U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H17ClN6O3
Molecular Weight 388.808
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESZOPICLONE

SMILES

CN1CCN(CC1)C(=O)O[C@@H]2N(C(=O)C3=C2N=CC=N3)C4=CC=C(Cl)C=N4

InChI

InChIKey=GBBSUAFBMRNDJC-INIZCTEOSA-N
InChI=1S/C17H17ClN6O3/c1-22-6-8-23(9-7-22)17(26)27-16-14-13(19-4-5-20-14)15(25)24(16)12-3-2-11(18)10-21-12/h2-5,10,16H,6-9H2,1H3/t16-/m0/s1

HIDE SMILES / InChI

Molecular Formula C17H17ClN6O3
Molecular Weight 388.808
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/eszopiclone.html

Eszopiclone is a nonbenzodiazepine hypnotic, pyrrolopyrazine derivative of the cyclopyrrolone class and is indicated for the short-term treatment of insomnia. While Eszopiclone is a hypnotic agent with a chemical structure unrelated to benzodiazepines, barbiturates, or other drugs with known hypnotic properties, it interacts with the gamma-aminobutyric acid-benzodiazepine (GABABZ) receptor complex. Subunit modulation of the GABABZ receptor chloride channel macromolecular complex is hypothesized to be responsible for some of the pharmacological properties of benzodiazepines, which include sedative, anxiolytic, muscle relaxant, and anticonvulsive effects in animal models. Eszopiclone binds selectively to the brain alpha subunit of the GABA A omega-1 receptor. The mechanism of action of Eszopiclone is not completely understood. It is thought that Eszopiclone acts on the benzodiazepine receptors as an agonist and interacts with GABA-receptor complexes. Used for the treatment of insomnia.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LUNESTA

Approved Use

LUNESTA is indicated for the treatment of insomnia.

Launch Date

2004
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6.15 ng/mL
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
19.88 ng/mL
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
40.28 ng/mL
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
10.29 ng/mL
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
25.48 ng/mL
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
54.68 ng/mL
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
9.58 ng/mL
1 mg 1 times / day multiple, oral
dose: 1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
26.18 ng/mL
3 mg 1 times / day multiple, oral
dose: 3 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
59.63 ng/mL
6 mg 1 times / day multiple, oral
dose: 6 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
54.76 ng × h/mL
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
166.21 ng × h/mL
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
338.26 ng × h/mL
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
62.96 ng × h/mL
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
187.76 ng × h/mL
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
379.04 ng × h/mL
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
66.05 ng × h/mL
1 mg 1 times / day multiple, oral
dose: 1 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
191.07 ng × h/mL
3 mg 1 times / day multiple, oral
dose: 3 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
409.31 ng × h/mL
6 mg 1 times / day multiple, oral
dose: 6 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.7 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ESZOPICLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
44.45%
ESZOPICLONE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
unlikely (co-administration study)
Comment: 5% decrease in AUC when paroxetine was the substrate and esopiclone the interacting drug
Page: 22;147
no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
yes
yes (co-administration study)
Comment: Coadministration with ketoconazole resulted in a 2.2-fold increase in exposure to eszopiclone
Page: 22.0
PubMed

PubMed

TitleDatePubMed
Evaluation of eszopiclone discontinuation after cotherapy with fluoxetine for insomnia with coexisting depression.
2007 Feb 15
Prolonged coma after eszopiclone overdose.
2007 Jul
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Insomnia Initial dose: 1 mg orally immediately before bedtime Maintenance dose: 1 to 3 mg orally immediately before bedtime Maximum dose: 3 mg orally immediately before bedtime
Route of Administration: Oral
10 uM Eszopiclone increased the mean amplitude of the IGV-induced outward current from 19.7 ± 3.9 pA to 47.1 ± 7.8 pA (n = 10) and increased duration from 396.5 ± 24.0 s to 568.8 ± 40.5 s in rat pedunculopontine neurons.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:13:33 GMT 2025
Edited
by admin
on Mon Mar 31 18:13:33 GMT 2025
Record UNII
UZX80K71OE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESZOPICLONE
HSDB   INN   JAN   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
ESTORRA
Preferred Name English
ESZOPICLONE [USAN]
Common Name English
Eszopiclone [WHO-DD]
Common Name English
1-PIPERAZINECARBOXYLIC ACID, 4-METHYL-, (5S)-6-(5-CHLORO-2-PYRIDINYL)-6,7-DIHYDRO-7-OXO-5H-PYRROLO(3,4-B)PYRAZIN-5-YL ESTER
Common Name English
ESZOPICLONE [JAN]
Common Name English
(+)-(5S)-6-(5-CHLOROPYRIDIN-2-YL)-7-OXO-6,7-DIHYDRO-5H-PYRROLO(3,4-B)PYRAZIN-5-YL 4-METHYLPIPERAZINE-1-CARBOXYLATE
Systematic Name English
ESZOPICLONE [VANDF]
Common Name English
ESZOPICLONE CIV [USP-RS]
Common Name English
LUNESTA
Brand Name English
ESZOPICLONE [MART.]
Common Name English
GSK-1755165
Code English
ZOPICLONE S-FORM [MI]
Common Name English
ESZOPICLONE [USP MONOGRAPH]
Common Name English
ESZOPICLONE [HSDB]
Common Name English
ZOPICLONE S-FORM
MI  
Common Name English
ESZOPICLON
Common Name English
ESZOPICLONE [ORANGE BOOK]
Common Name English
ESZOPICLONE CIV
USP-RS  
Common Name English
eszopiclone [INN]
Common Name English
(S)-ZOPICLONE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29756
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
WHO-VATC QN05CF04
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
WHO-ATC N05CF04
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
LIVERTOX NBK548047
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
Code System Code Type Description
MESH
C515051
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
RXCUI
461016
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY RxNorm
USAN
NN-76
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
NCI_THESAURUS
C65545
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
LACTMED
Eszopiclone
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
DRUG CENTRAL
1068
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
RS_ITEM_NUM
1255850
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
MERCK INDEX
m11663
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY Merck Index
PUBCHEM
969472
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
IUPHAR
7429
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
SMS_ID
100000092238
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
CAS
138729-47-2
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
FDA UNII
UZX80K71OE
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
ChEMBL
CHEMBL1522
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
DRUG BANK
DB00402
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
EVMPD
SUB21373
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
DAILYMED
UZX80K71OE
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
INN
8258
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
WIKIPEDIA
ESZOPICLONE
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
HSDB
7472
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
CHEBI
53760
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID8046086
Created by admin on Mon Mar 31 18:13:33 GMT 2025 , Edited by admin on Mon Mar 31 18:13:33 GMT 2025
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
TARGET->POSITIVE ALLOSTERIC MODULATOR (PAM)
EXCRETED UNCHANGED
URINE
BINDER->LIGAND
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
Binds to the GABA receptor with significantly lower potency than eszopiclone.
MAJOR
URINE
METABOLITE INACTIVE -> PARENT
MAJOR
URINE
METABOLITE INACTIVE -> PARENT
METABOLITE -> PARENT
METABOLITE INACTIVE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION