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Accession NumberDB01489
TypeSmall Molecule
GroupsApproved, Illicit

Camazepam 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. [Wikipedia]

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. [Wikipedia] 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.

CamazepamNot AvailableNot Available
CMZNot AvailableNot Available
CZNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
AlbegoBoehringer Ingelheim
Paxor Not Available
Brand mixturesNot Available
SaltsNot Available
CAS number36104-80-0
WeightAverage: 371.818
Monoisotopic: 371.103669164
Chemical FormulaC19H18ClN3O3
7-chloro-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl N,N-dimethylcarbamate
DescriptionThis compound 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
Sub Class1,4-benzodiazepines
Direct Parent1,4-benzodiazepines
Alternative Parents
  • 1,4-benzodiazepine
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Lactam
  • Ketimine
  • Carboxamide group
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Imine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
IndicationCamazepam has been used in placebo controlled studies for the treatment of patients suffering from anxiety and depression.
PharmacodynamicsNot Available
Mechanism of actionCamazepam 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.
AbsorptionAlmost completely absorbed into the bloodstream after oral administration. 90% bioavailability can be achieved in humans.
Volume of distributionNot Available
Protein bindingNot Available

Metabolized 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 eliminationRenally eliminated.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Predicted ADMET features
Human Intestinal Absorption+0.9966
Blood Brain Barrier+0.9578
Caco-2 permeable+0.5746
P-glycoprotein substrateSubstrate0.5311
P-glycoprotein inhibitor IInhibitor0.7291
P-glycoprotein inhibitor IIInhibitor0.7616
Renal organic cation transporterNon-inhibitor0.881
CYP450 2C9 substrateNon-substrate0.6792
CYP450 2D6 substrateNon-substrate0.8325
CYP450 3A4 substrateSubstrate0.7293
CYP450 1A2 substrateNon-inhibitor0.7304
CYP450 2C9 substrateNon-inhibitor0.6194
CYP450 2D6 substrateNon-inhibitor0.8758
CYP450 2C19 substrateInhibitor0.5491
CYP450 3A4 substrateNon-inhibitor0.7769
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6962
Ames testNon AMES toxic0.6493
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.9995 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9973
hERG inhibition (predictor II)Non-inhibitor0.6456
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Experimental Properties
melting point173-174Ferrari, G. and Casagrande, C.; U.S. Patent 3,799,920; March 26,1974; assigned to Siphar SA.
Predicted Properties
Water Solubility0.0182 mg/mLALOGPS
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area62.21 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.63 m3·mol-1ChemAxon
Polarizability38.05 Å3ChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Mass Spec (NIST)Not Available
Synthesis Reference

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

General Reference

1. Lu, Xiang-Lin, and Shen K. Yang. “Enantiomer resolution of camazepam and its derivatives and enantioselective metabolism of camazepam by human liver microsomes.” Journal of Chromatography A 666.1 (1994): 249-257.

2. Morino, Akira, et al. “Receptor-mediated model relating anticonvulsant effect to brain levels of camazepam in the presence of its active metabolites.” Journal of pharmacokinetics and biopharmaceutics 14.3 (1986): 309-321.

3. Morino, A. K. I. R. A., and M. A. K. O. T. O. Sugiyama. “Relation between time courses of pharmacological effects and of plasma levels of camazepam and its active metabolites in rats.” Journal of pharmacobio-dynamics 8.8 (1985): 597.

External Links
ATC CodesN05BA15
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Drug Interactions
AminophyllineTheophylline Derivatives may diminish the therapeutic effect of Benzodiazepines.
ClozapineMay enhance the adverse/toxic effect of CloZAPine.
FosphenytoinMay increase the serum concentration of Fosphenytoin. Short-term exposure to benzodiazepines may not present as much risk as chronic therapy. Exceptions: ALPRAZolam.
Gamma Hydroxybutyric AcidMay enhance the CNS depressant effect of Sodium Oxybate.
MethadoneMay enhance the CNS depressant effect of Methadone.
OlanzapineOLANZapine may enhance the adverse/toxic effect of Benzodiazepines.
PhenytoinMay increase the serum concentration of Phenytoin. Short-term exposure to benzodiazepines may not present as much risk as chronic therapy. Exceptions: ALPRAZolam.
TeduglutideTeduglutide may increase the serum concentration of Benzodiazepines.
TheophyllineTheophylline Derivatives may diminish the therapeutic effect of Benzodiazepines.
Food InteractionsNot Available
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Drug created on July 31, 2007 07:09 / Updated on April 02, 2014 11:39