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Compound Detail

CHEMBL1083659

SUVOREXANT
💊 Approved Drug
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💊 Approved Drug
Cc1ccc(-n2nccn2)c(C(=O)N2CCN(c3nc4cc(Cl)ccc4o3)CC[C@H]2C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1083659
Name SUVOREXANT
Phase Approved
Structure Type MOL
InChI Key JYTNQNCOQXFQPK-MRXNPFEDSA-N
Therapeutic ✓ Yes

Known Names

Belsomra MK-4305 MK4305 Suvorexant Suvorexant component of belsomra
5
Targets
27
Activities
2
Assay Types
30
PK Parameters
20
Publications
5
Known Names
11
Indications
1
Mechanisms

Molecular Properties

450.9
MW (Da)
4.11
ALogP
7
HBA
0
HBD
80.3
PSA (Ų)
0.47
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2014
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product First in Class
USAN Year 2010

Extended Properties

Molecular Formula C23H23ClN6O2
MW 450.93
Aromatic Rings 4
Heavy Atoms 32
NP-Likeness -1.63

Mechanism of Action

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

Indications

Sleep Initiation and Maintenance Disorders Delirium Alcoholism Alzheimer Disease Autistic Disorder Opioid-Related Disorders Restless Legs Syndrome Sleep Wake Disorders Smoking Cessation Sleep Apnea Syndromes Tobacco Use Disorder

ATC Classification

N05CJ01
suvorexant
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Activity Summary

Ki 15 meas. best 9.46
IC50 12 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Orexin receptor type 2
CHEMBL4792
 Ki 9.46 9.058 0.3 5
Orexin receptor type 2
CHEMBL4792
 IC50 9.4 7.4783 0.4 6
Orexin/Hypocretin receptor type 1
CHEMBL5113
 Ki 9.4 9.1486 0.4 7
Unchecked
CHEMBL612545
 IC50 9.22 9.22 0.6 1
Orexin/Hypocretin receptor type 1
CHEMBL2434819
 Ki 8.77 8.77 1.7 1
Unchecked
CHEMBL612545
 Ki 8.53 8.53 3.0 1
Orexin receptor type 2
CHEMBL2434818
 Ki 8.06 8.06 8.7 1
Orexin/Hypocretin receptor type 1
CHEMBL5113
 IC50 7.3 7.06 50.0 5

