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Identification
NameZopiclone
Accession NumberDB01198  (APRD00356)
TypeSmall Molecule
GroupsApproved
Description

Zopiclone is a novel hypnotic agent used in the treatment of insomnia. Its mechanism of action is based on modulating benzodiazepine receptors. In addition to zopiclone’s benzodiazepine pharmacological properties it also has some barbiturate like properties.

Structure
Thumb
Synonyms
(+-)-zopiclone
(±)-zopiclone
6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl-1-piperazinecarboxylate
Zopiclona
Zopiclone
Zopiclonum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Zopiclonetablet7.5 mgoralActavis Pharma Company2005-11-11Not applicableCanada
Act Zopiclonetablet5 mgoralActavis Pharma Company2005-11-11Not applicableCanada
Ava-zopiclonetablet7.5 mgoralAvanstra Inc2011-09-092014-08-21Canada
Ava-zopiclonetablet5 mgoralAvanstra Inc2011-08-112014-08-21Canada
Dom-zopiclonetablet7.5 mgoralDominion Pharmacal1999-11-23Not applicableCanada
Dom-zopiclonetablet5 mgoralDominion Pharmacal2009-05-25Not applicableCanada
Imovane - Tab 5mgtablet5.0 mgoralSanofi Aventis Canada Inc1998-02-10Not applicableCanada
Imovane 7.5 - Tab 7.5mgtablet7.5 mgoralSanofi Aventis Canada Inc1990-12-31Not applicableCanada
Ipg-zopiclonetablet7.5 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Ipg-zopiclonetablet5 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Jamp-zopiclonetablet5 mgoralJamp Pharma CorporationNot applicableNot applicableCanada
Jamp-zopiclonetablet7.5 mgoralJamp Pharma Corporation2011-11-02Not applicableCanada
Jamp-zopiclone Tabletstablet5 mgoralJamp Pharma Corporation2014-01-08Not applicableCanada
Jamp-zopiclone Tabletstablet7.5 mgoralJamp Pharma Corporation2014-11-19Not applicableCanada
Mar-zopiclonetablet7.5 mgoralMarcan Pharmaceuticals Inc2013-04-17Not applicableCanada
Mar-zopiclonetablet5 mgoralMarcan Pharmaceuticals Inc2013-04-17Not applicableCanada
Mint-zopiclonetablet5 mgoralMint Pharmaceuticals Inc2012-10-10Not applicableCanada
Mint-zopiclonetablet7.5 mgoralMint Pharmaceuticals Inc2012-10-10Not applicableCanada
Mylan-zopiclonetablet5 mgoralMylan Pharmaceuticals Ulc2007-06-27Not applicableCanada
Mylan-zopiclonetablet7.5 mgoralMylan Pharmaceuticals Ulc1998-08-12Not applicableCanada
Novo-zopiclonetablet7.5 mgoralNovopharm Limited2004-08-192015-10-26Canada
Novo-zopiclonetablet5 mgoralNovopharm Limited2004-08-192015-10-26Canada
Ntp-zopiclonetablet3.75 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-zopiclonetablet7.5 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-zopiclonetablet5 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Nu-zopiclonetablet7.5 mgoralNu Pharm IncNot applicableNot applicableCanada
Nu-zopiclonetablet5 mgoralNu Pharm IncNot applicableNot applicableCanada
Nu-zopiclone Tablets - 7.5mgtablet7.5 mgoralNu Pharm Inc1998-03-052012-09-04Canada
PHL-zopiclonetablet7.5 mgoralPharmel Inc2009-09-09Not applicableCanada
PHL-zopiclonetablet5 mgoralPharmel Inc2009-08-28Not applicableCanada
PMS-zopiclonetablet5 mgoralPharmascience Inc2001-02-15Not applicableCanada
PMS-zopiclonetablet7.5 mgoralPharmascience Inc1999-08-04Not applicableCanada
Priva-zopiclonetablet7.5 mgoralPharmapar Inc2015-06-03Not applicableCanada
Priva-zopiclonetablet5 mgoralPharmapar Inc2015-06-03Not applicableCanada
Pro-zopiclonetablet7.5 mgoralPro Doc Limitee2008-07-09Not applicableCanada
Pro-zopiclonetablet5 mgoralPro Doc Limitee2008-07-09Not applicableCanada
Q-zopiclonetablet5 mgoralQd Pharmaceuticals UlcNot applicableNot applicableCanada
Q-zopiclonetablet7.5 mgoralQd Pharmaceuticals Ulc2011-11-242015-08-21Canada
Ran-zopiclonetablet7.5 mgoralRanbaxy Pharmaceuticals Canada Inc.2005-07-05Not applicableCanada
Ran-zopiclonetablet5 mgoralRanbaxy Pharmaceuticals Canada Inc.2005-07-05Not applicableCanada
Ratio-zopiclonetablet7.5 mgoralTeva Canada Limited2001-04-18Not applicableCanada
Ratio-zopiclonetablet3.75 mgoralTeva Canada Limited2002-07-29Not applicableCanada
Ratio-zopiclonetablet5 mgoralTeva Canada Limited2002-12-18Not applicableCanada
Rhovanetablet7.5 mgoralSandoz Canada Incorporated1996-12-31Not applicableCanada
Riva Zopiclonetablet5 mgoralLaboratoire Riva Inc2006-10-10Not applicableCanada
Riva Zopiclonetablet7.5 mgoralLaboratoire Riva Inc2008-11-14Not applicableCanada
Sandoz Zopiclonetablet7.5 mgoralSandoz Canada Incorporated2004-08-18Not applicableCanada
Sandoz Zopiclonetablet5 mgoralSandoz Canada Incorporated2004-08-18Not applicableCanada
Septa-zopiclonetablet7.5 mgoralSepta Pharmaceuticals Inc2013-02-25Not applicableCanada
Septa-zopiclonetablet5 mgoralSepta Pharmaceuticals Inc2013-02-25Not applicableCanada
Si-zopiclonetablet7.5 mgoralSilas Healthcare IncNot applicableNot applicableCanada
Si-zopiclonetablet5 mgoralSilas Healthcare IncNot applicableNot applicableCanada
Zoclonetablet7.5 mgoralPrempharm Inc2004-09-162005-08-05Canada
Zopiclonetablet5 mgoralSanis Health Inc2010-02-25Not applicableCanada
Zopiclonetablet7.5 mgoralMeliapharm Inc2010-09-032014-06-25Canada
Zopiclonetablet7.5 mgoralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Zopiclonetablet5 mgoralMeliapharm Inc2010-09-032014-06-25Canada
Zopiclonetablet5 mgoralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Zopiclonetablet7.5 mgoralAbri Pharmaceuticals IncNot applicableNot applicableCanada
Zopiclonetablet5 mgoralAbri Pharmaceuticals IncNot applicableNot applicableCanada
Zopiclonetablet7.5 mgoralApotex IncNot applicableNot applicableCanada
Zopiclonetablet7.5 mgoralSivem Pharmaceuticals Ulc2012-06-11Not applicableCanada
Zopiclonetablet5 mgoralApotex IncNot applicableNot applicableCanada
Zopiclonetablet7.5 mgoralSanis Health Inc2010-02-25Not applicableCanada
Zopiclonetablet5 mgoralSivem Pharmaceuticals Ulc2012-06-11Not applicableCanada
Zopiclone-7.5 - Tab 7.5mgtablet7.5 mgoralPro Doc Limitee1997-06-252010-07-13Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-zopiclonetablet5 mgoralApotex Inc2002-06-04Not applicableCanada
Apo-zopiclone - Tab 7.5mgtablet7.5 mgoralApotex Inc1996-09-19Not applicableCanada
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AmobanNot Available
ImovaneNot Available
ZimovaneNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII03A5ORL08Q
CAS number43200-80-2
WeightAverage: 388.808
Monoisotopic: 388.105066147
Chemical FormulaC17H17ClN6O3
InChI KeyInChIKey=GBBSUAFBMRNDJC-UHFFFAOYSA-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
IUPAC Name
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)OC1N(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 DescriptorsNot Available
Pharmacology
IndicationFor the short-term treatment of insomnia.
PharmacodynamicsZopiclone is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class and is indicated for the short-term treatment of insomnia. While Zopiclone 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. Zopiclone binds selectively to the brain alpha subunit of the GABA A omega-1 receptor.
