CDEK
← All drugs Report issue

eszopiclone

Trade name: lunesta

Small moleculeapproved

Approved

Dec 15, 2004

Eszopiclone is a nonbenzodiazepine hypnotic, pyrrolopyrazine derivative of the cyclopyrrolone class and is indicated for the short-term treatment of insomnia. While Eszopiclone 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. Eszopiclone binds selectively to the brain alpha subunit of the GABA A omega-1 receptor. The mechanism of action of Eszopiclone is not completely understood. It is thought that Eszopiclone acts on the benzodiazepine receptors as an agonist and interacts with GABA-receptor complexes. Used for the treatment of insomnia. — NCATS

Clinical trial activity

68 trials · 42 clinical orgs · 23 marketing orgs

Phase 1
9
Phase 2
21
Phase 3
15
Phase 4
25

Earliest trial started Feb 1, 2001 (NCT01710631)

Timeline

2000s

  1. Jan 1, 2001

    Sunovion — Earliest Phase 3 Sponsor(trial)

  2. Jan 1, 2003

    Sunovion — Earliest Phase 2 Sponsor(trial)

  3. Jan 1, 2004

    Sunovion — Earliest Phase 1 Sponsor(trial)

  4. Dec 15, 2004

    Sunovion — Earliest FDA Approval

  5. Dec 15, 2004

    Waylis Therap — Marketing Organization

  6. Dec 15, 2004

    Sunovion — NDA Secondary Org

  7. Dec 15, 2004

    Sunovion — NDA Organization

  8. Dec 15, 2004

    Woodward — Marketing Organization

  9. Dec 15, 2004

    Woodward — NDA Secondary Org

2010s

  1. May 23, 2011

    Teva — Marketing Organization

  2. Jul 14, 2011

    Wockhardt — Marketing Organization

  3. Jul 14, 2011

    Chartwell Pharmaceuticals — Marketing Organization

  4. Sep 13, 2011

    Lupin — Marketing Organization

  5. Mar 26, 2013

    Mylan — Marketing Organization

  6. Apr 3, 2013

    Sun Pharmaceuticals — Marketing Organization

  7. Apr 15, 2014

    Dr. Reddy's Laboratories — Marketing Organization

  8. Apr 15, 2014

    Glenmark Pharmaceuticals — Marketing Organization

  9. Apr 15, 2014

    West-Ward Pharmaceutical — Marketing Organization

  10. Apr 15, 2014

    Hikma — Marketing Organization

  11. Jun 10, 2014

    Orbion Pharms — Marketing Organization

  12. Jun 10, 2014

    Orchid Pharma — Marketing Organization

  13. Jan 30, 2015

    Macleods Pharmaceuticals, Ltd — Marketing Organization

  14. Jan 30, 2015

    Neogen — Marketing Organization

  15. Sep 15, 2016

    Aurobindo Pharma — Marketing Organization

  16. May 8, 2019

    Nostrum Laboratories — Marketing Organization

  17. May 8, 2019

    Esteve Labs — Marketing Organization

  18. May 8, 2019

    PHARMOBEDIENT — Marketing Organization

2020s

  1. Dec 29, 2023

    IPCA Laboratories Ltd. — Marketing Organization

  2. Jan 4, 2024

    Hetero Labs Ltd — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedDec 15, 2004

Chemistry & pharmacology

Loading structure…

SMILES

CN1CCN(CC1)C(=O)O[C@@H]2N(C(=O)C3=C2N=CC=N3)C4=CC=C(Cl)C=N4
Mol. weight
388.808 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

No

Black box warning

Sources

Also known as

  • 1-piperazinecarobxylic acid,4-methyl-,(5s)-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5h-pyrrolo[3,4-b]pyrazin-5-yl ester
  • 1-piperazinecarobxylic acid,4-methyl-,(5s)-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5h-pyrrolo[3,4-b]pyrazin-5-yl ester
  • (+)-(5s)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5h-pyrrolo(3,4-b)pyrazin-5-yl 4-methylpiperazine-1-carboxylate
  • (+)-(5s)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5h-pyrrolo(3,4-b)pyrazin-5-yl 4-methylpiperazine-1-carboxylate
  • (+)-(5s)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazin-5-yl-4-methylpiperazine-1-carboxylate
  • (+)-(5s)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazin-5-yl-4-methylpiperazine-1-carboxylate
  • esopiclone
  • esopiclone
  • esopiclone
  • estorra
  • estorra
  • eszopiclone
  • eszopiclone
  • eszopiclone
  • eszopiclone
  • eszopiclone
  • eszopiclone
  • eszopiclone
  • eszopiclone
  • eszopiclone
  • eszopiclone
  • eszopiclone
  • lunesta
  • lunesta
  • lunesta
  • lunesta
  • (s)-6-(5-chloro-2-pyridinyl)- 7-oxo- 6,7-dihydro- 5h-pyrrolo[3,4-b]pyrazin-5-yl- 4-methyl- 1-piperazinecarboxylate
  • (s)-6-(5-chloro-2-pyridinyl)- 7-oxo- 6,7-dihydro- 5h-pyrrolo[3,4-b]pyrazin-5-yl- 4-methyl- 1-piperazinecarboxylate
  • (s)-zopiclone
  • (s)-zopiclone
  • (s)-zopiclone

