U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H17ClN6O3
Molecular Weight 388.808
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZOPICLONE, (R)-

SMILES

CN1CCN(CC1)C(=O)O[C@H]2N(C(=O)C3=C2N=CC=N3)C4=CC=C(Cl)C=N4

InChI

InChIKey=GBBSUAFBMRNDJC-MRXNPFEDSA-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-/m1/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
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1818054 | https://www.ncbi.nlm.nih.gov/pubmed/17870541 | https://www.ncbi.nlm.nih.gov/pubmed/11902799 | https://www.ncbi.nlm.nih.gov/pubmed/12404712 | http://www.who.int/medicines/areas/quality_safety/4.6ZopicloneCritReview.pdf

(R)-Zopiclone is the (R)-enantiomer of benzodiazepine modulator Zopiclone. (S)-Zopiclone binding at benzodiazepine recognition sites is about 50-fold higher than of the (R)-zopiclone, and the pharmacokinetics of the enantiomers varies between individuals differently. In rats, there is no stereo conversion from (S)- to (R)-Zopiclone, whereas (R)-Zopiclone converts to (S)-Zopiclone, which is preferentially distributed into the brain. (R)-Zopiclone is known to have sedative and anxiolytic effects and as well as effects towards locomotor activity reduction.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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
Determination of zopiclone enantiomers in plasma by liquid chromatography using a chiral cellulose carbamate column.
1991 Dec 6
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/7905394
RS-Zopiclone: 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
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:12:15 GMT 2023
Edited
by admin
on Sat Dec 16 11:12:15 GMT 2023
Record UNII
7A997Q53NR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZOPICLONE, (R)-
Common Name English
(-)-(5R)-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
ZOPICLONE R-ISOMER [USP IMPURITY]
Common Name English
1-PIPERAZINECARBOXYLIC ACID, 4-METHYL-, (5R)-6-(5-CHLORO-2-PYRIDINYL)-6,7-DIHYDRO-7-OXO-5H-PYRROLO(3,4-B)PYRAZIN-5-YL ESTER
Systematic Name English
(-)-ZOPICLONE
Common Name English
(R)-ZOPICLONE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID40160758
Created by admin on Sat Dec 16 11:12:15 GMT 2023 , Edited by admin on Sat Dec 16 11:12:15 GMT 2023
PRIMARY
PUBCHEM
941731
Created by admin on Sat Dec 16 11:12:15 GMT 2023 , Edited by admin on Sat Dec 16 11:12:15 GMT 2023
PRIMARY
FDA UNII
7A997Q53NR
Created by admin on Sat Dec 16 11:12:15 GMT 2023 , Edited by admin on Sat Dec 16 11:12:15 GMT 2023
PRIMARY
CAS
138680-08-7
Created by admin on Sat Dec 16 11:12:15 GMT 2023 , Edited by admin on Sat Dec 16 11:12:15 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP