You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:14 UTC
HMDB IDHMDB15527
Secondary Accession NumbersNone
Metabolite Identification
Common NamePrazepam
DescriptionPrazepam is only found in individuals that have used or taken this drug. It is a benzodiazepine that is used in the treatment of anxiety disorders. It is a schedule IV drug in the U.S. 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.
Structure
Thumb
Synonyms
ValueSource
CentraxKegg
Chemical FormulaC19H17ClN2O
Average Molecular Weight324.804
Monoisotopic Molecular Weight324.102940883
IUPAC Name7-chloro-1-(cyclopropylmethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
Traditional Nameprazepam
CAS Registry Number2955-38-6
SMILES
ClC1=CC2=C(C=C1)N(CC1CC1)C(=O)CN=C2C1=CC=CC=C1
InChI Identifier
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
InChI KeyInChIKey=MWQCHHACWWAQLJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,4-benzodiazepines
Alternative Parents
Substituents
  • 1,4-benzodiazepine
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Lactam
  • Ketimine
  • Carboxamide group
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Imine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-anxiety Agents
  • GABA Modulators
  • Hypnotics and Sedatives
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point145 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.99e-03 g/LNot Available
LogP3.73HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.004 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 RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-00r5-3391000000-0113e86cca51d223d412View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01588
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01588
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-0.3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-0.2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01588
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4721
KEGG Compound IDC07366
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPrazepam
NuGOwiki LinkHMDB15527
Metagene LinkHMDB15527
METLIN IDNot Available
PubChem Compound4890
PDB IDNot Available
ChEBI ID195969
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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. Epub 2009 Nov 24. [19934256 ]
General function:
Involved in ion transport
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:
GABRG2
Uniprot ID:
P18507
Molecular weight:
54161.8
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. [7773620 ]
General function:
Involved in ion transport
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:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
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. [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. [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. [9145922 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
General function:
Involved in ion transport
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
Molecular weight:
51325.9
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. [7773620 ]
General function:
Involved in ion transport
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
Molecular weight:
55164.1
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. [7773620 ]
General function:
Involved in ion transport
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
Molecular weight:
52145.6
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. [7773620 ]
General function:
Involved in ion transport
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:
GABRB1
Uniprot ID:
P18505
Molecular weight:
54234.1
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. [7773620 ]
General function:
Involved in ion transport
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:
GABRB2
Uniprot ID:
P47870
Molecular weight:
59149.9
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. [7773620 ]
General function:
Involved in ion transport
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:
GABRB3
Uniprot ID:
P28472
Molecular weight:
54115.0
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. [7773620 ]
General function:
Involved in ion transport
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
Molecular weight:
50707.8
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. [7773620 ]
General function:
Involved in ion transport
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
Molecular weight:
57971.2
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. [7773620 ]
General function:
Involved in ion transport
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
Molecular weight:
53594.5
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. [7773620 ]
General function:
Involved in ion transport
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
Molecular weight:
54288.2
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. [7773620 ]
General function:
Involved in ion transport
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 uterus, the function of the receptor appears to be related to tissue contractility. The binding of this pI subunit with other GABA(A) receptor subunits alters the sensitivity of recombinant receptors to modulatory agents such as pregnanolone
Gene Name:
GABRP
Uniprot ID:
O00591
Molecular weight:
50639.7
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. [7773620 ]
General function:
Involved in ion transport
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 receptor could play a role in retinal neurotransmission
Gene Name:
GABRR1
Uniprot ID:
P24046
Molecular weight:
55882.9
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. [7773620 ]
General function:
Involved in ion transport
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 receptor could play a role in retinal neurotransmission
Gene Name:
GABRR2
Uniprot ID:
P28476
Molecular weight:
56816.6
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. [7773620 ]
General function:
Involved in ion transport
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
Molecular weight:
54271.1
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. [7773620 ]