U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H33NO2
Molecular Weight 307.4708
Optical Activity NONE
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
Molecular Formula C19H33NO2
Molecular Weight 307.4708
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

CNS Active
3913
Curator's Comment: Fingolimod crosses the blood–brain barrier (BBB) and accumulates in the CNS.

Originator

Approval Year

2010
465
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 0.84 µM [IC50]
Agonist
2678
 2.1 µM [IC50]
Agonist
2678
 0.3 nM [EC50]
Agonist
2678
 0.3 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
GILENYA

Approved Use

GILENYA is indicated for the treatment of patients with relapsing forms of multiple sclerosis (MS) to reduce the frequency of clinical exacerbations and to delay the accumulation of physical disability. GILENYA is a sphingosine 1-phosphate receptor modulator indicated for the treatment of patients with relapsing forms of multiple sclerosis (MS) to reduce the frequency of clinical exacerbations and to delay the accumulation of physical disability. (1)

Launch Date

2010
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.65 ng/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/22149256
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FINGOLIMOD plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
149 ng × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/22149256
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FINGOLIMOD plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/22149256
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FINGOLIMOD plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
14 mg single, oral
Overdose
Dose: 14 mg
Route: oral
Route: single
Dose: 14 mg
Co-administed with::
phenoxymethylpenicillin(2000 mg, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24178903
unhealthy, 33 years
n = 1
Health Status: unhealthy
Condition: multiple sclerosis
Age Group: 33 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24178903
Other AEs: Bradycardia, Hypotension...
Other AEs:
Bradycardia (1 patient)
Hypotension (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24178903
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Other AEs: Appendicitis, Urinary tract infection...
Other AEs:
Appendicitis (serious, 1 patient)
Urinary tract infection (serious, 1 patient)
Hyperlipidemia (10.9%)
Leukopenia (10.9%)
Lymphopenia (17.4%)
Constipation (4.3%)
Diarrhea (13%)
Stomatitis (13%)
Alanine aminotransferase increased (2.2%)
Aspartate aminotransferase increased (2.2%)
Cystitis (15.2%)
Bronchitis (4.3%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
0.5 mg 1 times / day multiple, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 0.5 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022527s000lbl.pdf
unhealthy, 37 years
n = 425
Health Status: unhealthy
Condition: relapsing remitting MS
Age Group: 37 years
Sex: M+F
Population Size: 425
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022527s000lbl.pdf
Disc. AE: Transaminases increased...
AEs leading to
discontinuation/dose reduction:
Transaminases increased (3.8%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022527s000lbl.pdf
3.5 mg single, oral
Highest studied dose
Dose: 3.5 mg
Route: oral
Route: single
Dose: 3.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11912269/
unhealthy, 43.2 years
n = 3
Health Status: unhealthy
Age Group: 43.2 years
Sex: M+F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/11912269/
Other AEs: Bradycardia, Carbon monoxide diffusing capacity decreased...
Other AEs:
Bradycardia (2 patients)
Carbon monoxide diffusing capacity decreased (1 patient)
Electrocardiogram T wave abnormal (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11912269/
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022527s000lbl.pdf
unhealthy
n = 6
Health Status: unhealthy
Population Size: 6
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022527s000lbl.pdf
Other AEs: Chest tightness...
Other AEs:
Chest tightness (mild, 5 patients)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022527s000lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Bradycardia 1 patient
14 mg single, oral
Overdose
Dose: 14 mg
Route: oral
Route: single
Dose: 14 mg
Co-administed with::
phenoxymethylpenicillin(2000 mg, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24178903
unhealthy, 33 years
n = 1
Health Status: unhealthy
Condition: multiple sclerosis
Age Group: 33 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24178903
Hypotension 1 patient
14 mg single, oral
Overdose
Dose: 14 mg
Route: oral
Route: single
Dose: 14 mg
Co-administed with::
phenoxymethylpenicillin(2000 mg, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24178903
unhealthy, 33 years
n = 1
Health Status: unhealthy
Condition: multiple sclerosis
Age Group: 33 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24178903
Hyperlipidemia 10.9%
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Leukopenia 10.9%
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Diarrhea 13%
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Stomatitis 13%
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Cystitis 15.2%
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Lymphopenia 17.4%
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Alanine aminotransferase increased 2.2%
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Aspartate aminotransferase increased 2.2%
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Bronchitis 4.3%
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Constipation 4.3%
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Appendicitis serious, 1 patient
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Urinary tract infection serious, 1 patient
1.25 mg 1 times / day steady, oral
Highest studied dose
Dose: 1.25 mg, 1 times / day
Route: oral
Route: steady
Dose: 1.25 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
unhealthy, 36.0 years (range: 18–55 years)
n = 46
Health Status: unhealthy
Condition: relapsing multiple sclerosis
Age Group: 36.0 years (range: 18–55 years)
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/28129749
Transaminases increased 3.8%
Disc. AE
0.5 mg 1 times / day multiple, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 0.5 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022527s000lbl.pdf
unhealthy, 37 years
n = 425
Health Status: unhealthy
Condition: relapsing remitting MS
Age Group: 37 years
Sex: M+F
Population Size: 425
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022527s000lbl.pdf
Carbon monoxide diffusing capacity decreased 1 patient
3.5 mg single, oral
Highest studied dose
Dose: 3.5 mg
Route: oral
Route: single
Dose: 3.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11912269/
unhealthy, 43.2 years
n = 3
Health Status: unhealthy
Age Group: 43.2 years
Sex: M+F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/11912269/
Electrocardiogram T wave abnormal 1 patient
3.5 mg single, oral
Highest studied dose
Dose: 3.5 mg
Route: oral
Route: single
Dose: 3.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11912269/
unhealthy, 43.2 years
n = 3
Health Status: unhealthy
Age Group: 43.2 years
Sex: M+F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/11912269/
Bradycardia 2 patients
3.5 mg single, oral
Highest studied dose
Dose: 3.5 mg
Route: oral
Route: single
Dose: 3.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/11912269/
unhealthy, 43.2 years
n = 3
Health Status: unhealthy
Age Group: 43.2 years
Sex: M+F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/11912269/
Chest tightness mild, 5 patients
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022527s000lbl.pdf
unhealthy
n = 6
Health Status: unhealthy
Population Size: 6
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022527s000lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inhibitor
1587

