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Details

Stereochemistry ACHIRAL
Molecular Formula C19H33NO2
Molecular Weight 307.4708
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FINGOLIMOD

SMILES

CCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C1

InChI

InChIKey=KKGQTZUTZRNORY-UHFFFAOYSA-N
InChI=1S/C19H33NO2/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

HIDE SMILES / InChI

Description

Fingolimod (FTY720) is a sphingosine 1-phosphate receptor modulator indicated and approved for the treatment of relapsing-remitting multiple sclerosis. Fingolimod (trade name Gilenya, Novartis) is metabolized by sphingosine kinase to the active metabolite, fingolimod-phosphate. Fingolimod-phosphate is a sphingosine 1-phosphate receptor modulator, and binds with high affinity to sphingosine 1-phosphate receptors 1, 3, 4, and 5. Fingolimod-phosphate blocks the capacity of lymphocytes to egress from lymph nodes, reducing the number of lymphocytes in peripheral blood. The mechanism by which fingolimod exerts therapeutic effects in multiple sclerosis is unknown, but may involve reduction of lymphocyte migration into the central nervous system. Fingolimod was approved as a first-in-class, orally active drug for relapsing multiple sclerosis in 2010, and its applications in other disease conditions are currently under clinical trials.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
FTY720: a novel approach to the treatment of hepatic ischemia-reperfusion injury.
2002 Aug
Combined therapy of CTLA4Ig-gene transfection with FTY720 administration in rat lung allografts.
2002 Aug
T cell selective apoptosis by a novel immunosuppressant, FTY720, is closely regulated with Bcl-2.
2002 Dec
Prevention of autoimmune diabetes by FTY720 in nonobese diabetic mice.
2002 Dec 27
Different mechanisms for membrane and nuclear damages in apoptosis induced by an immunosuppressant, FTY720.
2002 Dec 31
Effects of mycophenolate sodium with or without FTY720 in a DA-to-Lewis rat heart transplantation model.
2002 Nov
Sirolimus and FTY720: new approaches to transplant immunosuppression.
2002 Nov
Efficacy of mycophenolate sodium as monotherapy and in combination with FTY720 in a DA-to-Lewis-rat heart-transplantation model.
2002 Nov 27
FTY720 pretreatment reduces warm hepatic ischemia reperfusion injury through inhibition of T-lymphocyte infiltration.
2002 Oct
FTY720: targeting G-protein-coupled receptors for sphingosine 1-phosphate in transplantation and autoimmunity.
2002 Oct
Transplantation.
2002 Oct
Oral efficacy of the new immunomodulator FTY720 in cynomolgus monkey kidney allotransplantation, given alone or in combination with cyclosporine or RAD.
2002 Oct 15
FTY720 alters the composition of T-lymphocyte subpopulations in the peripheral blood compartment of renal transplant patients.
2002 Sep
Effects of immunosuppressant FTY720 on renal and hepatic hemodynamics in the rat.
2002 Sep 15
Renal transplantation: basic concepts and evolution of therapy.
2003
The immune modulator FYT720 prevents autoimmune diabetes in nonobese diabetic mice.
2003 Apr
Sphingosine-1-phosphate receptor agonism impairs the efficiency of the local immune response by altering trafficking of naive and antigen-activated CD4+ T cells.
2003 Apr 1
Sphingosine 1-phosphate pathway therapeutics: a lipid ligand-receptor paradigm.
2003 Aug
Current immunosuppressive agents: efficacy, side effects, and utilization.
2003 Dec
Inhibition of Th1- and Th2-mediated airway inflammation by the sphingosine 1-phosphate receptor agonist FTY720.
2003 Dec 1
Pretreatment with FTY720 alone induced long-term survival of mouse heart allograft.
2003 Feb
FTY720: A new kid on the block for transplant immunosuppression.
2003 Jul
Pharmacodynamics of single doses of the novel immunosuppressant FTY720 in stable renal transplant patients.
2003 Jul
Ubiquitin pathway proteins influence the mechanism of action of the novel immunosuppressive drug FTY720 in Saccharomyces cerevisiae.
2003 Jul 18
Selective cancer cell apoptosis induced by FTY720; evidence for a Bcl-dependent pathway and impairment in ERK activity.
2003 Jul-Aug
New paradigms in immunosuppression.
2003 Jul-Sep
The effect of FTY 720 on engraftment in a model of spontaneous allograft acceptance.
2003 Jun
Induction of apoptosis in human bladder cancer cells in vitro and in vivo caused by FTY720 treatment.
2003 Jun
Elimination of cell-cycle regulators during caspase-3-dependent apoptosis caused by an immunosuppressant, FTY720.
2003 Mar
Graft-versus-host disease can be separated from graft-versus-lymphoma effects by control of lymphocyte trafficking with FTY720.
2003 Mar
FTY720 stimulates multidrug transporter- and cysteinyl leukotriene-dependent T cell chemotaxis to lymph nodes.
2003 Mar
FTY720 reduces T-cell recruitment into murine intestinal allograft and prevents activation of graft-infiltrating cells.
2003 May 15
Phosphorylation and action of the immunomodulator FTY720 inhibits vascular endothelial cell growth factor-induced vascular permeability.
2003 Nov 21
Significant prolongation of orthotopic corneal-graft survival in FTY720-treated mice.
2003 Nov 27
Phosphorylation of the immunomodulatory drug FTY720 by sphingosine kinases.
2003 Nov 28
The immunosuppressant FTY720 is phosphorylated by sphingosine kinase type 2.
2003 Nov 6
[Study the mechanisms and inducing transplantation immune tolerance of FTY720].
2003 Oct
Pharmacodynamics of FTY720, the first member of a new class of immune-modulating therapeutics in transplantation medicine.
2003 Oct
Pharmacodynamics, pharmacokinetics, and safety of multiple doses of FTY720 in stable renal transplant patients: a multicenter, randomized, placebo-controlled, phase I study.
2003 Oct 15
FTY720 does not abrogate acute graft-versus-host disease in the dog leukocyte antigen-nonidentical unrelated canine model.
2003 Oct 27
FTY720, a new immunosuppressant, as rescue therapy in mouse cardiac transplantation.
2003 Sep
Sphingosine 1-phosphate (S1P) receptor subtypes S1P1 and S1P3, respectively, regulate lymphocyte recirculation and heart rate.
2004 Apr 2
CD4+ CD25+ CD62+ T-regulatory cell subset has optimal suppressive and proliferative potential.
2004 Jan
Pharmacologic immunosuppression.
2004 Jan 1
Lymphocyte egress from thymus and peripheral lymphoid organs is dependent on S1P receptor 1.
2004 Jan 22
The sphingosine 1-phosphate receptor agonist FTY720 supports CXCR4-dependent migration and bone marrow homing of human CD34+ progenitor cells.
2004 Jun 15
FTY720-induced lymphocyte homing modulates post-transplant preservation/reperfusion injury.
2004 Mar
FTY720 exerts differential effects on CD4+ and CD8+ T-lymphocyte subpopulations expressing chemokine and adhesion receptors.
2004 Mar
The immunosuppressant FTY720 down-regulates sphingosine 1-phosphate G-protein-coupled receptors.
2004 Mar
Immune cell regulation and cardiovascular effects of sphingosine 1-phosphate receptor agonists in rodents are mediated via distinct receptor subtypes.
2004 May
Patents

