Description

Simple

A medication used to help with falling asleep and staying asleep.

Clinical

A sedative-hypnotic used in the treatment of insomnia, improving both the latency phase and the maintenance phase of sleep.

Overview

Eszopiclone, marketed by Sepracor under the brand-name Lunesta, is a nonbenzodiazepine hypnotic drug used to treat insomnia. It is the active stereoisomer of zopiclone, belonging to the class of drugs known as _cyclopyrrolones_.[1,12] Cyclopyrrolone drugs demonstrate high efficacy and low toxicity[9], offering a safer alternative to other drugs used for insomnia.

One major benefit of eszopiclone is that it is approved by the FDA for the long-term treatment of insomnia. This sets it apart from many other hypnotic sedatives, which are generally approved only for the relief of short-term (6-8 weeks) insomnia. Eszopiclone was initially approved by the FDA in 2004.[10]

Pharmacology

Indication

Eszopiclone is indicated for the treatment of insomnia.[10]

Pharmacodynamic

Eszopiclone rapidly induces sleep and decreases sleep latency. It also aids in the maintenance of sleep, preventing frequent awakenings.[ Read more

Mechanism of action

The exact mechanism of action of eszopiclone is unknown at this time but is thought to occur via binding with the GABA receptor complexes at binding sites located near benzodiazepine receptors, possibly explaining its hypnotic and sedative effects.[ Read more

Absorption

Eszopiclone is rapidly absorbed and the peak concentration is reached within about 1 hour after oral administration.[ Read more

Protein binding

This drug is 52-59% bound to plasma proteins.[10]

Volume of distribution

The volume of distribution of eszopiclone is estimated at 89.9L[11]

Clearance

The mean clearance of eszopiclone in young, healthy volunteers was 184 mL/min in one pharmacokinetic study.[ Read more

Half life

The half-life is 6.1 hours in healthy patients but is prolonged in various patients, including those with hepatic impairment, elderly patients, in addition to those taking CYP3A enzyme inhibiting drugs.[ Read more

Route of elimination

Only about 10% of an eszopiclone dose is found excreted in the urine as the parent drug.[ Read more

Toxicity

The oral LD50 of eszopiclone in rats is 980 mg/kg and 3200 mg/kg in rabbits.[13] Symptoms of overdose may include mental status changes and somnolence, demonstrating general exaggeration of the drug's pharmacological effe... Read more

Adverse Effects

Contraindications

  • Regions: Canada
  • Patient Conditions:
      • Name: Severe impairment of respiratory function
      • Drugbank Id: DBCOND0108382
  • Regions: Canada
  • Patient Conditions:
      • Name: Severe hepatic insufficiency
      • Drugbank Id: DBCOND0108038
      • Modification Of:
        • Base:
          • Name: Hepatic Insufficiency
          • Drugbank Id: DBCOND0031307
        • Severity:
          • Includes:
            • severe
  • Regions: Canada
  • Patient Conditions:
      • Name: Myasthenia Gravis
      • Drugbank Id: DBCOND0028961

Food Interactions

  • Avoid alcohol.
  • Do not take with or immediately after a high-fat meal. This decreases the absorption of eszopiclone.

