Identification
- Summary
Eszopiclone is a sedative-hypnotic used in the treatment of insomnia, improving both the latency phase and the maintenance phase of sleep.
- Brand Names
- Lunesta
- Generic Name
- Eszopiclone
- DrugBank Accession Number
- DB00402
- Background
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 toxicity9, 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
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Eszopiclone (DB00402)
- Weight
- Average: 388.808
Monoisotopic: 388.105066147 - Chemical Formula
- C17H17ClN6O3
- Synonyms
- (+)-(5S)-6-(5-Chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazin-5-yl 4-methylpiperazine-1-carboxylate
- (+)-(5S)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl-4-methylpiperazine-1-carboxylate
- (+)-Zopiclone
- (S)-6-(5-Chloro-2-pyridinyl)- 7-oxo- 6,7-dihydro- 5H-pyrrolo[3,4-b]pyrazin-5-yl- 4-methyl- 1-piperazinecarboxylate
- (S)-Zopiclone
- 1-Piperazinecarobxylic acid,4-methyl-,(5S)-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester
- Esopiclone
- Eszopiclone
- External IDs
- GSK-1755165
Pharmacology
- Indication
Eszopiclone is indicated for the treatment of insomnia.10
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Insomnia •••••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Eszopiclone rapidly induces sleep and decreases sleep latency. It also aids in the maintenance of sleep, preventing frequent awakenings.3,4,10 This drug has shown anticonvulsant and muscle relaxant properties in animals but is used in humans for its sedating effects.9
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.10 Complex sleep behaviors may result from eszopiclone use. Eszopiclone should be discontinued in these cases.15 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.14
- 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.3,10 It has particular affinity for GABA-A (or GABAA) receptor subunits 1, 3 and 5.5,6,7 Eszopiclone increases GABA-A channel currents significantly.5 GABA-A channels are major inhibitory channels that cause CNS depression when their receptors are activated.8
Target Actions Organism AGamma-aminobutyric acid receptor subunit alpha-1 potentiatorHumans AGABA(A) Receptor positive allosteric modulatorHumans UGamma-aminobutyric acid receptor subunit alpha-2 agonistHumans UGamma-aminobutyric acid receptor subunit alpha-3 agonistHumans UGamma-aminobutyric acid receptor subunit alpha-5 agonistHumans - Absorption
Eszopiclone is rapidly absorbed and the peak concentration is reached within about 1 hour after oral administration.3,10 The mean AUC after a 3 mg dose of eszopiclone was 278 ng/mL × h.1 The consumption of a high-fat has been shown to slow absorption. Steady-state concentrations of eszopiclone are reached within 24-48 hours.4
- Volume of distribution
The volume of distribution of eszopiclone is estimated at 89.9L11
- Protein binding
This drug is 52-59% bound to plasma proteins.10
- Metabolism
Following oral administration, eszopiclone is extensively biotransformed and the major metabolites are S-desmethylzopiclone and zopiclone-N-oxide, which are largely inactive.2. The enzymes involved in the metabolism of eszopiclone are CYP3A (the primary metabolizing enzyme), CYP2C8, and CYP2E1.2 The N-oxide derivative shows weak pharmacological activity in animals. The N-desmethyl metabolite is pharmacologically active.10
Hover over products below to view reaction partners
- Route of elimination
Only about 10% of an eszopiclone dose is found excreted in the urine as the parent drug.3,10 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.10
- 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.1,10
- Clearance
The mean clearance of eszopiclone in young, healthy volunteers was 184 mL/min in one pharmacokinetic study.1
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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 effects. Perform gastric lavage and offer supportive treatment if an overdose is suspected, including intravenous fluids as required. Flumazenil may be used. Vital signs should be closely monitored in addition to patient symptoms. Appropriate medical interventions should be employed. The possibility of an overdose with multiple drugs should be considered. Ensure to contact the local poison control center for the most updated management of hypnotic drug overdose.10
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when 1,2-Benzodiazepine is combined with Eszopiclone. Abacavir Eszopiclone may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Eszopiclone can be increased when it is combined with Abametapir. Abatacept The metabolism of Eszopiclone can be increased when combined with Abatacept. Abiraterone The metabolism of Eszopiclone can be decreased when combined with Abiraterone. - Food Interactions
- Avoid alcohol.
