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Compound Detail

CHEMBL3358920

ETRASIMOD
💊 Approved Drug
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💊 Approved Drug
O=C(O)C[C@H]1CCc2c1[nH]c1ccc(OCc3ccc(C4CCCC4)c(C(F)(F)F)c3)cc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3358920
Name ETRASIMOD
Phase Approved
Structure Type MOL
InChI Key MVGWUTBTXDYMND-QGZVFWFLSA-N
Therapeutic ✓ Yes

Known Names

APD-334 APD-334(FREE ACID) Apd334 Etrasimod
13
Targets
17
Activities
2
Assay Types
30
PK Parameters
20
Publications
4
Known Names
8
Indications
1
Mechanisms

Molecular Properties

457.5
MW (Da)
6.93
ALogP
2
HBA
2
HBD
62.3
PSA (Ų)
0.42
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2023
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral
USAN Stem -imod
USAN Year 2016

Extended Properties

Molecular Formula C26H26F3NO3
MW 457.49
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness -0.07

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Sphingosine 1-phosphate receptor Edg-1 agonist AGONIST Sphingosine 1-phosphate receptor 1 ✓ ✓

Indications

Colitis, Ulcerative Crohn Disease Alopecia Areata Dermatitis, Atopic Eosinophilic Esophagitis Inflammatory Bowel Diseases Liver Cirrhosis, Biliary Pyoderma

ATC Classification

L04AE05
etrasimod
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Activity Summary

