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MedKoo Cat#: 562332 | Name: (S)-FTY720P
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Description:

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

(S)-FTY720P is a potent immune modulator. It acts on S1P1, S1P3, S1P4, and S1P5.

Chemical Structure

(S)-FTY720P
(S)-FTY720P
CAS#402616-26-6

Theoretical Analysis

MedKoo Cat#: 562332

Name: (S)-FTY720P

CAS#: 402616-26-6

Chemical Formula: C19H34NO5P

Exact Mass: 387.2175

Molecular Weight: 387.45

Elemental Analysis: C, 58.90; H, 8.85; N, 3.62; O, 20.65; P, 7.99

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 750.00 2 Weeks
100mg USD 3,650.00 2 Weeks
1g USD 6,950.00 2 Weeks
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Synonym
(S)-FTY720P; (S) FTY720P; (S)FTY720P; S-FTY720P; (S)-FTY720 phosphate; FTY720 (S)-Phosphate; FTY-720 (S)-Phosphate;
IUPAC/Chemical Name
(S)-2-amino-2-(hydroxymethyl)-4-(4-octylphenyl)butyl dihydrogen phosphate
InChi Key
LRFKWQGGENFBFO-IBGZPJMESA-N
InChi Code
InChI=1S/C19H34NO5P/c1-2-3-4-5-6-7-8-17-9-11-18(12-10-17)13-14-19(20,15-21)16-25-26(22,23)24/h9-12,21H,2-8,13-16,20H2,1H3,(H2,22,23,24)/t19-/m0/s1
SMILES Code
CCCCCCCCC1=CC=C(CC[C@@](CO)(N)COP(O)(O)=O)C=C1
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 387.45 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: Al Alam N, Kreydiyyeh SI. FTY720P inhibits hepatic Na(+)-K(+) ATPase via S1PR2 and PGE2. Biochem Cell Biol. 2016 Aug;94(4):371-7. doi: 10.1139/bcb-2016-0025. Epub 2016 Aug 8. PubMed PMID: 27501354. 2: Tölle M, Klöckl L, Wiedon A, Zidek W, van der Giet M, Schuchardt M. Regulation of endothelial nitric oxide synthase activation in endothelial cells by S1P1 and S1P3. Biochem Biophys Res Commun. 2016 Aug 5;476(4):627-634. doi: 10.1016/j.bbrc.2016.06.009. Epub 2016 Jun 7. PubMed PMID: 27282481. 3: Park MK, Park S, Kim HJ, Kim EJ, Kim SY, Kang GJ, Byun HJ, Kim SH, Lee H, Lee CH. Novel effects of FTY720 on perinuclear reorganization of keratin network induced by sphingosylphosphorylcholine: Involvement of protein phosphatase 2A and G-protein-coupled receptor-12. Eur J Pharmacol. 2016 Mar 15;775:86-95. doi: 10.1016/j.ejphar.2016.02.024. Epub 2016 Feb 9. PubMed PMID: 26872988. 4: Gardner NM, Riley RT, Showker JL, Voss KA, Sachs AJ, Maddox JR, Gelineau-van Waes JB. Elevated Nuclear and Cytoplasmic FTY720-Phosphate in Mouse Embryonic Fibroblasts Suggests the Potential for Multiple Mechanisms in FTY720-Induced Neural Tube Defects. Toxicol Sci. 2016 Mar;150(1):161-8. doi: 10.1093/toxsci/kfv321. Epub 2015 Dec 29. PubMed PMID: 26719367; PubMed Central PMCID: PMC5009620. 5: Ottenlinger F, Schwiebs A, Pfarr K, Wagner A, Grüner S, Mayer CA, Pfeilschifter JM, Radeke HH. Fingolimod targeting protein phosphatase 2A differently affects IL-33 induced IL-2 and IFN-γ production in CD8(+) lymphocytes. Eur J Immunol. 2016 Apr;46(4):941-51. doi: 10.1002/eji.201545805. Epub 2016 Jan 13. PubMed PMID: 26683421. 6: Reeves PM, Kang YL, Kirchhausen T. Endocytosis of Ligand-Activated Sphingosine 1-Phosphate Receptor 1 Mediated by the Clathrin-Pathway. Traffic. 2016 Jan;17(1):40-52. doi: 10.1111/tra.12343. Epub 2015 Dec 9. PubMed PMID: 26481905; PubMed Central PMCID: PMC4688054. 7: Attiori Essis S, Laurier-Laurin ME, Pépin É, Cyr M, Massicotte G. GluN2B-containing NMDA receptors are upregulated in plasma membranes by the sphingosine-1-phosphate analog FTY720P. Brain Res. 2015 Oct 22;1624:349-358. doi: 10.1016/j.brainres.2015.07.055. Epub 2015 Aug 8. PubMed PMID: 26260438. 8: Janssen S, Schlegel C, Gudi V, Prajeeth CK, Skripuletz T, Trebst C, Stangel M. Effect of FTY720-phosphate on the expression of inflammation-associated molecules in astrocytes in vitro. Mol Med Rep. 2015 Oct;12(4):6171-7. doi: 10.3892/mmr.2015.4120. Epub 2015 Jul 27. PubMed PMID: 26239526. 9: Heinen A, Beyer F, Tzekova N, Hartung HP, Küry P. Fingolimod induces the transition to a nerve regeneration promoting Schwann cell phenotype. Exp Neurol. 