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Fingolimod hydrochloride

Oral drug for the treatment of multiple sclerosis
Fingolimod hydrochloride
Fingolimod hydrochloride structure
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

Fingolimod hydrochloride Properties

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)
EWG's Food Scores
1
FDA UNII
G926EC510T
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335-H412
Precautionary statements  P261-P273-P305+P351+P338
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)

Fingolimod hydrochloride price More Price(8)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0700 FTY720 ≥98% (HPLC) 162359-56-0 5mg $62.1 2021-03-22 Buy
Sigma-Aldrich SML0700 FTY720 ≥98% (HPLC) 162359-56-0 25mg $253 2021-03-22 Buy
TCI Chemical F1018 Fingolimod Hydrochloride >98.0%(HPLC)(T) 162359-56-0 200mg $117 2021-03-22 Buy
TCI Chemical F1018 Fingolimod Hydrochloride >98.0%(HPLC)(T) 162359-56-0 1g $351 2021-03-22 Buy
Cayman Chemical 10006292 Fingolimod (hydrochloride) ≥98% 162359-56-0 50mg $49 2021-03-22 Buy

Fingolimod hydrochloride Chemical Properties,Uses,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


Fingolimod hydrochloride Suppliers

Global( 299)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20010 60
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21237 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26711 60
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15950718863
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career henan chemical co
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Biochempartner
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candy@biochempartner.com CHINA 968 58
GIHI CHEMICALS CO.,LIMITED
08657186217390
sales@gihichemicals.com CHINA 310 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
Accela ChemBio Inc.
(+1)-858-699-3322
(+1)-858-876-1948 info@accelachem.com United States 19969 58

View Lastest Price from Fingolimod hydrochloride manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-07-29 Fingolimod hydrochloride
162359-56-0
US $10.00 / KG 1KG 99% 1000MT/Month Wuhan wingroup Pharmaceutical Co., Ltd
2021-07-22 Fingolimod hydrochloride
162359-56-0
US $95.00 / g 5g 99% 100kg Baoji Guokang Bio-Technology Co., Ltd.
2021-07-13 Fingolimod hydrochloride
162359-56-0
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd

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