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Revision as of 11:30, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{drugbox}} taken from revid 453722491 of page Eszopiclone for the Chem/Drugbox validation project (updated: 'DrugBank').		Latest revision as of 21:24, 11 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix
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			{{short description|Hypnotic medication}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
			{{cs1 config|name-list-style=vanc}}
	{{Drugbox		{{Drugbox
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 443737056		| verifiedrevid = 461095850
	| IUPAC_name = (''S'')-6-(5-Chloro-2-pyridinyl)- 7-oxo- 6,7-dihydro- 5''H''-pyrrolopyrazin-5-yl- 4-methyl- 1-piperazinecarboxylate
	| image = Eszopiclone.svg		| image = Eszopiclone.svg
			| image_class = skin-invert-image
			| alt =
	| image2 = Eszopiclone-3D-balls.png		| image2 = Eszopiclone-3D-balls.png
	| width2 = 180		| alt2 =
	<!--Clinical data-->		<!--Clinical data-->
	| tradename = Lunesta		| tradename = Lunesta, Eszop, others
	| Drugs.com = {{drugs.com|monograph|eszopiclone}}		| Drugs.com = {{drugs.com|monograph|eszopiclone}}
	| MedlinePlus = a605009		| MedlinePlus = a605009
			| DailyMedID = Eszopiclone
	| licence_US = Eszopiclone		| licence_US = Eszopiclone
			| routes_of_administration = ]
	| pregnancy_US = C
			| ATC_prefix = N05
			| ATC_suffix = CF04
			| ATC_supplemental =
			| legal_BR = B1
			| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
	| legal_US = Schedule IV		| legal_US = Schedule IV
			| legal_US_comment = <ref name="Lunesta FDA label">{{cite web | title=Lunesta- eszopiclone tablet, coated | website=DailyMed | date=24 May 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fd047b2b-05a6-4d99-95cb-955f14bf329f | access-date=7 July 2023}}</ref>
	| routes_of_administration = Oral
	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	| protein_bound = 52-59%		| protein_bound = 52–59%
	| metabolism = ] ] and demethylation (] and ]-mediated)		| metabolism = ] ] and demethylation (] and ]-mediated)
	| elimination_half-life = 6 hours		| elimination_half-life = 6 hours
	| excretion = ]		| excretion = ]
	<!--Identifiers-->		<!--Identifiers-->
			| IUPHAR_ligand = 7429
	| CASNo_Ref = {{cascite|correct|CAS}}
			| CAS_number_Ref = {{cascite|correct|??}}
	| CAS_number = 138729-47-2		| CAS_number = 138729-47-2
	| ATC_prefix = N05
	| ATC_suffix = CF04
	| ATC_supplemental = <ref>{{cite web | url = http://www.whocc.no/atcddd/new_atc_ddd.html#ATCDDD_FINAL | title = ATC/DDD Classification (FINAL): New ATC 5th level codes | date = August 27, 2008 | author = WHO International Working Group for Drug Statistics Methodology | publisher = WHO Collaborating Centre for Drug Statistics Methodology | accessdate = 2008-09-05 | archiveurl = http://web.archive.org/web/20080506023243/http://www.whocc.no/atcddd/new_atc_ddd.html#ATCDDD_FINAL <!-- Bot retrieved archive --> | archivedate = 2008-05-06}}</ref>
	| PubChem = 969472		| PubChem = 969472
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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	<!--Chemical data-->		<!--Chemical data-->
			| IUPAC_name = (''S'')-(+)-6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5''H''-pyrrolopyrazin-5-yl-4-methyl-1-piperazinecarboxylate
	| C=17 | H=17 | Cl=1 | N=6 | O=3
			| C=17 | H=17 | Cl=1 | N=6 | O=3
	| molecular_weight = 388.808 ]/]
	| smiles = O=C(O3c1nccnc1C(=O)N3c2ncc(Cl)cc2)N4CCN(C)CC4		| SMILES = O=C(O3c1nccnc1C(=O)N3c2ncc(Cl)cc2)N4CCN(C)CC4
	| InChI = 1/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
	| InChIKey = GBBSUAFBMRNDJC-INIZCTEOBX
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 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		| StdInChI = 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
