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MedKoo Cat#: 341299 | Name: Xaliproden

Description:

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

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
Xaliproden
CAS#135354-02-8 (free base)

Theoretical Analysis

MedKoo Cat#: 341299

Name: Xaliproden

CAS#: 135354-02-8 (free base)

Chemical Formula: C24H22F3N

Exact Mass: 381.1704

Molecular Weight: 381.44

Elemental Analysis: C, 75.57; H, 5.81; F, 14.94; N, 3.67

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
90494-79-4 (HCl) 135354-02-8 (free base)
Synonym
Xaliproden; SR 57746; SR-57746; SR57746.
IUPAC/Chemical Name
Pyridine, 1,2,3,6-tetrahydro-1-(2-(2-naphthalenyl)ethyl)-4-(3-(trifluoromethyl)phenyl)-
InChi Key
WJJYZXPHLSLMGE-UHFFFAOYSA-N
InChi Code
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
SMILES Code
FC(C1=CC(C2=CCN(CCC3=CC=C4C=CC=CC4=C3)CC2)=CC=C1)(F)F
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
Shelf Life
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 381.44 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.

Recalculate based on batch purity %
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
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. 3: 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(1):CD011776. doi: 10.1002/14651858.CD011776.pub2. PMID: 28072907; PMCID: PMC6469543. 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. 5: 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. PMID: 27110092; PMCID: PMC4818958. 6: 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. PMID: 25765877; PMCID: PMC4391771. 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. 18: Wilkes G. Peripheral neuropathy related to chemotherapy. Semin Oncol Nurs. 2007 Aug;23(3):162-73. doi: 10.1016/j.soncn.2007.05.001. PMID: 17693343. 19: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 Nov;28(9):657-78. PMID: 17200730. 20: 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. PMID: 16635277.