2015 Sep;271:25-35. doi: 10.1016/j.expneurol.2015.05.002. Epub 2015 May 7. PubMed PMID: 25957629. 10: Zhang DD, Linke B, Suo J, Zivkovic A, Schreiber Y, Ferreirós N, Henke M, Geisslinger G, Stark H, Scholich K. Antinociceptive effects of FTY720 during trauma-induced neuropathic pain are mediated by spinal S1P receptors. Biol Chem. 2015 Jun;396(6-7):783-94. doi: 10.1515/hsz-2014-0276. PubMed PMID: 25720064. 11: Schröder M, Arlt O, Schmidt H, Huwiler A, Angioni C, Pfeilschifter JM, Schwiebs A, Radeke HH. Subcellular distribution of FTY720 and FTY720-phosphate in immune cells - another aspect of Fingolimod action relevant for therapeutic application. Biol Chem. 2015 Jun;396(6-7):795-802. doi: 10.1515/hsz-2014-0287. PubMed PMID: 25720062. 12: Kułakowska A, Byfield FJ, Zendzian-Piotrowska M, Zajkowska JM, Drozdowski W, Mroczko B, Janmey PA, Bucki R. Increased levels of sphingosine-1-phosphate in cerebrospinal fluid of patients diagnosed with tick-borne encephalitis. J Neuroinflammation. 2014 Nov 25;11:193. doi: 10.1186/s12974-014-0193-4. PubMed PMID: 25421616; PubMed Central PMCID: PMC4258275. 13: Czubowicz K, Cieślik M, Pyszko J, Strosznajder JB, Strosznajder RP. Sphingosine-1-phosphate and its effect on glucose deprivation/glucose reload stress: from gene expression to neuronal survival. Mol Neurobiol. 2015;51(3):1300-8. doi: 10.1007/s12035-014-8807-5. Epub 2014 Jul 24. PubMed PMID: 25056275; PubMed Central PMCID: PMC4434862. 14: Aliouane L, Chao S, Brizuela L, Pfund E, Cuvillier O, Jean L, Renard PY, Lequeux T. Synthesis of fluorinated agonist of sphingosine-1-phosphate receptor 1. Bioorg Med Chem. 2014 Sep 1;22(17):4955-60. doi: 10.1016/j.bmc.2014.06.038. Epub 2014 Jun 27. PubMed PMID: 25047939. 15: Sykes DA, Riddy DM, Stamp C, Bradley ME, McGuiness N, Sattikar A, Guerini D, Rodrigues I, Glaenzel A, Dowling MR, Mullershausen F, Charlton SJ. Investigating the molecular mechanisms through which FTY720-P causes persistent S1P1 receptor internalization. Br J Pharmacol. 2014 Nov;171(21):4797-807. doi: 10.1111/bph.12620. PubMed PMID: 24641481; PubMed Central PMCID: PMC4294105. 16: Fayyaz S, Henkel J, Japtok L, Krämer S, Damm G, Seehofer D, Püschel GP, Kleuser B. Involvement of sphingosine 1-phosphate in palmitate-induced insulin resistance of hepatocytes via the S1P2 receptor subtype. Diabetologia. 2014 Feb;57(2):373-82. doi: 10.1007/s00125-013-3123-6. Epub 2013 Nov 29. PubMed PMID: 24292566. 17: Rutherford C, Childs S, Ohotski J, McGlynn L, Riddick M, MacFarlane S, Tasker D, Pyne S, Pyne NJ, Edwards J, Palmer TM. Regulation of cell survival by sphingosine-1-phosphate receptor S1P1 via reciprocal ERK-dependent suppression of Bim and PI-3-kinase/protein kinase C-mediated upregulation of Mcl-1. Cell Death Dis. 2013 Nov 21;4:e927. doi: 10.1038/cddis.2013.455. PubMed PMID: 24263101; PubMed Central PMCID: PMC3847331. 18: Nam JH, Kim WK, Kim BJ. Sphingosine and FTY720 modulate pacemaking activity in interstitial cells of Cajal from mouse small intestine. Mol Cells. 2013 Sep;36(3):235-44. doi: 10.1007/s10059-013-0091-0. Epub 2013 Aug 2. PubMed PMID: 23912597; PubMed Central PMCID: PMC3887975. 19: Doi Y, Takeuchi H, Horiuchi H, Hanyu T, Kawanokuchi J, Jin S, Parajuli B, Sonobe Y, Mizuno T, Suzumura A. Fingolimod phosphate attenuates oligomeric amyloid β-induced neurotoxicity via increased brain-derived neurotrophic factor expression in neurons. PLoS One. 2013 Apr 12;8(4):e61988. doi: 10.1371/journal.pone.0061988. Print 2013. PubMed PMID: 23593505; PubMed Central PMCID: PMC3625222. 20: Kim YD, Han KT, Lee J, Park CG, Kim MY, Shahi PK, Zuo DC, Choi S, Jun JY. Effects of sphingosine-1-phosphate on pacemaker activity of interstitial cells of Cajal from mouse small intestine. Mol Cells. 2013 Jan;35(1):79-86. doi: 10.1007/s10059-013-2282-0. Epub 2013 Jan 9. PubMed PMID: 23307289; PubMed Central PMCID: PMC3887851.

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