Identification
- Generic Name
- Camazepam
- DrugBank Accession Number
- DB01489
- Background
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.
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.
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
Structure for Camazepam (DB01489)
- Weight
- Average: 371.818
Monoisotopic: 371.103669164 - Chemical Formula
- C19H18ClN3O3
- Synonyms
- Camazepam
Pharmacology
- Indication
Camazepam has been used in placebo controlled studies for the treatment of patients suffering from anxiety and depression.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Camazepam 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.
Target Actions Organism AGABA(A) Receptor positive allosteric modulatorHumans AGABA(A) Receptor Benzodiazepine Binding Site ligandHumans - Absorption
Almost completely absorbed into the bloodstream after oral administration. 90% bioavailability can be achieved in humans.
- Volume of distribution
Not Available
- Protein binding
Not 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 elimination
Renally eliminated.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Camazepam is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Camazepam. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Camazepam. Agomelatine The risk or severity of CNS depression can be increased when Camazepam is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Camazepam. - Food Interactions
- Not Available
Products
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- Albego (Boehringer Ingelheim) / Limpidon (Crinos) / Paxor
Categories
- ATC Codes
- N05BA15 — Camazepam
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzodiazepines
- Sub Class
- 1,4-benzodiazepines
- Direct Parent
- 1,4-benzodiazepines
- Alternative Parents
- Alpha amino acids and derivatives / Benzene and substituted derivatives / Aryl chlorides / Tertiary carboxylic acid amides / Carbamate esters / Organic carbonic acids and derivatives / Lactams / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds show 5 more
- Substituents
- 1,4-benzodiazepine / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carbamic acid ester / Carbonic acid derivative / Carbonyl group show 18 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- HZ3XRH03C3
- CAS number
- 36104-80-0
- InChI Key
- PXBVEXGRHZFEOF-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
References
- Synthesis Reference
Ferrari, G. and Casagrande, C.; U.S. Patent 3,799,920; March 26,1974; assigned to Siphar SA.
- General References
- Lu XL, Yang SK: Enantiomer resolution of camazepam and its derivatives and enantioselective metabolism of camazepam by human liver microsomes. J Chromatogr A. 1994 Apr 22;666(1-2):249-57. [Article]
- Morino A, Sasaki H, Mukai H, Sugiyama M: Receptor-mediated model relating anticonvulsant effect to brain levels of camazepam in the presence of its active metabolites. J Pharmacokinet Biopharm. 1986 Jun;14(3):309-21. [Article]
- Morino A, Sugiyama M: Relation between time courses of pharmacological effects and of plasma levels of camazepam and its active metabolites in rats. J Pharmacobiodyn. 1985 Aug;8(8):597-606. [Article]
- External Links
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Pill - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 173-174 Ferrari, G. and Casagrande, C.; U.S. Patent 3,799,920; March 26,1974; assigned to Siphar SA. - Predicted Properties
Property Value Source Water Solubility 0.0182 mg/mL ALOGPS logP 2.48 ALOGPS logP 3.34 Chemaxon logS -4.3 ALOGPS pKa (Strongest Basic) -1.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 62.21 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 98.63 m3·mol-1 Chemaxon Polarizability 38.12 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.6194 CYP450 2D6 inhibitor Non-inhibitor 0.8758 CYP450 2C19 inhibitor Inhibitor 0.5491 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 177.07939 predictedDeepCCS 1.0 (2019) [M+H]+ 179.45134 predictedDeepCCS 1.0 (2019) [M+Na]+ 186.6125 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Positive allosteric modulator
- Curator comments
- The GABA(A) receptor is pentameric (i.e. comprising 5 subunit proteins) and therefore has a multitude of potential isoforms. The above target is a collection of all possible GABA(A) subunits that may participate in the formation of the pentameric receptor and is not meant to imply direct a drug-protein interaction for each individual subunit.
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
- Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Ligand
- Curator comments
- Benzodiazepines modulate GABA(A) function by binding at the interface between alpha (α) and gamma (γ) subunits. Of the 6 α-subunits, only 4 (α-1, -2, -3, and -5) participate in the formation of this binding site. The above target is a collection of all α- and γ-subunits that are known to participate in the formation of the benzodiazepine binding site.
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
- Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
Drug created at July 31, 2007 13:09 / Updated at February 21, 2021 18:51