Identification

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
Thumb
Synonyms
  • Prazepamum
External IDs
W 4020
International/Other Brands
Centrax / Demetrin / Lysanxia / Sedapran / Trepidan
Categories
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 drug. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. 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
AGamma-aminobutyric acid receptor subunit alpha-1
potentiator
Human
AGamma-aminobutyric acid receptor subunit alpha-2
potentiator
Human
AGamma-aminobutyric acid receptor subunit alpha-3
potentiator
Human
AGamma-aminobutyric acid receptor subunit alpha-5
potentiator
Human
AGamma-aminobutyric acid receptor subunit gamma-1
potentiator
Human
AGamma-aminobutyric acid receptor subunit gamma-2
potentiator
Human
AGamma-aminobutyric acid receptor subunit gamma-3
potentiator
Human
AGamma-aminobutyric acid receptor subunit beta-1
potentiator
Human
AGamma-aminobutyric acid receptor subunit beta-2
potentiator
Human
AGamma-aminobutyric acid receptor subunit beta-3
potentiator
Human
AGamma-aminobutyric acid receptor subunit delta
potentiator
Human
AGamma-aminobutyric acid receptor subunit epsilon
potentiator
Human
AGamma-aminobutyric acid receptor subunit pi
potentiator
Human
AGamma-aminobutyric acid receptor subunit rho-1
potentiator
Human
AGamma-aminobutyric acid receptor subunit rho-2
potentiator
Human
AGamma-aminobutyric acid receptor subunit rho-3
potentiator
Human
AGABA-A receptor (anion channel)
positive allosteric modulator
Human
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
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Prazepam.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Prazepam.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Prazepam is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe therapeutic efficacy of Prazepam can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Prazepam.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Prazepam.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Prazepam.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Prazepam.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Prazepam.
5-androstenedioneThe metabolism of Prazepam can be decreased when combined with 5-androstenedione.
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Avoid taking with grapefruit juice.
  • 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
ChEBI
8362
ChEMBL
CHEMBL969
Therapeutic Targets Database
DAP000689
PharmGKB
PA164776668
Wikipedia
Prazepam
ATC Codes
N05BA11 — Prazepam

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Physicians Total Care Inc.
Dosage forms
Not Available
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

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
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
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...
Gene Name
GABRA1
Uniprot ID
P14867
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-1
Molecular Weight
51801.395 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Amin J, Brooks-Kayal A, Weiss DS: Two tyrosine residues on the alpha subunit are crucial for benzodiazepine binding and allosteric modulation of gamma-aminobutyric acidA receptors. Mol Pharmacol. 1997 May;51(5):833-41. [PubMed:9145922]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA2
Uniprot ID
P47869
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-2
Molecular Weight
51325.85 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA3
Uniprot ID
P34903
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-3
Molecular Weight
55164.055 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Transporter activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA5
Uniprot ID
P31644
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-5
Molecular Weight
52145.645 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRG1
Uniprot ID
Q8N1C3
Uniprot Name
Gamma-aminobutyric acid receptor subunit gamma-1
Molecular Weight
53594.49 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
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...
Gene Name
GABRG2
Uniprot ID
P18507
Uniprot Name
Gamma-aminobutyric acid receptor subunit gamma-2
Molecular Weight
54161.78 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRG3
Uniprot ID
Q99928
Uniprot Name
Gamma-aminobutyric acid receptor subunit gamma-3
Molecular Weight
54288.16 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
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...
Gene Name
GABRB1
Uniprot ID
P18505
Uniprot Name
Gamma-aminobutyric acid receptor subunit beta-1
Molecular Weight
54234.085 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
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...
Gene Name
GABRB2
Uniprot ID
P47870
Uniprot Name
Gamma-aminobutyric acid receptor subunit beta-2
Molecular Weight
59149.895 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Gaba-gated chloride 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...
Gene Name
GABRB3
Uniprot ID
P28472
Uniprot Name
Gamma-aminobutyric acid receptor subunit beta-3
Molecular Weight
54115.04 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Gaba-a receptor activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRD
Uniprot ID
O14764
Uniprot Name
Gamma-aminobutyric acid receptor subunit delta
Molecular Weight
50707.835 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRE
Uniprot ID
P78334
Uniprot Name
Gamma-aminobutyric acid receptor subunit epsilon
Molecular Weight
57971.175 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Gaba-a receptor activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. In the ute...
Gene Name
GABRP
Uniprot ID
O00591
Uniprot Name
Gamma-aminobutyric acid receptor subunit pi
Molecular Weight
50639.735 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Gaba-a receptor activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-1 GABA...
Gene Name
GABRR1
Uniprot ID
P24046
Uniprot Name
Gamma-aminobutyric acid receptor subunit rho-1
Molecular Weight
55882.91 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Gaba-a receptor activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-2 GABA...
Gene Name
GABRR2
Uniprot ID
P28476
Uniprot Name
Gamma-aminobutyric acid receptor subunit rho-2
Molecular Weight
54150.41 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Potentiator
General Function
Gaba-a receptor activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRR3
Uniprot ID
A8MPY1
Uniprot Name
Gamma-aminobutyric acid receptor subunit rho-3
Molecular Weight
54271.1 Da
References
  1. Schove LT, Perez JJ, Loew GH: Molecular determinants of recognition and activation at the cerebellar benzodiazepine receptor site. Bioorg Med Chem. 1994 Oct;2(10):1029-49. [PubMed:7773620]

Enzymes

Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on August 29, 2007 09:29 / Updated on November 02, 2018 05:03