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Compound Detail

CHEMBL2107822

FILOREXANT
🧪 Phase II
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🧪 Phase II
Cc1ccc(-c2ncccn2)c(C(=O)N2C[C@H](COc3ccc(F)cn3)CC[C@H]2C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2107822
Name FILOREXANT
Phase Phase II
Structure Type MOL
InChI Key NPFDWHQSDBWQLH-QZTJIDSGSA-N

Known Names

Filorexant MK-6096
4
Targets
18
Activities
2
Assay Types
8
PK Parameters
20
Publications
2
Known Names
3
Indications
1
Mechanisms

Molecular Properties

420.5
MW (Da)
4.31
ALogP
5
HBA
0
HBD
68.2
PSA (Ų)
0.62
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Year 2012

Extended Properties

Molecular Formula C24H25FN4O2
MW 420.49
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -1.61

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Orexin receptor antagonist ANTAGONIST Orexin receptor ✓ ✓

Indications

Depressive Disorder, Major Diabetic Neuropathies Sleep Initiation and Maintenance Disorders

Activity Summary

Ki 14 meas. best 9.7
IC50 4 meas. best 7.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Orexin receptor type 2
CHEMBL4792
 Ki 9.7 9.55 0.2 6
Orexin receptor type 2
CHEMBL1275216
 Ki 9.51 9.51 0.3 1
Orexin/Hypocretin receptor type 1
CHEMBL5113
 Ki 9.2 8.7 0.6 6
Orexin/Hypocretin receptor type 1
CHEMBL1075232
 Ki 8.54 8.54 2.9 1
Orexin receptor type 2
CHEMBL4792
 IC50 7.96 7.865 11.0 2
Orexin/Hypocretin receptor type 1
CHEMBL5113
 IC50 7.96 7.88 11.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 67.0 mL.min-1.kg-1 Rattus norvegicus
CL 5.8 mL.min-1.kg-1 Canis lupus familiaris
F 25.0 % Rattus norvegicus
F 26.0 % Canis lupus familiaris
F 25.0 % Rattus norvegicus
F 26.0 % Canis lupus familiaris
T1/2 0.5 hr Rattus norvegicus
T1/2 2.3 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Orexin receptor type 2 Ki = 0.1995 nM 9.7 Displacement of [3H]4-(2,6-Difluoro-4-methoxybenzyl)-2-(5,6-dimethoxypyridin-3-y... 31860301
Orexin receptor type 2 Ki = 0.3 nM 9.52 Binding affinity to orexin receptor 2 (unknown origin) 23891187
Orexin receptor type 2 Ki = 0.3 nM 9.52 Antagonist activity at human OX2R by radioligand displacement assay 25577040
Orexin receptor type 2 Ki = 0.3 nM 9.52 Antagonist activity at orexin-2 receptor (unknown origin) 26045032
Orexin receptor type 2 Ki = 0.3 nM 9.52 Binding affinity to OX2R (unknown origin) 26317591
Orexin receptor type 2 Ki = 0.3 nM 9.52 Antagonist activity at human OX2R by FLIPR assay 30243589
Orexin receptor type 2 Ki = 0.31 nM 9.51 Radioligand Binding Assay: Radioligand binding assay described in Bergman et. al... -
Orexin/Hypocretin receptor type 1 Ki = 0.631 nM 9.2 Displacement of [3H]4-(2,6-Difluoro-4-methoxybenzyl)-2-(5,6-dimethoxypyridin-3-y... 31860301
Orexin/Hypocretin receptor type 1 Ki = 2.2 nM 8.66 Binding affinity to OX1R (unknown origin) 26317591
Orexin/Hypocretin receptor type 1 Ki = 2.5 nM 8.6 Antagonist activity at human OX1R by FLIPR assay 30243589
Orexin/Hypocretin receptor type 1 Ki = 2.5 nM 8.6 Antagonist activity at orexin-1 receptor (unknown origin) 26045032
Orexin/Hypocretin receptor type 1 Ki = 2.5 nM 8.6 Binding affinity to orexin receptor 1 (unknown origin) 23891187
Orexin/Hypocretin receptor type 1 Ki = 2.9 nM 8.54 Radioligand Binding Assay: Radioligand binding assay described in Bergman et. al... -
Orexin/Hypocretin receptor type 1 Ki = 2.9 nM 8.54 Antagonist activity at human OX1R by radioligand displacement assay 25577040
Orexin receptor type 2 IC50 = 11.0 nM 7.96 Antagonist activity at human OX2R expressed in CHO cell membranes assessed as in... 26317591
Orexin/Hypocretin receptor type 1 IC50 = 11.0 nM 7.96 Antagonist activity at human OX1R expressed in CHO cell membranes assessed as in... 26317591
Orexin/Hypocretin receptor type 1 IC50 = 16.0 nM 7.8 Antagonist activity at human OX1R by FLIPR assay 25577040
Orexin receptor type 2 IC50 = 17.0 nM 7.77 Antagonist activity at human OX2R by FLIPR assay 25577040

Literature References

PubMed DOI Target Context # Activities
26317591 10.1021/acs.jmedchem.5b00832 Rattus norvegicus 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
26317591 10.1021/acs.jmedchem.5b00832 Canis familiaris 4
26317591 10.1021/acs.jmedchem.5b00832 Molecular identity unknown 3
26317591 10.1021/acs.jmedchem.5b00832 Orexin/Hypocretin receptor type 1 2
30243589 10.1016/j.bmcl.2018.09.016 ADMET 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
26317591 10.1021/acs.jmedchem.5b00832 ADMET 2
26317591 10.1021/acs.jmedchem.5b00832 Orexin receptor type 2 2
25577040 10.1016/j.bmcl.2014.12.056 Orexin receptor type 2 2
25577040 10.1016/j.bmcl.2014.12.056 Orexin/Hypocretin receptor type 1 2
23891187 10.1016/j.bmcl.2013.06.057 Orexin receptor type 2 1
26045032 10.1016/j.bmcl.2015.05.012 Orexin receptor type 2 1
26045032 10.1016/j.bmcl.2015.05.012 Orexin/Hypocretin receptor type 1 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
31860301 10.1021/acs.jmedchem.9b01787 Orexin/Hypocretin receptor type 1 1
31860301 10.1021/acs.jmedchem.9b01787 Orexin receptor type 2 1
25577040 10.1016/j.bmcl.2014.12.056 Unchecked 1
30243589 10.1016/j.bmcl.2018.09.016 No relevant target 1

Data from ChEMBL 36 via Core Engine