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Identification
NameEszopiclone
Accession NumberDB00402  (APRD00431)
TypeSmall Molecule
GroupsApproved
Description

Eszopiclone, marketed by Sepracor under the brand-name Lunesta, is a nonbenzodiazepine hypnotic agent (viz., a sedative) used as a treatment for insomnia. Eszopiclone is the active stereoisomer of zopiclone, and belongs to the class of drugs known as cyclopyrrones.

Its main selling point is that it is approved by the U.S. Food and Drug Administration for long-term use, unlike almost all other hypnotic sedatives, which are approved only for the relief of short-term (6-8 weeks) insomnia.

Structure
Thumb
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
Estorra
Eszopiclone
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Lunestatablet, coated2 mg/1oralSt Marys Medical Park Pharmacy2005-04-04Not applicableUs
Lunestatablet, coated3 mg/1oralH.J. Harkins Company, Inc.2005-04-04Not applicableUs
Lunestatablet, coated2 mg/1oralRebel Distributors Corp2009-01-01Not applicableUs
Lunestatablet1 mgoralSunovion Pharmaceuticals Canada IncNot applicableNot applicableCanada
Lunestatablet, coated3 mg/1oralSt Marys Medical Park Pharmacy2005-04-04Not applicableUs
Lunestatablet, coated3 mg/1oralPd Rx Pharmaceuticals, Inc.2005-04-04Not applicableUs
Lunestatablet, coated3 mg/1oralUnit Dose Services2005-04-04Not applicableUs
Lunestatablet, coated3 mg/1oralDispensing Solutions, Inc.2005-04-04Not applicableUs
Lunestatablet, coated1 mg/1oralPhysicians Total Care, Inc.2006-09-29Not applicableUs
Lunestatablet, coated2 mg/1oralA S Medication Solutions Llc2005-04-04Not applicableUs
Lunestatablet, coated2 mg/1oralDispensing Solutions, Inc.2005-04-04Not applicableUs
Lunestatablet, coated3 mg/1oralPhysicians Total Care, Inc.2005-08-24Not applicableUs
Lunestatablet, coated3 mg/1oralA S Medication Solutions Llc2005-04-04Not applicableUs
Lunestatablet, coated2 mg/1oralbryant ranch prepack2005-04-04Not applicableUs
Lunestatablet, coated2 mg/1oralPhysicians Total Care, Inc.2005-04-27Not applicableUs
Lunestatablet, coated2 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-11-18Not applicableUs
Lunestatablet, coated3 mg/1oralbryant ranch prepack2005-04-04Not applicableUs
Lunestatablet, coated2 mg/1oralA S Medication Solutions Llc2005-04-04Not applicableUs
Lunestatablet, coated1 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-07-18Not applicableUs
Lunestatablet, coated3 mg/1oralSunovion Pharmaceuticals Inc.2005-04-04Not applicableUs
Lunestatablet, coated3 mg/1oralA S Medication Solutions Llc2005-04-04Not applicableUs
Lunestatablet, coated3 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-07-18Not applicableUs
Lunestatablet3 mgoralSunovion Pharmaceuticals Canada IncNot applicableNot applicableCanada
Lunestatablet, coated2 mg/1oralSunovion Pharmaceuticals Inc.2005-04-04Not applicableUs
Lunestatablet, coated1 mg/1oralSunovion Pharmaceuticals Inc.2005-04-04Not applicableUs
Lunestatablet, coated2 mg/1oralH.J. Harkins Company, Inc.2005-04-04Not applicableUs
Lunestatablet, coated3 mg/1oralRebel Distributors Corp2009-01-01Not applicableUs
Lunestatablet2 mgoralSunovion Pharmaceuticals Canada IncNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Eszopiclonetablet1 mg/1oralRoxane Laboratories, Inc.2014-04-15Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralGolden State Medical Supply, Inc.2016-01-19Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralPreferred Pharmaceuticals Inc.2015-08-18Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralGlenmark Pharmaceuticals Inc., Usa2014-04-15Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralSt. Mary's Medical Park Pharmacy2016-04-14Not applicableUs
Eszopiclonetablet, coated3 mg/1oralDr. Reddy's Laboratories Limited2014-04-15Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralA S Medication Solutions Llc2014-04-15Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralAv Kare, Inc.2014-05-15Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralGlenmark Pharmaceuticals Inc., Usa2014-04-15Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralProficient Rx LP2014-09-25Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralAv Kare, Inc.2014-05-15Not applicableUs
Eszopiclonetablet, coated2 mg/1oralDr. Reddy's Laboratories Limited2014-04-15Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralMylan Pharmaceuticals Inc.2013-03-26Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralGolden State Medical Supply, Inc.2016-01-19Not applicableUs
Eszopiclonetablet1 mg/1oralPreferred Pharmaceuticals, Inc.2014-10-20Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralA S Medication Solutions Llc2014-04-15Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralA S Medication Solutions Llc2014-04-15Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralGlenmark Pharmaceuticals Inc., Usa2014-04-15Not applicableUs
Eszopiclonetablet2 mg/1oralProficient Rx LP2014-04-15Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralAv Kare, Inc.2014-05-15Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralMylan Pharmaceuticals Inc.2013-03-26Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralGolden State Medical Supply, Inc.2016-01-19Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralPreferred Pharmaceuticals, Inc.2015-04-15Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralA S Medication Solutions Llc2014-04-15Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralSun Pharma Global FZE2014-04-15Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralLupin Pharmaceuticals, Inc.2014-04-15Not applicableUs
