Fingolimod | CAS#162359-55-9 | MS treatment

MedKoo Cat#: 584406 | Name: Fingolimod

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Description:

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

Fingolimod is used to treat multiple sclerosis, and has antineoplastic activity.

Chemical Structure

Fingolimod

CAS#162359-55-9 (free base)

Theoretical Analysis

MedKoo Cat#: 584406

Name: Fingolimod

CAS#: 162359-55-9 (free base)

Chemical Formula: C19H33NO2

Exact Mass: 307.2511

Molecular Weight: 307.48

Elemental Analysis: C, 74.22; H, 10.82; N, 4.56; O, 10.41

Price and Availability

Size	Price	Availability
50mg	USD 350.00	2 Weeks
100mg	USD 550.00	2 Weeks
250mg	USD 950.00	2 Weeks

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Related CAS #

162359-56-0 (HCl) 162359-55-9 (free base)

Synonym

Fingolimod; FTY720 (free base)

IUPAC/Chemical Name

1,3-Propanediol, 2-amino-2-(2-(4-octylphenyl)ethyl)-

InChi Key

KKGQTZUTZRNORY-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H33NO2/c1-2-3-4-5-6-7-8-17-9-11-18(12-10-17)13-14-19(20,15-21)16-22/h9-12,21-22H,2-8,13-16,20H2,1H3

SMILES Code

OCC(CCC1=CC=C(CCCCCCCC)C=C1)(N)CO

Appearance

Solid powder

Purity

>97% (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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Fingolimod (FTY720 free base) is a sphingosine 1-phosphate (S1P) antagonist with an IC50 of 0.033 nM in K562 and NK cells.

In vitro activity:

FTY720 decreased glioma cell viability in a dose-dependent manner in U251MG, U87MG, and U118MG (Figure 1a). Interestingly, although the pan-caspase inhibitor (z-VAD) completely blocked TNF-α plus cycloheximide (CHX)-induced cell death, z-VAD had no effect on cell death in FTY720-treated glioma cells (Figure 1b). Next, the possibility of necrosis was examined. When cells were treated with NecroX-5, a necrosis inhibitor, cell death by H2O2 was blocked, but FTY720-induced cell death did not change (Figure 1f). Therefore, these data indicate that FTY720 induces non-apoptotic and non-necrotic cell death in glioma cells. Reference: Cancers (Basel). 2020 Nov; 12(11): 3388. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7696845/

In vivo activity:

Compared with the sham mice group, the expressions of occludin and claudin-5 in the TBI group and the TBI + vehicle group were significantly decreased (p < 0.05), and both of them were significantly increased after FTY720 treatment (Fig. 3A, C, D). Immunofluorescent staining also showed that occludin and claudin-5 were down-regulated after TBI significantly and which were restored by FTY720 (Fig. 3E, F, G). Besides, activated (phosphorylated) ERK1/2, a key protein that transmits signals from surface receptors to the nucleus, was significantly elevated in the brain at 24 h after TBI. And this increase was reduced after treatment with FTY720 (p < 0.05) (Fig. 3A, B). Then the expression of the target of FTY720 was tested, and the result found that the expression of S1PR1 decreased significantly after using FTY720 (p < 0.05) (Supplementary Fig. C, D). But FTY720 had no effect on the content of S1P after TBI (p > 0.05) (Supplementary Fig. B). Reference: Int J Med Sci. 2021; 18(2): 304–313. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7757143/

	Solvent	mg/mL	mM
Solubility
	DMSO	8.3	27.09
	DMF	20.0	65.05
	Ethanol	5.0	16.26

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 307.48 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:

1. Min KJ, Kwon TK. Induction of Lysosomal Membrane Permeabilization Is a Major Event of FTY720-Mediated Non-Apoptotic Cell Death in Human Glioma Cells. Cancers (Basel). 2020 Nov 16;12(11):3388. doi: 10.3390/cancers12113388. PMID: 33207629; PMCID: PMC7696845. 2. Chang WT, Liu PY, Wu SN. Actions of FTY720 (Fingolimod), a Sphingosine-1-Phosphate Receptor Modulator, on Delayed-Rectifier K+ Current and Intermediate-Conductance Ca2+-Activated K+ Channel in Jurkat T-Lymphocytes. Molecules. 2020 Oct 2;25(19):4525. doi: 10.3390/molecules25194525. PMID: 33023219; PMCID: PMC7582672. 3. Zhu C, Wen S, Li J, Meng H, Zhang J, Zhao K, Wang L, Zhang Y. FTY720 Inhibits the Development of Collagen-Induced Arthritis in Mice by Suppressing the Recruitment of CD4+ T Lymphocytes. Drug Des Devel Ther. 2021 May 11;15:1981-1992. doi: 10.2147/DDDT.S293876. PMID: 34007158; PMCID: PMC8123953. 4. Cheng H, Di G, Gao CC, He G, Wang X, Han YL, Sun LA, Zhou ML, Jiang X. FTY720 Reduces Endothelial Cell Apoptosis and Remodels Neurovascular Unit after Experimental Traumatic Brain Injury. Int J Med Sci. 2021 Jan 1;18(2):304-313. doi: 10.7150/ijms.49066. PMID: 33390799; PMCID: PMC7757143.

