AUY-954 free base

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

MedKoo CAT#: 522593

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

Description: 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

CAS# 820240-77-5 (free base)

Instruction

Theoretical Analysis

MedKoo Cat#: 522593
Name: AUY-954 free base
CAS#: 820240-77-5 (free base)
Chemical Formula: C25H20F3NO2S
Exact Mass: 455.12
Molecular Weight: 455.495
Elemental Analysis: C, 65.92; H, 4.43; F, 12.51; N, 3.08; O, 7.02; S, 7.04

Price and Availability

Size	Price	Availability	Quantity
5mg	USD -2
10mg	USD -2
25mg	USD -2
50mg	USD -2
100mg	USD -2
200mg	USD -2
500mg	USD -2
1g	USD -1
2g	USD -1
5g	USD -1
10g	USD -1
20g	USD -1
50g	USD -1
100g	USD -1
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 #: 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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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: 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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