Pharmacokinetic Data

Parameter Value Units Species
AUC 766.58 ng.hr.mL-1 Rattus norvegicus
AUC 7620.72 ng.hr.mL-1 Canis lupus familiaris
CL 4.0 mL.min-1.kg-1 Canis lupus familiaris
CL 44.0 ml/mg/kg Rattus norvegicus
CL 44.0 mL.min-1.kg-1 Rattus norvegicus
CL 4.0 mL.min-1.kg-1 Canis lupus familiaris
Cmax 2100.0 nM Rattus norvegicus
Cmax 480.0 nM Rattus norvegicus
Cmax 3200.0 nM Canis lupus familiaris
F 56.0 % Canis lupus familiaris
F 19.0 % Rattus norvegicus
F 19.0 % Rattus norvegicus
F 56.0 % Canis lupus familiaris
Fu 0.0065 - Mus musculus
T1/2 0.6 hr Rattus norvegicus
T1/2 3.3 hr Canis lupus familiaris
T1/2 9.0 hr Homo sapiens
T1/2 12.0 hr Homo sapiens
T1/2 0.4 hr Homo sapiens
T1/2 3.5 hr Homo sapiens
T1/2 1.317 hr Homo sapiens
T1/2 1.317 hr Homo sapiens
T1/2 0.6 hr Rattus norvegicus
T1/2 3.3 hr Canis lupus familiaris
T1/2 8.0 hr Homo sapiens
T1/2 9.0 hr Homo sapiens
T1/2 12.0 hr Homo sapiens
T1/2 1.25 hr Homo sapiens
Tmax 0.5 hr Rattus norvegicus
Tmax 0.5 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 = 0.35 nM 9.46 Displacement of [3H](S)-N-(2-(1H-pyrrol-1-yl)phenyl)-1-(2-(1-methyl-1H-benzo[d]i... 20565075
Orexin receptor type 2 IC50 = 0.4 nM 9.4 Antagonist activity at human orexin 2 receptor expressed in CHO cells assessed a... 25613676
Orexin/Hypocretin receptor type 1 Ki = 0.3981 nM 9.4 Displacement of [3H]4-(2,6-Difluoro-4-methoxybenzyl)-2-(5,6-dimethoxypyridin-3-y... 31860301
Orexin receptor type 2 Ki = 0.4 nM 9.4 Displacement of [3H]radioligand from human orexin-2 receptor expressed in CHO ce... 24704030
Orexin receptor type 2 Ki = 0.4 nM 9.4 Binding affinity to orexin receptor 2 (unknown origin) 23891187
Orexin/Hypocretin receptor type 1 Ki = 0.55 nM 9.26 Displacement of [3H]N-cyclobutyl-5-methyl-N-(2-(1-methyl-1H-benzo[d]imidazol-2-y... 20565075
Orexin/Hypocretin receptor type 1 Ki = 0.55 nM 9.26 Displacement of [3H](S)-N-(biphenyl-2-yl)-1-(2-(1-methyl-1H-benzo[d]imidazol-2-y... 20565075
Unchecked IC50 = 0.6 nM 9.22 Antagonist activity at human orexin 1 receptor Ile408-Val mutant expressed in CH... 25613676
Orexin/Hypocretin receptor type 1 Ki = 0.6 nM 9.22 Displacement of [3H]radioligand from human orexin-1 receptor expressed in CHO ce... 24704030
Orexin/Hypocretin receptor type 1 Ki = 0.6 nM 9.22 Binding affinity to orexin receptor 1 (unknown origin) 23891187
Orexin/Hypocretin receptor type 1 Ki = 0.6761 nM 9.17 Displacement of 3H-SB-674042 from human Ox1R expressed in CHO cell membranes by ... 38295907
Orexin receptor type 2 Ki = 0.7943 nM 9.1 Displacement of [3H]4-(2,6-Difluoro-4-methoxybenzyl)-2-(5,6-dimethoxypyridin-3-y... 31860301
Orexin/Hypocretin receptor type 1 Ki = 1.698 nM 8.77 Antagonist activity at mouse OX1 receptor expressed in CHO cells assessed as inh... 23964859
Unchecked Ki = 2.951 nM 8.53 Displacement of [3H]-EMPA from human orexin 2 receptor expressed in CHO cells in... 32977721
Orexin/Hypocretin receptor type 1 Ki = 3.09 nM 8.51 Displacement of [3H]-SB67404 from human orexin 1 receptor expressed in CHO cells... 32977721
Orexin receptor type 2 Ki = 8.71 nM 8.06 Antagonist activity at mouse OX2 receptor expressed in HEK cells assessed as inh... 23964859
Orexin receptor type 2 Ki = 11.8 nM 7.93 Displacement of [125I]-Orexin A from human OX2R expressed in CHO cells after 30 ... 25267004
Orexin/Hypocretin receptor type 1 IC50 = 50.0 nM 7.3 Antagonist activity at human orexin-1 receptor expressed in CHO cells assessed a... 24704030
Orexin/Hypocretin receptor type 1 IC50 = 50.0 nM 7.3 Antagonist activity at human OX1R expressed in CHO cells assessed as inhibition ... 20565075
Orexin/Hypocretin receptor type 1 IC50 = 50.0 nM 7.3 Antagonist activity at OX1R (unknown origin) 26317591

Literature References

PubMed DOI Target Context # Activities
26317591 10.1021/acs.jmedchem.5b00832 Homo sapiens 34
20565075 10.1021/jm100541c Rattus norvegicus 14
20565075 10.1021/jm100541c Canis familiaris 8
20565075 10.1021/jm100541c ADMET 7
- 10.1039/C5MD00074B Rattus norvegicus 6
26317591 10.1021/acs.jmedchem.5b00832 Rattus norvegicus 5
23964859 10.1021/jm4007627 Mus musculus 5
20565075 10.1021/jm100541c No relevant target 4
26317591 10.1021/acs.jmedchem.5b00832 Canis familiaris 4
38295907 10.1016/j.bmcl.2024.129629 Orexin/Hypocretin receptor type 1 4
20565075 10.1021/jm100541c Plasma 3
28216404 10.1016/j.bmcl.2017.01.075 Rattus norvegicus 3
20565075 10.1021/jm100541c Orexin/Hypocretin receptor type 1 3
26317591 10.1021/acs.jmedchem.5b00832 Molecular identity unknown 3
- 10.1039/C5MD00027K Rattus norvegicus 2
24704030 10.1016/j.bmcl.2014.03.052 Orexin receptor type 2 2
25613676 10.1016/j.bmcl.2014.12.081 Liver microsome 2
24704030 10.1016/j.bmcl.2014.03.052 Orexin/Hypocretin receptor type 1 2
- 10.1039/C5MD00027K Orexin receptor type 2 2
23964859 10.1021/jm4007627 Brain 2

Data from ChEMBL 36 via Core Engine