Identification

Name
Prazepam
Accession Number
DB01588
Description

Prazepam is a benzodiazepine that is used in the treatment of anxiety disorders. It is a schedule IV drug in the U.S.

Type
Small Molecule
Groups
Approved, Illicit
Structure
Thumb
Weight
Average: 324.804
Monoisotopic: 324.102940883
Chemical Formula
C19H17ClN2O
Synonyms
  • Prazepamum
External IDs
  • W 4020

Pharmacology

Indication

For the treatment of anxiety disorders.

Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
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.

TargetActionsOrganism
AGABA(A) Receptor
positive allosteric modulator
Humans
AGABA(A) Receptor Benzodiazepine Binding Site
ligand
Humans
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
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
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.
DrugInteraction
AbametapirThe serum concentration of Prazepam can be increased when it is combined with Abametapir.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Prazepam.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Prazepam.
AclidiniumPrazepam may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Prazepam is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Prazepam.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Prazepam.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Prazepam.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Prazepam.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Prazepam.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    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.

Products

International/Other Brands
Centrax / Demetrin / Lysanxia / Sedapran / Trepidan

Categories

ATC Codes
N05BA11 — Prazepam
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 / 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 / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzodiazepine (CHEBI:8362)

Chemical Identifiers

UNII
Q30VCC064M
CAS number
2955-38-6
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

References

General References
Not Available
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

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Physicians Total Care Inc.
Dosage Forms
FormRouteStrength
Tablet10 mg/1
Tablet20 mg
Capsule10 mg
Capsule5 mg
Solution / dropsOral15 MG/ML
Tablet10 MG
Prices
Unit descriptionCostUnit
Doral 15 mg tablet3.41USD tablet
Doral 7.5 mg tablet3.37USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)145-146 °CPhysProp
logP3.73HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00399 mg/mLALOGPS
logP3.68ALOGPS
logP3.86ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)3.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity91.75 m3·mol-1ChemAxon
Polarizability34.77 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9821
Blood Brain Barrier+0.9934
Caco-2 permeable+0.6922
P-glycoprotein substrateSubstrate0.6631
P-glycoprotein inhibitor IInhibitor0.7452
P-glycoprotein inhibitor IIInhibitor0.6438
Renal organic cation transporterInhibitor0.6625
CYP450 2C9 substrateNon-substrate0.7317
CYP450 2D6 substrateNon-substrate0.8332
CYP450 3A4 substrateSubstrate0.7471
CYP450 1A2 substrateInhibitor0.861
CYP450 2C9 inhibitorInhibitor0.5153
CYP450 2D6 inhibitorNon-inhibitor0.7477
CYP450 2C19 inhibitorInhibitor0.7793
CYP450 3A4 inhibitorInhibitor0.6455
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7974
Ames testNon AMES toxic0.8623
CarcinogenicityNon-carcinogens0.8138
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8779 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9819
hERG inhibition (predictor II)Non-inhibitor0.5471
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-00r5-3391000000-0113e86cca51d223d412
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

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
  1. 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]
  2. 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
  1. 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]
  2. 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
  1. 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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