For research use only. Not for therapeutic Use.
Eszopiclone is a nonbenzodiazepine and active stereoisomer of zopiclone with hypnotic and sedative activity and without significant anxiolytic activity. 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.
CAS Number | 138729-47-2 |
Synonyms | [(9S)-8-(5-Chloropyridin-2-yl)-7-oxo-2,5,8-triazabicyclo[4.3.0]nona-1,3,5-trien-9-yl]4-methylpiperazine-1-carboxylate; Lunesta; (S)-Zopiclone |
Molecular Formula | C17H17ClN6O3 |
Purity | ≥95% |
Storage | 2°C to 8°C |
IUPAC Name | [(7S)-6-(5-chloropyridin-2-yl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate |
InChI | 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 |
InChIKey | GBBSUAFBMRNDJC-INIZCTEOSA-N |
SMILES | CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl |
Reference | </br>1:Eszopiclone-induced Parasomnia with Suicide Attempt: A Case Report. Pennington JG, Guina J.Innov Clin Neurosci. 2016 Oct 1;13(9-10):44-48. eCollection 2016 Sep-Oct. PMID: 27974999 Free PMC Article</br>2:Eszopiclone and Zolpidem Do Not Affect the Prevalence of the Low Arousal Threshold Phenotype. Smith PR, Sheikh KL, Costan-Toth C, Forsthoefel D, Bridges E, Andrada TF, Holley AB.J Clin Sleep Med. 2017 Jan 15;13(1):115-119. doi: 10.5664/jcsm.6402. PMID: 27784413 </br>3:New-Onset Visual Hallucinations With Eszopiclone. McGuire JM, Duquette M, Burghart SM, Ferri MJ.Prim Care Companion CNS Disord. 2016 Apr 14;18(2). doi: 10.4088/PCC.15l01859. eCollection 2016. No abstract available. PMID: 27486533 Free PMC Article</br>4:Eszopiclone versus zopiclone in the treatment of insomnia. Pinto Jr LR, Bittencourt LR, Treptow EC, Braga LR, Tufik S.Clinics (Sao Paulo). 2016 Jan;71(1):5-9. doi: 10.6061/clinics/2016(01)02. PMID: 26872077 Free PMC Article</br>5:Patient Background Factors Affecting the Therapeutic Outcomes in Response to Eszopiclone in Adult Patients with Chronic Insomnia: A Post Hoc Analysis of a Double-Blind Phase III Study in Japan. Inoue Y, Kamijo A, Nagai R.J Clin Sleep Med. 2015 Oct 15;11(10):1171-8. doi: 10.5664/jcsm.5094. PMID: 26094929 Free PMC Article</br>6:Zolpidem and eszopiclone prime α1β2γ2 GABAA receptors for longer duration of activity. Dixon CL, Harrison NL, Lynch JW, Keramidas A.Br J Pharmacol. 2015 Jul;172(14):3522-36. doi: 10.1111/bph.13142. Epub 2015 May 11. PMID: 25817320 Free PMC Article</br>7:The impact of eszopiclone on sleep and cognition in patients with schizophrenia and insomnia: a double-blind, randomized, placebo-controlled trial. Tek C, Palmese LB, Krystal AD, Srihari VH, DeGeorge PC, Reutenauer EL, Guloksuz S.Schizophr Res. 2014 Dec;160(1-3):180-5. doi: 10.1016/j.schres.2014.10.002. Epub 2014 Oct 29. PMID: 25454802 </br>8:Trial of Zolpidem, Eszopiclone, and Other GABA Agonists in a Patient with Progressive Supranuclear Palsy. Chang AY, Weirich E.Case Rep Med. 2014;2014:107064. doi: 10.1155/2014/107064. Epub 2014 Sep 16. PMID: 25371679 Free PMC Article</br>9:Efficacy of treatment of insomnia in migraineurs with eszopiclone (Lunesta®) and its effect on total sleep time, headache frequency, and daytime functioning: A randomized, double-blind, placebo-controlled, parallel-group, pilot study. Spierings EL, McAllister PJ, Bilchik TR.Cranio. 2015 Apr;33(2):115-21. doi: 10.1179/0886963414Z.00000000084. Epub 2014 Oct 16. PMID: 25323219 </br>10:Eszopiclone for insomnia associated with attention-deficit/hyperactivity disorder. Sangal RB, Blumer JL, Lankford DA, Grinnell TA, Huang H.Pediatrics. 2014 Oct;134(4):e1095-103. doi: 10.1542/peds.2013-4221. PMID: 25266438 Free Article |
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