In vitro protocol:

In vivo protocol:

1. Zhu C, Wen S, Li J, Meng H, Zhang J, Zhao K, Wang L, Zhang Y. FTY720 Inhibits the Development of Collagen-Induced Arthritis in Mice by Suppressing the Recruitment of CD4+ T Lymphocytes. Drug Des Devel Ther. 2021 May 11;15:1981-1992. doi: 10.2147/DDDT.S293876. PMID: 34007158; PMCID: PMC8123953. 2. Cheng H, Di G, Gao CC, He G, Wang X, Han YL, Sun LA, Zhou ML, Jiang X. FTY720 Reduces Endothelial Cell Apoptosis and Remodels Neurovascular Unit after Experimental Traumatic Brain Injury. Int J Med Sci. 2021 Jan 1;18(2):304-313. doi: 10.7150/ijms.49066. PMID: 33390799; PMCID: PMC7757143.

1: Ward MD, Jones DE, Goldman MD. Overview and safety of fingolimod hydrochloride use in patients with multiple sclerosis. Expert Opin Drug Saf. 2014 Jul;13(7):989-98. doi: 10.1517/14740338.2014.920820. Review. PubMed PMID: 24935480. 2: Derfuss T, Bergvall NK, Sfikas N, Tomic DL. Efficacy of fingolimod in patients with highly active relapsing-remitting multiple sclerosis. Curr Med Res Opin. 2015;31(9):1687-91. doi: 10.1185/03007995.2015.1067191. Epub 2015 Aug 20. PubMed PMID: 26121423. 3: Cruz VT, Fonseca J. Central effects of fingolimod. Rev Neurol. 2014 Aug 1;59(3):121-8. Review. English, Spanish. PubMed PMID: 25030072. 4: Fox E, Edwards K, Burch G, Wynn DR, LaGanke C, Crayton H, Hunter SF, Huffman C, Kim E, Pestreich L, McCague K, Barbato L; EPOC study investigators. Outcomes of switching directly to oral fingolimod from injectable therapies: Results of the randomized, open-label, multicenter, Evaluate Patient OutComes (EPOC) study in relapsing multiple sclerosis. Mult Scler Relat Disord. 2014 Sep;3(5):607-19. doi: 10.1016/j.msard.2014.06.005. Epub 2014 Jul 4. PubMed PMID: 26265273. 5: Hersh CM, Hara-Cleaver C, Rudick RA, Cohen JA, Bermel RA, Ontaneda D. Experience with fingolimod in clinical practice. Int J Neurosci. 2015;125(9):678-85. doi: 10.3109/00207454.2014.969839. Epub 2014 Oct 29. PubMed PMID: 25271798; PubMed Central PMCID: PMC4414718. 6: Camm J, Hla T, Bakshi R, Brinkmann V. Cardiac and vascular effects of fingolimod: mechanistic basis and clinical implications. Am Heart J. 2014 Nov;168(5):632-44. doi: 10.1016/j.ahj.2014.06.028. Epub 2014 Jul 11. Review. PubMed PMID: 25440790. 7: Karlsson G, Francis G, Koren G, Heining P, Zhang X, Cohen JA, Kappos L, Collins W. Pregnancy outcomes in the clinical development program of fingolimod in multiple sclerosis. Neurology. 2014 Feb 25;82(8):674-80. doi: 10.1212/WNL.0000000000000137. Epub 2014 Jan 24. PubMed PMID: 24463630; PubMed Central PMCID: PMC3945658. 8: Francis G, Kappos L, O'Connor P, Collins W, Tang D, Mercier F, Cohen JA. Temporal profile of lymphocyte counts and relationship with infections with fingolimod therapy. Mult Scler. 2014 Apr;20(4):471-80. doi: 10.1177/1352458513500551. Epub 2013 Aug 15. PubMed PMID: 23950550. 9: Sanford M. Fingolimod: a review of its use in relapsing-remitting multiple sclerosis. Drugs. 2014 Aug;74(12):1411-33. doi: 10.1007/s40265-014-0264-y. Review. PubMed PMID: 25063048. 10: Vanoli E, Pentimalli F, Botto G. Vagomimetic effects of fingolimod: physiology and clinical implications. CNS Neurosci Ther. 2014 Jun;20(6):496-502. doi: 10.1111/cns.12283. Review. PubMed PMID: 24836740; PubMed Central PMCID: PMC4204275. 