ml). Mice were later sacrificed to determine tissue accumulations.

Route of Administration: Intravenous

In Vitro Use Guide

Adult Sprague-Dawley rats were killed and their brains dissected and homogenized. Membranes were collected by centrifugation and the resuspended pellet was assayed for 5-HT binding. S-14506 was able to inhibit the specific binding of [3H]WAY-100635 to rat hippocampal membranes at nanomolar concentrations.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:15:40 UTC 2023` Edited by `admin` on `Sat Dec 16 08:15:40 UTC 2023`
Record UNII	YVO8LE53MI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

S-14506

Common Name

English

4-FLUORO-N-(2-(4-(7-METHOXY-1-NAPHTHYL)PIPERAZINE-1-YL)ETHYL)BENZAMIDE

Systematic Name

English

BENZAMIDE, 4-FLUORO-N-(2-(4-(7-METHOXY-1-NAPHTHALENYL)-1-PIPERAZINYL)ETHYL)-

Systematic Name

English

J485.975H

Code

English

N-(2-(4-(7-METHOXY-1-NAPHTHYL)PIPERAZINO)ETHYL)-4-FLUOROBENZAMIDE

Systematic Name

English

Code System Code Type Description

CHEBI

64101