Eszopiclonetablet1 mg/1oralProficient Rx LP2014-04-15Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralOrchid Pharma Inc2014-09-25Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralMylan Pharmaceuticals Inc.2013-03-26Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralMylan Institutional Inc.2014-11-11Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralSun Pharma Global FZE2014-04-15Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralLupin Pharmaceuticals, Inc.2014-04-15Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralDIRECT RX2015-12-01Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralOrchid Pharma Inc2014-09-25Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralTeva Pharmaceuticals USA Inc2014-04-14Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralA S Medication Solutions2014-04-14Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralPreferred Pharmaceuticals, Inc.2015-04-15Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralMylan Institutional Inc.2014-11-11Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralSun Pharma Global FZE2014-04-15Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralLupin Pharmaceuticals, Inc.2014-04-15Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralDIRECT RX2015-01-01Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralOrchid Pharma Inc2014-09-25Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralTeva Pharmaceuticals USA Inc2014-04-14Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralProficient Rx LP2014-09-25Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralPreferred Pharmaceuticals, Inc.2015-04-21Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralUnit Dose Services2014-04-14Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralMedsource Pharmaceuticals2014-04-15Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralbryant ranch prepack2014-04-15Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralDIRECT RX2014-01-01Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralMacleods Pharmaceuticals Limited2014-04-25Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralTeva Pharmaceuticals USA Inc2014-04-14Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralDIRECT RX2015-12-15Not applicableUs
Eszopiclonetablet3 mg/1oralPreferred Pharmaceuticals, Inc.2014-10-13Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralUnit Dose Services2014-04-14Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralMedsource Pharmaceuticals2014-04-15Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralbryant ranch prepack2014-04-15Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralDIRECT RX2015-01-01Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralMacleods Pharmaceuticals Limited2014-04-25Not applicableUs
Eszopiclonetablet3 mg/1oralRoxane Laboratories, Inc.2014-04-15Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralA S Medication Solutions2014-04-15Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralPreferred Pharmaceuticals Inc.2015-11-20Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralbryant ranch prepack2014-04-15Not applicableUs
Eszopiclonetablet, coated1 mg/1oralDr. Reddy's Laboratories Limited2014-04-15Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralMacleods Pharmaceuticals Limited2014-04-25Not applicableUs
Eszopiclonetablet2 mg/1oralRoxane Laboratories, Inc.2014-04-15Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralPreferred Pharmaceuticals, Inc.2014-04-15Not applicableUs
Eszopiclonetablet, film coated2 mg/1oralPreferred Pharmaceuticals Inc.2015-10-06Not applicableUs
Eszopiclonetablet, film coated1 mg/1oralUnit Dose Services2014-04-15Not applicableUs
Eszopiclonetablet, film coated3 mg/1oralMedsource Pharmaceuticals2014-04-15Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DorplenLKM
EsleepOpsonin
EszopSilesia
FulniteSun
InductalRoemmers
IsoklonTecnoquimicas
NirvanSaval
NopticAndromaco
PlessirMedipharm
SanilentSanitas
SleepilAristopharma
SonoAcme
ValnocDrugtech
Wen FeiTasly
ZopiloneIncepta
ZopinonChile
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIUZX80K71OE
CAS number138729-47-2
WeightAverage: 388.808
Monoisotopic: 388.105066147
Chemical FormulaC17H17ClN6O3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolopyrazines
Sub ClassCyclopyrrolones
Direct ParentCyclopyrrolones
Alternative Parents
Substituents
  • Cyclopyrrolone
  • Piperazine-1-carboxylic acid
  • N-alkylpiperazine
  • N-methylpiperazine
  • Aminopyridine
  • Imidolactam
  • Pyridine
  • Pyrazine
  • Piperazine
  • 1,4-diazinane
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactam
  • Carboxamide group
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of insomnia
PharmacodynamicsEszopiclone is a nonbenzodiazepine hypnotic, pyrrolopyrazine derivative of the cyclopyrrolone class and is indicated for the short-term treatment of insomnia. While Eszopiclone is a hypnotic agent with a chemical structure unrelated to benzodiazepines, barbiturates, or other drugs with known hypnotic properties, it interacts with the gamma-aminobutyric acid-benzodiazepine (GABABZ) receptor complex. Subunit modulation of the GABABZ receptor chloride channel macromolecular complex is hypothesized to be responsible for some of the pharmacological properties of benzodiazepines, which include sedative, anxiolytic, muscle relaxant, and anticonvulsive effects in animal models. Eszopiclone binds selectively to the brain alpha subunit of the GABA A omega-1 receptor.
Mechanism of actionThe mechanism of action of Eszopiclone is not completely understood. It is thought that Eszopiclone acts on the benzodiazepine receptors as an agonist and interacts with GABA-receptor complexes.
Related Articles
AbsorptionRapidly absorbed following oral administration
Volume of distributionNot Available
Protein binding52-59%
Metabolism

