Eszopiclone

Summary

Eszopiclone (CHEMBL1522) is an approved small-molecule central nervous system depressant (ATC N05CF04); indicated across 4 conditions including insomnia and obstructive sleep apnea syndrome.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: N05CF04
• Indications: 4 conditions
• Clinical trials: 68
• Chemistry: 388.8 Da · C17H17ClN6O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1522
Name	Eszopiclone
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	969472
ChEBI	CHEBI:53760
ATC	N05CF04
Molecular formula	C17H17ClN6O3
Molecular weight	388.8
InChIKey	GBBSUAFBMRNDJC-INIZCTEOSA-N

SMILES: CN1CCN(CC1)C(=O)O[C@H]2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl

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

ChEBI definition: The (5S)- (active) enantiomer of zopiclone. Unlike almost all other hypnotic sedatives, which are approved only for the relief of short-term (6-8 weeks) insomnia, eszopiclone is approved by the U.S. Food and Drug Administration for long-term use.

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

Also known as: (S)-ZOPICLONE, Estorra, Eszopiclon, Eszopiclona, Eszopiclone, Eszopiclone civ, GSK-1755165, Lunesta, Zopiclone s-form, eszopiclone, ESZOPICLONE, SID49666409

Patent coverage: 1,798 distinct patent families (6,548 SureChEMBL compound mentions), from 1 matched compound structure(s). 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: 4 (assay-derived). Sample: Gamma-aminobutyric acid receptor subunit alpha-1, GABA A receptor alpha-3/beta-2/gamma-2, GABA A receptor alpha-2/beta-2/gamma-2, Gamma-aminobutyric acid receptor subunit alpha-4.

Bioactivity

ChEMBL activities: 4 potent at pChembl ≥ 5 of 4 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
GABRA1	7.3	Ki	50.1	nM	CHEMBL_ACT_2401373
GABRA4	6.99	Ki	102	nM	CHEMBL_ACT_2401374
GABRG2	6.94	Ki	114	nM	CHEMBL_ACT_2401375
GABRG2	6.79	Ki	162	nM	CHEMBL_ACT_2401376

Target pathways

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

Indications & clinical

Indications

1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
insomnia	4	MONDO:0013600	EFO:0004698

3 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
obstructive sleep apnea syndrome	2	MONDO:0007147	EFO:0003918
generalized anxiety disorder	2	MONDO:0001942	EFO:1001892
cannabis dependence	1	MONDO:0005689	EFO:0007191

Clinical trials

Total trials: 68.

Phase distribution

Phase	Trials
PHASE4	25
PHASE3	14
Not specified	13
PHASE2	6
PHASE1	6
PHASE2/PHASE3	2
PHASE1/PHASE2	1
EARLY_PHASE1	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
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?
NCT00460993	PHASE4	COMPLETED	Efficacy & Safety of Eszopiclone (Lunesta) in Nursing Home Patients
NCT00507117	PHASE4	COMPLETED	Ezopiclone Improves the Quality of Overnight Polysomnography
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
NCT01605253	PHASE4	COMPLETED	Eszopiclone for the Treatment of Posttraumatic Stress Disorder
NCT02456532	PHASE4	COMPLETED	Safety and Efficacy of Chronic Hypnotic Use 2
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
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
NCT00857220	PHASE3	COMPLETED	Long Term Safety Study of Study Drug (Eszopiclone) in Children and Adolescents With ADHD -Associated Insomnia
NCT01100164	PHASE3	COMPLETED	A Non-inferiority Study With Two Treatment Arms Eszopiclone 3 mg Versus Zopiclone 7.5 mg - for the Treatment of Insomnia
NCT01710631	PHASE3	COMPLETED	Twelve Month Study of the Safety of Eszopiclone in Adult Subjects With Insomnia
NCT03668041	PHASE3	COMPLETED	National Adaptive Trial for PTSD Related Insomnia
NCT04875364	PHASE2	RECRUITING	Do Endotypes Predict Response and Sequelae in OSA Patients
NCT05293600	PHASE1/PHASE2	RECRUITING	Rescue Pharmacotherapy for OSA
NCT06928766	PHASE2	NOT_YET_RECRUITING	Effects of Eszopiclone and Lemborexant in People With OSA With a Low Arousal Threshold Who Have Difficulty Sleeping
NCT00616655	PHASE2	COMPLETED	Generalized Anxiety Disorder Proof of Concept Efficacy and Safety Study of SEP-225441 (Eszopiclone) In GAD Subjects
NCT00685269	PHASE2	COMPLETED	Safety and Efficacy of Eszopiclone With Mild to Moderate Obstructive Sleep Apnea Syndrome (OSAS)
NCT04639193	PHASE2	COMPLETED	Combination Drug-Therapy for Patients With Untreated Obstructive Sleep Apnea
NCT05951023	PHASE2	COMPLETED	Endotype-Targeted Therapy to Rescue OSA Patients Struggling With CPAP Adherence (TOP-CPAP)
NCT00368160	PHASE1	COMPLETED	Study of an Evening Dose of Eszopiclone on Next Day Driving Ability & Psychomotor/Memory Function in Healthy Volunteers
NCT00893269	PHASE1	COMPLETED	The Effect of Marijuana and Prescription Medications in Mood, Performance and Sleep
NCT01055834	PHASE1	COMPLETED	A Bioequivalence and Food Effect Study of SEP-190 in Japanese Healthy Subjects (Study SEP 190-102)
NCT01887691	PHASE1	TERMINATED	Sleep Effectiveness and Insulin and Glucose Homeostasis
NCT02322645	PHASE1	COMPLETED	Bioequivalence Study of Eszopiclone Tablets, 3 mg Under Fasting Conditions
NCT02322658	PHASE1	COMPLETED	Bioequivalence Study of Eszopiclone Tablets, 3 mg Under Fed Conditions
NCT01102270	EARLY_PHASE1	COMPLETED	The Effect of Eszopiclone on the Arousal Threshold in Sleep Apnea Syndrome
NCT00374192	Not specified	COMPLETED	The Treatment of Insomnia in Symptomatic Peri- and Postmenopausal Women
NCT00374556	Not specified	COMPLETED	Insomnia and Osteoarthritis Study
NCT00555750	Not specified	COMPLETED	Sleep Loss and Mechanisms of Impaired Glucose Metabolism
NCT00594087	Not specified	COMPLETED	Eszopiclone for Improving Sleep in Multiple Sclerosis (MS)
NCT00645944	Not specified	COMPLETED	Randomized, Controlled, Double Blind Trial of Eszopiclone for Insomnia Associated With Schizophrenia
NCT00811746	Not specified	COMPLETED	Hypnotics to Improve Polysomnography Yield: Eszopiclone vs Ramelteon?
NCT00833547	Not specified	COMPLETED	Effects of Eszopiclone on Sleep-dependent Learning in Schizophrenia
NCT00900159	Not specified	COMPLETED	Effects of Daytime Eszopiclone Administration in Shift Workers
NCT01641900	Not specified	COMPLETED	Effects of Eszopiclone on Sleep and Memory in Schizophrenia
NCT02087488	Not specified	COMPLETED	Auricular Acupuncture for Primary Insomnia
NCT02452684	Not specified	COMPLETED	Investigation of the Safety and Efficacy of Eszopiclone in Insomnia Patients
NCT02455271	Not specified	COMPLETED	Investigation of the Safety and Efficacy of Long Term Administration of Eszopiclone in Insomnia Patients
NCT06452953	Not specified	COMPLETED	Modified Suanzaoren Decoction Versus Eszopiclone for the Treatment of Chronic Insomnia Disorder

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).