Interactions

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  • Paracetamol(acetaminophen)
  • Paxil(paroxetine)
  • Pamelor(nortriptyline)
  • Panadol(acetaminophen)
  • Patanol(olopatadine ophthalmic)
  • Pataday(olopatadine ophthalmic)
  • Parnate(tranylcypromine)
  • Pazeo(olopatadine ophthalmic)
(R)-warfarin
The metabolism of (R)-warfarin can be decreased when combined with Eszopiclone.
(S)-Warfarin
The metabolism of (S)-Warfarin can be decreased when combined with Eszopiclone.
2,5-Dimethoxy-4-ethylthioamphetamine
The risk or severity of CNS depression can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Eszopiclone.
4-Bromo-2,5-dimethoxyamphetamine
The risk or severity of CNS depression can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Eszopiclone.
4-Methoxyamphetamine
The risk or severity of CNS depression can be increased when 4-Methoxyamphetamine is combined with Eszopiclone.
5-methoxy-N,N-dimethyltryptamine
The risk or severity of CNS depression can be increased when 5-methoxy-N,N-dimethyltryptamine is combined with Eszopiclone.
6-Deoxyerythronolide B
The metabolism of Eszopiclone can be decreased when combined with 6-Deoxyerythronolide B.
7-ethyl-10-hydroxycamptothecin
The metabolism of Eszopiclone can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
7-Nitroindazole
The risk or severity of CNS depression can be increased when 7-Nitroindazole is combined with Eszopiclone.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline
The risk or severity of CNS depression can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Eszopiclone.
Abacavir
Eszopiclone may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abatacept
The metabolism of Eszopiclone can be increased when combined with Abatacept.
Abiraterone
The metabolism of Eszopiclone can be decreased when combined with Abiraterone.
Acalabrutinib
The metabolism of Eszopiclone can be decreased when combined with Acalabrutinib.
Acarbose
Acarbose may decrease the excretion rate of Eszopiclone which could result in a higher serum level.
Aceclofenac
Aceclofenac may decrease the excretion rate of Eszopiclone which could result in a higher serum level.
Acemetacin
Acemetacin may decrease the excretion rate of Eszopiclone which could result in a higher serum level.
Acepromazine
The risk or severity of CNS depression can be increased when Acepromazine is combined with Eszopiclone.
Aceprometazine
The risk or severity of CNS depression can be increased when Aceprometazine is combined with Eszopiclone.
Acetaminophen
The serum concentration of Eszopiclone can be decreased when it is combined with Acetaminophen.
15 References
  1. 1 . Greenblatt DJ, Zammit GK: Pharmacokinetic evaluation of eszopiclone: clinical and therapeutic implications. Expert Opin Drug Metab Toxicol. 2012 Dec;8(12):1609-18. doi: 10.1517/17425255.2012.741588. Epub 2012 Nov 6.PubMed: 23126273
  2. 2 . Carlson JN, Haskew R, Wacker J, Maisonneuve IM, Glick SD, Jerussi TP: Sedative and anxiolytic effects of zopiclone's enantiomers and metabolite. Eur J Pharmacol. 2001 Mar;415(2-3):181-9. doi: 10.1016/s0014-2999(01)00851-2.PubMed: 11274997
  3. 3 . Brielmaier BD: Eszopiclone (Lunesta): a new nonbenzodiazepine hypnotic agent. Proc (Bayl Univ Med Cent). 2006 Jan;19(1):54-9. doi: 10.1080/08998280.2006.11928127.PubMed: 16424933
  4. 4 . Halas CJ: Eszopiclone. Am J Health Syst Pharm. 2006 Jan 1;63(1):41-8. doi: 10.2146/ajhp050357.PubMed: 16373464
  5. 5 . Dixon CL, Harrison NL, Lynch JW, Keramidas A: Zolpidem and eszopiclone prime alpha1beta2gamma2 GABAA receptors for longer duration of activity. Br J Pharmacol. 2015 Jul;172(14):3522-36. doi: 10.1111/bph.13142. Epub 2015 May 11.PubMed: 25817320
  6. 6 . Nutt DJ, Stahl SM: Searching for perfect sleep: the continuing evolution of GABAA receptor modulators as hypnotics. J Psychopharmacol. 2010 Nov;24(11):1601-12. doi: 10.1177/0269881109106927. Epub 2009 Nov 26.PubMed: 19942638
  7. 7 . Hanson SM, Morlock EV, Satyshur KA, Czajkowski C: Structural requirements for eszopiclone and zolpidem binding to the gamma-aminobutyric acid type-A (GABAA) receptor are different. J Med Chem. 2008 Nov 27;51(22):7243-52. doi: 10.1021/jm800889m.PubMed: 18973287
  8. 8 . Goetz T, Arslan A, Wisden W, Wulff P: GABA(A) receptors: structure and function in the basal ganglia. Prog Brain Res. 2007;160:21-41. doi: 10.1016/S0079-6123(06)60003-4.PubMed: 17499107
  9. 9 . Goa KL, Heel RC: Zopiclone. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy as an hypnotic. Drugs. 1986 Jul;32(1):48-65. doi: 10.2165/00003495-198632010-00003.PubMed: 2874974
  10. 10 . Eszopiclone FDA Label Link
  11. 11 . FDA review, Eszopiclone Link
  12. 12 . Pubchem, Eszopiclone Link
  13. 13 . MSDS, Eszopiclone Link
  14. 14 . Lunesta label 2019 Link
  15. 15 . FDA news Link