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Fingolimod hydrochloride

Fingolimod hydrochloride structure

CAS No:
162359-56-0
Formula:
C19H33NO2.ClH
Chemical Name:
Fingolimod hydrochloride
Synonyms:
1,3-Propanediol,2-amino-2-[2-(4-octylphenyl)ethyl]-,hydrochloride (1:1);1,3-Propanediol,2-amino-2-[2-(4-octylphenyl)ethyl]-,hydrochloride;FTY 720;Fingolimod hydrochloride;2-Amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol hydrochloride;Gilenya;Imusera;2-Amino-[2-(4-octylphenyl)ethyl]-1,3-propanediol hydrochloride
Categories:
Active Pharmaceutical Ingredients > Inhibitor Drugs

Description

White SolidChEBI: The hydrochloride salt of 2-amino-2-[2-(4-octylphenyl) ethyl]-1,3-propanediol (fingolimod).Approved by the U.S. FDA in September 2010, fingolimod (also referredto as FTY720) is the first approved oral therapy for the relapsing-remittingform ofmultiple sclerosis (RRMS). Because of fingolimod’s structuralresemblance to sphingosine, a metabolite of sphingolipids that constitutesthe cell membrane of all eukaryotic cells, it was hypothesized thatfingolimod may be affectin

Fingolimod hydrochloride is the hydrochloride salt of 2-amino-2-[2-(4-octylphenyl) ethyl]-1,3-propanediol (fingolimod). It has a role as a sphingosine-1-phosphate receptor agonist, an immunosuppressive agent and a prodrug. It is a hydrochloride and an organic salt. It contains a fingolimod(1+).|Fingolimod Hydrochloride is the hydrochloride salt form of fingolimod, an orally available derivate of myriocin and sphingosine-1-phosphate receptor 1 (S1PR1, S1P1) modulator, with potential anti-inflammatory and immunomodulating activities. Upon oral administration, fingolimod, as a structural analogue of sphingosine, selectively targets and binds to S1PR1 on lymphocytes and causes transient receptor activation followed by S1PR1 internalization and degradation. This results in the sequestration of lymphocytes in lymph nodes. By preventing egress of lymphocytes. fingolimod reduces both the amount of circulating peripheral lymphocytes and the infiltration of lymphocytes into target tissues. This prevents a lymphocyte-mediated immune response and may reduce inflammation. S1PR1, a G-protein coupled receptor, plays a key role in lymphocyte migration from lymphoid tissues. Fingolimod also shifts macrophages to an anti-inflammatory M2 phenotype, and modulates their proliferation, morphology, and cytokine release via inhibition of the transient receptor potential cation channel, subfamily M, member 7 (TRPM7).|A sphingosine-derivative and IMMUNOSUPPRESSIVE AGENT that blocks the migration and homing of LYMPHOCYTES to the CENTRAL NERVOUS SYSTEM through its action on SPHINGOSINE 1-PHOSPHATE RECEPTORS. It is used in the treatment of MULTIPLE SCLEROSIS.

Fingolimod hydrochloride Basic Attributes

Molecular Weight：

343.93

Exact Mass：

343.227814

EC Number：

1308068-626-2

UNII：

G926EC510T

DSSTox ID：

DTXSID00167364

NCI Thesaurus Code：

C72782

ATC Code：

L04AA27

HScode：

29221990

Characteristics

PSA：

66.5

XLogP3：

4.70660

Appearance：

white to beige

Density：

1.016g/cm3

Melting Point：

107-108 °C

Boiling Point：

479.5ºC at 760 mmHg

Flash Point：

243.8ºC

Refractive Index：

1.531

Water Solubility：

water: soluble10mg/mL, clear

Storage Conditions：

-20°C Freezer

Vapor Pressure：

5.28E-10mmHg at 25°C

Toxicity：

LD50 orally in rats: 300-600 mg/kg (Troncoso)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-52/53

safety instructions：

26-61

RTECS Number：

TY3130000

Marks：

Precautionary statement(s)：

P261-P273-P305 + P351 + P338

Hazard Statements：

H315-H319-H335-H412

GHS Classification：

|Warning|H315 (84.91%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P260, P261, P263, P264, P270, P271, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 107 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Gilenya is indicated as single disease modifying therapy in highly active relapsing remitting multiple sclerosis for the following groups of adult patients and paediatric patients aged 10 years and older:Patients with highly active disease despite a full and adequate course of treatment with at least one disease modifying therapy (for exceptions and information about washout periods see sections 4.4 and 5.1).orPatients with rapidly evolving severe relapsing remitting multiple sclerosis defined by 2 or more disabling relapses in one year, and with 1 or more Gadolinium enhancing lesions on brain MRI or a significant increase in T2 lesion load as compared to a previous recent MRI.

MeSH：

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)|Agents that affect the function of G-protein coupled SPHINGOSINE 1-PHOSPHATE RECEPTORS. Their binding to the receptors blocks lymphocyte migration and are often used as IMMUNOSUPPRESSANTS. (See all compounds classified as Sphingosine 1 Phosphate Receptor Modulators.)

MeSH Entry Terms：

2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol hydrochloride

Fingolimod hydrochloride Use and Manufacturing

Uses

A cell-permeable aminopropanediol immunosuppressive agent that displays lymphocyte sequestration properties. Fingolimod is a sphingosine-l-phosphate (S1PR) receptor modulator, which binds to the s1P receptor on the surface of lymphocytes after phosphorylation in the body, changes the migration of lymphocytes, and promotes cells to enter lymphatic tissues. Prevent it from leaving the lymphatic tissue and enter the graft, thereby preventing these cells from infiltrating the central nervous system (CNS), thereby achieving the effect of immunosuppression.

Use Classification：

Human drugs -> Gilenya -> EMA Drug Category|Immunosuppressants -> Human pharmacotherapeutic group|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:343.9
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:12
Exact Mass:343.2278070
Monoisotopic Mass:343.2278070
Topological Polar Surface Area:66.5
Heavy Atom Count:23
Complexity:258
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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