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	| StdInChIKey = GBBSUAFBMRNDJC-INIZCTEOSA-N		| StdInChIKey = GBBSUAFBMRNDJC-INIZCTEOSA-N
	}}		}}
			<!-- Definition and medical uses -->
			'''Eszopiclone''', sold under the brand name '''Lunesta''' among others, is a ] used in the treatment of ].<ref name="Lunesta FDA label" /><ref name=TB2012/> Evidence supports slight to moderate benefit up to six months.<ref name=AHFS2019/><ref name=TB2012/><ref>{{cite journal | vauthors = Rösner S, Englbrecht C, Wehrle R, Hajak G, Soyka M | title = Eszopiclone for insomnia | journal = The Cochrane Database of Systematic Reviews | volume = 2018 | issue = 10 | pages = CD010703 | date = October 2018 | pmid = 30303519 | pmc = 6492503 | doi = 10.1002/14651858.CD010703.pub2 }}</ref> It is taken ].<ref name="Lunesta FDA label" /><ref name=AHFS2019>{{cite web |title=Eszopiclone Monograph for Professionals |url=https://www.drugs.com/monograph/eszopiclone.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=6 April 2019 }}</ref>
			<!-- Side effects and mechanism -->
			Common side effects include headache, ], nausea, and dizziness.<ref name=AHFS2019/> Severe side effects may include ], ]s, and ].<ref name=AHFS2019/> Rapid decreasing of the dose may result in withdrawal.<ref name=AHFS2019/> Eszopiclone is classified as a ] or ] and a ] and ] of the ] group.<ref name = Davis2017/> It is the S-] of ].<ref name=AHFS2019/><ref>{{cite journal | vauthors = Rösner S, Englbrecht C, Wehrle R, Hajak G, Soyka M | title = Eszopiclone for insomnia | journal = The Cochrane Database of Systematic Reviews | volume = 2018 | issue = 10 | pages = CD010703 | date = October 2018 | pmid = 30303519 | pmc = 6492503 | doi = 10.1002/14651858.CD010703.pub2 }}</ref> It works by interacting with the ]s.<ref name = Davis2017/>
			<!-- History and culture -->
			Approved for medical use in the United States in 2004,<ref name="Lunesta FDA label" /> eszopiclone is available as a ].<ref name=AHFS2019/> In 2020, it was the 232nd most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title = The Top 300 of 2020 | url = https://clincalc.com/DrugStats/Top300Drugs.aspx | website = ClinCalc | access-date = 7 October 2022}}</ref><ref>{{cite web | title = Eszopiclone - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Eszopiclone | access-date = 7 October 2022}}</ref> Eszopiclone is not sold in the European Union; as of 2009, the ] (EMA) ruled that it was too similar to ] to be considered a new active substance.<ref>{{cite web | title=Lunivia: Withdrawn application | website=European Medicines Agency | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/withdrawn-applications/lunivia | access-date=19 February 2023}}</ref><ref name=CBS2009>{{cite news | vauthors = Edwards J |title=End of Sepracor-GSK Deal Raises Question in Lunesta Patent Fight |url=https://www.cbsnews.com/news/end-of-sepracor-gsk-deal-raises-question-in-lunesta-patent-fight/ |access-date=7 April 2019 |work=www.cbsnews.com |date=13 June 2009}}</ref><ref>{{cite web |title=Sepracor Pharmaceuticals Ltd withdraws its marketing authorisation application for Lunivia (eszopiclone) |url=http://www.ema.europa.eu/ema/index.jsp?curl=pages/news_and_events/news/2009/11/news_detail_000083.jsp&jsenabled=true |website=European Medicines Agency |access-date=7 April 2019 |date=15 June 2009 |archive-date=3 August 2012 |archive-url=https://archive.today/20120803035436/http://www.ema.europa.eu/ema/index.jsp?curl=pages/news_and_events/news/2009/11/news_detail_000083.jsp&jsenabled=true |url-status=dead }}</ref>
			==Medical uses==
