XALIPRODEN HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H22F3N.ClH
Molecular Weight	417.894
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.FC(F)(F)C1=CC=CC(=C1)C2=CCN(CCC3=CC=C4C=CC=CC4=C3)CC2

InChI

InChIKey=WVHBEIJGAINUBW-UHFFFAOYSA-N

InChI=1S/C24H22F3N.ClH/c25-24(26,27)23-7-3-6-22(17-23)20-11-14-28(15-12-20)13-10-18-8-9-19-4-1-2-5-21(19)16-18;/h1-9,11,16-17H,10,12-15H2;1H

HIDE SMILES / InChI

Description
Sources: http://www.alzforum.org/therapeutics/xaliproden | http://adisinsight.springer.com/drugs/800001601 | https://www.ncbi.nlm.nih.gov/pubmed/19616185 | https://www.ncbi.nlm.nih.gov/pubmed/19814656

Xaliproden is an orally active 5HT1-A receptor antagonist that was being developed by Sanofi. It has been evaluated for the treatment of Alzheimer's disease and amyotrophic lateral sclerosis (ALS), and protection against peripheral neurotoxicity associated with certain cancer chemotherapies. Two large, 18-month, clinical trials of xaliproden (monotherapy or adjunctive therapy, respectively) in patients with mild to moderate AD (MMSE, 16–26, inclusive) were completed in 2007. Failure to demonstrate sufficient efficacy in both trials resulted in cancelation of the xaliproden development program for AD in September 2007.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19814656 \| https://www.ncbi.nlm.nih.gov/pubmed/8314196	Agonist 2678		4.3 nM [IC50]
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19508400	Agonist 2678		9.0 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 272 Sources: http://www.alzforum.org/therapeutics/xaliproden https://clinicaltrials.gov/ct2/show/NCT00103649	Primary	Phase III 656	Unknown Approved Use Unknown
Amyotrophic lateral sclerosis 41 Sources: http://www.alzforum.org/therapeutics/xaliproden http://adisinsight.springer.com/drugs/800001601 https://www.ncbi.nlm.nih.gov/pubmed/19814656	Primary	Phase III 656	Unknown Approved Use Unknown
Cancer pain 10 Sources: http://adisinsight.springer.com/drugs/800001601	Palliative	Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Xaliproden in amyotrophic lateral sclerosis: early clinical trials.	2004 Jun	15204011
Effects of paliroden (SR57667B) and xaliproden on adult brain neurogenesis.	2006 Feb	16472201
SR 57746A/xaliproden, a non-peptide neurotrophic compound: prospects and constraints for the treatment of nervous system diseases.	2009 Nov	19814656

Patents

Sample Use Guides

In Vivo Use Guide

Patients with clinically probable or definite ALS of more than 6 months and less than 5 years duration were randomly assigned to placebo, 1 mg or 2 mg xaliproden orally once daily as monotherapy in Study 1

Route of Administration: Oral

In Vitro Use Guide

Xaliproden (1 uM) increases the phenotypic survival of embryonic purified mouse motoneurons in vitro to the same extent as brain-derived neurotrophic factor (100 ng/ml), and increases the outgrowth and number of their neurites. It acts in a dose-dependent manner up to 1 uM which is the optimal concentration. Above this concentration, its neurotrophic effect decreases.

Name

Type

Language

XALIPRODEN HYDROCHLORIDE

Common Name

English

XALIPRODEN HYDROCHLORIDE [JAN]

Common Name

English

SR-57746A

Common Name

English

SR 57746A

Common Name

English

XALIPRODEN HYDROCHLORIDE [MI]

Common Name

English

1,2,3,6-TETRAHYDRO-1-(2-(2-NAPHTHALENYL)ETHYL)-4-(3-(TRIFLUOROMETHYL)PHENYL)PYRIDINE HYDROCHLORIDE

Systematic Name

English

XALIPRODEN HCL

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/00/015