Overview
| Generic Names: | (+-)-zopiclone; Zopiclona [INN-Spanish]; Zopiclone [Ban:Inn:Jan]; Zopiclonum [INN-Latin] |
|---|---|
| IUPAC Name: | [6-(5-chloropyridin-2-yl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate |
| Trade Names: | Amoban; Amovane; Imovance; Imovane; Novo-zopiclone; Nu-Zopiclone; Ran-zopiclone; Rhovane; Sopivan; Ximovan; Zimovane |
| PharmGKB Accession Id: | PA10236 |
Description
Zopiclone is a novel hypnotic agent used in the treatment of insomnia. Its mechanism of action is based on modulating benzodiazepine receptors. In addition to zopiclone's benzodiazepine pharmacological properties it also has some barbiturate like properties.
Indication
For the short-term treatment of insomnia.
ATC Therapeutic Category
- N05CF:Benzodiazepine related drugs
Pharmacology and Interactions
Mechanism Of Action
Zopiclone exerts its action by binding on the benzodiazepine receptor complex and modulation of the GABABZ receptor chloride channel macromolecular complex.
Pharmacology
Zopiclone is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class and is indicated for the short-term treatment of insomnia. While Zopiclone 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. Zopiclone binds selectively to the brain alpha subunit of the GABA A omega-1 receptor.
Absorption, Distribution, Metabolism, Elimination & Toxicity
Biotransformation
Extensively metabolized in the liver via decarboxylation (major pathway), demethylation, and side chain oxidation. Metabolites include an N-oxide derivative (weakly active; approximately 12% of a dose) and an N-desmethyl metabolite (inactive; approximately 16%). Approximately 50% of a dose is converted to other inactive metabolites via decarboxylation. Hepatic microsomal enzymes are apparently not involved in zopiclone clearance.
Protein Binding
Approximately 45%
Absorption
Rapidly absorbed following oral administration.
Half Life
Elimination half life is approximately 5 hours (range 3.8 to 6.5 hours) and is prolonged to 11.9 hours in patients with hepatic insufficiency.
Toxicity
Rare individual instances of fatal outcomes following overdose with racemic zopiclone have been reported in European postmarketing reports, most often associated with overdose with other CNS-depressant agent. Signs and symptoms of overdose effects of CNS depressants can be expected to present as exaggerations of the pharmacological effects noted in preclinical testing.
Chemical Properties
Chemical Formula:
C17H17ClN6O3
SMILES Code:
CN1CCN(CC1)C(=O)OC2c3c(nccn3)C(=O)N2c4ccc(cn4)Cl
(Format: OpenEye Isomeric)
Molecular Weight ( average / monoisotopic )
388.808 / 388.1051
Non-Curated Information
A list of non-curated publications that mention this drug along with other genes is available.
Metabolizing Enzymes
Drug Targets
Non-Curated Information
A list of non-curated publications that mention this drug along with other drugs is available.
Non-Curated Information
A list of non-curated publications that mention this drug along with other diseases is available.
Additional Datasets
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.