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
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
| 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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26715391 | https://www.ncbi.nlm.nih.gov/pubmed/23518370
Curator's Comment: Fingolimod crosses the blood–brain barrier (BBB) and accumulates in the CNS.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 0.84 µM [IC50] | |||
| 2.1 µM [IC50] | |||
| 0.3 nM [EC50] | |||
| 0.3 nM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | GILENYA Approved UseGILENYA 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 Date2010 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Dose | Population | Adverse events |
|---|---|---|
14 mg single, oral Overdose |
unhealthy, 33 years |
Other AEs: Bradycardia, Hypotension... Other AEs: Bradycardia (1 patient) Sources: Hypotension (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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
Other AEs: Appendicitis, Urinary tract infection... Other AEs: Appendicitis (serious, 1 patient) Sources: 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%) |
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: |
unhealthy, 37 years Health Status: unhealthy Age Group: 37 years Sex: M+F Sources: |
Disc. AE: Transaminases increased... AEs leading to discontinuation/dose reduction: Transaminases increased (3.8%) Sources: |
3.5 mg single, oral Highest studied dose |
unhealthy, 43.2 years Health Status: unhealthy Age Group: 43.2 years Sex: M+F Sources: |
Other AEs: Bradycardia, Carbon monoxide diffusing capacity decreased... Other AEs: Bradycardia (2 patients) Sources: Carbon monoxide diffusing capacity decreased (1 patient) Electrocardiogram T wave abnormal (1 patient) |
40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Chest tightness... Other AEs: Chest tightness (mild, 5 patients) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Bradycardia | 1 patient | 14 mg single, oral Overdose |
unhealthy, 33 years |
| Hypotension | 1 patient | 14 mg single, oral Overdose |
unhealthy, 33 years |
| 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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
| 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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
| 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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
| 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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
| 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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
| 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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
| 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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
| 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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
| 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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
| 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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
| 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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
| 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: |
unhealthy, 36.0 years (range: 18–55 years) Health Status: unhealthy Age Group: 36.0 years (range: 18–55 years) Sex: M+F Sources: |
| 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: |
unhealthy, 37 years Health Status: unhealthy Age Group: 37 years Sex: M+F Sources: |
| Carbon monoxide diffusing capacity decreased | 1 patient | 3.5 mg single, oral Highest studied dose |
unhealthy, 43.2 years Health Status: unhealthy Age Group: 43.2 years Sex: M+F Sources: |
| Electrocardiogram T wave abnormal | 1 patient | 3.5 mg single, oral Highest studied dose |
unhealthy, 43.2 years Health Status: unhealthy Age Group: 43.2 years Sex: M+F Sources: |
| Bradycardia | 2 patients | 3.5 mg single, oral Highest studied dose |
unhealthy, 43.2 years Health Status: unhealthy Age Group: 43.2 years Sex: M+F Sources: |
| Chest tightness | mild, 5 patients | 40 mg single, oral Overdose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
Drug as perpetrator
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: (ClinPharm) 11, 54, 55, 56-57, 207-210 |
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 |
||
| minor [Km 73 uM] | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022527Orig1s000clinpharmr.pdf#page=89 Page: (ClinPharm) 89 |
no | |||
| yes [Km 117 uM] | ||||
| yes [Km 76 uM] |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Immunosuppressive drugs in paediatric liver transplantation. | 2001 |
|
| Long-term graft acceptance in rat heart transplantation by CTLA4Ig gene transfection combined with FTY720 treatment. | 2001 Apr |
|
| Coexpression of CD4 and CD8alpha on rat T-cells in whole blood: a sensitive marker for monitoring T-cell immunosuppressive drugs. | 2001 Aug 1 |
|
| Combined FTY720/cyclosporine A treatment promotes graft survival and lowers the peripheral lymphocyte count in DA to lewis heart and skin transplantation models. | 2001 Feb |
|
| FTY 720 prevents ischemic reperfusion damage in rat kidneys. | 2001 Feb-Mar |
|
| FTY720, a novel immunosuppressive agent with insulinotropic activity, prolongs graft survival in a mouse islet transplantation model. | 2001 Feb-Mar |
|
| FTY720 prevents chronic rejection of rat heterotopic cardiac allografts. | 2001 Feb-Mar |
|
| FTY720 alters lymphocyte homing and protects allografts without inducing general immunosuppression. | 2001 Feb-Mar |
|
| New immunosuppressive drugs: an update. | 2001 Mar |
|
| FTY-720 is efficacious in monkey kidney transplantation. | 2001 May |
|
| Therapeutic effects of FTY720, a new immunosuppressive agent, in a murine model of acute viral myocarditis. | 2001 May |
|
| FTY720, a novel transplantation drug, modulates lymphocyte migratory responses to chemokines. | 2001 Nov-Dec |
|
| Activation of caspases and mitochondria in FTY720-mediated apoptosis in human T cell line Jurkat. | 2001 Oct |
|
| [What is new on transplantation in 2001?]. | 2001 Sep 1 |
|
| Effects of FTY720 in MRL-lpr/lpr mice: therapeutic potential in systemic lupus erythematosus. | 2002 Apr |
|
| 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 |
|
| L-selectin-dependent lymphoid occupancy is required to induce alloantigen-specific tolerance. | 2002 Feb 15 |
|
| A novel immunosuppressive drug, FTY720, prevents the cancer progression induced by cyclosporine. | 2002 Jul 26 |
|
| Combination treatment with FTY720 and CTLA4IgG preserves the respiratory epithelium and prevents obliterative disease in a murine airway model. | 2002 Jun |
|
| FTY720 pretreatment reduces warm hepatic ischemia reperfusion injury through inhibition of T-lymphocyte infiltration. | 2002 Oct |
|
| Effects of immunosuppressant FTY720 on renal and hepatic hemodynamics in the rat. | 2002 Sep 15 |
|
| FTY720: A new kid on the block for transplant immunosuppression. | 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 |
|
| FTY720 stimulates multidrug transporter- and cysteinyl leukotriene-dependent T cell chemotaxis to lymph nodes. | 2003 Mar |
|
| [Study the mechanisms and inducing transplantation immune tolerance of FTY720]. | 2003 Oct |
|
| Lymphocyte egress from thymus and peripheral lymphoid organs is dependent on S1P receptor 1. | 2004 Jan 22 |
|
| 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
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
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
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on
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| Record UNII |
3QN8BYN5QF
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Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
305910
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EU-Orphan Drug |
EU/3/09/718
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LIVERTOX |
NBK548384
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WHO-VATC |
QL04AA27
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NDF-RT |
N0000181816
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NCI_THESAURUS |
C308
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WHO-ATC |
L04AA27
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| Code System | Code | Type | Description | ||
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FINGOLIMOD
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C74202
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8341
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SUB31908
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1012892
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3QN8BYN5QF
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CHEMBL314854
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2407
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Fingolimod
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DB08868
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100000124172
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C098720
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4167
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N0000181815
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PRIMARY | Sphingosine 1-Phosphate Receptor Modulators [MoA] | ||
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63115
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107970
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162359-55-9
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DTXSID40167363
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m5384
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PRIMARY | Merck Index | ||
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3QN8BYN5QF
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63112
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| Related Record | Type | Details | ||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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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
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Volume of Distribution | PHARMACOKINETIC |
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| Volume of Distribution | PHARMACOKINETIC |
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| Tmax | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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