- Do not take with or immediately after a high-fat meal. This decreases the absorption of eszopiclone.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Dorplen (LKM) / Esleep (Opsonin) / Eszop (Silesia) / Fulnite (Sun) / Inductal (Roemmers) / Isoklon (Tecnoquimicas) / Nirvan (Saval) / Noptic (Andromaco) / Plessir (Medipharm) / Sanilent (Sanitas) / Sleepil (Aristopharma) / Sono (Acme) / Valnoc (Drugtech) / Wen Fei (Tasly) / Zopilone (Incepta) / Zopinon (Chile)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Lunesta Tablet, coated 3 mg/1 Oral Unit Dose Services 2005-04-04 2017-12-31 US 
Lunesta Tablet, coated 1 mg/1 Oral Waylis Therapeutics LLC 2023-08-15 Not applicable US Lunesta Tablet, coated 3 mg/1 Oral Caremark L.L.C. 2009-01-01 2012-07-31 US Lunesta Tablet, coated 3 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 2005-04-04 Not applicable US Lunesta Tablet 1 mg Oral Sunovion 2020-10-20 Not applicable Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Eszopiclone Tablet, film coated 3 mg/1 Oral Proficient Rx LP 2014-09-25 Not applicable US Eszopiclone Tablet, film coated 1 mg/1 Oral bryant ranch prepack 2015-01-31 Not applicable US Eszopiclone Tablet, film coated 1 mg/1 Oral Sun Pharmaceutical Industries, Inc. 2014-04-15 Not applicable US Eszopiclone Tablet, film coated 1 mg/1 Oral Golden State Medical Supply, Inc. 2013-03-26 Not applicable US Eszopiclone Tablet, film coated 1 mg/1 Oral AvKARE, Inc. 2014-05-15 2018-09-17 US 
Categories
- ATC Codes
- N05CF04 — Eszopiclone
- Drug Categories
- Benzodiazepine hypnotics and sedatives
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Drugs that are Mainly Renally Excreted
- Hypnotics (Nonbenzodiazepine)
- Hypnotics and Sedatives
- Miscellaneous Anxiolytics Sedatives and Hypnotics
- Muscle Relaxants
- Muscle Relaxants, Centrally Acting Agents
- Nervous System
- Photosensitizing Agents
- Piperazines
- Psycholeptics
- Pyrazines
- Pyridines
- Zopiclone and prodrugs
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cyclopyrrolones. These are compounds belonging to a family of pyridin-2-ylpyrrole based chemicals. The pyrrole is usually fused to a benzene, pyrimidine, or dithiin.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyrrolopyrazines
- Sub Class
- Cyclopyrrolones
- Direct Parent
- Cyclopyrrolones
- Alternative Parents
- Piperazine carboxylic acids / 2-heteroaryl carboxamides / N-methylpiperazines / Pyridines and derivatives / Pyrazines / Aryl chlorides / Imidolactams / Tertiary carboxylic acid amides / Carbamate esters / Heteroaromatic compounds show 9 more
- Substituents
- 1,4-diazinane / 2-heteroaryl carboxamide / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Carbamic acid ester / Carbonic acid derivative show 25 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- zopiclone (CHEBI:53760)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- UZX80K71OE
- CAS number
- 138729-47-2
- InChI Key
- GBBSUAFBMRNDJC-INIZCTEOSA-N
- 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
- IUPAC Name
- (5S)-6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate
- SMILES
- CN1CCN(CC1)C(=O)O[C@@H]1N(C(=O)C2=NC=CN=C12)C1=NC=C(Cl)C=C1
References
- Synthesis Reference
Marioara MENDELOVICI, Anita LIBERMAN, Alex MAINFELD, Nina FINKELSTEIN, "METHODS FOR PREPARING ESZOPICLONE CRYSTALLINE FORM A, SUBSTANTIALLY PURE ESZOPICLONE AND OPTICALLY ENRICHED ESZOPICLONE." U.S. Patent US20070270590, issued November 22, 2007.
