Record Information
Version1.0
Creation Date2014-09-08 02:40:14 UTC
Update Date2016-11-09 01:09:10 UTC
Accession NumberCHEM003605
Identification
Common NameLoprazolam
ClassSmall Molecule
DescriptionLoprazolam (Triazulenone) marketed under the brand names Dormonoct, Havlane, Sonin, Somnovit, is a drug which is an imidazole benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. It is available in 1 mg and 2 mg tablets. It is licensed and marketed for the short term treatment of moderately severe insomnia.
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Drug
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
DormonoctKegg
Triazulenone mesylateMeSH
8-nitro-6-(O-Chlorophenyl)-1,2-dihydro-2-(N-methylpiperazin-1-yl)methylene-1H,4H-imidazo (1,2-a)(1,4)benzodiazepin-1-one methanesulfonateMeSH
TriazulenoneMeSH
Triazulenone, (Z)-isomerMeSH
Chemical FormulaC23H21ClN6O3
Average Molecular Mass464.904 g/mol
Monoisotopic Mass464.136 g/mol
CAS Registry Number61197-73-7
IUPAC Name(4Z)-9-(2-chlorophenyl)-4-[(4-methylpiperazin-1-yl)methylidene]-12-nitro-2,5,8-triazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),5,8,11,13-pentaen-3-one
Traditional Nameloprazolam
SMILES[H]\C(N1CCN(C)CC1)=C1\N=C2CN=C(C3=CC=CC=C3Cl)C3=C(C=CC(=C3)N(=O)=O)N2C1=O
InChI IdentifierInChI=1S/C23H21ClN6O3/c1-27-8-10-28(11-9-27)14-19-23(31)29-20-7-6-15(30(32)33)12-17(20)22(25-13-21(29)26-19)16-4-2-3-5-18(16)24/h2-7,12,14H,8-11,13H2,1H3/b19-14-
InChI KeyUTEFBSAVJNEPTR-RGEXLXHISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,4-benzodiazepines
Alternative Parents
Substituents
  • 1,4-benzodiazepine
  • Alpha-amino acid or derivatives
  • Nitroaromatic compound
  • N-methylpiperazine
  • N-alkylpiperazine
  • Halobenzene
  • Chlorobenzene
  • Piperazine
  • Aryl chloride
  • Imidazolinone
  • Benzenoid
  • Aryl halide
  • 1,4-diazinane
  • Monocyclic benzene moiety
  • 2-imidazoline
  • Vinylogous amide
  • C-nitro compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amino acid or derivatives
  • Ketimine
  • Organic nitro compound
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Enamine
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic zwitterion
  • Imine
  • Organooxygen compound
  • Organonitrogen compound
  • Organohalogen compound
  • Carbonyl group
  • Organochloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
  • Microsome
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
AnticonvulsantsNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.092 g/LALOGPS
logP2.8ALOGPS
logP2.68ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)19.13ChemAxon
pKa (Strongest Basic)8.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area97.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity126.87 m³·mol⁻¹ChemAxon
Polarizability48.07 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-6351bd74cc903e32a15fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-1400900000-9d17c4afce9246b44cceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gr-9400000000-8271a21835963d7b0a27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-48e97ae451c1d96f6072Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01p2-5900500000-548d28c7fcada0857245Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-9400000000-ce46d276c0d5c7b237a1Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityBenzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesLoprazolam is licensed and marketed for the short term treatment of moderately severe insomnia.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentGeneral supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended.
Concentrations
Not Available
DrugBank IDDB13643
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLoprazolam
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID3033860
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available