Oral drug for the treatment of multiple sclerosis
ChemicalBook > CAS DataBase List > Fingolimod hydrochloride

Fingolimod hydrochloride

Oral drug for the treatment of multiple sclerosis
Product Name
Fingolimod hydrochloride
CAS No.
162359-56-0
Chemical Name
Fingolimod hydrochloride
Synonyms
Gilenya;FTY720;Fingolimod HCl;Fin;2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol hydrochloride;FY720;CS-290;FTY-720A;FTY720 . HCl;Fingolimod HC
CBNumber
CB4244536
Molecular Formula
C19H34ClNO2
Formula Weight
343.93
MOL File
162359-56-0.mol
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Fingolimod hydrochloride Property

Melting point:
102-107°C
storage temp. 
-20°C
solubility 
water: soluble10mg/mL, clear
form 
powder
color 
white to beige
biological source
synthetic
Water Solubility 
water: 10mg/mL, clear
Merck 
14,4083
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChI
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
InChIKey
SWZTYAVBMYWFGS-UHFFFAOYSA-N
SMILES
C1(C=CC(CCCCCCCC)=CC=1)CCC(N)(CO)CO.Cl
CAS DataBase Reference
162359-56-0(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38-52/53
Safety Statements 
26-61
WGK Germany 
3
RTECS 
TY3130000
HS Code 
29221990
Toxicity
LD50 orally in rats: 300-600 mg/kg (Troncoso)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P314Get medical advice/attention if you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0700
Product name
FTY720
Purity
≥98% (HPLC)
Packaging
5mg
Price
$74.1
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0700
Product name
FTY720
Purity
≥98% (HPLC)
Packaging
25mg
Price
$303
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR2790
Product name
Fingolimod Hydrochloride
Packaging
500MG
Price
$956
Updated
2022/05/15
Sigma-Aldrich
Product number
1270480
Product name
Fingolimod Hydrochloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
300MG
Price
$3600
Updated
2022/05/15
TCI Chemical
Product number
F1018
Product name
Fingolimod Hydrochloride
Purity
>98.0%(HPLC)(T)
Packaging
200mg
Price
$139
Updated
2024/03/01
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Fingolimod hydrochloride Chemical Properties,Usage,Production

Oral drug for the treatment of multiple sclerosis

Fingolimod hydrochloride is the first oral drug for the treatment of multiple sclerosis. It is successfully developed by the pharmaceutical company Novartis, and it has been approved for marketing by the US Food and Drug Administration (FDA). The recommended dose is 0.5mg once a day for oral administration.
Multiple sclerosis is a debilitating neurological disease that can cause the patient to lose a sense of balance, appear muscle spasms and other movement disorders. The disease has been treated with injectable drugs. This kind of medication brought great inconvenience to patients.
Fingolimod is a sphingosine-l-phosphate (S1PR) receptor modulator. After phosphorylation, It is bound to s1P receptor that is on the surface of lymphocyte, which will change lymphocyte migration, and promote cells into the lymphatic tissue, and prevent lymphocytes from leaving the lymphoid tissue and get into the graft. Thereby, it will prevent these cells from infiltrating the central nervous system (CNS), which achieves the effect of immunosuppression. According to the drug's introduction, drugmaker Novartis said that this process of pharmacological effects is reversible. If medication is stopped, the level of lymphocytes in circulating system will return to normal.
The above information is edited by the chemicalbook of Kui Ming.

Description

Approved by the U.S. FDA in September 2010, fingolimod (also referred to as FTY720) is the first approved oral therapy for the relapsing-remitting form ofmultiple sclerosis (RRMS). Because of fingolimod’s structural resemblance to sphingosine, a metabolite of sphingolipids that constitutes the cell membrane of all eukaryotic cells, it was hypothesized that fingolimod may be affecting sphingolipid metabolism in cells. A series of elegant in vitro and in vivo studies confirmed that fingolimod is converted to (S)-fingolimod phosphate primarily by sphingosine kinase- 2 and that (S)-fingolimod phosphate mediates multiple biological processes by binding to novel GPCR’s referred to as sphingosine-1-phosphate (S1P) receptors. S1P receptors are divided into five subtypes, S1P1–5, which have varying tissue and cellular distribution. S1P1–3 receptors are ubiquitously expressed in the immune, cardiovascular, and central nervous systems, S1P4 is restricted to the hematopoietic system, and S1P5 is mostly localized in the white matter of CNS. S1P1–3 receptors play important roles in endothelial barrier function, maintaining vascular tone, regulating heart rate and allowing for lymphocyte egress fromsecondary lymphoid organs. The functional role of S1P4 is unknown,while the S1P5 receptor is thought to be involved in natural killer cell trafficking and oligodendrocyte function.

Chemical Properties

White Solid

Originator

Yoshitomi Pharmaceutical Industries (now Mitsubishi Tanabe Pharma) (United States)

Uses

A derivative of ISP-1 (myriocin), a fungal metabolite of the Chinese herb Iscaria sinclarii as well as a structural analogue of Sphingosine. It is a novel immune modulator that prolongs allograft transplant survival in numberour models by inhibitin

Uses

FTY720 is a derivative of ISP-1 (myriocin), a fungal metabolite of the Chinese herb Iscaria sinclarii as well as a structural analogue of Sphingosine. FTY720 is a novel immune modulator that prolong s allograft transplant survival in numberour models by inhibiting lymphocyte emigration from lymphoid organs. FTY720 us reported to be phosphorylated by sphingosine kinase to FTY720-P, which has been shown to potently stimulate GTPgS binding activity in S1P-transfected CHO cells (EC50 = 210 pM, 4.9 nM, 4.3 nM, and 1 nM for S1P1, S1P3, S1P4 and S1P5, respectively).