Sample Use Guides

In Vivo Use Guide
The recommended dose of GILENYA is 0.5 mg orally once-daily. Fingolimod doses higher than 0.5 mg are associated with a greater incidence of adverse reactions without additional benefit. GILENYA can be taken with or without food.
Route of Administration: Oral
In Vitro Use Guide
Astrocytes derived from human fetal CNS specimens and maintained in dissociated cultures were exposed to 100 nM of the biologically active form of Fingolimod (FTY720) over a dosing regimen that ranged from a single exposure (with or without washout after 1 h) to daily exposures up to 5 days, a single addition of FTY720 inhibited subsequent S1PR ligand-induced pERK1/2 signaling for >24 h. Daily FTY720 treatments (3-5 days) maintained this effect together with a loss of proliferative responses to the natural ligand S1P. Repeated FTY720 dosing concurrently maintained a functional cell response as measured by the inhibition of intracellular calcium release when stimulated by the cytokine IL-1β. Recurrent FTY720 treatments did not inhibit serum- or IL-1β-induced pERK1/2.
Name Type Language
FINGOLIMOD
DASH   INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
FTY-720
Code English
FTY720
Code English
FINGOLIMOD [MART.]
Common Name English
FINGOLIMOD [MI]
Common Name English
FINGOLIMOD [WHO-DD]
Common Name English
2-AMINO-2-(2-(4-OCTYLPHENYL)ETHYL)PROPANE-1,3-DIOL
Systematic Name English
FINGOLIMOD [INN]
Common Name English
FINGOLIMOD [ORANGE BOOK]
Common Name English
1,3-PROPANEDIOL, 2-AMINO-2-(2-(4-OCTYLPHENYL)ETHYL)-
Systematic Name English
FINGOLIMOD [VANDF]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/09/718
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
LIVERTOX 412
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
WHO-VATC QL04AA27
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
NDF-RT N0000181816
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
NCI_THESAURUS C308
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
WHO-ATC L04AA27
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
FDA ORPHAN DRUG 305910
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
Code System Code Type Description
WIKIPEDIA
FINGOLIMOD
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY
NCI_THESAURUS
C74202
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY
INN
8341
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY
EVMPD
SUB31908
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY
RXCUI
1012892
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL314854
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY
IUPHAR
2407
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY
DRUG BANK
DB08868
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY
MESH
C098720
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY
NDF-RT
N0000181815
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY Sphingosine 1-Phosphate Receptor Modulators [MoA]
PUBCHEM
107970
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY
CAS
162359-55-9
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY
EPA CompTox
162359-55-9
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY
MERCK INDEX
M5384
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY Merck Index
LactMed
162359-55-9
Created by admin on Mon Oct 21 20:45:25 UTC 2019 , Edited by admin on Mon Oct 21 20:45:25 UTC 2019
PRIMARY