Mechanism of actionZopiclone exerts its action by binding on the benzodiazepine receptor complex and modulation of the GABABZ receptor chloride channel macromolecular complex. Both zopiclone and benzodiazepines act indiscriminately at the benzodiazepine binding site on α1, α2, α3 and α5 GABAA containing receptors as full agonists causing an enhancement of the inhibitory actions of GABA to produce the therapeutic (hypnotic and anxiolytic) and adverse effects of zopiclone.
Related Articles
AbsorptionRapidly absorbed following oral administration.
Volume of distributionNot Available
Protein bindingApproximately 45%
Metabolism

Extensively metabolized in the liver via decarboxylation (major pathway), demethylation, and side chain oxidation. Metabolites include an N-oxide derivative (weakly active; approximately 12% of a dose) and an N-desmethyl metabolite (inactive; approximately 16%). Approximately 50% of a dose is converted to other inactive metabolites via decarboxylation. Hepatic microsomal enzymes are apparently not involved in zopiclone clearance.

SubstrateEnzymesProduct
Zopiclone
Zopiclone N-oxideDetails
Zopiclone
Carbon dioxideDetails
Zopiclone
zopiclone-N-oxideDetails
Zopiclone
N-desmethylzopicloneDetails
Route of eliminationNot Available
Half lifeElimination half life is approximately 5 hours (range 3.8 to 6.5 hours) and is prolonged to 11.9 hours in patients with hepatic insufficiency.
ClearanceNot Available
ToxicityRare individual instances of fatal outcomes following overdose with racemic zopiclone have been reported in European postmarketing reports, most often associated with overdose with other CNS-depressant agent. Signs and symptoms of overdose effects of CNS depressants can be expected to present as exaggerations of the pharmacological effects noted in preclinical testing.
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
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral5.0 mg
Tabletoral7.5 mg
Tabletoral5 mg
Tabletoral3.75 mg
Prices
Unit descriptionCostUnit
Imovane 7.5 mg Tablet1.41USD tablet
Imovane 5 mg Tablet1.11USD tablet
Apo-Zopiclone 7.5 mg Tablet0.49USD tablet
Co Zopiclone 7.5 mg Tablet0.49USD tablet
Mylan-Zopiclone 7.5 mg Tablet0.49USD tablet
Novo-Zopiclone 7.5 mg Tablet0.49USD tablet
Nu-Zopiclone 7.5 mg Tablet0.49USD tablet
Pms-Zopiclone 7.5 mg Tablet0.49USD tablet
Ran-Zopiclone 7.5 mg Tablet0.49USD tablet
Ratio-Zopiclone 7.5 mg Tablet0.49USD tablet
Rhovane 7.5 mg Tablet0.49USD tablet
Sandoz Zopiclone 7.5 mg Tablet0.49USD tablet
Zopiclone 7.5 mg Tablet0.49USD tablet
Apo-Zopiclone 5 mg Tablet0.23USD tablet
Co Zopiclone 5 mg Tablet0.23USD tablet
Mylan-Zopiclone 5 mg Tablet0.23USD tablet
Novo-Zopiclone 5 mg Tablet0.23USD tablet
Pms-Zopiclone 5 mg Tablet0.23USD tablet
Ran-Zopiclone 5 mg Tablet0.23USD tablet
Ratio-Zopiclone 5 mg Tablet0.23USD tablet
Sandoz Zopiclone 5 mg Tablet0.23USD tablet
Zopiclone 5 mg Tablet0.23USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point178 °CPhysProp
water solubility0.151 mg/mL at 25 °CMEYLAN,WM et al. (1996)
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
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-0007-6950000000-c1583a92e3cbc5066186View in MoNA
1D NMR13C NMR SpectrumNot Available
References
Synthesis Reference

Thomas Jerussi, “Compositions comprising zopiclone derivatives and methods of making and using the same.” U.S. Patent US20040147521, issued July 29, 2004.

