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Eszopiclone

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Collated from PsychonautWiki, TripSit, Pharmacology, DrugCentral, DailyMed. Where sources differ (e.g. dosing), Compare shows them side by side.

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HallucinogenDepressantHypnoticCyclopyrroloneHabit-formingPW

Also known as Lunesta, EszopPW

This page has not been fully approved by the PsychonautWiki administrators. It may contain incorrect information, particularly with respect to dosage, duration, subjective effects, toxicity and other risks. It may also not meet PW style and grammar standards.PW

Addiction potentialPW
extremely physically and psychologically addictive
ToxicityPW
low toxicity; potentially lethal when mixed with depressants like benzodiazepines, alcohol or opioids
TolerancePW
full tolerance within a couple of weeks of daily use; baseline after 7 - 14 days
Cross-tolerancePW
benzodiazepines

Oral

Route dataPsychonautWiki

Dose
WeakerStronger
ThresholdLightCommonStrongHeavy
0.5 mg1–1.5 mg2–3 mg4–5 mg6 mg+
07.5 mg
LightCommonStrongHeavy
Duration
ShorterLonger
Onset10–20 minutes
Peak30–90 minutes
Total6–8 hours
OnsetCome-upPeakOffset

🧬 Receptor activityPHDC

TargetActionAffinitySource
Unchecked—Ki 0.83 nMCHEMBL
Gamma-aminobutyric acid receptor subunit alpha-1—Ki 50.1 nMCHEMBL
Gamma-aminobutyric acid receptor subunit alpha-4—Ki 102 nMCHEMBL
GABA A receptor alpha-2/beta-2/gamma-2—Ki 114 nMCHEMBL
GABA A receptor alpha-3/beta-2/gamma-2—Ki 162 nMCHEMBL
Gamma-aminobutyric acid receptor subunit alpha-5—Ki 15000 nMCHEMBL
GABA A receptor alpha-6/beta-2/gamma-2—Ki 15000 nMCHEMBL
GABA A receptor alpha-3/beta-2/gamma-2 (GABRG2)Positive allosteric modulator—DRUGCENTRAL
GABA A receptor alpha-3/beta-2/gamma-3 (GABRA3)Positive allosteric modulator—DRUGCENTRAL
GABA A receptor alpha-5/beta-2/gamma-2 (GABRG2)Positive allosteric modulator—DRUGCENTRAL
GABA A receptor alpha-5/beta-2/gamma-3 (GABRA5)Positive allosteric modulator—DRUGCENTRAL
GABA-A receptor alpha-1/beta-2/gamma-2 (GABRA1)Positive allosteric modulator—DRUGCENTRAL
GABA-A receptor alpha-1/beta-2/gamma-3 (GABRA1)Positive allosteric modulator—DRUGCENTRAL
Gamma-aminobutyric acid receptor subunit alpha-2 (GABRA2)Positive allosteric modulator6.94 KiDRUGCENTRAL
Gamma-aminobutyric acid receptor subunit alpha-4 (GABRA4)Positive allosteric modulator6.99 KiDRUGCENTRAL
Gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1)—7.3 KiDRUGCENTRAL
Gamma-aminobutyric acid receptor subunit alpha-3 (GABRA3)—6.79 KiDRUGCENTRAL
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Mechanism of actionPHDM

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. It has particular affinity for GABA-A (or GABAA) receptor subunits 1, 3 and 5. Eszopiclone increases GABA-A channel currents significantly. GABA-A channels are major inhibitory channels that cause CNS depression when their receptors are activated.
Eszopiclone, the S-enantiomer of zopiclone (not commercially available in the US), is a sedative and hypnotic agent that is structurally unrelated to benzadiazepines and other sedative and hypnotic agents that are commercially available in the US, including barbiturates, imidazopyridines (e.g., zolpidem), and pyrazolopyrimidines (e.g., zaleplon). Eszopiclone is pharmacologically similar to zaleplon and zolpidem; all of these agents have been shown to interact with the CNS gamma-aminobutyric acid (GABA) receptor complex at binding domains located close to or allosterically coupled to benzodiazepine receptors.
The precise mechanism of action of eszopiclone as a hypnotic is unknown. Its pharmalogic effect is believed to result from its interaction with GABA-receptor complexes at binding domains located close to or allosterically coupled to benzodiazepine receptors.

