Cloxazolam (CHEM003529)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2014-08-30 21:05:48 UTC
Update Date2016-11-09 01:09:09 UTC
Accession NumberCHEM003529
Identification
Common NameCloxazolam
ClassSmall Molecule
DescriptionCloxazolam is a benzodiazepine with anxiolytic, sedative/hypnotic, muscle relaxant, and antiepileptic effects. It is marketed in the Argentina, Australia, Portugal, Belgium, Switzerland, Luxembourg, Germany, Taiwan and Japan -- mainly for anti-anxiety. The usual dose of cloxazolam in adults is 3-12mg/day for anti-anxiety. Although less commonly noted, it has also been reported as clinically effective in the treatment of depression, schizophrenia, and neurosis. As well, it has also been studied in Japan in doses of 15-30mg/day as an adjunct in the treatment of intractable epilepsy, for which it has demonstrated effectiveness.
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Benzodiazepine
  • Drug
  • Ether
  • Hypnotic and Sedative
  • Neuromuscular Agent
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SepazonKegg
OlcadilMeSH
10-chloro-11b-(2-Chlorophenyl)-2,3,5,6,7,11b-hexahydrobenzo(6,7)-1,4-diazepino(5,4-b)oxazol-6-oneMeSH
10-chloro-11b-(2-Chlorophenyl)-2,3,7,11b(5H)-tetrahydro-oxazolo(3,2-D)(1,4)benzodiazepine-6-oneMeSH
Former cas registry number OF cloxazolamMeSH
Chemical FormulaC17H14Cl2N2O2
Average Molecular Mass349.211 g/mol
Monoisotopic Mass348.043 g/mol
CAS Registry Number24166-13-0
IUPAC Name13-chloro-2-(2-chlorophenyl)-3-oxa-6,9-diazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),11,13-trien-8-one
Traditional Namecloxazolam
SMILESClC1=CC2=C(NC(=O)CN3CCOC23C2=CC=CC=C2Cl)C=C1
InChI IdentifierInChI=1S/C17H14Cl2N2O2/c18-11-5-6-15-13(9-11)17(12-3-1-2-4-14(12)19)21(7-8-23-17)10-16(22)20-15/h1-6,9H,7-8,10H2,(H,20,22)
InChI KeyZIXNZOBDFKSQTC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,3-oxazolobenzo-1,4-diazepines. These are aromatic heteropolycyclic compounds containing a 1,3-oxazole ring fused to the 1,-4-diazepine moiety of a 1,4-benzodiazepine ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,3-oxazolobenzo-1,4-diazepines
Alternative Parents
Substituents
  • 1,3-oxazolobenzo-1,4-diazepine
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Cyclic carboximidic acid
  • Oxazolidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point202-204°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP3.56ALOGPS
logP4.13ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.69ChemAxon
pKa (Strongest Basic)2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.05 m³·mol⁻¹ChemAxon
Polarizability33.62 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4u-5691000000-8bb3e7cf2ded84037340Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-ca402478d99c37c19b25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0019000000-9a3935cb9c7797213c9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-1961000000-e20556ccb3c2898cfe7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-2b25bbd53c59b8f11315Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-e76b768dbe8c36250ee1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-8798000000-c105d9d5ffe1a2275eb5Spectrum
MSMass Spectrum (Electron Ionization)splash10-0bt9-1493000000-ab9e03b63d47a52579abSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityCloxazolam is a long acting benzodiazepine. It acts as a prodrug, with pharmacologically active metabolites, which bind to to the GABAa receptor, which other benzodiazepines bind to, to illicit a physiological response.
MetabolismCloxazolam is metabolised by the liver into the active metabolite chlordesmethyldiazepam (delorazepam). [5] Route of Elimination: Renal elimination. Half Life: 65 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed primarily as an anti-anxiety agent. Typically used short term, and may be given as a single dose of up to 100mcg/kg to reduce anxiety and tension experienced prior to surgery.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsDrowsiness and ataxia are dose related. Central nervous system toxicity may result in respiratory depression and loss of consciousness. As such, pre-existing central nervous system depression and severe hepatic impairment are two particular contraindications for use.
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 IDDB01553
HMDB IDHMDB0259410
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCloxazolam
Chemspider ID2714
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Tachikawa, R., Takagi, H., Kamioka, T., Fukunaga, M., Kawano, Y. and Miyadera, T.; US. Patents 3,696,094; October 3,1972; and 3,772,371; November 13, 1973; both assigned to Sankyo Company Limited, Japan.

MSDSNot Available
General ReferencesNot Available