US20040147521
General References
  1. Liu HJ, Sato K, Shih HC, Shibuya T, Kawamoto H, Kitagawa H: Pharmacologic studies of the central action of zopiclone: effects on locomotor activity and brain monoamines in rats. Int J Clin Pharmacol Ther Toxicol. 1985 Mar;23(3):121-8. [PubMed:2581904 ]
  2. Sato K, Hong YL, Yang MS, Shibuya T, Kawamoto H, Kitagawa H: Pharmacologic studies of central actions of zopiclone: influence on brain monoamines in rats under stressful condition. Int J Clin Pharmacol Ther Toxicol. 1985 Apr;23(4):204-10. [PubMed:2860074 ]
  3. Dundar Y, Dodd S, Strobl J, Boland A, Dickson R, Walley T: Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis. Hum Psychopharmacol. 2004 Jul;19(5):305-22. [PubMed:15252823 ]
  4. Blanchard JC, Julou L: Suriclone: a new cyclopyrrolone derivative recognizing receptors labeled by benzodiazepines in rat hippocampus and cerebellum. J Neurochem. 1983 Mar;40(3):601-7. [PubMed:6298365 ]
  5. Julou L, Bardone MC, Blanchard JC, Garret C, Stutzmann JM: Pharmacological studies on zopiclone. Pharmacology. 1983;27 Suppl 2:46-58. [PubMed:6142468 ]
External Links
ATC CodesN05CF01
AHFS Codes
  • 28:24.92
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AprepitantThe serum concentration of Zopiclone can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of Zopiclone can be increased when it is combined with Atazanavir.
AzelastineZopiclone 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 Zopiclone.
BexaroteneThe serum concentration of Zopiclone can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Zopiclone can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Zopiclone can be decreased when it is combined with Bosentan.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Zopiclone.
BuprenorphineZopiclone may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
CeritinibThe serum concentration of Zopiclone can be increased when it is combined with Ceritinib.
ClarithromycinThe serum concentration of Zopiclone can be increased when it is combined with Clarithromycin.
CobicistatThe serum concentration of Zopiclone can be increased when it is combined with Cobicistat.
ConivaptanThe serum concentration of Zopiclone can be increased when it is combined with Conivaptan.
CrizotinibThe serum concentration of Zopiclone can be increased when it is combined with Crizotinib.
DabrafenibThe serum concentration of Zopiclone can be decreased when it is combined with Dabrafenib.
DapsoneThe risk or severity of adverse effects can be increased when Dapsone is combined with Zopiclone.
DarunavirThe serum concentration of Zopiclone can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Zopiclone can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Zopiclone can be decreased when it is combined with Deferasirox.
DelavirdineThe serum concentration of Zopiclone can be increased when it is combined with Delavirdine.
DiltiazemThe serum concentration of Zopiclone can be increased when it is combined with Diltiazem.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Zopiclone.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Zopiclone.
DronedaroneThe serum concentration of Zopiclone can be increased when it is combined with Dronedarone.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Zopiclone.
ErythromycinThe serum concentration of Zopiclone can be increased when it is combined with Erythromycin.
EthanolThe risk or severity of adverse effects can be increased when Ethanol is combined with Zopiclone.
FluconazoleThe serum concentration of Zopiclone can be increased when it is combined with Fluconazole.
FlumazenilFlumazenil may decrease the sedative activities of Zopiclone.
FosamprenavirThe serum concentration of Zopiclone can be increased when it is combined with Fosamprenavir.
FosaprepitantThe serum concentration of Zopiclone can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Zopiclone can be increased when it is combined with Fusidic Acid.
HydrocodoneZopiclone may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Zopiclone.
IdelalisibThe serum concentration of Zopiclone can be increased when it is combined with Idelalisib.
ImatinibThe serum concentration of Zopiclone can be increased when it is combined with Imatinib.
IndinavirThe serum concentration of Zopiclone can be increased when it is combined with Indinavir.
IsavuconazoniumThe serum concentration of Zopiclone can be increased when it is combined with Isavuconazonium.
ItraconazoleThe serum concentration of Zopiclone can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Zopiclone can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Zopiclone can be increased when it is combined with Ketoconazole.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Zopiclone.
LuliconazoleThe serum concentration of Zopiclone can be increased when it is combined with Luliconazole.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Zopiclone.
MethotrimeprazineZopiclone may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
MetyrosineZopiclone may increase the sedative activities of Metyrosine.
MifepristoneThe serum concentration of Zopiclone can be increased when it is combined with Mifepristone.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Zopiclone.
MirtazapineZopiclone may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
MitotaneThe serum concentration of Zopiclone can be decreased when it is combined with Mitotane.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Zopiclone.
