Camazepam (CHEM003526)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2014-08-30 21:05:24 UTC
Update Date2016-11-09 01:09:09 UTC
Accession NumberCHEM003526
Identification
Common NameCamazepam
ClassSmall Molecule
DescriptionCamazepam is a benzodiazepine which is a dimethyl carbamate ester of tamzepam, a metabolite of diazepam. Similarly to other drugs in its class, it has antxiolytic, anticonvulsant, hypnotic, and skeletal muscle relaxant properties. However, unlike other benzodiapeines camazepam is predominantly anxiolytic and is relatively weak as an anticonvulsant, hypnotic and skeletal muscle relaxant. Camazepam also has less side effects, such as impaired cognition and reaction times, compared to other benzodiazepines. However, impairment of cognition and disrupted sleep patterns will occur at doses higher than 40mg of carazepam.]Camazepam is also believed to increase attention, and is associated with skin disorders. In the United States camazepam is regulated as a Schedule IV controlled substance.
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Benzodiazepine
  • Drug
  • Ether
  • Hypnotic and Sedative
  • Neuromuscular Agent
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC19H18ClN3O3
Average Molecular Mass371.818 g/mol
Monoisotopic Mass371.104 g/mol
CAS Registry Number36104-80-0
IUPAC Name7-chloro-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl N,N-dimethylcarbamate
Traditional Namecamazepam
SMILESCN(C)C(=O)OC1N=C(C2=CC=CC=C2)C2=C(C=CC(Cl)=C2)N(C)C1=O
InChI IdentifierInChI=1S/C19H18ClN3O3/c1-22(2)19(25)26-17-18(24)23(3)15-10-9-13(20)11-14(15)16(21-17)12-7-5-4-6-8-12/h4-11,17H,1-3H3
InChI KeyPXBVEXGRHZFEOF-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
  • Carbamic acid ester
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Ketimine
  • Lactam
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Imine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen 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 Point173-174°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP2.48ALOGPS
logP3.34ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area62.21 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.63 m³·mol⁻¹ChemAxon
Polarizability38.05 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-00di-1009000000-823c63921e078c0416dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-4129000000-882e1f6e37c13e988a26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9620000000-4f609372fd4f6171c750Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3029000000-d4cb6289ec62182ee71eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-2079000000-10339e966393eac9544eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00y3-9000000000-e9c3496236445c282b83Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-9260000000-edfba1a5fcbe9ca50d1dSpectrum
Toxicity Profile
Route of ExposureAlmost completely absorbed into the bloodstream after oral administration. 90% bioavailability can be achieved in humans.
Mechanism of ToxicityCamazepam has been shown to bind competitively to benzodiazepine receptors in the brain with a relatively low affinity in animal models. This binding of benzodiazepine receptors by camazepam and its active metabolites is responsible for its anticonvulsant effects. Notably, only three metabolites were shown to exert anticonvulsant activity, temazepam, oxazepam, and hydroxy camazepam. The anxiolytic properties of camazepam are also attributed to their ability to bind benzodiazepine receptors, also known as GABA receptors. When benzodiazepines bind to GABA receptors they increase the efficiency with which the inhibitory neurotransmitter GABA binds.
MetabolismMetabolized by the liver into more than 10 metabolites, some of which are also active and posses anticonvulsant properties. [3] One active metabolite of note is temazepam which has roughly equal in effectiveness as an anxiolytic, but is less anticonvulsant, sedating, and motor-impairing. Camazepam undergoes enantioselective metabolism by human liver microsomes. [1] Route of Elimination: Renally eliminated.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCamazepam has been used in placebo controlled studies for the treatment of patients suffering from anxiety and depression.
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 IDDB01489
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 LinkCamazepam
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID37367
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Ferrari, G. and Casagrande, C.; U.S. Patent 3,799,920; March 26,1974; assigned to Siphar SA.

MSDSNot Available
General ReferencesNot Available