inducer
781
inhibitor
1767

inducer
389
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2A6
707

CYP2C19
1478

CYP2E1
882

CYP4A9/11
37

CYP2B6
810

CYP3A4/5
278

CYP2C8
911

BSEP
402

MRP2
383

P-gp
1461

OATP1B1
788

OATP1B3
706

NTCP
34
CYP2E1
667

CYP1A1
349

CYP2J2
56

FMO3
67
CYP1A2
701

CYP2B6
547

CYP2C8
168

CYP2C19
293

P-gp
257
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1692
 no [IC50 >10 uM]
AML627
3
CYP1A2
1692
 no [IC50 >10 uM]
AML629
3
CYP2A6
739
 no [IC50 >10 uM]
AML627
3
CYP2A6
739
 no [IC50 >10 uM]
AML629
3
CYP2C19
1553
 no [IC50 >10 uM]
AML627
3
CYP2C19
1553
 no [IC50 >10 uM]
AML629
3
CYP2C8
965
 no [IC50 >10 uM]
AML627
3
CYP2C8
965
 no [IC50 >10 uM]
AML629
3
CYP2C9
1819
 no [IC50 >10 uM]
AML627
3
CYP2C9
1819
 no [IC50 >10 uM]
AML629
3
CYP2D6
1891
 no [IC50 >10 uM]
AML627
3
CYP2D6
1891
 no [IC50 >10 uM]
AML629
3
CYP3A4
1925
 no [IC50 >10 uM]
AML629
3
CYP2C19
1553
 no [IC50 >900 uM]
BSEP
403
 no
BSEP
403
 no
AML629
3
CYP1A2
1692
 no
CYP2B6
1001
 no
CYP2C19
1553
 no
CYP2C8
965
 no
CYP2C9
1819
 no
CYP3A4
1925
 no
MRP2
475
 no
MRP2
475
 no
AML629
3
NTCP
35
 no
NTCP
35
 no
AML629
3
OATP1B1
803
 no
OATP1B1
803
 no
AML629
3
OATP1B3
715
 no
OATP1B3
715
 no
AML629
3
P-gp
1650
 no
P-gp
1650
 no
AML629
3
CYP2C9
1819
 weak [IC50 110 uM]
CYP2E1
970
 weak [IC50 12.5 uM]
AML627
3
CYP3A4
1925
 weak [IC50 17 uM]
AML627
3
CYP2E1
970
 weak [IC50 180 uM]
CYP3A4/5
335
 weak [IC50 35 uM]
CYP2B6
1001
 weak [IC50 36 uM]
CYP2D6
1891
 weak [IC50 51 uM]
CYP2A6
739
 weak [IC50 53 uM]
CYP1A2
1692
 weak [IC50 80 uM]
CYP4A9/11
37
 weak [IC50 80 uM]
P-gp
1650
 yes [IC50 84 uM]
CYP2E1
970
 yes [IC50 9.9 uM]
AML629
3
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1737
 minor [Km 107 uM]
unlikely (co-administration study)
Comment: Recombinant human CYP3A4, Vmax = 1423 pmol/(min.nmol CYP); Cyclosporine did not modify fingolimod overall exposure AUC(0-tz) or peak concentration (Cmax). The pharmacokinetics of steady-state cyclosporine were not altered during coadministration with singledose fingolimod.
Page: (ClinPharm) 11, 54, 55, 56-57, 207-210
CYP2E1
667
 minor [Km 73 uM]
FMO3
67
 no
CYP1A1
349
 yes [Km 117 uM]
CYP2J2
56
 yes [Km 76 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
hERG
1647
FTY720-P
3
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:63115
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63115
ChemicalBook
CB92498299
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB92498299
MolPort
MolPort-003-847-513
https://www.molport.com/shop/molecule-link/MolPort-003-847-513
ZINC
ZINC000001542002
http://zinc15.docking.org/substances/ZINC000001542002
eMolecules
6843670
https://www.emolecules.com/cgi-bin/more?vid=6843670
PubMed

