zopiclone

Also known as RP-27267, Zimovane®, 6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl-1-piperazinecarboxylate, (±)-zopiclone

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 458773669
Drug.IUPAC_name: (RS)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate
Drug.image: Zopiclone structure.svg
Drug.image_class: skin-invert-image
Drug.width: 200
Drug.caption: Above: molecular structure of zopiclone Below: 3D representation of the (S)-zopiclone molecule
Drug.image2: Zopiclone 3D.png
Drug.image_class2: bg-transparent
Drug.width2: 230
Drug.tradename: Imovane, Zimovane, Dopareel, others
Drug.pregnancy_AU: C
Drug.legal_AU: S4
Drug.dependency_liability: High
Drug.routes_of_administration: Oral tablets, 3.75 mg or 7.5mg (UK), 5 mg, 7.5 mg, or 10 mg (JP)
Drug.bioavailability: 75–80%
Drug.protein_bound: 52–59%
Drug.metabolism: Hepatic through CYP3A4 and CYP2E1

via Wikipedia infobox

Chemical data

Formula: C17H17ClN6O3
Molecular weight: 388.8 g/mol
IUPAC name: [6-(5-chloro-2-pyridinyl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate
SMILES: CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
InChIKey: GBBSUAFBMRNDJC-UHFFFAOYSA-N
XLogP: 0.5
Polar surface area: 91.8 Å²
H-bond donors: 0
H-bond acceptors: 7
Formal charge: 0

via PubChem

Research

1,580 papers

Zopiclone to treat insomnia in older adults: A systematic review.European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology · 2021
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
Zopiclone induced methemoglobinemia and hemolytic anemia.International journal of clinical pharmacology and therapeutics · 2014
Zopiclone: is there any dependence and abuse potential?Journal of neurology · 1997
Zopiclone as a Potent Positive Control for Assessing the Residual Effects of Hypnotic Drugs on Next Day Driving Performance: A Systematic Review.Human psychopharmacology · 2025

via PubMed

Wikidata facts

Mass: 388.105066

Show 5 more facts

chemical formula: C₁₇H₁₇ClN₆O₃
defined daily dose: 7.5
Commons category: Zopiclone
canonical SMILES: CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
World Health Organisation international non-proprietary name: zopiclone

Sources (8)

via Wikidata · CC0

~19 min read

Article

18 sections

Contents

Medical uses
Specific populations
Elderly
Liver disease
Adverse reactions
Contraindications
EEG and sleep
Overdose
Interactions
Pharmacology
Pharmacokinetics
Chemistry
Detection in biological fluids
History
Society and culture
Recreational use
References
External links

Zopiclone, sold under the brand name Imovane among others, is a nonbenzodiazepine, specifically a cyclopyrrolone, used to treat insomnia. While molecularly distinct from benzodiazepine drugs, Zopiclone's mechanism of action is similar; it increases the normal transmission of the neurotransmitter gamma-aminobutyric acid (GABA) in the central nervous system, via positive allosteric modulation at GABAA neurons.

Zopiclone is considered a sedative and CNS depressant. After prolonged use, the body can become accustomed to the effects of zopiclone. When the dose is then reduced or the drug is abruptly stopped, withdrawal symptoms may result. These can include a range of symptoms similar to those of benzodiazepine withdrawal. Although withdrawal symptoms from therapeutic doses of zopiclone and its isomers (i.e., eszopiclone) do not typically present with convulsions and are therefore not considered life-threatening, patients may experience such significant agitation or anxiety that they seek emergency medical attention.