Oxazolam (CHEM003609)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2014-09-08 02:40:55 UTC
Update Date2016-11-09 01:09:10 UTC
Accession NumberCHEM003609
Identification
Common NameOxazolam
ClassSmall Molecule
DescriptionOxazolam is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. It is a prodrug for desmethyldiazepam.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Drug
  • Ether
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC18H17ClN2O2
Average Molecular Mass328.793 g/mol
Monoisotopic Mass328.098 g/mol
CAS Registry Number24143-17-7
IUPAC Name(2S,4R)-13-chloro-4-methyl-2-phenyl-3-oxa-6,9-diazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),8,11,13-tetraen-8-ol
Traditional Nameoxazolam
SMILES[H][C@@]1(C)CN2CC(O)=NC3=C(C=C(Cl)C=C3)[C@@]2(O1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C18H17ClN2O2/c1-12-10-21-11-17(22)20-16-8-7-14(19)9-15(16)18(21,23-12)13-5-3-2-4-6-13/h2-9,12H,10-11H2,1H3,(H,20,22)/t12-,18+/m1/s1
InChI KeyVCCZBYPHZRWKFY-XIKOKIGWSA-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
  • Alpha-amino acid or derivatives
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxazolidine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Lactam
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.047 g/LALOGPS
logP2.9ALOGPS
logP4.52ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)2.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.42 m³·mol⁻¹ChemAxon
Polarizability33.72 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-004i-0009000000-24513d579c89720abe56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0019000000-a373f8e65433527acd68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-7940000000-e0e8ca100da998be3deeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-8bd2568d91a72c0116f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0059000000-a04ec06ad36c3fab9d8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9440000000-09641ffca0adcefa4f43Spectrum
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/SourcesNot Available
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 IDNot Available
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 LinkOxazolam
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID62779
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available