			A 2018 Cochrane review found that it produced moderate improvement in sleep onset and maintenance. The authors suggest that where preferred non-pharmacological treatment strategies have been exhausted, eszopiclone provides an efficient treatment for insomnia.<ref>{{cite journal | vauthors = Rösner S, Englbrecht C, Wehrle R, Hajak G, Soyka M | title = Eszopiclone for insomnia | journal = The Cochrane Database of Systematic Reviews | volume = 2018 | issue = 10 | pages = CD010703 | date = October 2018 | pmid = 30303519 | pmc = 6492503 | doi = 10.1002/14651858.CD010703.pub2 }}</ref> In 2014, the US ] asked that the starting dose be lowered from 2 ]s to 1 milligram after it was observed in a study that even eight hours after taking the drug at night, some people were not able to cope with their next-day activities like driving and other activities that require full alertness.<ref>{{cite web | title=FDA warns of next-day impairment with sleep aid Lunesta | website=U.S. ] (FDA) | date=15 January 2016 | url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-fda-warns-next-day-impairment-sleep-aid-lunesta-eszopiclone-and-lowers | access-date=7 July 2023}}</ref>
			Eszopiclone is slightly effective in the treatment of insomnia where difficulty in falling asleep is the primary complaint.<ref name="TB2012">{{cite journal | vauthors = Huedo-Medina TB, Kirsch I, Middlemass J, Klonizakis M, Siriwardena AN | title = Effectiveness of non-benzodiazepine hypnotics in treatment of adult insomnia: meta-analysis of data submitted to the Food and Drug Administration | journal = BMJ | volume = 345 | pages = e8343 | date = December 2012 | pmid = 23248080 | pmc = 3544552 | doi = 10.1136/bmj.e8343 }}</ref> The benefit over placebo was found to be of questionable clinical significance.<ref name=TB2012/> Although the drug effect and the placebo response were rather small and of questionable clinical importance, the two together produce a reasonably large clinical response.<ref name=TB2012/>
			===Elderly===
			Sedative hypnotic drugs including eszopiclone are more commonly prescribed to the elderly than to younger patients despite benefits of medication being generally unimpressive.<ref>{{cite journal | vauthors = Tariq SH, Pulisetty S | title = Pharmacotherapy for insomnia | journal = Clinics in Geriatric Medicine | volume = 24 | issue = 1 | pages = 93–105, vii | date = February 2008 | pmid = 18035234 | doi = 10.1016/j.cger.2007.08.009 }}</ref>
			In 2015, the ] reviewed the safety information about eszopiclone and similar drugs and concluded that the "nonbenzodiazepine, benzodiazepine receptor agonist hypnotics (eszopiclone, ], ]) are to be avoided without consideration of duration of use because of their association with harms balanced with their minimal efficacy in treating insomnia."
			The review made this determination both because of the relatively large dangers to elderly individuals from zolpidem and other "z-drugs" together with the fact the drugs have "minimal efficacy in treating insomnia." This was a change from the 2012 AGS recommendation, which suggested limiting use to 90 days or less. The review stated: "the 90‐day‐use caveat removed from nonbenzodiazepine, benzodiazepine receptor agonist hypnotics, resulting in an unambiguous 'avoid' statement (without caveats) because of the increase in the evidence of harm in this area since the 2012 update."<ref>{{cite journal | author = American Geriatrics Society 2015 Beers Criteria Update Expert Panel | title = American Geriatrics Society 2015 Updated Beers Criteria for Potentially Inappropriate Medication Use in Older Adults | journal = Journal of the American Geriatrics Society | volume = 63 | issue = 11 | pages = 2227–2246 | date = November 2015 | pmid = 26446832 | doi = 10.1111/jgs.13702 | s2cid = 38797655 <!-- | author-link1 = Donna M. Fick --> | doi-access = }}</ref>
			An extensive review of the medical literature regarding the management of insomnia and the elderly found that there is considerable evidence of the effectiveness and durability of non-drug treatments for insomnia in adults of all ages and that these interventions are underutilized. Compared with the benzodiazepines, the ] sedative-hypnotics, including eszopiclone appeared to offer few, if any, significant clinical advantages in efficacy or tolerability in elderly persons. It was found that newer agents with novel mechanisms of action and improved safety profiles, such as the ], hold promise for the management of chronic insomnia in elderly people. Long-term use of sedative-hypnotics for insomnia lacks an evidence base and has traditionally been discouraged for reasons that include concerns about such potential adverse drug effects as cognitive impairment (]), daytime sedation, motor incoordination, and increased risk of ]s and falls. In addition, the effectiveness and safety of long-term use of these agents remain to be determined. It was concluded that more research is needed to evaluate the long-term effects of treatment and the most appropriate management strategy for elderly persons with chronic insomnia.<ref>{{cite journal | vauthors = Bain KT | title = Management of chronic insomnia in elderly persons | journal = The American Journal of Geriatric Pharmacotherapy | volume = 4 | issue = 2 | pages = 168–192 | date = June 2006 | pmid = 16860264 | doi = 10.1016/j.amjopharm.2006.06.006 }}</ref>
			A 2009 meta-analysis found a higher rate of ]s.<ref>{{cite journal | vauthors = Joya FL, Kripke DF, Loving RT, Dawson A, Kline LE | title = Meta-analyses of hypnotics and infections: eszopiclone, ramelteon, zaleplon, and zolpidem | journal = Journal of Clinical Sleep Medicine | volume = 5 | issue = 4 | pages = 377–383 | date = August 2009 | pmid = 19968019 | pmc = 2725260 | doi = 10.5664/jcsm.27552 }}</ref>
			==Adverse effects==
			Sleeping pills, including eszopiclone, have been associated with an increased risk of death.<ref>{{cite journal | vauthors = Kripke DF | title = Mortality Risk of Hypnotics: Strengths and Limits of Evidence | journal = Drug Safety | volume = 39 | issue = 2 | pages = 93–107 | date = February 2016 | pmid = 26563222 | doi = 10.1007/s40264-015-0362-0 | s2cid = 7946506 | doi-access = free | title-link = doi | url = https://escholarship.org/content/qt08d9f3d5/qt08d9f3d5.pdf?t=nz1gjv }}</ref>
			] to eszopiclone is a contraindication to its use. The presence of liver impairment, lactation and activities requiring mental alertness (e.g., driving) may be considered when determining frequency and dosage.<ref name = Davis2017/>
			{{div col|colwidth=20em}}
			* ]<ref name = Davis2017/>
			* ]<ref name = Davis2017/>
			* ]<ref name = Davis2017/><ref name="lunestasefxab"/>
			* ]<ref name = Davis2017/>
			* ]<ref name = Davis2017/>
			* ]<ref name = Davis2017/>
			* ]<ref name = Davis2017/><ref name="lunestasefxab"/>
			* ]<ref name = Davis2017/><ref name="lunestasefxab"/>
			* ]<ref name = Davis2017/> and ]
			* ]<ref name = Davis2017/>
			* ]<ref name = Davis2017/><ref name="lunestasefxab"/>
			* altered ]<ref name = Davis2017/>
			* impaired ]<ref name = Davis2017/>
			* ]<ref name = Davis2017/>
			* daytime drowsiness<ref name = Davis2017/>
			<!--* ]-like ]s
			* pain
			* dry mouth
			* daytime ]
			* ]
			* ]
			* ]
			* decreased ]
			* painful ] (periods)
			* ]
			* Sedation, drowsiness, and sleepiness, these side effects aren't referenced at this time-->
			* ]ing<ref name="lunestasefxab"/>
			* ] or ]<ref name="lunestasefxab"/>
			* ]<ref name="lunestasefxab"/>
			* ] behavior<ref name="lunestasefxab"/>
			* ]<ref name="lunestasefxab"/>
			* ]<ref name="lunestasefxab"/>
			* ]<ref name="lunestasefxab"/>
			* ]<ref name="lunestasefxab"/>
			* ]<ref name="lunestasefxab">{{cite web |url= http://www.rxlist.com/cgi/generic/lunesta_ad.htm |title= Lunesta |access-date= 15 April 2017 |date= 26 October 2016 |author= Rxlist |archive-url= https://web.archive.org/web/20081205095238/http://www.rxlist.com/cgi/generic/lunesta_ad.htm |archive-date= 5 December 2008 |url-status= dead }}</ref>
			{{div col end}}
			A 2009 meta-analysis found a 44% higher rate of mild ]s, such as ] or ], in people taking eszopiclone or other hypnotic drugs compared to those taking a placebo.<ref>{{cite journal | vauthors = Joya FL, Kripke DF, Loving RT, Dawson A, Kline LE | title = Meta-analyses of hypnotics and infections: eszopiclone, ramelteon, zaleplon, and zolpidem | journal = Journal of Clinical Sleep Medicine | volume = 5 | issue = 4 | pages = 377–383 | date = August 2009 | pmid = 19968019 | pmc = 2725260 | doi = 10.5664/jcsm.27552 }}</ref>
			===Dependence===
			In the United States, eszopiclone is a schedule IV controlled substance under the ]. Use of eszopiclone may lead to physical and psychological dependence.<ref name = Davis2017/><ref name = Brie2006/> The risk of non-medical use and dependence increases with the dose and duration of usage and concomitant use of other psychoactive substances. The risk is also greater in patients with a history of ] or other ] or history of psychiatric disorders. Tolerance may develop after repeated use of benzodiazepines and benzodiazepine-like drugs for a few weeks.
			A study funded and carried out by ], the manufacturer of eszopiclone, found no signs of tolerance or dependence in a group of patients followed for up to six months.<ref name="Brie2006">{{cite journal | vauthors = Brielmaier BD | title = Eszopiclone (Lunesta): a new nonbenzodiazepine hypnotic agent | journal = Proceedings | volume = 19 | issue = 1 | pages = 54–59 | date = January 2006 | pmid = 16424933 | pmc = 1325284 | doi = 10.1080/08998280.2006.11928127 }}</ref>
			===Non-medical use===
			A study of non-medical use potential of eszopiclone found that in persons with a known history of non-medical ] use, eszopiclone at doses of 6 and 12&nbsp;mg produced effects similar to those of ] 20&nbsp;mg. The study found that at these doses which are two or more times greater than the maximum recommended doses, a dose-related increase in reports of amnesia, sedation, sleepiness, and hallucinations was observed for both eszopiclone (Lunesta) as well as for diazepam (]).<ref name="lunestasefxab"/>
			===Overdose===
			Overdoses of eszopiclone up to 90 times the recommended dose have been reported in which the patient fully recovered.<ref name="Lunesta FDA label" /> Fatalities have been reported only in cases in which eszopiclone was combined with other drugs or ].<ref name="Lunesta FDA label" /> Overdose may be successfully treated with ], a GABA<sub>A</sub> receptor antagonist used also for benzodiazepine overdose.<ref>{{cite book | vauthors = Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA |title=Goldfrank's toxicologic emergencies |publisher=McGraw-Hill, Medical Pub. Division |location=New York |year=2006 |isbn=978-0-07-147914-1 }}</ref>
			]s reported that between 2005 and 2006 there were 525 total eszopiclone overdoses recorded in the state of ], the majority of which were intentional ]s.<ref>{{cite journal | vauthors = Forrester MB | title = Eszopiclone ingestions reported to Texas poison control centers, 2005 2006 | journal = Human & Experimental Toxicology | volume = 26 | issue = 10 | pages = 795–800 | date = October 2007 | pmid = 18025051 | doi = 10.1177/0960327107084045 | bibcode = 2007HETox..26..795F | s2cid = 25102558 }}</ref>
			If consumed within the last hour, eszopiclone overdose can be treated with the administration of ] or via ].<ref>{{ cite web| url= http://www.mhra.gov.uk/Howweregulate/Medicines/Licensingofmedicines/Informationforlicenceapplicants/Guidance/OverdosesectionsofSPCs/Genericoverdosesections/Zopiclone/index.htm |archive-date=December 6, 2014 |title=Zopiclone overdose |website=MHRA |publisher=Medicines and Healthcare Products Regulatory Agency |archive-url= http://webarchive.nationalarchives.gov.uk/20141206094902/http://www.mhra.gov.uk/Howweregulate/Medicines/Licensingofmedicines/Informationforlicenceapplicants/Guidance/OverdosesectionsofSPCs/Genericoverdosesections/Zopiclone/index.htm}}</ref>