PubMed

TitleDatePubMed
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
Renal transplantation: basic concepts and evolution of therapy.
2003
The immune modulator FYT720 prevents autoimmune diabetes in nonobese diabetic mice.
2003 Apr
A novel immunosuppressive agent FTY720 induced Akt dephosphorylation in leukemia cells.
2003 Apr
Amelioration of experimental autoimmune encephalomyelitis in Lewis rats by FTY720 treatment.
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
FTY720, an immunosuppressant that alters lymphocyte trafficking, abrogates chronic rejection in combination with cyclosporine A.
2003 Apr 15
Immunosuppression with FTY720 and cyclosporine A inhibits rejection of adult porcine islet xenografts in rats.
2003 Apr 27
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
CTLA4Ig-gene transfection with FTY720 administration markedly inhibits the obliterative airway disease in heterotopically transplanted rat tracheas.
2003 Feb
[Effects of three different immunosuppressive drugs on SD rat islet cell viability].
2003 Feb
Linking Chinese medicine and G-protein-coupled receptors.
2003 Jan
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
Egress: a receptor-regulated step in lymphocyte trafficking.
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

Patents

US20120184617
3
WO2017058364A1
3

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:29:18 GMT 2023
Edited
by admin
on Fri Dec 15 15:29:18 GMT 2023
Record UNII
3QN8BYN5QF
Record Status Validated (UNII)
Record Version
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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
2-AMINO-2-(2-(4-OCTYLPHENYL)ETHYL)PROPANE-1,3-DIOL
Systematic Name English
fingolimod [INN]
Common Name English
Fingolimod [WHO-DD]
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
FDA ORPHAN DRUG 305910
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
EU-Orphan Drug EU/3/09/718
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
LIVERTOX NBK548384
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
WHO-VATC QL04AA27
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
NDF-RT N0000181816
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
NCI_THESAURUS C308
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
WHO-ATC L04AA27
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
Code System Code Type Description
WIKIPEDIA
FINGOLIMOD
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
NCI_THESAURUS
C74202
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
INN
8341
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
EVMPD
SUB31908
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
RXCUI
1012892
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY RxNorm
DAILYMED
3QN8BYN5QF
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
ChEMBL
CHEMBL314854
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
IUPHAR
2407
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
LACTMED
Fingolimod
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
DRUG BANK
DB08868
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
SMS_ID
100000124172
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
MESH
C098720
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
DRUG CENTRAL
4167
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
NDF-RT
N0000181815
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY Sphingosine 1-Phosphate Receptor Modulators [MoA]
CHEBI
63115
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
PUBCHEM
107970
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
CAS
162359-55-9
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID40167363
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
MERCK INDEX
m5384
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY Merck Index
FDA UNII
3QN8BYN5QF
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
CHEBI
63112
Created by admin on Fri Dec 15 15:29:18 GMT 2023 , Edited by admin on Fri Dec 15 15:29:18 GMT 2023
PRIMARY
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of FINGOLIMOD LAURYL SULFATE
SALT/SOLVATE -> PARENT
Structure of FINGOLIMOD HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of FINGOLIMOD
EXCRETED UNCHANGED
After an oral administration, about 81% of the dose is slowly excreted in the urine as inactive metabolites. Fingolimod and fingolimod-P are not excreted intact in urine but are the major components in the feces with amounts representing less than 2.5% of the dose each.
FECAL
CYTOCHROME P450 4F2
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
Structure of DES(4-OCTYL) FINGOLIMOD-4-ACETIC ACID
METABOLITE -> PARENT
Structure of FINGOLIMOD PALMITAMIDE
METABOLITE -> PARENT
Structure of FINGOLIMOD OCTANOIC ACID
METABOLITE -> PARENT
Structure of FINGOLIMOD HEXANOIC ACID
METABOLITE -> PARENT
Structure of FINGOLIMOD PHOSPHATE ESTER, (S)-
METABOLITE ACTIVE -> PRODRUG
Structure of FINGOLIMOD STEARAMIDE
METABOLITE -> PARENT
Structure of 4-(3-AMINO-4-HYDROXY-3-(HYDROXYMETHYL)BUTYL)BENZENEBUTANOIC ACID
METABOLITE -> PARENT
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
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