US20070270590- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Halas CJ: Eszopiclone. Am J Health Syst Pharm. 2006 Jan 1;63(1):41-8. doi: 10.2146/ajhp050357. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- FDA Approved Drug Products: Lunesta (eszopiclone) oral tablets [Link]
- FDA review, Eszopiclone [Link]
- Pubchem, Eszopiclone [Link]
- MSDS, Eszopiclone [Link]
- Lunesta label 2019 [Link]
- FDA news [Link]
- External Links
- Human Metabolome Database
- HMDB0014546
- PubChem Compound
- 969472
- PubChem Substance
- 46505809
- ChemSpider
- 839530
- BindingDB
- 50247998
- 461016
- ChEBI
- 53760
- ChEMBL
- CHEMBL1522
- ZINC
- ZINC000019632834
- Therapeutic Targets Database
- DAP000933
- PharmGKB
- PA162630444
- RxList
- RxList Drug Page
- Wikipedia
- Eszopiclone
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Basic Science Insomnia 1 4 Completed Diagnostic Obstructive Sleep Apnea (OSA) 1 4 Completed Other Insomnia / Migraine 1 4 Completed Supportive Care Acute Coronary Syndrome (ACS) / Sleep disorders and disturbances 1 4 Completed Supportive Care Obstructive Sleep Apnea (OSA) 1
Pharmacoeconomics
- Manufacturers
- Sepracor inc
- Sepracor Inc.
- Packagers
- A-S Medication Solutions LLC
- Caremark LLC
- Centaur Pharmaceuticals Pvt Ltd.
- DispenseXpress Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- H.J. Harkins Co. Inc.
- Innoviant Pharmacy Inc.
- Lake Erie Medical and Surgical Supply
- Lupin Pharmaceuticals Inc.
- Mckesson Corp.
- Murfreesboro Pharmaceutical Nursing Supply
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- Patheon Inc.
- PD-Rx Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Rebel Distributors Corp.
- Sepracor Pharmaceuticals Inc.
- Southwood Pharmaceuticals
- Stat Rx Usa
- Dosage Forms
Form Route Strength Tablet, film coated Oral 2 mg Tablet, film coated 1 MG Tablet, film coated 2 MG Tablet, film coated 3 MG Tablet, film coated Oral 1 MG Tablet Oral 1 mg/1 Tablet Oral 2 mg/1 Tablet Oral 3 mg/1 Tablet, film coated Oral 1 mg/1 Tablet, film coated Oral 2 mg/1 Tablet, film coated Oral 3 mg/1 Tablet, film coated Oropharyngeal 3 mg/1 Tablet, coated Oral 1 mg Tablet, coated Oral 3 mg Tablet Oral 1 mg Tablet Oral 2 mg Tablet Oral 3 mg Tablet, coated Oral 1 mg/1 Tablet, coated Oral 2 mg/1 Tablet, coated Oral 3 mg/1 Tablet, coated Oral 2 mg Tablet, film coated Oral 3 mg Capsule, liquid filled Oral 3 mg Capsule, liquid filled Oral 1 mg Capsule, liquid filled Oral 2 mg Tablet, coated Oral 200000 mg Tablet, coated Oral 300000 mg - Prices
Unit description Cost Unit Lunesta 2 mg tablet 8.08USD tablet Lunesta 3 mg tablet 7.28USD tablet Lunesta 1 mg tablet 7.24USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6444673 No 2002-09-03 2014-02-14 US US6319926 No 2001-11-20 2012-01-16 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 202-203 https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3711352.htm boiling point (°C) 487.2 https://www.lookchem.com/Timolol/ water solubility soluble in water https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3711352.htm logP 0.81 http://www.t3db.ca/toxins/T3D4552 pKa 9.