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Compound Detail

CHEMBL314854

FINGOLIMOD
💊 Approved Drug
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💊 Approved Drug
CCCCCCCCc1ccc(CCC(N)(CO)CO)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL314854
Name FINGOLIMOD
Phase Approved
Structure Type MOL
InChI Key KKGQTZUTZRNORY-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL366208

Known Names

Fingolimod FTY-720
27
Targets
49
Activities
4
Assay Types
16
PK Parameters
20
Publications
2
Known Names
17
Indications

Molecular Properties

307.5
MW (Da)
3.20
ALogP
3
HBA
3
HBD
66.5
PSA (Ų)
0.52
QED
0
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2010
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product First in Class Prodrug
USAN Stem -imod
USAN Year 2005

Extended Properties

Molecular Formula C19H33NO2
MW 307.48
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness 0.66

Indications

Multiple Sclerosis Multiple Sclerosis, Chronic Progressive Multiple Sclerosis, Chronic Progressive Multiple Sclerosis, Relapsing-Remitting Polyradiculoneuropathy, Chronic Inflammatory Demyelinating Asthma Optic Neuritis Schizophrenia Severe Acute Respiratory Syndrome Stroke Uveitis Breast Neoplasms Cerebral Hemorrhage Renal Insufficiency Rett Syndrome Astrocytoma Glioblastoma

ATC Classification

L04AE01
fingolimod
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Activity Summary

IC50 36 meas. best 8.21
EC50 10 meas. best 9.52
Kd 2 meas. best 5.3
Ki 1 meas. best 5.67