PharmacodynamicsPH

Eszopiclone rapidly induces sleep and decreases sleep latency. It also aids in the maintenance of sleep, preventing frequent awakenings. This drug has shown anticonvulsant and muscle relaxant properties in animals but is used in humans for its sedating effects. Eszopiclone is a central nervous system depressant with various effects. These include changes in alertness and motor coordination and the risk of next morning impairment, increasing with the amount of eszopiclone administered. Exercise caution and advise against driving a motor vehicle or activities that require full mental alertness the next morning. Complex sleep behaviors may result from eszopiclone use. Eszopiclone should be discontinued in these cases. Avoid the use of alcohol and other CNS depressants when eszopiclone is administered. Advise patients to skip the eszopiclone dose if alcohol has been consumed before bed or during the evening. Use the smallest dose of eszopiclone as possible, especially in elderly patients, who may experience exaggerated drug effects. Though the potential for dependence and abuse with eszopiclone is lower than for other hypnotic drugs, this drug has been abused and is known to cause dependence.

Pharmacokinetics

Half-lifePH

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.
Eszopiclone has an intermediate duration of action (i.e., possesses a half-life of approximately 5-7 hours).

AbsorptionPHDM

Eszopiclone is rapidly absorbed and the peak concentration is reached within about 1 hour after oral administration. The mean AUC after a 3 mg dose of eszopiclone was 278 ng/mL × h. The consumption of a high-fat has been shown to slow absorption. Steady-state concentrations of eszopiclone are reached within 24-48 hours.
Only about 10% of an eszopiclone dose is found excreted in the urine as the parent drug. As much as 75% of an orally administered dose of racemic zopiclone as is found to be excreted in the urine in the form of metabolites. Eszopiclone, the S-isomer of racemic zopiclone, would likely show the same excretion pattern.
The volume of distribution of eszopiclone is estimated at 89.9L
The mean clearance of eszopiclone in young, healthy volunteers was 184 mL/min in one pharmacokinetic study.
Eszopiclone is rapidly absorbed following oral administration. Peak plasma concentrations are achieved within approximately 1 hour after oral administration. Eszopiclone is weakly bound to plasma protein (52-59%). The large free fraction suggests that eszopiclone disposition should not be affected by drug-drug interactions caused by protein binding. The blood-to-plasma ratio for eszopiclone is less than one, indicating no selective uptake by red blood cells.
Onset of action may be reduced if taken with or immediately after a high-fat or heavy meal.

MetabolismPH

Following oral administration, eszopiclone is extensively biotransformed and the major metabolites are S-desmethylzopiclone and zopiclone-N-oxide, which are largely inactive.. The enzymes involved in the metabolism of eszopiclone are CYP3A (the primary metabolizing enzyme), CYP2C8, and CYP2E1. The N-oxide derivative shows weak pharmacological activity in animals. The N-desmethyl metabolite is pharmacologically active.
Extensively metabolized by CYP3A4 and CYP2E1 via oxidation and demethylation. The two primary metabolites are (S)-zopiclone-N-oxide (inactive) and (S)-N-demethylzopiclone which binds to GABA receptors with lower potency then eszopiclone.
Eszopiclone has known human metabolites that include N-desmethyl-zopiclone and N-oxide-zopiclone.
Following oral administration, eszopiclone is extensively metabolized by oxidation and demethylation.
Route of Elimination: Up to 75% of an oral dose of racemic zopiclone is excreted in the urine, primarily as metabolites.
Half Life: 6 hours

Protein bindingPH

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

Plan when to take Eszopiclone — see where onset, peak and comedown land on the clock

Fact-sheets from PsychonautWiki. Harm-reduction reference only — not medical advice.