Following oral administration, eszopiclone is extensively metabolized by oxidation and demethylation.

SubstrateEnzymesProduct
Eszopiclone
Zopiclone N-oxideDetails
Eszopiclone
nopiclone N-oxideDetails
Eszopiclone
zopiclone-N-oxideDetails
Eszopiclone
N-desmethylzopicloneDetails
Eszopiclone
Carbon dioxideDetails
Route of eliminationUp to 75% of an oral dose of racemic zopiclone is excreted in the urine, primarily as metabolites.
Half life6 hours
ClearanceNot Available
ToxicitySide effects include viral infection, dry mouth, dizziness, hallucinations, infection, rash, and unpleasant taste, with this relationship clearest for unpleasant taste depending on doses.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9382
Caco-2 permeable+0.5805
P-glycoprotein substrateSubstrate0.6917
P-glycoprotein inhibitor IInhibitor0.6381
P-glycoprotein inhibitor IIInhibitor0.5
Renal organic cation transporterNon-inhibitor0.6785
CYP450 2C9 substrateNon-substrate0.7158
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.6775
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorInhibitor0.8995
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.689
Ames testAMES toxic0.5332
CarcinogenicityNon-carcinogens0.9174
BiodegradationNot ready biodegradable0.9941
Rat acute toxicity2.6411 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7838
hERG inhibition (predictor II)Non-inhibitor0.5688
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Sepracor inc
  • Sepracor Inc.
Packagers
Dosage forms
FormRouteStrength
Tabletoral1 mg/1
Tabletoral2 mg/1
Tabletoral3 mg/1
Tablet, film coatedoral1 mg/1
Tablet, film coatedoral2 mg/1
Tablet, film coatedoral3 mg/1
Tabletoral1 mg
Tabletoral2 mg
Tabletoral3 mg
Tablet, coatedoral1 mg/1
Tablet, coatedoral2 mg/1
Tablet, coatedoral3 mg/1
Prices
Unit descriptionCostUnit
Lunesta 2 mg tablet8.08USD tablet
Lunesta 3 mg tablet7.28USD tablet
Lunesta 1 mg tablet7.24USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6319926 No1995-01-162012-01-16Us
US6444673 No1994-02-142014-02-14Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityvery slightly solubleNot Available
logP0.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.885 mg/mLALOGPS
logP0.97ALOGPS
logP0.81ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)13.04ChemAxon
pKa (Strongest Basic)6.89ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area91.76 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.89 m3·mol-1ChemAxon
Polarizability37.67 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 ReferencesNot Available
External Links
ATC CodesN05CF04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (252 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AprepitantThe serum concentration of Eszopiclone can be increased when it is combined with Aprepitant.
AzelastineEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Eszopiclone.
BexaroteneThe serum concentration of Eszopiclone can be decreased when it is combined with Bexarotene.
BosentanThe serum concentration of Eszopiclone can be decreased when it is combined with Bosentan.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Eszopiclone.
BuprenorphineEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
ConivaptanThe serum concentration of Eszopiclone can be increased when it is combined with Conivaptan.
DabrafenibThe serum concentration of Eszopiclone can be decreased when it is combined with Dabrafenib.
DasatinibThe serum concentration of Eszopiclone can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Eszopiclone can be decreased when it is combined with Deferasirox.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Eszopiclone.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Eszopiclone.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Eszopiclone.
EthanolEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
FluconazoleThe metabolism of Eszopiclone can be decreased when combined with Fluconazole.
FlumazenilFlumazenil may decrease the sedative activities of Eszopiclone.
FosaprepitantThe serum concentration of Eszopiclone can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Eszopiclone can be increased when it is combined with Fusidic Acid.
Gamma Hydroxybutyric AcidEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Gamma Hydroxybutyric Acid.
HydrocodoneEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Eszopiclone.
IdelalisibThe serum concentration of Eszopiclone can be increased when it is combined with Idelalisib.
IvacaftorThe serum concentration of Eszopiclone can be increased when it is combined with Ivacaftor.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Eszopiclone.
LuliconazoleThe serum concentration of Eszopiclone can be increased when it is combined with Luliconazole.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Eszopiclone.
MethotrimeprazineEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
MetyrosineEszopiclone may increase the sedative activities of Metyrosine.
MifepristoneThe serum concentration of Eszopiclone can be increased when it is combined with Mifepristone.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Eszopiclone.
MirtazapineEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
MitotaneThe serum concentration of Eszopiclone can be decreased when it is combined with Mitotane.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Eszopiclone.
