Xaliproden | SR57746 | CAS# 90494-79-4

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. The SR57746A activates PI3-K/AKT- and ERK-signaling in IECs. Depending on ERK- and AKT activation, SR57746A potently prevents apoptosis of IECs without inducing proliferation or migration in these cells. Moreover, SR57746A prevented apoptosis in EGCs in vitro. Topical SR57746A treatment significantly reduced mucosal injury in 2 experimental murine colitis models and was as effective as intraperitoneal infliximab treatment.

Chemical Structure

Xaliproden HCl

CAS# 90494-79-4 (HCl)

Instruction

Theoretical Analysis

MedKoo Cat#: 203180
Name: Xaliproden HCl
CAS#: 90494-79-4 (HCl)
Chemical Formula: C24H23ClF3N
Exact Mass: 381.17
Molecular Weight: 417.900
Elemental Analysis: C, 68.98; H, 5.55; Cl, 8.48; F, 13.64; N, 3.35

Price and Availability

Size	Price	Availability
25mg	USD 250	2 Weeks
50mg	USD 450	2 Weeks
100mg	USD 750	2 Weeks
200mg	USD 1350	2 Weeks
500mg	USD 2650	2 Weeks
1g	USD 3850	2 Weeks
2g	USD 6450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

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).

HS Tariff Code: 2934.99.9001

More Info: 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.

Instruction:

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In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 417.90 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Francisco SG, Rowan S. Repurposing Drugs for Treatment of Age-Related Macular Degeneration. Adv Exp Med Biol. 2023;1415:73-77. doi: 10.1007/978-3-031-27681-1_12. PMID: 37440017.

2: Walldorf J, Porzner M, Neumann M, Joodi G, Niess JH, von Boyen G, Mäder K, Weissbach J, Kleger A, Seufferlein T. The Selective 5-HT1A Agonist SR57746A Protects Intestinal Epithelial Cells and Enteric Glia Cells and Promotes Mucosal Recovery in Experimental Colitis. Inflamm Bowel Dis. 2022 Mar 2;28(3):423-433. doi: 10.1093/ibd/izab191. PMID: 34417821.

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4: 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. PMID: 27562704.

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7: 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. PMID: 24070812.

8: 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. PMID: 23936211; PMCID: PMC3723823.

9: 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. PMID: 22513921.

10: 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. PMID: 20192884.

11: 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. PMID: 19814656.

12: 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. PMID: 19616185; PMCID: PMC2948028.

13: 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. PMID: 19508400; PMCID: PMC2795245.

14: 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. PMID: 19506136.

15: Douillet P, Orgogozo JM. What we have learned from the Xaliproden Sanofi- aventis trials. J Nutr Health Aging. 2009 Apr;13(4):365-6. doi: 10.1007/s12603-009-0045-6. PMID: 19300882.

16: 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(Suppl 1):213-25. doi: 10.1016/j.neuropharm.2008.07.049. Epub 2008 Aug 13. PMID: 18762202; PMCID: PMC2635340.

17: 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. PMID: 18571399.

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