Uses

A cell-permeable aminopropanediol immunosuppressive agent that displays lymphocyte sequestration properties.

Uses

Oral medicine for the treatment of multiple sclerosis

Uses

Fingolimod Hydrochloride is a derivative of ISP-1 (myriocin), a fungal metabolite of the Chinese herb Iscaria sinclarii as well as a structural analogue of Sphingosine. Fingolimod is a novel immune modulator that prolongs allograft transplant survival in numerous models by inhibiting lymphocyte emigration from lymphoid organs. Fingolimod is reported to be phosphorylated by sphingosine kinase to FTY720-P, which has been shown to potently stimulate GTPgS binding activity in S1P-transfected CHO cells (EC50 = 210 pM, 4.9 nM, 4.3 nM, and 1 nM for S1P1, S1P3, S1P4 and S1P5, respectively).

Definition

ChEBI: The hydrochloride salt of 2-amino-2-[2-(4-octylphenyl) ethyl]-1,3-propanediol (fingolimod).

brand name

Gilenya

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.

Clinical Use

Fingolimod hydrochloride is an immunosuppressive drug developed by Novartis and approved in the U.S., Europe, and Australia in 2010 for the treatment of multiple sclerosis. The structure of fingolimod derives from the naturally-occurring myriocin (ISP-1) metabolite of the fungus I. sinclairii and the aminoalcohol functionality within the drug possesses structural similarity to the sphingosine family of natural products.

Synthesis

Although several convenient preparations of fingolimod (FTY720) have been reported in the literature, the route most closely resembling the process-scale approach is described in the scheme. Friedel-Crafts acylation of commercial toluene derivative 89 with bromoacetyl chloride followed by ethoxide-mediated N-acylated aminomalonate (91) attack onto the resulting -bromoketone 90 gave rise to ketoamide 92 in good overall yield. Next, separate hydride reduction protocols were employed to furnish diol 93. Presumably, triethylsilyl hydride reduced the ketone and both ethyl esters within 92 to the corresponding diacid, which then underwent lithium aluminum hydride treatment to arrive at diol 93. Careful attention to stoichiometry was required to avoid over reduction of amide 93, which was critical to achieve high-yielding (76%) salt formation of fingolimod HCl (VI) through the use of 6 N ethanolic hydrochloric acid.

target

COX | PGE | Histamine Receptor | PAK | p21 | S1P

storage

+4°C

References

1) Brinkmann et al. (2002), The immune modulator FTY720 targets spingosine-1-phosphate receptors; J. Biol. Chem., 277 21453 2) Wolf et al. (2009), The sphingosine 1-phosphate receptor agonist FTY720 potently inhibits regulatory T cell proliferation in vitro and in vivo; J. Immunol., 183 3751 3) Awojoodu et al. (2013), Sphingosine 1-phosphate receptor 3 regulates recruitment of anti-inflammatory monocytes to microvessels during implant arteriogenesis; Proc. Natl. Acad. Sci. USA, 110 13785 4) Chiba (2005), FTY720, a new class of immunomodulator, inhibits lymphocyte egress from secondary lymphoid tissues and thymus by agonistic activity at sphingosine 1-phosphate receptors; Pharmacol. Ther., 108 308

Fingolimod hydrochloride Preparation Products And Raw materials

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Preparation Products

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View Lastest Price from Fingolimod hydrochloride manufacturers

Wuhan Circle Star Chem-medical Technology Co.,Ltd
Product
Fingolimod hydrochloride 162359-56-0
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98
Supply Ability
1000
Release date
2025-01-07
Hebei Zhuanglai Chemical Trading Co Ltd
Product
Fingolimod hydrochloride 162359-56-0
Price
US $99.00-45.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-11-26
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Fingolimod Hydrochloride 162359-56-0
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-09-19

162359-56-0, Fingolimod hydrochlorideRelated Search:

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  • Fingolimod (FTY720) hydrochloride
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  • 2-AMINO-2-[2-(4-OCTYLPHENYL)ETHYL]-1,3-PROPANEDIOL, HYDROCHLORIDE
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  • Fingolimod hydrochloride 2-Amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol hydrochloride
  • Fingolimod (FTY-720A, FTY720)
  • FTY-720A
  • 1,3-Propanediol, 2-amino-2-(2-(4-octylphenyl)ethyl)-, hydrochloride
  • Unii-G926ec510t
  • FTY720(Fingolimod)
  • FY720
  • FTY720 B-0720
  • Fingolimod hydrochloride(FTY720)
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  • Fingolimod hydrochlorid
  • 2-aMino-2-(4-octylphenethyl)propane-1,3-diol hydrochloride
  • Gilenya
  • Fingolimod hydrochloride, 98%, S1P antagonist
  • FTY720 hydrochloride, >=99%
  • Fingolimod HLC
  • GILENIA;FTY720;FTY 720
  • CS-290
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  • FingolimodHydrochloride&gt
  • Fingolimod Hydrochloride (300 mg)
  • 1,3-Propanediol, 2-amino-2-[2-(4-octylphenyl)ethyl]-, hydrochloride (1:1)
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  • 162359-56-0
  • 62359-55-9
  • C19H34ClNO2
  • C19H33NO2HCl
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