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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Prazepam
- Accession Number
- DB01588
- Type
- Small Molecule
- Groups
- Approved, Illicit
- Description
Prazepam is a benzodiazepine that is used in the treatment of anxiety disorders. It is a schedule IV drug in the U.S.
- Structure
Structure for Prazepam (DB01588)
- Synonyms
- Prazepamum
- External IDs
- W 4020
- International/Other Brands
- Centrax / Demetrin / Lysanxia / Sedapran / Trepidan
- Categories
- Anti-Anxiety Agents
- Benzazepines
- Benzodiazepines and benzodiazepine derivatives
- Benzodiazepinones
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- GABA Agents
- GABA Modulators
- Heterocyclic Compounds, Fused-Ring
- Nervous System
- Neurotransmitter Agents
- Psycholeptics
- Psychotropic Drugs
- Tranquilizing Agents
- UNII
- Q30VCC064M
- CAS number
- 2955-38-6
- Weight
- Average: 324.804
Monoisotopic: 324.102940883 - Chemical Formula
- C19H17ClN2O
- InChI Key
- MWQCHHACWWAQLJ-UHFFFAOYSA-N
- InChI
- InChI=1S/C19H17ClN2O/c20-15-8-9-17-16(10-15)19(14-4-2-1-3-5-14)21-11-18(23)22(17)12-13-6-7-13/h1-5,8-10,13H,6-7,11-12H2
- IUPAC Name
- 7-chloro-1-(cyclopropylmethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
- SMILES
- ClC1=CC2=C(C=C1)N(CC1CC1)C(=O)CN=C2C1=CC=CC=C1
Pharmacology
- Indication
For the treatment of anxiety disorders.
- Pharmacodynamics
Prazepam is a benzodiazepine derivative with anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant activity. Benzodiazepines may be habit-forming (causing mental or physical dependence), especially when taken for a long time or in high doses.
- Mechanism of action
Prazepam is believed to stimulate GABA receptors in the ascending reticular activating system. Since GABA is inhibitory, receptor stimulation increases inhibition and blocks both cortical and limbic arousal following stimulation of the brain stem reticular formation.
Target Actions Organism AGABA(A) Receptor positive allosteric modulatorHumans AGABA(A) Receptor Benzodiazepine Binding Site ligandHumans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
Hepatic.
- Route of elimination
- Not Available
- Half life
36-200 hours
- Clearance
- Not Available
- Toxicity
Symptoms of overdose include somnolence, confusion, coma, and diminished reflexes. Respiration, pulse and blood pressure should be monitored.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Unlock Additional Data2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of adverse effects can be increased when Prazepam is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 3-isobutyl-1-methyl-7H-xanthine The therapeutic efficacy of Prazepam can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Prazepam. 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Prazepam. 5-methoxy-N,N-dimethyltryptamine The risk or severity of adverse effects can be increased when Prazepam is combined with 5-methoxy-N,N-dimethyltryptamine. 6-O-benzylguanine The therapeutic efficacy of Prazepam can be decreased when used in combination with 6-O-benzylguanine. 7-Deazaguanine The therapeutic efficacy of Prazepam can be decreased when used in combination with 7-Deazaguanine. 7-Nitroindazole The risk or severity of adverse effects can be increased when Prazepam is combined with 7-Nitroindazole. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The risk or severity of adverse effects can be increased when Prazepam is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline. 7,9-Dimethylguanine The therapeutic efficacy of Prazepam can be decreased when used in combination with 7,9-Dimethylguanine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid alcohol.
- Avoid grapefruit products.
- Limit caffeine intake.
- Take with food.
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015527
- KEGG Drug
- D00470
- KEGG Compound
- C07366
- PubChem Compound
- 4890
- PubChem Substance
- 46505417
- ChemSpider
- 4721
- RxNav
- 8627
- ChEBI
- 8362
- ChEMBL
- CHEMBL969
- ZINC
- ZINC000000001971
- Therapeutic Targets Database
- DAP000689
- PharmGKB
- PA164776668
- Wikipedia
- Prazepam
- ATC Codes
- N05BA11 — Prazepam
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Physicians Total Care Inc.
- Dosage forms
- Not Available
- Prices
Unit description Cost Unit Doral 15 mg tablet 3.41USD tablet Doral 7.5 mg tablet 3.37USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 145-146 °C PhysProp logP 3.73 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.00399 mg/mL ALOGPS logP 3.68 ALOGPS logP 3.86 ChemAxon logS -4.9 ALOGPS pKa (Strongest Basic) 3.06 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 32.67 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 91.75 m3·mol-1 ChemAxon Polarizability 34.77 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9821 Blood Brain Barrier + 0.9934 Caco-2 permeable + 0.6922 P-glycoprotein substrate Substrate 0.6631 P-glycoprotein inhibitor I Inhibitor 0.7452 P-glycoprotein inhibitor II Inhibitor 0.6438 Renal organic cation transporter Inhibitor 0.6625 CYP450 2C9 substrate Non-substrate 0.7317 CYP450 2D6 substrate Non-substrate 0.8332 CYP450 3A4 substrate Substrate 0.7471 CYP450 1A2 substrate Inhibitor 0.861 CYP450 2C9 inhibitor Inhibitor 0.5153 CYP450 2D6 inhibitor Non-inhibitor 0.7477 CYP450 2C19 inhibitor Inhibitor 0.7793 CYP450 3A4 inhibitor Inhibitor 0.6455 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7974 Ames test Non AMES toxic 0.8623 Carcinogenicity Non-carcinogens 0.8138 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 1.8779 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9819 hERG inhibition (predictor II) Non-inhibitor 0.5471
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-00r5-3391000000-0113e86cca51d223d412 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- 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 / Lactams / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Organochlorides show 3 more
- 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 show 16 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- benzodiazepine (CHEBI:8362)
Targets
- 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. [PubMed:23038269]
- 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. [PubMed:29950725]
- 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. [PubMed:23038269]
- 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. [PubMed:29950725]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Dinis-Oliveira RJ: Metabolic profile of oxazepam and related benzodiazepines: clinical and forensic aspects. Drug Metab Rev. 2017 Nov;49(4):451-463. doi: 10.1080/03602532.2017.1377223. Epub 2017 Sep 14. [PubMed:28903606]
Drug created on August 29, 2007 09:29 / Updated on June 12, 2020 10:51
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