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SML0700

Sigma-Aldrich

FTY720

≥98% (HPLC), powder, immunomodulating drug

Synonym(s):

2-Amino-2-[2-(4-octyl-phenyl)-ethyl]-propane-1,3-diol hydrochloride, Fingolimod hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C19H33NO2 · HCl
CAS Number:
162359-56-0
Molecular Weight:
343.93
UNSPSC Code:
12352211
NACRES:
NA.77

product name

FTY720, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

water: 10 mg/mL, clear

storage temp.

−20°C

InChI

1S/C19H33NO2.ClH/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;1H

InChI key

SWZTYAVBMYWFGS-UHFFFAOYSA-N

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Application

FTY720 has been used as an immunomodulator and is used to investigate its effect on in vitro gastrulation model of P19C5 stem cells. It is also used to determine its efficacy in prolonging the survival corneal transplantation. FTY720 has been used to study its effect on the proliferation and differentiation of cultured embryonic hippocampal neural stem cells (NSCs) using the 5-bromo-2-deoxyuridine incorporation assay, the neurosphere formation assay and western blot analysis.

Biochem/physiol Actions

FTY720 is an immunomodulating drug and sphingosine 1-phosphate (S1P) receptor modulator. Phosphorylation of FTY270 by sphingosine kinase causes S1P1R internalization, which sequesters lymphocytes in lymph nodes, preventing them from taking part in an autoimmune response. Clinically, it has been approved for the treatment of multiple sclerosis (MS). It has also been shown to block and reverse paclitaxel-induced chemotherapy induced peripheral neuropathy (CIPN) through S1PR inhibition as well as inhibit the activity of histone deacetylases in the hippocampus of mouse brains, thereby modulating memory.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H373

Precautionary Statements

P260 - P314 - P501

Hazard Classifications

STOT RE 2

Target Organs

Immune system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M Mehling et al.
Neurology, 76(8 Suppl 3), S20-S27 (2011-02-26)
The oral sphingosine 1-phosphate (S1P) receptor (S1PR) modulator fingolimod has been shown to be effective in the treatment of patients with relapsing multiple sclerosis (MS). The drug binds with high affinity to 4 of the 5 G-protein-coupled S1P receptors (S1P(1-5)).
Goeril Karlsson et al.
Neurology, 82(8), 674-680 (2014-01-28)
To report outcomes of pregnancies that occurred during the fingolimod clinical development program. Pregnancy outcomes from phase II, phase III, and phase IV clinical studies (with optional extensions) were reported by clinical trial investigators. Fingolimod exposure in utero was defined
Fingolimod and teriflunomide attenuate neurodegeneration in mouse models of neuronal ceroid lipofuscinosis.
Groh J, et al.
Molecular Therapy, 25(8), 1889-1899 (2017)
M Kipp et al.
Multiple sclerosis (Houndmills, Basingstoke, England), 18(3), 258-263 (2012-03-03)
FTY720 (fingolimod; Gilenya®), a sphingosine 1-phosphate (S1P) receptor modulator, is the first oral disease-modifying therapy to be approved for the treatment of relapsing-remitting multiple sclerosis. FTY720 is rapidly converted in vivo to the active S-fingolimod-phosphate, which binds to S1P receptors.
The sphingosine-1-phosphate analogue, FTY-720, promotes the proliferation of embryonic neural stem cells, enhances hippocampal neurogenesis and learning and memory abilities in adult mice.
Sun Y, et al.
British Journal of Pharmacology, 173(18), 2793-2807 (2016)
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