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Details

Stereochemistry ACHIRAL
Molecular Formula C24H22F3N
Molecular Weight 381.4334
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of XALIPRODEN

SMILES

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

InChI

InChIKey=WJJYZXPHLSLMGE-UHFFFAOYSA-N
InChI=1S/C24H22F3N/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

HIDE SMILES / InChI
Molecular Formula C24H22F3N
Molecular Weight 381.4334
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Sanofi-Aventis
63
Curator's Comment: The drug was originated by Sanofi, and in mid-1999, Sanofi merged with Synthélabo to form Sanofi-Synthélabo.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 4.3 nM [IC50]
Agonist
2752
 9.0 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
665
Unknown

Approved Use

Unknown
Primary
Phase III
665
Unknown

Approved Use

Unknown
Palliative
Phase III
665
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
2 mg 1 times / day multiple, oral
MTD
Dose: 2 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/15204011/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/15204011/
Sources:
https://pubmed.ncbi.nlm.nih.gov/15204011/
PubMed

PubMed

TitleDatePubMed
SR 57746A/xaliproden, a non-peptide neurotrophic compound: prospects and constraints for the treatment of nervous system diseases.
2009-11
5-HT1A receptors are involved in the effects of xaliproden on G-protein activation, neurotransmitter release and nociception.
2009-09
Drug development for Alzheimer's disease: where are we now and where are we headed?
2009-06
Defining survival as an outcome measure in amyotrophic lateral sclerosis.
2009-06
Amyotrophic lateral sclerosis.
2009-02-03
Role of oxaliplatin in the treatment of colorectal cancer.
2009-02
Current and emerging treatments for amyotrophic lateral sclerosis.
2009
Towards a quantitative representation of the cell signaling mechanisms of hallucinogens: measurement and mathematical modeling of 5-HT1A and 5-HT2A receptor-mediated ERK1/2 activation.
2009
Small molecule activators of the Trk receptors for neuroprotection.
2008-12-03
Chemotherapy-induced peripheral neuropathy: prevention and treatment strategies.
2008-07
Peripheral neuropathy related to chemotherapy.
2007-08
Xaliproden lessens oxaliplatin-mediated neuropathy.
2006-04
Highlights From: the 2006 American Society of Clinical Oncology Gastrointestinal Cancers Symposium San Francisco, CA, January 2006.
2006-03
Effects of paliroden (SR57667B) and xaliproden on adult brain neurogenesis.
2006-02
Pharmacological strategies for the prevention of Alzheimer's disease.
2006-01
Xaliproden (SR57746A) induces 5-HT1A receptor-mediated MAP kinase activation in PC12 cells.
2005-05-13
MAPK activation via 5-hydroxytryptamine 1A receptor is involved in the neuroprotective effects of xaliproden.
2005-02-09
Quantification of neurotrophin mRNA expression in PMN mouse: modulation by xaliproden.
2004-06-03
Efficacy and safety of xaliproden in amyotrophic lateral sclerosis: results of two phase III trials.
2004-06
Xaliproden in amyotrophic lateral sclerosis: early clinical trials.
2004-06
Xaliproden: SR 57746, SR 57746A, xaliproden hydrochloride, xaliprodene.
2003
Magnetic resonance imaging of the neuroprotective effect of xaliproden in rats.
2002-06
Patents

Patents

07320982
2

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:24:12 GMT 2025
Edited
by admin
on Mon Mar 31 18:24:12 GMT 2025
Record UNII
V8QL94KNQO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
XALIPRODEN
INN   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
SR-57746
Preferred Name English
XALIPRODEN [USAN]
Common Name English
PYRIDINE, 1,2,3,6-TETRAHYDRO-1-(2-(2-NAPHTHALENYL)ETHYL)-4-(3-(TRIFLUOROMETHYL)PHENYL)-
Systematic Name English
XALIPRODEN [MI]
Common Name English
Xaliproden [WHO-DD]
Common Name English
xaliproden [INN]
Common Name English
SR57746
Code English
Classification Tree Code System Code
NCI_THESAURUS C1509
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
WHO-VATC QN07XX03
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
WHO-ATC N07XX03
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
Code System Code Type Description
DRUG BANK
DB06393
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
USAN
LL-101
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
FDA UNII
V8QL94KNQO
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
INN
7622
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
CHEBI
48520
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
WIKIPEDIA
XALIPRODEN
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
EPA CompTox
DTXSID9048306
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
NCI_THESAURUS
C152924
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
EVMPD
SUB00091MIG
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
MERCK INDEX
m11522
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1512580
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
PUBCHEM
128919
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
SMS_ID
100000079348
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
CAS
135354-02-8
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
MESH
C462299
Created by admin on Mon Mar 31 18:24:12 GMT 2025 , Edited by admin on Mon Mar 31 18:24:12 GMT 2025
PRIMARY
Related Record Type Details
5-HYDROXYTRYPTAMINE RECEPTOR 1A
TARGET -> AGONIST
Structure of XALIPRODEN HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of XALIPRODEN
ACTIVE MOIETY
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