EC50 11 meas. best 10.4
IC50 6 meas. best 8.73

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 EC50 10.4 9.2 0.0 4
Sphingosine 1-phosphate receptor 1
CHEMBL1914263
 EC50 9.49 9.49 0.3 1
Sphingosine 1-phosphate receptor 1
CHEMBL3559675
 EC50 9.49 9.49 0.3 1
Sphingosine-1-phosphate receptor 1
CHEMBL3559680
 EC50 9.47 9.47 0.3 1
Sphingosine 1-phosphate receptor 1
CHEMBL1914262
 EC50 9.36 9.36 0.4 1
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 IC50 8.73 8.73 1.9 1
Sphingosine 1-phosphate receptor 5
CHEMBL2274
 EC50 7.61 7.61 24.4 1
Unchecked
CHEMBL612545
 EC50 7.52 7.52 29.9 1
Rattus norvegicus
CHEMBL376
 IC50 7.29 7.29 51.0 1
Canis familiaris
CHEMBL373
 IC50 7.24 7.24 58.0 1
Rhesus monkey
CHEMBL614875
 IC50 7.01 7.01 98.0 1
Mus musculus
CHEMBL375
 IC50 7.0 7.0 101.0 1
Sphingosine 1-phosphate receptor 4
CHEMBL3230
 EC50 6.83 6.83 147.0 1
Adenosine receptor A3
CHEMBL256
 IC50 5.48 5.48 3300.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 23100.0 ng.hr.mL-1 Macaca mulatta
AUC 164000.0 ng.hr.mL-1 Canis lupus familiaris
AUC 3790.0 ng.hr.mL-1 Rattus norvegicus
AUC 10300.0 ng.hr.mL-1 Mus musculus
CL 2.23 % Macaca mulatta
CL 0.746 % Canis lupus familiaris
CL 3.45 % Rattus norvegicus
CL 2.0 % Mus musculus
CL 0.9467 mL.min-1.kg-1 Macaca mulatta
CL 0.23 mL.min-1.kg-1 Canis lupus familiaris
CL 2.417 mL.min-1.kg-1 Rattus norvegicus
CL 1.833 mL.min-1.kg-1 Mus musculus
Cmax 182700.0 nM Rattus norvegicus
Cmax 135700.0 nM Rattus norvegicus
Cmax 6273.36 nM Macaca mulatta
Cmax 8109.47 nM Canis lupus familiaris
Cmax 476.51 nM Rattus norvegicus
Cmax 1704.96 nM Mus musculus
Cmax 789.09 nM Rattus norvegicus
F 43.8 % Macaca mulatta
F 73.2 % Canis lupus familiaris
F 54.0 % Rattus norvegicus
F 100.0 % Mus musculus
F 54.0 % Rattus norvegicus
T1/2 6.37 hr Macaca mulatta
T1/2 28.8 hr Canis lupus familiaris
T1/2 9.64 hr Rattus norvegicus
T1/2 12.3 hr Mus musculus
T1/2 1.0 hr Macaca mulatta
T1/2 1.0 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sphingosine 1-phosphate receptor 1 EC50 = 0.04 nM 10.4 Agonist activity at human S1P1 receptor assessed as cAMP accumulation by HTRF as... 25516790
Sphingosine 1-phosphate receptor 1 EC50 = 0.102 nM 9.99 Homogenous Time-Resolved Fluorescence (HTRF) Assay for Direct cAMP Measurement: ... -
Sphingosine 1-phosphate receptor 1 EC50 = 0.32 nM 9.49 Agonist activity at monkey S1P1 receptor assessed as cAMP accumulation by HTRF a... 25516790
Sphingosine 1-phosphate receptor 1 EC50 = 0.32 nM 9.49 Agonist activity at rat S1P1 receptor assessed as cAMP accumulation by HTRF assa... 25516790
Sphingosine-1-phosphate receptor 1 EC50 = 0.34 nM 9.47 Agonist activity at dog S1P1 receptor assessed as cAMP accumulation by HTRF assa... 25516790
Sphingosine 1-phosphate receptor 1 EC50 = 0.44 nM 9.36 Agonist activity at mouse S1P1 receptor assessed as cAMP accumulation by HTRF as... 25516790
Sphingosine 1-phosphate receptor 1 IC50 = 1.88 nM 8.73 Induction of internalization of HA-tagged human S1P1 receptor expressed in CHO c... 25516790
Sphingosine 1-phosphate receptor 1 EC50 = 6.1 nM 8.21 Agonist activity at human S1P1 receptor by beta-arrestin recruitment assay 25516790
Sphingosine 1-phosphate receptor 1 EC50 = 6.31 nM 8.2 Modulation of S1PR1 (unknown origin) 36758307
Sphingosine 1-phosphate receptor 5 EC50 = 24.4 nM 7.61 Agonist activity at human S1P5 receptor by beta-arrestin recruitment assay 25516790
Unchecked EC50 = 29.9 nM 7.52 Activation of Inward rectifier potassium channel in human atrial myocytes 25516790
Rattus norvegicus IC50 = 51.0 nM 7.29 Reduction in peripheral lymphocyte count in orally dosed rat measured after 24 h... 25516790
Canis familiaris IC50 = 58.0 nM 7.24 Reduction in peripheral lymphocyte count in orally dosed dog measured after 24 h... 25516790
Rhesus monkey IC50 = 98.0 nM 7.01 Reduction in peripheral lymphocyte count in orally dosed monkey measured after 2... 25516790
Mus musculus IC50 = 101.0 nM 7.0 Reduction in peripheral lymphocyte count in orally dosed mouse measured after 24... 25516790
Sphingosine 1-phosphate receptor 4 EC50 = 147.0 nM 6.83 Agonist activity at human S1P4 receptor by beta-arrestin recruitment assay 25516790
Adenosine receptor A3 IC50 = 3300.0 nM 5.48 Binding affinity to human adenosine A3 receptor 25516790

Literature References

PubMed DOI Target Context # Activities
25516790 10.1021/ml500389m Rattus norvegicus 25
25516790 10.1021/ml500389m Canis familiaris 13
25516790 10.1021/ml500389m Mus musculus 13
25516790 10.1021/ml500389m Sphingosine 1-phosphate receptor 1 11
32223194 10.1021/acs.jmedchem.9b01663 Mus musculus 11
- 10.6019/CHEMBL4689842 HEK-293T 10
- 10.6019/CHEMBL4689842 Fibroblast 10
- 10.6019/CHEMBL4689842 U2OS 9
25516790 10.1021/ml500389m Rhesus monkey 9
37948883 10.1016/j.ejmech.2023.115921 Staphylococcus aureus 8
25516790 10.1021/ml500389m Plasma 3
37948883 10.1016/j.ejmech.2023.115921 Erythrocyte 3
25516790 10.1021/ml500389m Liver microsome 3
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 2
- 10.6019/CHEMBL5209801 G-protein coupled receptor 35 2
25516790 10.1021/ml500389m Salmonella typhimurium 2
25516790 10.1021/ml500389m ADMET 2
25516790 10.1021/ml500389m Sphingosine 1-phosphate receptor 4 2
25516790 10.1021/ml500389m Voltage-gated inwardly rectifying potassium channel KCNH2 2

Data from ChEMBL 36 via Core Engine