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Compound Detail

CHEMBL1522

ESZOPICLONE
💊 Approved Drug
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💊 Approved Drug
CN1CCN(C(=O)O[C@H]2c3nccnc3C(=O)N2c2ccc(Cl)cn2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1522
Name ESZOPICLONE
Phase Approved
Structure Type MOL
InChI Key GBBSUAFBMRNDJC-INIZCTEOSA-N
Therapeutic ✓ Yes

Known Names

(S)-ZOPICLONE Estorra Eszopiclon Eszopiclona Eszopiclone Eszopiclone civ GSK-1755165 Lunesta Zopiclone s-form
5
Targets
26
Activities
1
Assay Types
5
PK Parameters
20
Publications
9
Known Names
4
Indications
1
Mechanisms

Molecular Properties

388.8
MW (Da)
1.57
ALogP
7
HBA
0
HBD
91.8
PSA (Ų)
0.77
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2004
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -clone
USAN Year 2002

Extended Properties

Molecular Formula C17H17ClN6O3
MW 388.82
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -0.99

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
GABA-A receptor; anion channel positive allosteric modulator POSITIVE ALLOSTERIC MODULATOR GABA-A receptor; anion channel ✓ ✓

Indications

Sleep Initiation and Maintenance Disorders Anxiety Disorders Sleep Apnea, Obstructive Marijuana Abuse

ATC Classification

N05CF04
eszopiclone
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Drug Warnings

Black Box Warning
misuse
Country: United States
Black Box Warning
General Warning
Country: United States

Activity Summary

Ki 26 meas. best 9.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.08 7.0605 0.8 22
Gamma-aminobutyric acid receptor subunit alpha-1
CHEMBL1962
 Ki 7.3 7.3 50.1 1
Gamma-aminobutyric acid receptor subunit alpha-4
CHEMBL2472
 Ki 6.99 6.99 102.0 1
GABA A receptor alpha-2/beta-2/gamma-2
CHEMBL2111413
 Ki 6.94 6.94 114.0 1
GABA A receptor alpha-3/beta-2/gamma-2
CHEMBL2111339
 Ki 6.79 6.79 162.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 80.0 % Homo sapiens
F 80.0 % Homo sapiens
T1/2 6.0 hr Homo sapiens
T1/2 5.0 hr Homo sapiens
Tmax 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.83 nM 9.08 Displacement of [3H]Ro15-1788 from benzodiazepine binding site of GABAA alpha-1 ... 18973287
Unchecked Ki = 22.4 nM 7.65 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-... 18973287
Unchecked Ki = 33.8 nM 7.47 Displacement of [3H]Ro15-1788 from benzodiazepine binding site of GABAA alpha1 T... 18973287
Unchecked Ki = 34.9 nM 7.46 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha1 S... 18973287
Unchecked Ki = 46.3 nM 7.33 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-... 18973287
Gamma-aminobutyric acid receptor subunit alpha-1 Ki = 50.1 nM 7.3 Displacement of [3H]Ro15-1788 from benzodiazepine binding site of GABAA alpha-1-... 18973287
Unchecked Ki = 57.9 nM 7.24 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha1 S... 18973287
Unchecked Ki = 60.4 nM 7.22 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha1 A... 18973287
Unchecked Ki = 62.4 nM 7.21 Displacement of [3H]Ro15-1788 from benzodiazepine binding site of GABAA alpha-1 ... 18973287
Unchecked Ki = 67.0 nM 7.17 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-... 18973287
Unchecked Ki = 70.9 nM 7.15 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-... 18973287
Unchecked Ki = 71.9 nM 7.14 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-... 18973287
Unchecked Ki = 75.2 nM 7.12 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-... 18973287
Unchecked Ki = 82.4 nM 7.08 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-... 18973287
Unchecked Ki = 102.0 nM 6.99 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-... 18973287
Gamma-aminobutyric acid receptor subunit alpha-4 Ki = 102.0 nM 6.99 Displacement of [3H]Ro-154513 from benzodiazepine binding site of GABAA alpha-4-... 18973287
Unchecked Ki = 110.0 nM 6.96 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-... 18973287
GABA A receptor alpha-2/beta-2/gamma-2 Ki = 114.0 nM 6.94 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-2-... 18973287
Unchecked Ki = 119.0 nM 6.92 Displacement of [3H]Ro15-1788 from benzodiazepine binding site of GABAA alpha-1 ... 18973287
GABA A receptor alpha-3/beta-2/gamma-2 Ki = 162.0 nM 6.79 Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-3-... 18973287

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
18973287 10.1021/jm800889m Unchecked 47
34213340 10.1021/acs.jmedchem.1c00790 ADMET 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
18973287 10.1021/jm800889m Gamma-aminobutyric acid receptor subunit alpha-5 1
18973287 10.1021/jm800889m GABA A receptor alpha-6/beta-2/gamma-2 1
23956101 10.1093/toxsci/kft176 Bile salt export pump 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 2 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 3 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 4 1
18973287 10.1021/jm800889m GABA A receptor alpha-3/beta-2/gamma-2 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
18973287 10.1021/jm800889m GABA A receptor alpha-2/beta-2/gamma-2 1
31307886 10.1016/j.bmcl.2019.06.043 ADMET 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
18973287 10.1021/jm800889m Gamma-aminobutyric acid receptor subunit alpha-4 1
18973287 10.1021/jm800889m Gamma-aminobutyric acid receptor subunit alpha-1 1

Data from ChEMBL 36 via Core Engine