			== Interactions ==
			There is an increased risk of ] ] when eszopiclone is taken together with other CNS depressant agents, including ]s, sedative hypnotics (like ] or benzodiazepines), ], ], ], and some antidepressants. There is also increased risk of ] with other medications that inhibit the metabolic activities of the ] enzyme system of the ]. Substances that inhibit this enzyme system include ], ], ], ], ] and ]. Alcohol also has an additive effect when used concurrently with eszopiclone.<ref name = Davis2017/> Eszopiclone is most effective if it is not taken after a heavy meal with high fat content.<ref name =Davis2017>{{cite web | title = Eszopiclone | publisher = F.A. Davis | date = 2017 | access-date = April 15, 2017 | url = http://davisplus.fadavis.com/3976/meddeck/pdf/eszopiclone.pdf | archive-date = October 8, 2017 | archive-url = https://web.archive.org/web/20171008100344/http://davisplus.fadavis.com/3976/meddeck/pdf/eszopiclone.pdf | url-status = dead }}</ref>
			==Pharmacology==
			Eszopiclone acts on ] binding site situated on ] as a ].<ref>{{cite journal | vauthors = Jufe GS | title = | journal = Vertex | volume = 18 | issue = 74 | pages = 294–299 | date = July–August 2007 | pmid = 18265473 }}</ref>
			Eszopiclone is rapidly absorbed after oral administration, with serum levels peaking between .45 and 1.3 hours.<ref>{{cite journal | vauthors = Halas CJ | title = Eszopiclone | journal = American Journal of Health-System Pharmacy | volume = 63 | issue = 1 | pages = 41–48 | date = January 2006 | pmid = 16373464 | doi = 10.2146/ajhp050357 }}</ref><ref name = Davis2017/> The elimination half-life of eszopiclone is approximately 6 hours and it is extensively metabolized by oxidation and demethylation. Approximately 52% to 59% of a dose is weakly bound to plasma protein. Cytochrome P450 (CYP) isozymes ] and ] are involved in the biotransformation of eszopiclone; thus, drugs that induce or inhibit these CYP isozymes may affect the metabolism of eszopiclone. Less than 10% of the orally administered dose is excreted in the urine as racemic zopiclone.<ref>{{cite journal | vauthors = Najib J | title = Eszopiclone, a nonbenzodiazepine sedative-hypnotic agent for the treatment of transient and chronic insomnia | journal = Clinical Therapeutics | volume = 28 | issue = 4 | pages = 491–516 | date = April 2006 | pmid = 16750462 | doi = 10.1016/j.clinthera.2006.04.014 }}</ref><ref>{{cite journal | vauthors = Morinan A, Keaney F | title = Long-term misuse of zopiclone in an alcohol dependent woman with a history of anorexia nervosa: a case report | journal = Journal of Medical Case Reports | volume = 4 | issue = 1 | pages = 403 | date = December 2010 | pmid = 21143957 | pmc = 3014964 | doi = 10.1186/1752-1947-4-403 | doi-access = free }}</ref> In terms of benzodiazepine receptor binding and relevant potency, 3&nbsp;mg of eszopiclone is equivalent to 10&nbsp;mg of ].<ref>{{cite web | url= http://www.benzo.org.uk/bzequiv.htm |title= Benzodiazepine Equivalence Table | work = benzo.org.uk |access-date= 21 March 2008 | vauthors = Ashton CH |date=April 2007}}</ref>
			==History==
			In a controversial 2009 article in the '']'', "Lost in Transmission — FDA Drug Information That Never Reaches Clinicians", it was reported that the largest of three Lunesta trials found that compared to placebo Lunesta "was superior to placebo" while it only shortened initial time falling asleep by 15 minutes on average. "Clinicians who are interested in the drug’s efficacy cannot find efficacy information in the label: it states only that Lunesta is superior to placebo. The FDA’s medical review provides efficacy data, albeit not until page 306 of the 403-page document. In the longest, largest phase 3 trial, patients in the Lunesta group reported falling asleep an average of 15 minutes faster and sleeping an average of 37 minutes longer than those in the placebo group. However, on average, Lunesta patients still met criteria for insomnia and reported no clinically meaningful improvement in next-day alertness or functioning."