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
Fin;FY720;FTY720;CS-290;Gilenya;FTY-720A;FTY720 . HCl;Fingolimod HCl;FTY720 B-0720;Fingolimod HLC
CBNumber
CB4244536
Molecular Formula
C19H34ClNO2
Formula Weight
343.93
MOL File
162359-56-0.mol
More
Less

Fingolimod hydrochloride Property

Melting point:
102-107°C
storage temp. 
-20°C Freezer
solubility 
water: soluble10mg/mL, clear
form 
powder
color 
white to beige
Merck 
14,4083
InChIKey
SWZTYAVBMYWFGS-UHFFFAOYSA-N
CAS DataBase Reference
162359-56-0(CAS DataBase Reference)
More
Less

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)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0700
Product name
FTY720
Purity
≥98% (HPLC)
Packaging
5mg
Price
$62.1
Updated
2021/03/22
Sigma-Aldrich
Product number
SML0700
Product name
FTY720
Purity
≥98% (HPLC)
Packaging
25mg
Price
$253
Updated
2021/03/22
TCI Chemical
Product number
F1018
Product name
Fingolimod Hydrochloride
Purity
>98.0%(HPLC)(T)
Packaging
200mg
Price
$117
Updated
2021/03/22
TCI Chemical
Product number
F1018
Product name
Fingolimod Hydrochloride
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$351
Updated
2021/03/22
Cayman Chemical
Product number
10006292
Product name
Fingolimod (hydrochloride)
Purity
≥98%
Packaging
50mg
Price
$49
Updated
2021/03/22
More
Less

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

Oral medicine for the treatment of multiple sclerosis

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.

Definition

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

brand name

Gilenya

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.

Chemical 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.

Fingolimod hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Fingolimod hydrochloride Suppliers

TCI Europe
Tel
320-37350700-
Fax
+32 (0)37350701
Email
sales@tcieurope.eu
Country
Europe
ProdList
23696
Advantage
75
More
Less

View Lastest Price from Fingolimod hydrochloride manufacturers

Wuhan wingroup Pharmaceutical Co., Ltd
Product
Fingolimod hydrochloride 162359-56-0
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1000MT/Month
Release date
2021-07-16
Baoji Guokang Bio-Technology Co., Ltd.
Product
Fingolimod hydrochloride 162359-56-0
Price
US $95.00/g
Min. Order
5g
Purity
99%
Supply Ability
100kg
Release date
2021-06-04
Zhuozhou Wenxi import and Export Co., Ltd
Product
Fingolimod hydrochloride 162359-56-0
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10

162359-56-0, Fingolimod hydrochlorideRelated Search:


  • Fingolimod (FTY720) hydrochloride
  • Fin
  • limod hydrochloride
  • fingolimod hydrochloride
  • FTY720
  • 2-AMINO-2-[2-(4-OCTYLPHENYL)ETHYL]-1,3-PROPANEDIOL, HYDROCHLORIDE
  • 2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol hydrochloride
  • Fingolimod HCl
  • FTY720 HYDROCHLORIDE
  • 2-Amino-2-(2-(4-octylphenyl)ethyl)propane-1,3-diol,HCl
  • Fingolimod HCL(FTY720)
  • 2-AMINO-2-[2-(4-OCTYLPHENYL)-ETHYL]-1,3-PROPANEDIOL
  • FingoliMod FTY120
  • FTY720 . HCl
  • FingoliMod (FTY720) HCl
  • 2-(4-octylphenethyl)-2-aminopropane-1,3-diol hydrochloride
  • 2-Amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol hydrochloride Fingolimod (FTY720) HCl
  • 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)
  • FTY720(FingoliMod HCL)
  • 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
  • Fingolimod hydrochloride CRS
  • FingolimodHydrochloride&gt
  • Fingolimod Hydrochloride (300 mg)
  • 1,3-Propanediol, 2-amino-2-[2-(4-octylphenyl)ethyl]-, hydrochloride (1:1)
  • 2-Amino-2-[2-(4-n-octylphenyl)ethyl]propane-1,3-diol Hydrochloride
  • Fingolimod hydrochloride USP/EP/BP
  • 162359-56-0
  • 62359-55-9
  • C19H34ClNO2
  • C19H33NO2HCl
  • Pharmaceuticals
  • Aromatics
  • Intermediates & Fine Chemicals
  • Metabolites & Impurities
  • Other APIs
  • API
  • Pharmaceutical intermediate
  • Inhibitors
  • Metabolites
  • All Inhibitors