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07018557Phase 4Jun 4, 2025Eurofarma Laboratorios S.A., University of Sao Paulo
NCT06928766Phase 2May 1, 2025Flinders University
NCT05953610Phase 2Dec 1, 2023National Heart, Lung, and Blood Institute (NHLBI), University of California, Los Angeles
NCT05951023Phase 2Aug 31, 2023American Academy of Sleep Medicine, University of California, San Diego
NCT06017921Phase 4Aug 24, 2023University of Sao Paulo
NCT05293600Phase 1/Phase 2 (Phase 2)Sep 1, 2022Harvard University
NCT05349396Phase 1Apr 11, 2022Grunenthal
NCT04875364Phase 2Jan 1, 2022University of California, San Diego
NCT04639193Phase 2Dec 1, 2020University of California, San Diego
NCT06452953N/ASep 10, 2020Central South University
NCT03937713Phase 4Oct 1, 2019Department of Veteran Affairs
NCT03668041Phase 3Aug 1, 2019Department of Veteran Affairs
NCT02456532Phase 4Jul 1, 2015Henry Ford Health System
NCT02087488N/AMar 1, 2014Chengdu University of Traditional Chinese Medicines
NCT01887691Phase 1Oct 1, 2012Harvard University
NCT01633827N/AAug 1, 2012Harvard University, National Heart, Lung, and Blood Institute (NHLBI)
NCT01641900N/AJul 1, 2012Harvard University, Mclean Hospital
NCT01605253Phase 4Mar 1, 2012National Institute of Mental Health (NIMH), Rush University
NCT01100164Phase 3Mar 1, 2011Eurofarma Laboratorios S.A.
NCT01055834Phase 1Jan 1, 2010Eisai
Showing 20 of 68 trials
Page 1 / 4

Organizations

Research & Development (42)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
SunovionFor profit341452001
Harvard UniversityAcademic/Hospital101042005
University of California, San DiegoAcademic/Hospital5522006
Department of Veteran AffairsGovernment4332007
EisaiFor profit3322008
National Heart, Lung, and Blood Institute (NHLBI)Government3032009
BA Research India LtdFor profit2012008
Dr. Reddy's LaboratoriesFor profit2212008
Eurofarma Laboratorios S.A.For profit2122011
Johns Hopkins UniversityAcademic/Hospital2222006
Mclean HospitalAcademic/Hospital2012006
National Institute of Mental Health (NIMH)Government2012005
Rutgers UniversityAcademic/Hospital2022006
United States ArmyGovernment2212007
University of California, Los AngelesAcademic/Hospital2222008
University of Medicine and Dentistry of New JerseyAcademic/Hospital2222006
University of Sao PauloAcademic/Hospital2212023
Yale UniversityAcademic/Hospital2222007
Abiant, Inc.For profit1012008
American Academy of Sleep MedicineAcademic/Hospital1012023
42 organizations
Page 1 / 3

Marketing (31)

OrganizationOrg typeRelationshipDate
Aurobindo PharmaFor profitMKTGSep 15, 2016
Aurobindo PharmaFor profitSYNSep 15, 2016
Chartwell PharmaceuticalsFor profitMKTGJul 14, 2011
Dr. Reddy's LaboratoriesFor profitMKTGApr 15, 2014
Dr. Reddy's LaboratoriesFor profitSYNApr 15, 2014
Esteve LabsFor profitSYNMay 8, 2019
Esteve LabsFor profitMKTGMay 8, 2019
Glenmark PharmaceuticalsFor profitSYNApr 15, 2014
Glenmark PharmaceuticalsFor profitMKTGApr 15, 2014
Hetero Labs LtdFor profitMKTGJan 4, 2024
HikmaFor profitMKTGApr 15, 2014
HikmaFor profitSYNApr 15, 2014
IPCA Laboratories Ltd.For profitMKTGDec 29, 2023
LupinFor profitMKTGSep 13, 2011
Macleods Pharmaceuticals, LtdFor profitMKTGJan 30, 2015
MylanFor profitMKTGMar 26, 2013
NeogenFor profitMKTGJan 30, 2015
Nostrum LaboratoriesFor profitMKTGMay 8, 2019
Orbion PharmsFor profitMKTGJun 10, 2014
Orchid PharmaFor profitMKTGJun 10, 2014
PHARMOBEDIENTFor profitMKTGMay 8, 2019
Sun PharmaceuticalsFor profitMKTGApr 3, 2013
Sun PharmaceuticalsFor profitSYNApr 3, 2013
SunovionFor profitNDA2Dec 15, 2004
SunovionFor profitNDADec 15, 2004
TevaFor profitMKTGMay 23, 2011
Waylis TherapFor profitMKTGDec 15, 2004
West-Ward PharmaceuticalFor profitMKTGApr 15, 2014
WockhardtFor profitMKTGJul 14, 2011
WoodwardFor profitMKTGDec 15, 2004
WoodwardFor profitNDA2Dec 15, 2004