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Identification
NameCamazepam
Accession NumberDB01489
Typesmall molecule
Groupsapproved, illicit
Description

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.

Structure
Thumb
Synonyms
SynonymLanguageCode
CamazepamNot AvailableNot Available
CMZNot AvailableNot Available
CZNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
AlbegoBoehringer Ingelheim
LimpidonCrinos
Paxor Not Available
Brand mixturesNot Available
Categories
CAS number36104-80-0
WeightAverage: 371.818
Monoisotopic: 371.103669164
Chemical FormulaC19H18ClN3O3
InChI KeyPXBVEXGRHZFEOF-UHFFFAOYSA-N
InChI
InChI=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
IUPAC Name
7-chloro-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl N,N-dimethylcarbamate
SMILES
CN(C)C(=O)OC1N=C(C2=CC=CC=C2)C2=C(C=CC(Cl)=C2)N(C)C1=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzodiazepines
SubclassNot Available
Direct parentBenzodiazepines
Alternative parentsChlorobenzenes; Aryl Chlorides; Tertiary Carboxylic Acid Amides; Tertiary Amines; Carbamic Acids and Derivatives; Ethers; Carboxylic Acids; Polyamines; Organochlorides
Substituentschlorobenzene; aryl chloride; aryl halide; benzene; tertiary carboxylic acid amide; carboxamide group; tertiary amine; carbamic acid derivative; carboxylic acid derivative; ether; polyamine; carboxylic acid; organochloride; organohalogen; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms).
Pharmacology
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
Metabolism

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
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9966
Blood Brain Barrier + 0.9578
Caco-2 permeable + 0.5746
P-glycoprotein substrate Substrate 0.5311
P-glycoprotein inhibitor I Inhibitor 0.7291
P-glycoprotein inhibitor II Inhibitor 0.7616
Renal organic cation transporter Non-inhibitor 0.881
CYP450 2C9 substrate Non-substrate 0.6792
CYP450 2D6 substrate Non-substrate 0.8325
CYP450 3A4 substrate Substrate 0.7293
CYP450 1A2 substrate Non-inhibitor 0.7304
CYP450 2C9 substrate Non-inhibitor 0.6194
CYP450 2D6 substrate Non-inhibitor 0.8758
CYP450 2C19 substrate Inhibitor 0.5491
CYP450 3A4 substrate Non-inhibitor 0.7769
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6962
Ames test Non AMES toxic 0.6493
Carcinogenicity Non-carcinogens 0.7149
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 1.9995 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9973
hERG inhibition (predictor II) Non-inhibitor 0.6456
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point173-174Ferrari, G. and Casagrande, C.; U.S. Patent 3,799,920; March 26,1974; assigned to Siphar SA.
Predicted Properties
PropertyValueSource
water solubility1.82e-02 g/lALOGPS
logP2.48ALOGPS
logP3.34ChemAxon
logS-4.3ALOGPS
pKa (strongest basic)-1.7ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count0ChemAxon
polar surface area62.21ChemAxon
rotatable bond count3ChemAxon
refractivity98.63ChemAxon
polarizability38.05ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
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
ResourceLink
KEGG DrugD07315
PubChem Compound37367
PubChem Substance46505921
ChemSpider34285
WikipediaCamazepam
ATC CodesN05BA15
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on July 31, 2007 07:09 / Updated on April 02, 2014 11:39