ESZOPICLONE

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 Search

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
Sources: http://www.drugbank.ca/drugs/DB00402
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: http://www.genome.jp/dbget-bin/www_bget?D02624	Agonist 2752
GABA receptor alpha-1 subunit 19 Target ID: CHEMBL1962 Sources: http://www.genome.jp/dbget-bin/www_bget?D02624	Agonist 2752	50.1 nM [Ki]
GABA receptor alpha-2 subunit 7 Target ID: CHEMBL4956 Sources: http://www.genome.jp/dbget-bin/www_bget?D02624	Agonist 2752	114.0 nM [Ki]
GABA receptor alpha-4 subunit 2 Target ID: CHEMBL2472 Sources: http://www.genome.jp/dbget-bin/www_bget?D02624	Agonist 2752	102.0 nM [Ki]
GABA receptor alpha-3 subunit 6 Target ID: CHEMBL3026 Sources: http://www.genome.jp/dbget-bin/www_bget?D02624	Agonist 2752	162.0 nM [Ki]
Translocator protein 12 Target ID: CHEMBL5742 Sources: http://www.drugbank.ca/drugs/DB00402	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 111 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021476s030lbl.pdf	Primary		Approved 8583	LUNESTA Approved Use LUNESTA is indicated for the treatment of insomnia. Launch Date 2004

C_max

Value	Dose	Analyte	Population
6.15 ng/mL REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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

Value	Dose	Analyte	Population
54.76 ng × h/mL REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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 REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.7 h REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
44.45% REVIEW https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-lunivia_en.pdf			ESZOPICLONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087	inhibitor 2438 inducer 440	inhibitor 2507 inducer 109

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060	CYP2E1 729	CYP1A2 832 CYP2A6 86 CYP2C19 329 CYP2E1 131

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	no
CYP2A6 911	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	no
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	no
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	no
CYP2E1 1146	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22;147	no	unlikely (co-administration study) Comment: 5% decrease in AUC when paroxetine was the substrate and esopiclone the interacting drug Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22;147
CYP2D6 2546	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22;147	no	unlikely Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22;147

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	likely
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0	yes		yes (co-administration study) Comment: Coadministration with ketoconazole resulted in a 2.2-fold increase in exposure to eszopiclone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021476_Lunesta_biopharmr.PDF#page=22 Page: 22.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:53760	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:53760
ChemicalBook	CB1468825	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1468825
eMolecules	2728749	https://www.emolecules.com/cgi-bin/more?vid=2728749
ZINC	ZINC000019632834	http://zinc15.docking.org/substances/ZINC000019632834

PubMed

Title	Date	PubMed
Evaluation of eszopiclone discontinuation after cotherapy with fluoxetine for insomnia with coexisting depression.	2007 Feb 15	17557453
Prolonged coma after eszopiclone overdose.	2007 Jul	17606111

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

In Vitro Use Guide

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

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Name

Type

Language

ESZOPICLONE

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

Common Name

English

ESZOPICLON

Common Name

English

ESZOPICLONE [ORANGE BOOK]

Common Name

English

ESZOPICLONE CIV

Common Name

English

eszopiclone [INN]

Common Name

English

(S)-ZOPICLONE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29756