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MedKoo Cat#: 522593 | Name: AUY-954 free base

Description:

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

AUY-954 is a potent and selective S1P(1) modulator. AUY-954 prevents experimental autoimmune neuritis. In EAN rats, AUY954 greatly prevented paraparesis if administrated from the day of immunization. T cell, B cell, and macrophage infiltration, inflammatory demyelination, and local expression of interleukine-17 and matrix metalloproteinase-9 in sciatic nerves of EAN rats were significantly decreased by AUY954 treatment. Therefore, S1P(1) modulation might be a potential treatment option for inflammatory neuropathies.

Chemical Structure

AUY-954 free base
AUY-954 free base
CAS#820240-77-5 (free base)

Theoretical Analysis

MedKoo Cat#: 522593

Name: AUY-954 free base

CAS#: 820240-77-5 (free base)

Chemical Formula: C25H20F3NO2S

Exact Mass: 455.1167

Molecular Weight: 455.50

Elemental Analysis: C, 65.92; H, 4.43; F, 12.51; N, 3.08; O, 7.02; S, 7.04

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 #
820240-78-6 (HCl) 820240-77-5 (free base)
Synonym
NVP-AUY954, AUY954, AUY-954, AUY 954.
IUPAC/Chemical Name
3-(((2-(2-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)benzo[b]thiophen-5-yl)methyl)amino)propanoic acid
InChi Key
SKYYWSWIUKISCX-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H20F3NO2S/c26-25(27,28)21-13-18(7-8-20(21)17-4-2-1-3-5-17)23-14-19-12-16(6-9-22(19)32-23)15-29-11-10-24(30)31/h1-9,12-14,29H,10-11,15H2,(H,30,31)
SMILES Code
FC(F)(F)C1=CC(C2=CC3=CC(CNCCC(O)=O)=CC=C3S2)=CC=C1C4=CC=CC=C4
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
>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 455.50 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: Montrose DC, Scherl EJ, Bosworth BP, Zhou XK, Jung B, Dannenberg AJ, Hla T. S1P₁ localizes to the colonic vasculature in ulcerative colitis and maintains blood vessel integrity. J Lipid Res. 2013 Mar;54(3):843-51. doi: 10.1194/jlr.M034108. Epub 2013 Jan 7. PubMed PMID: 23296878; PubMed Central PMCID: PMC3617958. 2: Galicia-Rosas G, Pikor N, Schwartz JA, Rojas O, Jian A, Summers-Deluca L, Ostrowski M, Nuesslein-Hildesheim B, Gommerman JL. A sphingosine-1-phosphate receptor 1-directed agonist reduces central nervous system inflammation in a plasmacytoid dendritic cell-dependent manner. J Immunol. 2012 Oct 1;189(7):3700-6. Epub 2012 Aug 29. PubMed PMID: 22933630. 3: Trifilieff A, Fozard JR. Sphingosine-1-phosphate-induced airway hyper-reactivity in rodents is mediated by the sphingosine-1-phosphate type 3 receptor. J Pharmacol Exp Ther. 2012 Aug;342(2):399-406. doi: 10.1124/jpet.112.191585. Epub 2012 May 8. PubMed PMID: 22570366. 4: Jackson SJ, Giovannoni G, Baker D. Fingolimod modulates microglial activation to augment markers of remyelination. J Neuroinflammation. 2011 Jul 5;8:76. doi: 10.1186/1742-2094-8-76. PubMed PMID: 21729281; PubMed Central PMCID: PMC3152910. 5: Marsolais D, Yagi S, Kago T, Leaf N, Rosen H. Modulation of chemokines and allergic airway inflammation by selective local sphingosine-1-phosphate receptor 1 agonism in lungs. Mol Pharmacol. 2011 Jan;79(1):61-8. doi: 10.1124/mol.110.066811. Epub 2010 Oct 8. PubMed PMID: 20935081; PubMed Central PMCID: PMC3014274. 6: Shea BS, Brooks SF, Fontaine BA, Chun J, Luster AD, Tager AM. Prolonged exposure to sphingosine 1-phosphate receptor-1 agonists exacerbates vascular leak, fibrosis, and mortality after lung injury. Am J Respir Cell Mol Biol. 2010 Dec;43(6):662-73. doi: 10.1165/rcmb.2009-0345OC. Epub 2010 Jan 15. PubMed PMID: 20081052; PubMed Central PMCID: PMC2993087. 7: Walsh KB, Marsolais D, Welch MJ, Rosen H, Oldstone MB. Treatment with a sphingosine analog does not alter the outcome of a persistent virus infection. Virology. 2010 Feb 20;397(2):260-9. doi: 10.1016/j.virol.2009.08.043. Epub 2009 Dec 3. PubMed PMID: 19962171; PubMed Central PMCID: PMC2821988. 8: Zhang ZY, Zhang Z, Zug C, Nuesslein-Hildesheim B, Leppert D, Schluesener HJ. AUY954, a selective S1P(1) modulator, prevents experimental autoimmune neuritis. J Neuroimmunol. 2009 Nov 30;216(1-2):59-65. doi: 10.1016/j.jneuroim.2009.09.010. Epub 2009 Oct 4. PubMed PMID: 19804913. 9: Blé FX, Cannet C, Zurbruegg S, Gérard C, Frossard N, Beckmann N, Trifilieff A. Activation of the lung S1P(1) receptor reduces allergen-induced plasma leakage in mice. Br J Pharmacol. 2009 Nov;158(5):1295-301. doi: 10.1111/j.1476-5381.2009.00391.x. Epub 2009 Sep 25. PubMed PMID: 19785648; PubMed Central PMCID: PMC2782338. 10: Niessen F, Furlan-Freguia C, Fernández JA, Mosnier LO, Castellino FJ, Weiler H, Rosen H, Griffin JH, Ruf W. Endogenous EPCR/aPC-PAR1 signaling prevents inflammation-induced vascular leakage and lethality. Blood. 2009 Mar 19;113(12):2859-66. doi: 10.1182/blood-2008-12-192385. Epub 2009 Jan 13. Retraction in: Blood. 2011 Jun 30;117(26):7188. PubMed PMID: 19141861; PubMed Central PMCID: PMC2661868. 11: van Der Lee MM, Bras M, van Koppen CJ, Zaman GJ. beta-Arrestin recruitment assay for the identification of agonists of the sphingosine 1-phosphate receptor EDG1. J Biomol Screen. 2008 Dec;13(10):986-98. doi: 10.1177/1087057108326144. Epub 2008 Nov 25. PubMed PMID: 19036707. 12: Mullershausen F, Craveiro LM, Shin Y, Cortes-Cros M, Bassilana F, Osinde M, Wishart WL, Guerini D, Thallmair M, Schwab ME, Sivasankaran R, Seuwen K, Dev KK. Phosphorylated FTY720 promotes astrocyte migration through sphingosine-1-phosphate receptors. J Neurochem. 2007 Aug;102(4):1151-61. PubMed PMID: 17488279. 13: Pan S, Mi Y, Pally C, Beerli C, Chen A, Guerini D, Hinterding K, Nuesslein-Hildesheim B, Tuntland T, Lefebvre S, Liu Y, Gao W, Chu A, Brinkmann V, Bruns C, Streiff M, Cannet C, Cooke N, Gray N. A monoselective sphingosine-1-phosphate receptor-1 agonist prevents allograft rejection in a stringent rat heart transplantation model. Chem Biol. 2006 Nov;13(11):1227-34. PubMed PMID: 17114004.

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