<ref>{{cite journal | vauthors = Schwartz LM, Woloshin S | title = Lost in transmission--FDA drug information that never reaches clinicians | journal = The New England Journal of Medicine | volume = 361 | issue = 18 | pages = 1717–1720 | date = October 2009 | pmid = 19846841 | doi = 10.1056/NEJMp0907708 | doi-access = free }}</ref>
			===Availability in Europe===
			On September 11, 2007, Sepracor signed a marketing deal with British pharmaceutical company ] for the rights to sell eszopiclone (under the name Lunivia rather than Lunesta) in ].<ref name=autogenerated1>{{Cite web|url=http://www.gsk.com/media/pressreleases/2007/2007_09_11_GSK1114.htm|archive-url=https://web.archive.org/web/20101227035822/http://www.gsk.com/media/pressreleases/2007/2007_09_11_GSK1114.htm|url-status=dead|title=GlaxoSmithKline and Sepracor Inc. announce international alliance for commercialisation of Lunivia|archive-date=December 27, 2010}}</ref> Sepracor was expected to receive approximately $155 million if the deal went through.<ref name=autogenerated1 /> In 2008 Sepracor submitted an application to the ] (the ] equivalent to the U.S. ]) for authorization to market the drug in the EU, and initially received a favorable response.<ref>{{Dead link|date=March 2024 |bot=InternetArchiveBot |fix-attempted=yes }} – ]/], 23 Oct 2010</ref> However, Sepracor withdrew its authorization application in 2009 after the EMA stated it would not be granting eszopiclone 'new active substance' status, as it was essentially pharmacologically and therapeutically too similar to ] to be considered a new patentable product.<ref>{{cite web | url = http://www.ema.europa.eu/ema/index.jsp?curl=pages/news_and_events/news/2009/11/news_detail_000083.jsp&jsenabled=true | title = Sepracor Pharmaceuticals Ltd withdraws its marketing authorisation application for Lunivia (eszopiclone) | archive-url = https://web.archive.org/web/20171201043407/http://www.ema.europa.eu/ema/index.jsp?curl=pages%2Fnews_and_events%2Fnews%2F2009%2F11%2Fnews_detail_000083.jsp&jsenabled=true | archive-date = 1 December 2017 | work = ] | date = 15 May 2009 }}</ref> Since the ] on zopiclone has expired, this ruling would have allowed rival companies to also legally produce cheaper ] versions of eszopiclone for the European market.<ref>{{cite web | vauthors = Smillie M | date = 23 April 2010 | url = http://www.twobirds.com/English/News/Articles/Pages/Data_exclusivity_definition_new_active_substance.Aspx | title = Data exclusivity and definition of a new active substance: suspension of generic escitalopram-containing medicines by CHMP | archive-url = https://web.archive.org/web/20100523214527/http://www.twobirds.com/English/NEWS/ARTICLES/Pages/Data_exclusivity_definition_new_active_substance.Aspx | archive-date = 23 May 2010| work = Bird and Bird Commercial Law }}</ref> {{As of|2012|11}}, Sepracor has not resubmitted its authorization application and eszopiclone is not available in Europe. The deal with GSK fell through, and GSK instead launched a $3.3 billion deal to market Actelion's ] sleeping tablet, which entered phase 3 medical trials before development was abandoned due to side effects.<ref>{{Cite web|title=Almorexant for Treatment of Primary Insomnia | work = Clinical Trials Arena |url= https://www.clinicaltrialsarena.com/projects/almorexant/ |access-date=2021-08-04 }}</ref>{{citation needed|date=May 2020}}
			== References ==
			{{reflist}}
			{{Hypnotics and sedatives}}
			{{Insomnia pharmacotherapies}}
			{{GABAAR PAMs}}
			{{Portal bar | Medicine}}
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