II. Mechanism

  1. Nonbenzodiazepine Hypnotic Agent (Benzodiazepine Receptor Agonist)
  2. Acts at gamma-aminobutyric acid receptors
  3. Isomer of Zopiclone (Imovane)
  4. Schedule IV Controlled Substance

III. Indication

IV. Dosing

  1. Starting dose: 1 mg orally at bedtime
  2. Maximum dosing of 1 mg indications
    1. Severe liver disease
    2. Concurrent use of CYP 3A4 inhibitor
  3. Maximum dosing of 2 mg indications
    1. Older patients (age over 65 years old): 1 mg
  4. Maximum of 3 mg indications
    1. Younger, healthy patients

V. Precaution

  1. These agents have a duration of effect that extends past the time patients awaken
  2. Eszopiclone (Lunesta) at 3 mg dose can impair driving, coordination and memory for up to 11 hours
  3. In 2014 FDA released a safety warning to limit maximum dosing of Lunesta and to start at 1 mg in all patients (similar to the 2013 Ambien warning)
  4. FDA Warning
    1. http://www.fda.gov/Drugs/DrugSafety/ucm397260.htm

VI. Pharmacokinetics

  1. Onset of action: 10-18 minutes
  2. Half-Life: 4-6 hours (5-7 hours in some reviews)
  3. Duration of action: 6-8 hours
  4. Metabolism: CYP450 3A4
  5. Delayed activity if taken after a fatty meal

VII. Adverse effects

  1. Nonbenzodiazepine Hypnotic Agent for common effects
  2. Metallic Taste
    1. Reported in up to 34% of patients on 3 mg
    2. Very bothersome - discontinuation is common
  3. Amnesia
  4. Hallucinations
  5. Worsening depression

VIII. Advantages

IX. Disadvantages

  1. Expensive: Over $100 for 1 month supply

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Cost: Medications

lunesta (on 10/19/2016 at Medicaid.Gov Survey of pharmacy drug pricing)
LUNESTA 3 MG TABLET Generic $0.28 each
eszopiclone (on 5/17/2017 at Medicaid.Gov Survey of pharmacy drug pricing)
ESZOPICLONE 1 MG TABLET Generic $0.54 each
ESZOPICLONE 2 MG TABLET Generic $0.35 each
ESZOPICLONE 3 MG TABLET Generic $0.28 each

Ontology: Eszopiclone (C1436328)

Definition (NCI) A nonbenzodiazepine, cyclopyrrolone and active stereoisomer of zopiclone with hypnotic and sedative activity and without significant anxiolytic activity. Although the exact mechanism of action remains to be fully elucidated, eszopiclone is able to bind to and activate the omega-1 subtype of the alpha subunit of the gamma-aminobutyric acid-benzodiazepine GABA receptor complex (GABA-A), a chloride ionophore complex in the central nervous system (CNS). This leads to the opening of chloride channels, causing hyperpolarization, inhibition of neuronal firing, and enhancement of the inhibitory effect of GABA. This eventually leads to a hypnotic effect and allows for an induction of sleep.
Concepts Organic Chemical (T109) , Pharmacologic Substance (T121)
MSH C515051
SnomedCT 409421001, 409420000
English eszopiclone, (+)-(5S)-6(chloropyridine-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo(3,4-b)-pyrazin-5-yl-4-methyl-piperazine-1-carboxylate, eszopiclone (medication), (S)-Zopiclone, (+)-(5S)-6-(5-Chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazin-5-yl 4-methylpiperazine-1-carboxylate, ESZOPICLONE, eszopiclone [Chemical/Ingredient], Eszopiclone (product), Eszopiclone (substance), Eszopiclone
Spanish eszopiclona (producto), eszopiclona (sustancia), eszopiclona

Ontology: Lunesta (C1579761)

Concepts Organic Chemical (T109) , Pharmacologic Substance (T121)
MSH C515051
English Lunesta