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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:46:17 UTC
Update Date2019-07-23 06:35:11 UTC
HMDB IDHMDB0041890
Secondary Accession Numbers
  • HMDB41890
Metabolite Identification
Common NameEtizolam
DescriptionAccording to the Italian P.I. sheet etizolam belongs to a new class of diazepines, thienotriazolodiazepines. This new class is easily oxidized, rapidly metabolized, and has a lower risk of accumulation, even after prolonged treatment. Etizolam has an anxiolytic action about 6 times greater than that of diazepam. Etizolam produces, especially at higher dosages, a reduction in time taken to fall asleep, an increase in total sleep time and a reduction in the number of awakenings. During tests there were not substantial changes in deep sleep. There is a reduction of REM sleep. In EEG tests of healthy volunteers Etizolam showed some characteristics of tricyclic antidepressants. Etizolam (marketed under the brand name Etilaam, Etizola, Sedekopan, Pasaden or Depas) is a thienodiazepine drug which is a benzodiazepine analog. The etizolam molecule differs from a benzodiazepine in that the benzene ring has been replaced by a thiophene ring. It possesses amnesic, anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties.
Structure
Data?1563863711
Synonyms
ValueSource
SedekopanKegg
Etizolam fine granulesHMDB
Etizolam tabletsHMDB
Etizolam, 14C-labeledHMDB
Chemical FormulaC17H15ClN4S
Average Molecular Weight342.846
Monoisotopic Molecular Weight342.070594897
IUPAC Name7-(2-chlorophenyl)-4-ethyl-13-methyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.0²,⁶]trideca-2(6),4,7,10,12-pentaene
Traditional Nameetizolam
CAS Registry Number40054-69-1
SMILES
CCC1=CC2=C(S1)N1C(C)=NN=C1CN=C2C1=CC=CC=C1Cl
InChI Identifier
InChI=1S/C17H15ClN4S/c1-3-11-8-13-16(12-6-4-5-7-14(12)18)19-9-15-21-20-10(2)22(15)17(13)23-11/h4-8H,3,9H2,1-2H3
InChI KeyVMZUTJCNQWMAGF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thienodiazepines. These are heteropolycyclic containing a thiophene ring fused to a diazepine ring. Thiophene is 5-membered ring consisting of four carbon and one sulfur atoms. Diazepine is a 7-membered ring consisting of five carbon and two nitrogen atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThienodiazepines
Sub ClassNot Available
Direct ParentThienodiazepines
Alternative Parents
Substituents
  • Thieno-para-diazepine
  • 2,3,5-trisubstituted thiophene
  • Para-diazepine
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Azole
  • 1,2,4-triazole
  • Thiophene
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Imine
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP10(2.98) g/LALOGPS
logP10(2.98) g/LChemAxon
logS10(-3.9) g/LALOGPS
pKa (Strongest Acidic)18.28ChemAxon
pKa (Strongest Basic)4.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity104.72 m³·mol⁻¹ChemAxon
Polarizability35.64 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Etizolam GC-MS (Non-derivatized) - 70eV, Positivesplash10-06tf-8189000000-7a2ceb12ff7824adfa152017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etizolam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etizolam 10V, Positive-QTOFsplash10-0006-0039000000-6aa13f3ed55cdf58c0b32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etizolam 20V, Positive-QTOFsplash10-0006-1119000000-93d7efb06b709134261b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etizolam 40V, Positive-QTOFsplash10-052p-6941000000-d4507f862b8b2305babe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etizolam 10V, Negative-QTOFsplash10-000f-0069000000-275219bc80bff427a3da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etizolam 20V, Negative-QTOFsplash10-001i-0192000000-c324182ddc3f898153362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etizolam 40V, Negative-QTOFsplash10-03nm-0890000000-c508188c0bd16231d74d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etizolam 10V, Negative-QTOFsplash10-0006-0009000000-fa3ca2e1cd79c37341942021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etizolam 20V, Negative-QTOFsplash10-000x-4039000000-48e95c6351ad62de00cd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etizolam 40V, Negative-QTOFsplash10-001j-8293000000-65ab65f011e0fe3e35322021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etizolam 10V, Positive-QTOFsplash10-0006-0009000000-7a706823cbf79cb06f312021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etizolam 20V, Positive-QTOFsplash10-0006-0009000000-860d3e752f1da782d5042021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etizolam 40V, Positive-QTOFsplash10-03fs-4698000000-1e803a56b7dcb176ceda2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 IDDB09166
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3191
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEtizolam
METLIN IDNot Available
PubChem Compound3307
PDB IDNot Available
ChEBI IDNot Available
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