NefazodoneThe serum concentration of Zopiclone can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Zopiclone can be increased when it is combined with Nelfinavir.
NilotinibThe serum concentration of Zopiclone can be increased when it is combined with Nilotinib.
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Zopiclone.
OrphenadrineZopiclone may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
PalbociclibThe serum concentration of Zopiclone can be increased when it is combined with Palbociclib.
ParaldehydeZopiclone may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Zopiclone is combined with Paroxetine.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Zopiclone.
PhenytoinThe metabolism of Zopiclone can be increased when combined with Phenytoin.
PosaconazoleThe serum concentration of Zopiclone can be increased when it is combined with Posaconazole.
PramipexoleZopiclone may increase the sedative activities of Pramipexole.
PrilocaineThe risk or severity of adverse effects can be increased when Zopiclone is combined with Prilocaine.
RitonavirThe serum concentration of Zopiclone can be increased when it is combined with Ritonavir.
RopiniroleZopiclone may increase the sedative activities of Ropinirole.
RotigotineZopiclone may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Zopiclone.
SaquinavirThe serum concentration of Zopiclone can be increased when it is combined with Saquinavir.
SiltuximabThe serum concentration of Zopiclone can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Zopiclone can be increased when it is combined with Simeprevir.
Sodium NitriteThe risk or severity of adverse effects can be increased when Zopiclone is combined with Sodium Nitrite.
Sodium oxybateZopiclone may increase the central nervous system depressant (CNS depressant) activities of Sodium oxybate.
St. John's WortThe serum concentration of Zopiclone can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Zopiclone can be increased when it is combined with Stiripentol.
SuvorexantZopiclone may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Zopiclone.
TelaprevirThe serum concentration of Zopiclone can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Zopiclone can be increased when it is combined with Telithromycin.
ThalidomideZopiclone may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TocilizumabThe serum concentration of Zopiclone can be decreased when it is combined with Tocilizumab.
VerapamilThe serum concentration of Zopiclone can be increased when it is combined with Verapamil.
VoriconazoleThe serum concentration of Zopiclone can be increased when it is combined with Voriconazole.
ZolpidemZopiclone 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 ]
  3. Sanger DJ: The pharmacology and mechanisms of action of new generation, non-benzodiazepine hypnotic agents. CNS Drugs. 2004;18 Suppl 1:9-15; discussion 41, 43-5. [PubMed:15291009 ]
  4. Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [PubMed:6135616 ]
  5. Ramerstorfer J, Furtmuller R, Vogel E, Huck S, Sieghart W: The point mutation gamma 2F77I changes the potency and efficacy of benzodiazepine site ligands in different GABAA receptor subtypes. Eur J Pharmacol. 2010 Jun 25;636(1-3):18-27. doi: 10.1016/j.ejphar.2010.03.015. Epub 2010 Mar 19. [PubMed:20303942 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
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 ]
  3. Ramerstorfer J, Furtmuller R, Vogel E, Huck S, Sieghart W: The point mutation gamma 2F77I changes the potency and efficacy of benzodiazepine site ligands in different GABAA receptor subtypes. Eur J Pharmacol. 2010 Jun 25;636(1-3):18-27. doi: 10.1016/j.ejphar.2010.03.015. Epub 2010 Mar 19. [PubMed:20303942 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
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 ]
  3. Ramerstorfer J, Furtmuller R, Vogel E, Huck S, Sieghart W: The point mutation gamma 2F77I changes the potency and efficacy of benzodiazepine site ligands in different GABAA receptor subtypes. Eur J Pharmacol. 2010 Jun 25;636(1-3):18-27. doi: 10.1016/j.ejphar.2010.03.015. Epub 2010 Mar 19. [PubMed:20303942 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
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 ]
  3. Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [PubMed:6135616 ]
  4. Ramerstorfer J, Furtmuller R, Vogel E, Huck S, Sieghart W: The point mutation gamma 2F77I changes the potency and efficacy of benzodiazepine site ligands in different GABAA receptor subtypes. Eur J Pharmacol. 2010 Jun 25;636(1-3):18-27. doi: 10.1016/j.ejphar.2010.03.015. Epub 2010 Mar 19. [PubMed:20303942 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
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 ]

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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. 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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. 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 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13