Xaliproden HCl
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 203180

CAS#: 90494-79-4 (HCl)

Description: Xaliproden, also known as SR57746, is a drug which acts as a 5HT1A agonist. It has neurotrophic and neuroprotective effects in vitro, and has been proposed for use in the treatment of several neurodegenerative conditions including amyotrophic lateral sclerosis and Alzheimer's disease.


Price and Availability

Size
Price

10mg
USD 250
Size
Price

20mg
USD 450
Size
Price

50mg
USD 950

Xaliproden, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 203180
Name: Xaliproden HCl
CAS#: 90494-79-4 (HCl)
Chemical Formula: C24H23ClF3N
Exact Mass: 381.17043
Molecular Weight: 417.9
Elemental Analysis: C, 68.98; H, 5.55; Cl, 8.48; F, 13.64; N, 3.35


Related CAS #: 90494-79-4 (HCl)   135354-02-8 (free base)  

Synonym: SR57746; SR-57746; SR 57746; SR 57746A; SR-57746A; SR 57746A; Xaliproden HCl; Xaliproden hydrochloride

IUPAC/Chemical Name: 1-[2-(2-naphthyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine hydrochloride

InChi Key: WVHBEIJGAINUBW-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: FC(C1=CC(C2=CCN(CCC3=CC=C4C=CC=CC4=C3)CC2)=CC=C1)(F)F.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Xaliproden (codenamed SR57746) is a drug which acts as a 5HT1A agonist  It has neurotrophic and neuroprotective effects in vitro, and has been proposed for use in the treatment of several neurodegenerative conditions including amyotrophic lateral sclerosis (ALS) and Alzheimer's disease. Development of xaliproden for these two indications was discontinued in 2007 following analysis of Phase III data. While the drug did show an effect on hippocampal volume (suggesting perhaps a slowing of cell loss), there was insufficient evidence for efficacy in counteracting Alzheimer's related cognitive decline. Similarly while there were some indicators of efficacy in ALS, including a small but clinically noteworthy effect on some functional parameters, the overall benefit did not reach statistical significance when results across several Phase III trials were averaged. Xaliproden remains under investigation for treatment of peripheral neuropathy associated with chemotherapy. see wikepedia.com.
 
 
 


References

 1: Ng L, Khan F, Young CA, Galea M. Symptomatic treatments for amyotrophic lateral sclerosis/motor neuron disease. Cochrane Database Syst Rev. 2017 Jan 10;1:CD011776. doi: 10.1002/14651858.CD011776.pub2. Review. PubMed PMID: 28072907.

2: Andoh T, Sakamoto A, Kuraishi Y. 5-HT1A receptor agonists, xaliproden and tandospirone, inhibit the increase in the number of cutaneous mast cells involved in the exacerbation of mechanical allodynia in oxaliplatin-treated mice. J Pharmacol Sci. 2016 Aug;131(4):284-7. doi: 10.1016/j.jphs.2016.07.008. Epub 2016 Aug 4. PubMed PMID: 27562704.

3: Ahmed CM, Biswal MR, Li H, Han P, Ildefonso CJ, Lewin AS. Repurposing an orally available drug for the treatment of geographic atrophy. Mol Vis. 2016 Apr 2;22:294-310. eCollection 2016. PubMed PMID: 27110092; PubMed Central PMCID: PMC4818958.

4: Avan A, Postma TJ, Ceresa C, Avan A, Cavaletti G, Giovannetti E, Peters GJ. Platinum-induced neurotoxicity and preventive strategies: past, present, and future. Oncologist. 2015 Apr;20(4):411-32. doi: 10.1634/theoncologist.2014-0044. Epub 2015 Mar 12. Review. PubMed PMID: 25765877; PubMed Central PMCID: PMC4391771.

5: Andoh T, Sakamoto A, Kuraishi Y. Effects of xaliproden, a 5-HT₁A agonist, on mechanical allodynia caused by chemotherapeutic agents in mice. Eur J Pharmacol. 2013 Dec 5;721(1-3):231-6. doi: 10.1016/j.ejphar.2013.09.030. Epub 2013 Sep 23. PubMed PMID: 24070812.

6: Boerma M, Wang J, Sridharan V, Herbert JM, Hauer-Jensen M. Pharmacological induction of transforming growth factor-beta1 in rat models enhances radiation injury in the intestine and the heart. PLoS One. 2013 Jul 25;8(7):e70479. doi: 10.1371/journal.pone.0070479. Print 2013. PubMed PMID: 23936211; PubMed Central PMCID: PMC3723823.