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.885 mg/mL ALOGPS logP 0.97 ALOGPS logP 0.52 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 8.04 Chemaxon pKa (Strongest Basic) 6.86 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 91.76 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 95.89 m3·mol-1 Chemaxon Polarizability 37.82 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9382 Caco-2 permeable + 0.5805 P-glycoprotein substrate Substrate 0.6917 P-glycoprotein inhibitor I Inhibitor 0.6381 P-glycoprotein inhibitor II Inhibitor 0.5 Renal organic cation transporter Non-inhibitor 0.6785 CYP450 2C9 substrate Non-substrate 0.7158 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Substrate 0.6775 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Inhibitor 0.8995 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.689 Ames test AMES toxic 0.5332 Carcinogenicity Non-carcinogens 0.9174 Biodegradation Not ready biodegradable 0.9941 Rat acute toxicity 2.6411 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7838 hERG inhibition (predictor II) Non-inhibitor 0.5688
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 196.2478232 predictedDarkChem Lite v0.1.0 [M-H]- 187.75032 predictedDeepCCS 1.0 (2019) [M+H]+ 196.9037232 predictedDarkChem Lite v0.1.0 [M+H]+ 190.12737 predictedDeepCCS 1.0 (2019) [M+Na]+ 195.9800232 predictedDarkChem Lite v0.1.0 [M+Na]+ 197.03639 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
- Gene Name
- GABRA1
- Uniprot ID
- P14867
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-1
- Molecular Weight
- 51801.395 Da
References
- 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. [Article]
- 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. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Positive allosteric modulator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Doble A, Canton T, Malgouris C, Stutzmann J, Piot O, Bardone M, Pauchet C, Blanchard J: The mechanism of action of zopiclone. Eur Psychiatry. 1995;10 Suppl 3:117s-28s. doi: 10.1016/0924-9338(96)80093-9. [Article]
- Wadworth AN, McTavish D: Zopiclone. A review of its pharmacological properties and therapeutic efficacy as an hypnotic. Drugs Aging. 1993 Sep-Oct;3(5):441-59. doi: 10.2165/00002512-199303050-00006. [Article]
- 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. [Article]
- ChEMBL Compound Report Card [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRA2
- Uniprot ID
- P47869
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-2
- Molecular Weight
- 51325.85 Da
References
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRA3
- Uniprot ID
- P34903
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-3
- Molecular Weight
- 55164.055 Da
References
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Transporter activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRA5
- Uniprot ID
- P31644
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-5
- Molecular Weight
- 52145.645 Da
References
- 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. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Lalovic B, Phillips B, Risler LL, Howald W, Shen DD: Quantitative contribution of CYP2D6 and CYP3A to oxycodone metabolism in human liver and intestinal microsomes. Drug Metab Dispos. 2004 Apr;32(4):447-54. [Article]
- 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. [Article]
- Becquemont L, Mouajjah S, Escaffre O, Beaune P, Funck-Brentano C, Jaillon P: Cytochrome P-450 3A4 and 2C8 are involved in zopiclone metabolism. Drug Metab Dispos. 1999 Sep;27(9):1068-73. [Article]
- FDA Approved Drug Products: Lunesta (eszopiclone) oral tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Lalovic B, Phillips B, Risler LL, Howald W, Shen DD: Quantitative contribution of CYP2D6 and CYP3A to oxycodone metabolism in human liver and intestinal microsomes. Drug Metab Dispos. 2004 Apr;32(4):447-54. [Article]
- Becquemont L, Mouajjah S, Escaffre O, Beaune P, Funck-Brentano C, Jaillon P: Cytochrome P-450 3A4 and 2C8 are involved in zopiclone metabolism. Drug Metab Dispos. 1999 Sep;27(9):1068-73. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 05, 2023 12:31