Zopiclone

Identification

Summary

Zopiclone is a nonbenzodiazepine hypnotic used for the short-term management of insomnia.

Brand Names
Imovane
Generic Name
Zopiclone
DrugBank Accession Number
DB01198
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 388.808
Monoisotopic: 388.105066147
Chemical Formula
C17H17ClN6O3
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 IDs
  • RP 27267
  • RP-27267

Pharmacology

Indication

For the short-term treatment of insomnia.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofInsomnia••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Zopiclone 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 action

Zopiclone 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.

TargetActionsOrganism
AGamma-aminobutyric acid receptor subunit alpha-1
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-2
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-3
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-5
potentiator
Humans
UTranslocator protein
agonist
Humans
Absorption

Rapidly absorbed following oral administration.

Volume of distribution

Not Available

Protein binding

Approximately 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.

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Elimination 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.

Clearance

Not Available

Adverse Effects
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Toxicity

Rare 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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Zopiclone.
AbametapirThe serum concentration of Zopiclone can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Zopiclone can be increased when combined with Abatacept.
AbirateroneThe metabolism of Zopiclone can be decreased when combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Zopiclone.
Food Interactions
  • Avoid alcohol. Ingesting alcohol may potentiate the CNS depressant actions of zopiclone.
  • Avoid grapefruit products. Grapefruit may reduce the CYP3A4 metabolism of zopiclone, increasing its sedative effects.

Products

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International/Other Brands
Amoban / Zimovane
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act ZopicloneTablet7.5 mgOralTEVA Canada Limited2005-11-11Not applicableCanada flag
Act ZopicloneTablet5 mgOralTEVA Canada Limited2005-11-11Not applicableCanada flag
ImovaneTablet7.5 mgOralSanofi Aventis1990-12-31Not applicableCanada flag
ImovaneTablet5.0 mgOralSanofi Aventis1998-02-102022-05-24Canada flag
M-zopicloneTablet7.5 mgOralMantra Pharma Inc2018-04-16Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-zopicloneTablet3.75 mgOralAngita Pharma Inc.2018-12-21Not applicableCanada flag
Ag-zopicloneTablet7.5 mgOralAngita Pharma Inc.2018-07-25Not applicableCanada flag
Ag-zopicloneTablet5 mgOralAngita Pharma Inc.2018-07-25Not applicableCanada flag
Apo-zopicloneTablet7.5 mgOralApotex Corporation1996-09-19Not applicableCanada flag
Apo-zopicloneTablet5 mgOralApotex Corporation2002-06-04Not applicableCanada flag

Categories

ATC Codes
N05CF01 — Zopiclone
Drug Categories
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
pyrrolopyrazine, monochloropyridine (CHEBI:32315)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
03A5ORL08Q
CAS number
43200-80-2
InChI Key
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

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Julou L, Bardone MC, Blanchard JC, Garret C, Stutzmann JM: Pharmacological studies on zopiclone. Pharmacology. 1983;27 Suppl 2:46-58. [Article]
Human Metabolome Database
HMDB0015329
KEGG Drug
D01372
PubChem Compound
5735
PubChem Substance
46505233
ChemSpider
5533
BindingDB
50054136
RxNav
40001
ChEBI
32315
ChEMBL
CHEMBL135400
Therapeutic Targets Database
DAP000427
PharmGKB
PA10236
Drugs.com
Drugs.com Drug Page
Wikipedia
Zopiclone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAnxiety1
4CompletedTreatmentInsomnia1
4CompletedTreatmentInsomnia / Sleep1
4TerminatedSupportive CareSleep Apnea, Central / Ventricular Dysfunction1
3CompletedTreatmentBalance1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Centaur Pharmaceuticals Pvt Ltd.
Dosage Forms
FormRouteStrength
TabletOral
TabletOral5 mg
TabletOral7.5 mg
TabletOral5.0 mg
Tablet, film coatedOral7.5 MG
TabletOral3.75 mg
Tablet, coatedOral
Tablet, film coatedOral3.75 MG
Tablet, coatedOral7.5 mg
Tablet, coatedOral750000 mg
Tablet, film coatedOral
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)178 °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
logP0.52Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.04Chemaxon
pKa (Strongest Basic)6.86Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area91.76 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity95.89 m3·mol-1Chemaxon
Polarizability38.22 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-05bb-9212000000-b3e4c2874ff86d2544e1
Mass Spectrum (Electron Ionization)MSsplash10-0007-6950000000-c1583a92e3cbc5066186
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kb-0090000000-9d80e08080f406848221
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0092000000-977d45f9a516242be80f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0090000000-397a508c11f66c161327
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014j-0090000000-abc6a676659114a83d08
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0790000000-74d7c73e854e61700433
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00lr-0920000000-2c17f6282d1031cb4d50
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-c0f92aba9374337ff737
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-003r-5900000000-46755df8b5cfb7f46bf9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-9300000000-091d5434bc674d5bf9a4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-9000000000-87365fa01fb0854897ca
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-ecc43b453bcef84eb6dd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0019000000-856593370c65f718fda8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0019000000-1e8ff416debdbb051176
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-056a-0394000000-3169034c01e3fd5ad2c9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-1945000000-a1bb6829667ca9894ef3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0019-9621000000-be3e21df1b3a2d39364c
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-198.1988232
predicted
DarkChem Lite v0.1.0
[M-H]-185.05937
predicted
DeepCCS 1.0 (2019)
[M+H]+199.0918232
predicted
DarkChem Lite v0.1.0
[M+H]+187.57133
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.7405232
predicted
DarkChem Lite v0.1.0
[M+Na]+194.7325
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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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
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-2
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-3
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-5
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
Curator comments
This is a potential target based on the benzodiazepine drug-class mechanism, however, direct evidence is not readily available in the literature.
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 l...
Gene Name
TSPO
Uniprot ID
P30536
Uniprot Name
Translocator protein
Molecular Weight
18827.81 Da
References
  1. Rupprecht R, Papadopoulos V, Rammes G, Baghai TC, Fan J, Akula N, Groyer G, Adams D, Schumacher M: Translocator protein (18 kDa) (TSPO) as a therapeutic target for neurological and psychiatric disorders. Nat Rev Drug Discov. 2010 Dec;9(12):971-88. doi: 10.1038/nrd3295. [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
  1. 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]
  2. 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]
  3. IMOVANE (Zopiclone) Product Monograph [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
  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. [Article]
  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. [Article]
  3. 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]
  4. IMOVANE (Zopiclone) Product Monograph [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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
Kind
Protein
Organism
Humans
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 gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48