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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014546
Secondary Accession Numbers
  • HMDB14546
Metabolite Identification
Common NameEszopiclone
DescriptionEszopiclone, 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
Data?1582753191
Synonyms
ValueSource
(+)-(5S)-6-(5-Chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazin-5-yl 4-methylpiperazine-1-carboxylateChEBI
(+)-ZopicloneChEBI
(S)-ZopicloneChEBI
EsopicloneChEBI
EstorraKegg
LunestaKegg
(+)-(5S)-6-(5-Chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazin-5-yl 4-methylpiperazine-1-carboxylic acidGenerator
Chemical FormulaC17H17ClN6O3
Average Molecular Weight388.808
Monoisotopic Molecular Weight388.105066147
IUPAC Name(5S)-6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate
Traditional Namelunesta
CAS Registry Number138729-47-2
SMILES
CN1CCN(CC1)C(=O)O[C@@H]1N(C(=O)C2=NC=CN=C12)C1=NC=C(Cl)C=C1
InChI Identifier
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
InChI KeyGBBSUAFBMRNDJC-INIZCTEOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclopyrrolones. Cyclopyrrolones 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
  • 2-heteroaryl carboxamide
  • N-methylpiperazine
  • N-alkylpiperazine
  • Aryl chloride
  • Aryl halide
  • Imidolactam
  • Pyridine
  • Pyrazine
  • Piperazine
  • 1,4-diazinane
  • Heteroaromatic compound
  • Carbamic acid ester
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactam
  • Carbonic acid derivative
  • Azacycle
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organochloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.88 g/LNot Available
LogP0.8Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.88 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.89 m³·mol⁻¹ChemAxon
Polarizability37.67 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-221.99630932474
DeepCCS[M+Na]+197.03630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EszopicloneCN1CCN(CC1)C(=O)O[C@@H]1N(C(=O)C2=NC=CN=C12)C1=NC=C(Cl)C=C13770.0Standard polar33892256
EszopicloneCN1CCN(CC1)C(=O)O[C@@H]1N(C(=O)C2=NC=CN=C12)C1=NC=C(Cl)C=C13195.2Standard non polar33892256
EszopicloneCN1CCN(CC1)C(=O)O[C@@H]1N(C(=O)C2=NC=CN=C12)C1=NC=C(Cl)C=C13197.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Eszopiclone GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bb-9212000000-b3e4c2874ff86d2544e12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Eszopiclone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Eszopiclone , positive-QTOFsplash10-0002-0190000000-979bdecccd14f99834e72017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eszopiclone 10V, Positive-QTOFsplash10-000i-0009000000-58198ad5b8e6fb5075fc2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eszopiclone 20V, Positive-QTOFsplash10-004i-5917000000-fed7a3a68ceccd2f26be2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eszopiclone 40V, Positive-QTOFsplash10-0ac0-9000000000-ef1623aed48bd5073d7b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eszopiclone 10V, Negative-QTOFsplash10-000i-0309000000-e2a958d8569e44198c062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eszopiclone 20V, Negative-QTOFsplash10-004i-1901000000-d74484c0d625330ab7cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eszopiclone 40V, Negative-QTOFsplash10-056r-9510000000-15dec99e5a95379575582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eszopiclone 10V, Positive-QTOFsplash10-000i-0009000000-8fbf9af9d2708ba6bc8c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eszopiclone 20V, Positive-QTOFsplash10-000j-0049000000-0d0bcaed2a13fc359e642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eszopiclone 40V, Positive-QTOFsplash10-03e9-2695000000-54c5cabfed200237305e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eszopiclone 10V, Negative-QTOFsplash10-000i-0019000000-8858df62be2425d6d12c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eszopiclone 20V, Negative-QTOFsplash10-000b-0296000000-2ee50c7aa4e487c881282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eszopiclone 40V, Negative-QTOFsplash10-001i-5591000000-d23576e5504d2099b1042021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00402 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00402 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00402
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID839530
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEszopiclone
METLIN IDNot Available
PubChem Compound969472
PDB IDNot Available
ChEBI ID53760
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available