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sphingosine 1-phosphate receptor 5
CHEMBL2274
 EC50 9.52 7.51 0.3 2
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 EC50 9.52 7.932 0.3 5
Sphingosine 1-phosphate receptor 4
CHEMBL3230
 EC50 9.52 9.52 0.3 1
Sphingosine 1-phosphate receptor 3
CHEMBL3892
 EC50 8.52 7.06 3.0 2
Mus musculus
CHEMBL375
 IC50 8.21 7.69 6.1 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.21 5.884 6.1 5
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 IC50 6.22 6.15 603.8 2
Transient receptor potential cation channel subfamily M member 7
CHEMBL3714706
 IC50 6.14 6.14 720.0 1
Sphingosine 1-phosphate receptor 5
CHEMBL2274
 IC50 5.68 5.68 2100.0 1
FL5.12
CHEMBL4296414
 IC50 5.68 5.65 2100.0 2
Ceramide synthase 2
CHEMBL5291553
 Ki 5.67 5.67 2150.0 1
MDA-MB-231
CHEMBL400
 IC50 5.54 5.42 2900.0 2
G-protein coupled receptor 183
CHEMBL3259470
 IC50 5.38 5.38 4219.1 1
SH-SY5Y
CHEMBL614910
 IC50 5.33 5.33 4710.0 1
MCF7
CHEMBL387
 IC50 5.3 5.3 5000.0 1
HCT-116
CHEMBL394
 IC50 5.3 5.3 5000.0 1
Troponin C, slow skeletal and cardiac muscles
CHEMBL2066
 Kd 5.3 5.255 5000.0 2
SW-620
CHEMBL612262
 IC50 5.3 5.3 5000.0 1
SK-BR-3
CHEMBL613834
 IC50 5.3 5.3 5000.0 1
Unchecked
CHEMBL612545
 IC50 5.26 5.1733 5500.0 3
SK-N-AS
CHEMBL1075578
 IC50 5.21 5.21 6110.0 1
BV-173
CHEMBL2366145
 IC50 5.2 5.2 6300.0 1
Ceramide synthase 2
CHEMBL5291553
 IC50 5.19 5.19 6400.0 1
DU-145
CHEMBL613508
 IC50 5.19 5.19 6500.0 1
CCRF-CEM
CHEMBL382
 IC50 5.17 5.17 6800.0 1
BT-474
CHEMBL614529
 IC50 5.07 5.07 8500.0 1
NALM-6
CHEMBL614187
 IC50 5.02 5.02 9600.0 1
PC-3
CHEMBL390
 IC50 5.01 5.01 9800.0 1
Sphingosine-1-phosphate lyase 1
CHEMBL3286061
 IC50 4.77 4.525 17000.0 2
Troponin C, slow skeletal and cardiac muscles
CHEMBL2066
 IC50 4.54 4.54 29100.0 1
Sphingosine-1-phosphate lyase 1
CHEMBL5009
 IC50 4.28 4.28 52400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 200.0 ng.hr.mL-1 Rattus norvegicus
AUC 319.0 ng.hr.mL-1 Rattus norvegicus
CL - - Homo sapiens
Cmax 110.58 nM Rattus norvegicus
Cmax 42.93 nM Rattus norvegicus
T1/2 216.0 hr Homo sapiens
T1/2 89.0 hr Homo sapiens
T1/2 32.0 hr Rattus norvegicus
T1/2 4.1 hr Rattus norvegicus
T1/2 18.9 hr Rattus norvegicus
T1/2 120.0 hr Homo sapiens
T1/2 216.0 hr Homo sapiens
t1/2 - - Homo sapiens
T1/2 168.0 hr Homo sapiens
T1/2 144.0 hr Homo sapiens
Tmax 8.4 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sphingosine 1-phosphate receptor 4 EC50 = 0.3 nM 9.52 Agonist activity at S1P4 receptor (unknown origin) 24125884
Sphingosine 1-phosphate receptor 1 EC50 = 0.3 nM 9.52 Agonist activity at S1P1 receptor (unknown origin) 24125884
Sphingosine 1-phosphate receptor 5 EC50 = 0.3 nM 9.52 Agonist activity at S1P5 receptor (unknown origin) 24125884
Sphingosine 1-phosphate receptor 1 EC50 = 2.0 nM 8.7 Agonist activity at human S1P1 receptor expressed in human U2OS cells co-express... 22104144
Sphingosine 1-phosphate receptor 3 EC50 = 3.0 nM 8.52 Agonist activity at S1P3 receptor (unknown origin) 24125884
Mus musculus IC50 = 6.1 nM 8.21 In vitro ability to inhibit mouse allogenic mixed leukocyte response (MLR) -
NON-PROTEIN TARGET IC50 = 6.1 nM 8.21 Immunosuppressive activity in BALB/c/C57BL/6 mouse T cells assessed as inhibitio... 21456524
Sphingosine 1-phosphate receptor 1 EC50 = 7.2 nM 8.14 Agonist activity at human S1P1 receptor expressed in EDG1-bla U2OS cells incubat... 26687487
Sphingosine 1-phosphate receptor 1 EC50 = 62.65 nM 7.2 GPCR PRESTO-Tango dose-response in agonist mode with target: S1PR1 -
Mus musculus IC50 = 67.4 nM 7.17 Compound was tested for its effect on mouse allogenic mixed lymphocyte reaction(... -
Sphingosine 1-phosphate receptor 1 IC50 = 603.75 nM 6.22 Inhibition of S1PR1 (unknown origin) 34905377
Transient receptor potential cation channel subfamily M member 7 IC50 = 720.0 nM 6.14 Inhibition of HA-tagged mouse TRPM7 transfected in HEK293 cells assessed as inhi... 38537009
Sphingosine 1-phosphate receptor 1 EC50 = 794.33 nM 6.1 Modulation of S1PR1 (unknown origin) 36758307
Sphingosine 1-phosphate receptor 1 IC50 = 840.0 nM 6.08 Displacement of [33P]sphingosine 1 phosphate from human S1P1 receptor expressed ... 15615513
FL5.12 IC50 = 2100.0 nM 5.68 Cytotoxicity against mouse FL5.12 cells after 48 hrs by DAPI or propidium iodide... 30292898
Sphingosine 1-phosphate receptor 5 IC50 = 2100.0 nM 5.68 Displacement of [33P]sphingosine 1 phosphate from human S1P5 receptor expressed ... 15615513
Ceramide synthase 2 Ki = 2150.0 nM 5.67 Competitive inhibition of CerS2 in HPAC cells using DHSph as substrate by LC/MS/... 33395289
FL5.12 IC50 = 2400.0 nM 5.62 Cytotoxicity against mouse FL5.12A cells after 48 hrs by DAPI staining-based flo... 27475534
Sphingosine 1-phosphate receptor 3 EC50 = 2511.89 nM 5.6 Agonist activity at human S1P3 receptor expressed in CHO cells assessed as incre... 29254642
MDA-MB-231 IC50 = 2900.0 nM 5.54 Cytotoxicity against human MDA-MB-231 cells assessed as inhibition of cell growt... 37974956

Literature References

PubMed DOI Target Context # Activities
36598820 10.1021/acs.jnatprod.2c00798 Mus musculus 66
27913115 10.1016/j.bmc.2016.11.015 SK-N-SH 53
27913115 10.1016/j.bmc.2016.11.015 SH-SY5Y 53
27913115 10.1016/j.bmc.2016.11.015 U-118-MG 44
26985316 10.1021/acsmedchemlett.5b00448 Mus musculus 16
- 10.1016/0960-894X(95)00127-F Rattus norvegicus 11
- 10.6019/CHEMBL5058564 HEK-293T 8
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 8
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 8
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 8
- 10.6019/CHEMBL5058564 Fibroblast 8
- 10.6019/CHEMBL5058564 U2OS 8
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 8
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 8
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 8
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 8
- 10.6019/CHEMBL5209801 Apelin receptor 8
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 8
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 8
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 8

Data from ChEMBL 36 via Core Engine