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
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
| 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 |
| 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 |
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.
Originator
Sources: http://adisinsight.springer.com/drugs/800001601 | https://www.ncbi.nlm.nih.gov/pubmed/14584974
Curator's Comment: The drug was originated by Sanofi, and in mid-1999, Sanofi merged with Synthélabo to form Sanofi-Synthélabo.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Magnetic resonance imaging of the neuroprotective effect of xaliproden in rats. | 2002 Jun |
|
| Xaliproden: SR 57746, SR 57746A, xaliproden hydrochloride, xaliprodene. | 2003 |
|
| Efficacy and safety of xaliproden in amyotrophic lateral sclerosis: results of two phase III trials. | 2004 Jun |
|
| Xaliproden in amyotrophic lateral sclerosis: early clinical trials. | 2004 Jun |
|
| Quantification of neurotrophin mRNA expression in PMN mouse: modulation by xaliproden. | 2004 May-Aug |
|
| Xaliproden (SR57746A) induces 5-HT1A receptor-mediated MAP kinase activation in PC12 cells. | 2005 Apr-Jun |
|
| MAPK activation via 5-hydroxytryptamine 1A receptor is involved in the neuroprotective effects of xaliproden. | 2005 Jan-Mar |
|
| Effects of paliroden (SR57667B) and xaliproden on adult brain neurogenesis. | 2006 Feb |
|
| Pharmacological strategies for the prevention of Alzheimer's disease. | 2006 Jan |
|
| Highlights From: the 2006 American Society of Clinical Oncology Gastrointestinal Cancers Symposium San Francisco, CA, January 2006. | 2006 Mar |
|
| Peripheral neuropathy related to chemotherapy. | 2007 Aug |
|
| Small molecule activators of the Trk receptors for neuroprotection. | 2008 Dec 3 |
|
| Chemotherapy-induced peripheral neuropathy: prevention and treatment strategies. | 2008 Jul |
|
| 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 |
|
| Role of oxaliplatin in the treatment of colorectal cancer. | 2009 Feb |
|
| Amyotrophic lateral sclerosis. | 2009 Feb 3 |
|
| Drug development for Alzheimer's disease: where are we now and where are we headed? | 2009 Jun |
|
| Defining survival as an outcome measure in amyotrophic lateral sclerosis. | 2009 Jun |
|
| SR 57746A/xaliproden, a non-peptide neurotrophic compound: prospects and constraints for the treatment of nervous system diseases. | 2009 Nov |
|
| 5-HT1A receptors are involved in the effects of xaliproden on G-protein activation, neurotransmitter release and nociception. | 2009 Sep |
Patents
Sample Use Guides
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
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
Edited
Fri Dec 15 19:42:09 GMT 2023
by
admin
on
Fri Dec 15 19:42:09 GMT 2023
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| Record UNII |
44D5EE8E26
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| Record Status |
Validated (UNII)
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EU-Orphan Drug |
EU/3/00/015
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NCI_THESAURUS |
C1509
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100000151936
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C61328
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DBSALT002009
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128918
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m11522
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