eszopiclone

Also known as (S)-zopiclone, Lunesta®, (+)-(5S)-6-(5-Chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazin-5-yl 4-methylpiperazine-1-carboxylate, (+)-Zopiclone, Esopiclone, 1-Piperazinecarobxylic acid,4-methyl-,(5S)-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester, (+)-(5S)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl-4-methylpiperazine-1-carboxylate

thumb|1mg Dexzopiclone (Eszopiclone) tablets from China

In the Vinony graph

Within Vinony's link graph, eszopiclone is referenced by 827 other articles, and connects out to amylene hydrate, hallucination and barbiturates.

It is catalogued under topics including 4-Methylpiperazin-1-yl compounds, Carbamates and Chloropyridines.

Its subject is documented across 17 Wikipedia language editions.

Chemical data

Formula: C17H17ClN6O3
Molecular weight: 388.8 g/mol
IUPAC name: [(7S)-6-(5-chloro-2-pyridinyl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate
SMILES: CN1CCN(CC1)C(=O)O[C@H]2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
InChIKey: GBBSUAFBMRNDJC-INIZCTEOSA-N
XLogP: 0.5
Polar surface area: 91.8 Å²
H-bond donors: 0
H-bond acceptors: 7
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2004
Admin. routes: oral
Indications: insomnia, obstructive sleep apnea, cannabis dependence, generalized anxiety disorder

via ChEMBL · EBI

Research

396 papers

Eszopiclone.2006
Eszopiclone.2012
Eszopiclone for insomnia.The Cochrane database of systematic reviews · 2018
Comparative effects of pharmacological interventions for the acute and long-term management of insomnia disorder in adults: a systematic review and network meta-analysis.Lancet (London, England) · 2022
Eszopiclone for insomnia.The Annals of pharmacotherapy · 2005

via PubMed

Wikidata facts

Subclass of: zopiclone
Mass: 388.105066
Has use: medication

Show 7 more facts

medical condition treated: insomnia
chemical formula: C₁₇H₁₇ClN₆O₃
isomeric SMILES: CN1CCN(CC1)C(=O)O[C@H]2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
canonical SMILES: CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
World Health Organisation international non-proprietary name: eszopiclone
Commons category: Eszopiclone
legal status (medicine): boxed warning

Sources (4)

via Wikidata · CC0

~12 min read

Encyclopedic overview

11 sections

Contents

Medical uses
Elderly
Adverse effects
Dependence
Non-medical use
Overdose
Interactions
Pharmacology
History
Availability in Europe
References

thumb|1mg Dexzopiclone (Eszopiclone) tablets from China

Eszopiclone, sold under the brand name Lunesta among others, is a nonbenzodiazepine medication used in the treatment of short-term and long-term insomnia. It is one of the few FDA-approved hypnotic medications with a controlled substance designation that does not have restrictions on its length of use. Evidence supports benefits up to six months, with some studies suggesting similar efficacy after 12 months. It is taken by mouth.

Excerpted from Wikipedia’s “eszopiclone” article, available under the CC BY-SA 4.0 licence.