Eszopiclone

Eszopiclone
Clinical data
Trade namesLunesta, Eszop, others
AHFS/Drugs.comMonograph
MedlinePlusa605009
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding52–59%
MetabolismLiver oxidation and demethylation (CYP3A4 and CYP2E1-mediated)
Elimination half-life6 hours
ExcretionKidney
Identifiers
  • (S)-(+)-6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl-4-methyl-1-piperazinecarboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.149.304 Edit this at Wikidata
Chemical and physical data
FormulaC17H17ClN6O3
Molar mass388.81 g·mol−1
3D model (JSmol)
  • O=C(O[C@H]3c1nccnc1C(=O)N3c2ncc(Cl)cc2)N4CCN(C)CC4
  • 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-/m0/s1 checkY
  • Key:GBBSUAFBMRNDJC-INIZCTEOSA-N checkY
  (verify)

Eszopiclone, sold under the brand name Lunesta among others, is a medication used in the treatment of insomnia.[3][4] Evidence supports slight to moderate benefit up to six months.[5][4][6] It is taken by mouth.[3][5]

Common side effects include headache, dry mouth, nausea, and dizziness.[5] Severe side effects may include suicidal thoughts, hallucinations, and angioedema.[5] Rapid decreasing of the dose may result in withdrawal.[5] Eszopiclone is classified as a nonbenzodiazepine or Z-drug and a sedative and hypnotic of the cyclopyrrolone group.[7] It is the S-stereoisomer of zopiclone.[5][8] It works by interacting with the GABA receptors.[7]

Approved for medical use in the United States in 2004,[3] eszopiclone is available as a generic medication.[5] In 2020, it was the 232nd most commonly prescribed medication in the United States, with more than 1 million prescriptions.[9][10] Eszopiclone is not sold in the European Union; as of 2009, the European Medicines Agency (EMA) ruled that it was too similar to zopiclone to be considered a new active substance.[11][12][13]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  3. ^ a b c d "Lunesta- eszopiclone tablet, coated". DailyMed. 24 May 2023. Retrieved 7 July 2023.
  4. ^ a b Cite error: The named reference TB2012 was invoked but never defined (see the help page).
  5. ^ a b c d e f g "Eszopiclone Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 6 April 2019.
  6. ^ Rösner S, Englbrecht C, Wehrle R, Hajak G, Soyka M (October 2018). "Eszopiclone for insomnia". The Cochrane Database of Systematic Reviews. 2018 (10): CD010703. doi:10.1002/14651858.CD010703.pub2. PMC 6492503. PMID 30303519.
  7. ^ a b Cite error: The named reference Davis2017 was invoked but never defined (see the help page).
  8. ^ Rösner S, Englbrecht C, Wehrle R, Hajak G, Soyka M (October 2018). "Eszopiclone for insomnia". The Cochrane Database of Systematic Reviews. 2018 (10): CD010703. doi:10.1002/14651858.CD010703.pub2. PMC 6492503. PMID 30303519.
  9. ^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  10. ^ "Eszopiclone - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  11. ^ "Lunivia: Withdrawn application". European Medicines Agency. 17 September 2018. Retrieved 19 February 2023.
  12. ^ Edwards J (13 June 2009). "End of Sepracor-GSK Deal Raises Question in Lunesta Patent Fight". www.cbsnews.com. Retrieved 7 April 2019.
  13. ^ "Sepracor Pharmaceuticals Ltd withdraws its marketing authorisation application for Lunivia (eszopiclone)". European Medicines Agency. 15 June 2009. Archived from the original on 3 August 2012. Retrieved 7 April 2019.