NelfinavirThe metabolism of Eszopiclone can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Eszopiclone can be increased when it is combined with Netupitant.
OrphenadrineEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
PalbociclibThe serum concentration of Eszopiclone can be increased when it is combined with Palbociclib.
ParaldehydeEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Eszopiclone is combined with Paroxetine.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Eszopiclone.
PhenytoinThe metabolism of Eszopiclone can be increased when combined with Phenytoin.
PramipexoleEszopiclone may increase the sedative activities of Pramipexole.
RopiniroleEszopiclone may increase the sedative activities of Ropinirole.
RotigotineEszopiclone may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Eszopiclone.
SiltuximabThe serum concentration of Eszopiclone can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Eszopiclone can be increased when it is combined with Simeprevir.
Sodium oxybateEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Sodium oxybate.
St. John's WortThe serum concentration of Eszopiclone can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Eszopiclone can be increased when it is combined with Stiripentol.
SuvorexantEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Eszopiclone.
ThalidomideEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TocilizumabThe serum concentration of Eszopiclone can be decreased when it is combined with Tocilizumab.
ZolpidemEszopiclone may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By si...
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular Weight:
51801.395 Da
References
  1. 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 ]
  2. 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 ]
Kind
Protein
Organism
Human
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
Molecular Weight:
51325.85 Da
References
  1. 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 ]
  2. 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 ]
Kind
Protein
Organism
Human
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
Molecular Weight:
55164.055 Da
References
  1. 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 ]
  2. 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 ]
Kind
Protein
Organism
Human
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
Molecular Weight:
52145.645 Da
References
  1. 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 ]
  2. 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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Cholesterol binding
Specific Function:
Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism (PubMed:24814875), but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Was initially identified as peripheral-type benz...
Gene Name:
TSPO
Uniprot ID:
P30536
Molecular Weight:
18827.81 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Becker PM, Sattar M: Treatment of sleep dysfunction and psychiatric disorders. Curr Treat Options Neurol. 2009 Sep;11(5):349-57. [PubMed:19744401 ]
  4. Jufe GS: [New hypnotics: perspectives from sleep physiology]. Vertex. 2007 Jul-Aug;18(74):294-9. [PubMed:18265473 ]
Kind
Protein group
Organism
Human
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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Components:
NameUniProt IDDetails
Gamma-aminobutyric acid receptor subunit alpha-1P14867 Details
Gamma-aminobutyric acid receptor subunit alpha-2P47869 Details
Gamma-aminobutyric acid receptor subunit alpha-3P34903 Details
Gamma-aminobutyric acid receptor subunit alpha-4P48169 Details
Gamma-aminobutyric acid receptor subunit alpha-5P31644 Details
Gamma-aminobutyric acid receptor subunit alpha-6Q16445 Details
Gamma-aminobutyric acid receptor subunit beta-1P18505 Details
Gamma-aminobutyric acid receptor subunit beta-2P47870 Details
Gamma-aminobutyric acid receptor subunit beta-3P28472 Details
Gamma-aminobutyric acid receptor subunit deltaO14764 Details
Gamma-aminobutyric acid receptor subunit epsilonP78334 Details
Gamma-aminobutyric acid receptor subunit gamma-1Q8N1C3 Details
Gamma-aminobutyric acid receptor subunit gamma-2P18507 Details
Gamma-aminobutyric acid receptor subunit gamma-3Q99928 Details
Gamma-aminobutyric acid receptor subunit piO00591 Details
Gamma-aminobutyric acid receptor subunit thetaQ9UN88 Details
References
  1. ChEMBL Compound Report Card [Link]

Enzymes

Kind
Protein
Organism
Human
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. 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. [PubMed:19515014 ]
  2. 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. [PubMed:15039299 ]
Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. 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. [PubMed:19515014 ]
  2. 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. [PubMed:15039299 ]
Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. 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. [PubMed:19515014 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. 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. [PubMed:19515014 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10