7: Baldinger R, Katzberg HD, Weber M. Treatment for cramps in amyotrophic lateral sclerosis/motor neuron disease. Cochrane Database Syst Rev. 2012 Apr 18;(4):CD004157. doi: 10.1002/14651858.CD004157.pub2. Review. PubMed PMID: 22513921.

8: Sanjak M, Salachas F, Frija-Orvoen E, Theys P, Hutchinson D, Verheijde J, Pianta T, Stewart H, Brooks BR, Meininger V, Douillet P; Xaliproden [SR57746A] ALS International Study Group. Quality control of vital capacity as a primary outcome measure during phase III therapeutic clinical trial in amyotrophic lateral sclerosis. Amyotroph Lateral Scler. 2010 Aug;11(4):383-8. doi: 10.3109/17482960903486083. PubMed PMID: 20192884.

9: Porzner M, Müller T, Seufferlein T. SR 57746A/xaliproden, a non-peptide neurotrophic compound: prospects and constraints for the treatment of nervous system diseases. Expert Opin Investig Drugs. 2009 Nov;18(11):1765-72. doi: 10.1517/13543780903329089. Review. PubMed PMID: 19814656.

10: Sabbagh MN. Drug development for Alzheimer's disease: where are we now and where are we headed? Am J Geriatr Pharmacother. 2009 Jun;7(3):167-85. doi: 10.1016/j.amjopharm.2009.06.003. Review. PubMed PMID: 19616185; PubMed Central PMCID: PMC2948028.

11: Martel JC, Assié MB, Bardin L, Depoortère R, Cussac D, Newman-Tancredi A. 5-HT1A receptors are involved in the effects of xaliproden on G-protein activation, neurotransmitter release and nociception. Br J Pharmacol. 2009 Sep;158(1):232-42. doi: 10.1111/j.1476-5381.2009.00249.x. Epub 2009 Jun 5. PubMed PMID: 19508400; PubMed Central PMCID: PMC2795245.

12: Gordon PH, Corcia P, Lacomblez L, Pochigaeva K, Abitbol JL, Cudkowicz M, Leigh PN, Meininger V. Defining survival as an outcome measure in amyotrophic lateral sclerosis. Arch Neurol. 2009 Jun;66(6):758-61. doi: 10.1001/archneurol.2009.1. PubMed PMID: 19506136.

13: Douillet P, Orgogozo JM. What we have learned from the Xaliproden Sanofi-aventis trials. J Nutr Health Aging. 2009 Apr;13(4):365-6. PubMed PMID: 19300882.

14: Chang CW, Poteet E, Schetz JA, Gümüş ZH, Weinstein H. 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. Neuropharmacology. 2009;56 Suppl 1:213-25. doi: 10.1016/j.neuropharm.2008.07.049. Epub 2008 Aug 13. PubMed PMID: 18762202; PubMed Central PMCID: PMC2635340.

15: Wolf S, Barton D, Kottschade L, Grothey A, Loprinzi C. Chemotherapy-induced peripheral neuropathy: prevention and treatment strategies. Eur J Cancer. 2008 Jul;44(11):1507-15. doi: 10.1016/j.ejca.2008.04.018. Epub 2008 Jun 18. Review. PubMed PMID: 18571399.

16: Wilkes G. Peripheral neuropathy related to chemotherapy. Semin Oncol Nurs. 2007 Aug;23(3):162-73. Review. PubMed PMID: 17693343.

17: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 Nov;28(9):657-78. PubMed PMID: 17200730.

18: Gibson TB, Ranganathan A, D'Orazio A; American Society of Clinical Oncology. Highlights From: the 2006 American Society of Clinical Oncology Gastrointestinal Cancers Symposium San Francisco, CA, January 2006. Clin Colorectal Cancer. 2006 Mar;5(6):398-402. PubMed PMID: 16635277.

19: Susman E. Xaliproden lessens oxaliplatin-mediated neuropathy. Lancet Oncol. 2006 Apr;7(4):288. PubMed PMID: 16598880.

20: Labie C, Canolle B, Chatelin S, Lafon C, Fournier J. Effects of paliroden (SR57667B) and xaliproden on adult brain neurogenesis. Curr Alzheimer Res. 2006 Feb;3(1):35-6. Review. PubMed PMID: 16472201.