Zopiclone

Summary

Zopiclone (CHEMBL135400) is an approved small-molecule central nervous system depressant (ATC N05CF01); indicated across 9 conditions including insomnia and anxiety.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: N05CF01
• Indications: 9 conditions
• Clinical trials: 90
• Chemistry: 388.8 Da · C17H17ClN6O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL135400
Name	Zopiclone
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	5735
ChEBI	CHEBI:32315
ATC	N05CF01
Molecular formula	C17H17ClN6O3
Molecular weight	388.8
InChIKey	GBBSUAFBMRNDJC-UHFFFAOYSA-N

SMILES: CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl

IUPAC name: [6-(5-chloro-2-pyridinyl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate

ChEBI definition: A pyrrolo[3,4-b]pyrazine compound having a 4-methylpiperazine-1-carboxyl group at the 5-position, a 5-chloropyridin-2-yl group at the 6-position and an oxo-substituent at the 7-position.

Pharmacological roles (ChEBI): central nervous system depressant, sedative.

Also known as: Amoban, Imovane, NSC-758463, RP-27267, Zileze 3.75, Zileze 7.5, Zimovane, Zimovane ls, Zopiclona, Zopiclone, SID26747152, SID866104

Patent coverage: 2,720 distinct patent families (9,760 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 9,569 (98%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 5 (assay-derived). Sample: Microtubule-associated protein tau, ATP-dependent DNA helicase Q1, GABA-A receptor; anion channel, Adenosine receptor A3, Gamma-aminobutyric acid receptor subunit alpha-1.

Bioactivity

ChEMBL activities: 5 potent at pChembl ≥ 5 of 6 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
O09028	7.54	IC50	29	nM	CHEMBL_ACT_994803
P62813	7.03	AC50	93	nM	CHEMBL_ACT_25130641
MAPT	6.05	Potency	891.3	nM	CHEMBL_ACT_4041715
MAPT	6	Potency	1000	nM	CHEMBL_ACT_3968982
RECQL	5.85	Potency	1412	nM	CHEMBL_ACT_3673523

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

9 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
insomnia	3	MONDO:0013600	EFO:0004698
anxiety	3	MONDO:0011918	EFO:0005230
obstructive sleep apnea syndrome	3	MONDO:0007147	EFO:0003918
dementia	3	MONDO:0001627	HP:0000726
depressive disorder	3	MONDO:0002050	MONDO:0002050
sleep disorder	3	MONDO:0100081	EFO:0008568
major depressive disorder	1	MONDO:0002009	MONDO:0002009

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 90.