11: Simula S, Laitinen T, Laitinen TM, Tarkiainen T, Hartikainen JE, Hartikainen P. Effects of Three Months Fingolimod Therapy on Heart Rate. J Neuroimmune Pharmacol. 2015 Dec;10(4):651-4. doi: 10.1007/s11481-015-9619-8. Epub 2015 Jun 20. PubMed PMID: 26092537. 12: Bermel RA, Hashmonay R, Meng X, Randhawa S, von Rosenstiel P, Sfikas N, Kantor D. Fingolimod first-dose effects in patients with relapsing multiple sclerosis concomitantly receiving selective serotonin-reuptake inhibitors. Mult Scler Relat Disord. 2015 May;4(3):273-80. doi: 10.1016/j.msard.2015.04.002. Epub 2015 Apr 13. PubMed PMID: 26008945. 13: Efstathopoulos P, Kourgiantaki A, Karali K, Sidiropoulou K, Margioris AN, Gravanis A, Charalampopoulos I. Fingolimod induces neurogenesis in adult mouse hippocampus and improves contextual fear memory. Transl Psychiatry. 2015 Nov 24;5:e685. doi: 10.1038/tp.2015.179. PubMed PMID: 26795749; PubMed Central PMCID: PMC5545691. 14: Ziemssen T, Kern R, Cornelissen C. The PANGAEA study design - a prospective, multicenter, non-interventional, long-term study on fingolimod for the treatment of multiple sclerosis in daily practice. BMC Neurol. 2015 Jun 18;15:93. doi: 10.1186/s12883-015-0342-0. PubMed PMID: 26084334; PubMed Central PMCID: PMC4472406. 15: DiMarco JP, O'Connor P, Cohen JA, Reder AT, Zhang-Auberson L, Tang D, Collins W, Kappos L. First-dose effects of fingolimod: Pooled safety data from three phase 3 studies. Mult Scler Relat Disord. 2014 Sep;3(5):629-38. doi: 10.1016/j.msard.2014.05.005. Epub 2014 Jun 17. PubMed PMID: 26265275. 16: David OJ, Pryce M, Meiser K, Picard F, Emotte C, Kobalava Z, Moiseev V, Schmouder R. Pharmacokinetics of fingolimod and metabolites in subjects with severe renal impairment: An open-label, single-dose, parallel-group study. Int J Clin Pharmacol Ther. 2015 Oct;53(10):847-54. doi: 10.5414/CP202356. PubMed PMID: 26308173. 17: Tanasescu R, Constantinescu CS. Pharmacokinetic evaluation of fingolimod for the treatment of multiple sclerosis. Expert Opin Drug Metab Toxicol. 2014 Apr;10(4):621-30. doi: 10.1517/17425255.2014.894019. Epub 2014 Mar 1. Review. PubMed PMID: 24579791. 18: Montalban X, Comi G, Antel J, O'Connor P, de Vera A, Cremer M, Sfikas N, von Rosenstiel P, Kappos L. Long-term results from a phase 2 extension study of fingolimod at high and approved dose in relapsing multiple sclerosis. J Neurol. 2015 Dec;262(12):2627-34. doi: 10.1007/s00415-015-7834-0. Epub 2015 Sep 4. PubMed PMID: 26338810. 19: Zhang J, Zhang ZG, Li Y, Ding X, Shang X, Lu M, Elias SB, Chopp M. Fingolimod treatment promotes proliferation and differentiation of oligodendrocyte progenitor cells in mice with experimental autoimmune encephalomyelitis. Neurobiol Dis. 2015 Apr;76:57-66. doi: 10.1016/j.nbd.2015.01.006. Epub 2015 Feb 11. PubMed PMID: 25680941. 20: Li YJ, Chang GQ, Liu Y, Gong Y, Yang C, Wood K, Shi FD, Fu Y, Yan Y. Fingolimod alters inflammatory mediators and vascular permeability in intracerebral hemorrhage. Neurosci Bull. 2015 Dec;31(6):755-62. doi: 10.1007/s12264-015-1532-2. Epub 2015 May 10. PubMed PMID: 25958190; PubMed Central PMCID: PMC5563722.