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Details

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

SHOW SMILES / InChI
Structure of ZOPICLONE

SMILES

CN1CCN(CC1)C(=O)OC2N(C(=O)C3=C2N=CC=N3)C4=CC=C(Cl)C=N4

InChI

InChIKey=GBBSUAFBMRNDJC-UHFFFAOYSA-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

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8863805 | http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021476s030lbl.pdf | https://www.drugbank.ca/drugs/DB01198 | https://www.ncbi.nlm.nih.gov/pubmed/6086398 | https://www.ncbi.nlm.nih.gov/pubmed/16399882

Zopiclone (brand names Zimovane and Imovane) is a nonbenzodiazepine hypnotic agent used in the treatment of insomnia. The therapeutic pharmacological properties of zopiclone include hypnotic, anxiolytic, anticonvulsant, and myorelaxant properties. Zopiclone and benzodiazepines bind to different sites on GABAA-containing receptors, causing an enhancement of the actions of GABA to produce the therapeutic and adverse effects of zopiclone. The metabolite of zopiclone called desmethylzopiclone is also pharmacologically active, although it has predominately anxiolytic properties. One study found some slight selectivity for zopiclone on α1 and α5 subunits, although it is regarded as being unselective in its binding to α1, α2, α3, and α5 GABAA benzodiazepine receptor complexes. Desmethylzopiclone has been found to have partial agonist properties, unlike the parent drug zopiclone, which is a full agonist. The mechanism of action of zopiclone is similar to benzodiazepines, with similar effects on locomotor activity and on dopamine and serotonin turnover. A meta-analysis of randomised controlled clinical trials that compared benzodiazepines to zopiclone or other Z drugs such as zolpidem and zaleplon has found few clear and consistent differences between zopiclone and the benzodiazepines in sleep onset latency, total sleep duration, number of awakenings, quality of sleep, adverse events, tolerance, rebound insomnia, and daytime alertness. After oral administration, zopiclone is rapidly absorbed, with a bioavailability around 75–80%. Time to peak plasma concentration is 1–2 hours. High-fat meal preceding zopiclone administration does not change absorption (as measured by AUC), but reduces peak plasma levels and delays its occurrence, thus may delay the onset of therapeutic effects. The pharmacokinetics of zopiclone in humans are stereoselective. After oral administration of the racemic mixture, Cmax (time to maximum plasma concentration), area under the plasma time-concentration curve (AUC) and terminal elimination half-life values are higher for the dextrorotatory enantiomers, owing to the slower total clearance and smaller volume of distribution (corrected by the bioavailability), compared with the levorotatory enantiomer. In urine, the concentrations of the dextrorotatory enantiomers of the N-dimethyl and N-oxide metabolites are higher than those of the respective antipodes. Zopiclone is sometimes used as a method of suicide. It has a similar fatality index to that of benzodiazepine drugs, apart from temazepam, which is particularly toxic in overdose.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
29.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LUNESTA

Approved Use

Zopiclone is indicated for the short-term treatment of insomnia characterized by difficulty in falling asleep, frequent nocturnal awakenings, and/or early morning awakenings. Since sleep disturbances may be the presenting symptom of a physical and/or psychiatric disorder, the patient should be carefully evaluated before pharmacologic treatment is initiated. Insomnia that continues after 7 to 10 days of treatment may indicate the presence of a primary psychiatric and/or medical illness.

Launch Date

2004
PubMed

PubMed

TitleDatePubMed
Pharmacologic studies of central actions of zopiclone: influence on brain monoamines in rats under stressful condition.
1985 Apr
Pharmacologic studies of the central action of zopiclone: effects on locomotor activity and brain monoamines in rats.
1985 Mar
Subjective effects during administration and on discontinuation of zopiclone and temazepam in normal subjects.
1987 Mar
[First-degree heart block caused by voluntary zopiclone poisoning].
1990 Mar-Apr
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
Dasatinib-induced acute hepatitis.
2008 Aug
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Oral, 5 mg to 7.5 mg at bedtime.
Route of Administration: Oral
To study the effects of Zopiclone , GABA currents were repeatedly elicited by puffer application of 3 mkM GABA every 12 s, and test substances were applied by bath perfusion. A pressurized (10 p.s.i.) puffer pipette (~2 mkm tip diameter) was positioned near the recorded cell, and GABA (3 mkM) was applied by opening a computer-controlled solenoid valve (50–100 ms). This activated a peak inward current (200–2000 pA) that rapidly decayed. Because the small volume of GABA released from the puffer pipette was rapidly diluted in the external bath, the neurons were exposed to a maximum concentration of <3 mkM GABA. This is less than the EC50 of GABA for native and cloned GABAA receptors and provided a reliable starting point to measure potentiation of the current by positive allosteric modulators. Drugs were applied for 3 min (15 evoked GABA currents), which was sufficient for an equilibrium response to be established. Drugs were washed out for at least 3 min. If the GABA current recovered to predrug control amplitude, a higher concentration of drug was applied
Name Type Language
ZOPICLONE
EP   INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
6-(5-CHLOROPYRID-2-YL)-5-(4-METHYLPIPERAZIN-1-YL)CARBONYLOXY-7-OXO-6,7-DIHYDRO-5H-PYRROLO(3,4-B)PYRAZINE
Systematic Name English
ZOPICLONE [MART.]
Common Name English
IMOVANE
Common Name English
AMOBAN
Brand Name English
Zopiclone [WHO-DD]
Common Name English
ZOPICLONE [JAN]
Common Name English
NSC-758463
Code English
ZOPICLONE [MI]
Common Name English
ZIMOVANE
Brand Name English
4-METHYL-1-PIPERAZINECARBOXYLIC ACID ESTER WITH 6-(5-CHLORO-2-PYRIDYL)-6,7-DIHYDRO-7-HYDROXY-5H-PYRROLO(3,4-B)PYRAZIN-5-ONE
Common Name English
ZOPICLONE [EP MONOGRAPH]
Common Name English
RP-27267
Code English
ZOPICLONE [EP IMPURITY]
Common Name English
4-METHYL-1-PIPERAZINECARBOXYLIC ACID 6-(5-CHLORO-2-PYRIDINYL)-6,7-DIHYDRO-7-OXO-5H-PYRROLO(3,4-B)PYRAZIN-5-YL ESTER
Systematic Name English
zopiclone [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29756
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
DEA NO. 2784
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
WHO-VATC QN05CF01
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
WHO-ATC N05CF01
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
256-138-9
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
PRIMARY
DRUG BANK
DB01198
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
PRIMARY
CAS
43200-80-2
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
PRIMARY
DRUG CENTRAL
2873
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
PRIMARY
MERCK INDEX
m11663
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PRIMARY Merck Index
FDA UNII
03A5ORL08Q
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PRIMARY
PUBCHEM
5735
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EPA CompTox
DTXSID4041155
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MESH
C515050
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PRIMARY
CHEBI
32315
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PRIMARY
EVMPD
SUB00188MIG
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PRIMARY
IUPHAR
7430
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PRIMARY
INN
4462
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PRIMARY
NCI_THESAURUS
C80279
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PRIMARY
CHEBI
53762
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
PRIMARY
RXCUI
40001
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
PRIMARY RxNorm
NSC
758463
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
PRIMARY
WIKIPEDIA
ZOPICLONE
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL135400
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
PRIMARY
SMS_ID
100000092519
Created by admin on Sat Dec 16 17:14:23 GMT 2023 , Edited by admin on Sat Dec 16 17:14:23 GMT 2023
PRIMARY