Halazepam (CHEM002274)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:40 UTC
Update Date2026-03-27 01:49:55 UTC
Accession NumberCHEM002274
Identification
Common NameHalazepam
ClassSmall Molecule
DescriptionHalazepam is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. It is a trifluoromethyl derivative of nordazepam. While its structure may be similar to chlordiazepoxide and diazepam, it has both less toxicity and less tendency to cause paradoxical hostility and aggression than either of them. Halazepam is no longer marketed in the United States, and was withdrawn by Schering-Plough due to poor sales. [Wikipedia]
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Anti-Anxiety Agent
  • Benzodiazepine
  • Drug
  • Hypnotic and Sedative
  • Metabolite
  • Muscle Relaxant
  • Neuromuscular Agent
  • Organic Compound
  • Organochloride
  • Organofluoride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PaxipamKegg
Chemical FormulaC17H12ClF3N2O
Average Molecular Mass352.738 g/mol
Monoisotopic Mass352.059 g/mol
CAS Registry Number23092-17-3
IUPAC Name7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
Traditional Namehalazepam
SMILESFC(F)(F)CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1
InChI IdentifierInChI=1S/C17H12ClF3N2O/c18-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)22-9-15(24)23(14)10-17(19,20)21/h1-8H,9-10H2
InChI KeyWYCLKVQLVUQKNZ-UHFFFAOYSA-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
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Ketimine
  • Lactam
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Alkyl fluoride
  • Organochloride
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Imine
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alkyl halide
  • 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 Point165°C
Boiling PointNot Available
Solubility1.70e-03 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP3.52ALOGPS
logP4.03ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)18.88ChemAxon
pKa (Strongest Basic)2.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity85.26 m³·mol⁻¹ChemAxon
Polarizability31.82 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05rr-3195000000-ee23c72fc85d145762eaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-3613dceb7b1256e06244Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0069000000-8dabf1a4514ba621b833Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9370000000-a894bef7dd81fc02637eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-5ba7cf7ccc8558500e2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1029000000-6f8810f1bd36737fb1e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pir-9275000000-089a2ee2c344b5970d64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-0396a703d7308a53d437Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-47e0e15dbee408226062Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016u-2291000000-ffb22ade26715179fd8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-54e12ef7918a315b480dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-a630743e54db0681b32fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0wn9-2094000000-06e2671a6cb9c9eec9c9Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fmi-3539000000-76854e3f82279b906a7fSpectrum
Toxicity Profile
Route of ExposureOral
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 GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
MetabolismHepatic.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed to relieve anxiety, nervousness, and tension associated with anxiety disorders.
Minimum Risk LevelNot Available
Health EffectsWithdrawal symptoms include anxiety, convulsions, and possible death. They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
Symptoms"Barbs" cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
TreatmentThe patient should be evaluated to determine adequacy of airway, breathing and circulation. Continue clinical observation until evidence of toxicity has resolved. Intravenous access should be available for administration of fluid. Endotracheal intubation, assisted ventilation and supplemental oxygen may be required on rare occasions, more commonly when benzodiazepines are ingested in large amounts or with other CNS depressants. (3)
Concentrations
Not Available
DrugBank IDDB00801
HMDB IDHMDB0014939
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHalazepam
Chemspider ID29343
ChEBI ID195970
PubChem Compound ID31640
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

U.S. Patents 3,429,874 and 3,641,147.

MSDSNot Available
General References
1. Fann WE, Pitts WM, Wheless JC: Pharmacology, efficacy, and adverse effects of halazepam, a new benzodiazepine. Pharmacotherapy. 1982 Mar-Apr;2(2):72-9.