Phase distribution

Phase	Trials
PHASE4	27
PHASE3	18
PHASE1	18
Not specified	15
PHASE2	7
PHASE2/PHASE3	2
EARLY_PHASE1	2
PHASE1/PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT07018557	PHASE4	RECRUITING	Impact of Eszopiclone on Blood Pressure in Patients With Insomnia and Hypertension (PRYSMA-HTN)
NCT00120250	PHASE4	COMPLETED	Eszopiclone for Sleep Disturbance and Nightmares in Post-Traumatic Stress Disorder
NCT00235508	PHASE4	COMPLETED	Safety and Efficacy of Eszopiclone in Patients With Generalized Anxiety Disorder
NCT00247624	PHASE4	COMPLETED	Improving Sleep and Psychological Functioning in People With Depression and Insomnia
NCT00295386	PHASE4	COMPLETED	Cognitive-Behavioural and Hypnotic Treatment of Chronic Primary Insomnia Among the Elderly
NCT00365261	PHASE4	COMPLETED	Effect of Eszopiclone on Sleep Disturbance and Pain in Cancer
NCT00365976	PHASE4	COMPLETED	Study of the Insomnia in Patients With Low Back Pain
NCT00386334	PHASE4	COMPLETED	A Long-Term Safety and Efficacy Study of Eszopiclone in Elderly With Primary Chronic Insomnia
NCT00392041	PHASE4	COMPLETED	Eszopiclone in the Treatment of Insomnia and Fibromyalgia
NCT00414037	PHASE4	TERMINATED	How do Sleeping Pills Affect Pain in the Brain?
NCT00511134	PHASE4	TERMINATED	Study of Lunesta Versus Placebo for Sleep Problems Related to Smoking Cessation and Zyban
NCT00612157	PHASE4	COMPLETED	Continuous Positive Airway Pressure (CPAP) Promotion And Prognosis - the Army Sleep Apnea Program (ASAP)
NCT00628914	PHASE4	UNKNOWN	Brain Mechanisms and Targeting Insomnia in Major Depression
NCT00724282	PHASE4	COMPLETED	Treatment of Insomnia and Glucose Metabolism
NCT00781482	PHASE4	WITHDRAWN	Positron Emission Tomography Assessment of the Central Nervous System Effects of Eszopiclone and Zolpidem
NCT00812214	PHASE4	COMPLETED	Treatment of Insomnia in Migraineurs
NCT00813735	PHASE4	COMPLETED	Eszopiclone Co-Administered With Escitalopram for Insomnia in Elderly Adults With Major Depressive Disorder
NCT00822679	PHASE4	COMPLETED	Eszopiclone and Inflammatory Mediators in Patients With Acute Coronary Syndrome
NCT00826111	PHASE4	COMPLETED	The Effects of Eszopiclone and Lexapro on Prefrontal Glutamate and GABA in Depression With Anxiety and Insomnia
NCT00889200	PHASE4	COMPLETED	Eszopiclone Treatment & Cortisol Responsivity
NCT01549691	PHASE4	COMPLETED	Reassessment of Premedication in Surgery
NCT01605253	PHASE4	COMPLETED	Eszopiclone for the Treatment of Posttraumatic Stress Disorder
NCT02456532	PHASE4	COMPLETED	Safety and Efficacy of Chronic Hypnotic Use 2
NCT02807922	PHASE4	COMPLETED	Pharmacological Treatment of Insomnia in Palliative Care
NCT02820441	PHASE4	TERMINATED	Benefit of One Month Zopiclone Intake on Adaptative Servoventilation Compliance
NCT03937713	PHASE4	COMPLETED	Effectiveness of Combining Behavioral and Pharmacologic Therapy for Complex Insomnia in Veterans With PTSD
NCT06017921	PHASE4	COMPLETED	Effect of Eszopiclone on Adherence to CPAP and Severity of Insomnia in Patients With COMISA
NCT07332442	PHASE3	RECRUITING	Continuous Positive Airway Pressure, Arousability and Links to Mechanisms in Obstructive Sleep Apnea
NCT00237497	PHASE3	COMPLETED	Safety and Efficacy of Ramelteon in Adults With Chronic Insomnia
NCT00324896	PHASE3	COMPLETED	Treatment of Insomnia in Patients With Parkinson’s Disease: A Multi-site, Placebo-controlled Study of Eszopiclone
NCT00352144	PHASE3	COMPLETED	6-Month Chronic Efficacy & Safety Study of Eszopiclone in Adult Subjects With Primary Insomnia
NCT00366093	PHASE3	COMPLETED	Study of Eszopiclone Compared to Placebo in the Treatment of Insomnia Secondary to Perimenopause/Menopause
NCT00367965	PHASE3	COMPLETED	Study of Eszopiclone Compared to Placebo on Daytime Function in Subjects With Insomnia Related to Rheumatoid Arthritis
NCT00368030	PHASE3	COMPLETED	A Study of Eszopiclone in Subjects With Insomnia Related to Major Depressive Disorder
NCT00368056	PHASE3	COMPLETED	Effects of One Evening Dose of 3 mg Eszopiclone on Next Day Driving Ability
NCT00435279	PHASE3	COMPLETED	A Study of Eszopiclone Co-administered With Venlafaxine in Subjects With Major Depressive Disorder and Insomnia
NCT00515177	PHASE2/PHASE3	COMPLETED	Mindfulness Versus Pharmacotherapy for Chronic Insomnia: A Pilot Study
NCT00770510	PHASE2/PHASE3	COMPLETED	A Phase II/III Study of SEP-190 (Eszopiclone) in Patients With Primary Insomnia (Study 190-126)
NCT00770692	PHASE3	COMPLETED	A Phase III Study of Eszopiclone in Patients With Insomnia (Study SEP 190-150)
NCT00856973	PHASE3	COMPLETED	Safety & Efficacy Study of Study Drug (Eszopiclone) in Children and Adolescents With Attention-deficit/Hyperactivity Disorder - Associated Insomnia

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).