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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 UTC
HMDB IDHMDB0015527
Secondary Accession Numbers
  • HMDB15527
Metabolite Identification
Common NamePrazepam
DescriptionPrazepam, also known as demetrin or centrax, 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. Prazepam is a drug which is used for the treatment of anxiety disorders. Prazepam is a strong basic compound (based on its pKa). Prazepam is a potentially toxic compound. Abrupt or over-rapid discontinuation of prazepam after long-term use, even at low dosage, may result in a protracted withdrawal syndrome. Side effects of prazepam are less profound than with other benzodiazepines. Benzodiazepines require special precaution if used in the elderly, during pregnancy, in children, alcohol or drug-dependent individuals and individuals with comorbid psychiatric disorders. Animal studies have found prazepam taken during pregnancy results in delayed growth and causes reproductive abnormalities.
Structure
Data?1582753306
Synonyms
ValueSource
CentraxKegg
Parke davis brand OF prazepamHMDB
Warner-lambert brand OF prazepamHMDB
DemetrinHMDB
Pfizer brand OF prazepamHMDB
ReapamHMDB
LysanxiaHMDB
mono DemetrinHMDB
United drug brand OF prazepamHMDB
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 KeyMWQCHHACWWAQLJ-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Alpha-amino acid or derivatives
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Ketimine
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Imine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point145 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.004 g/LNot Available
LogP3.73HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM174.030932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP3.68ALOGPS
logP3.86ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)3.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity91.75 m³·mol⁻¹ChemAxon
Polarizability34.77 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+172.77530932474
DeepCCS[M-H]-170.41730932474
DeepCCS[M-2H]-204.32130932474
DeepCCS[M+Na]+179.61430932474
AllCCS[M+H]+175.532859911
AllCCS[M+H-H2O]+172.232859911
AllCCS[M+NH4]+178.632859911
AllCCS[M+Na]+179.432859911
AllCCS[M-H]-179.332859911
AllCCS[M+Na-2H]-178.632859911
AllCCS[M+HCOO]-178.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PrazepamClC1=CC2=C(C=C1)N(CC1CC1)C(=O)CN=C2C1=CC=CC=C14077.3Standard polar33892256
PrazepamClC1=CC2=C(C=C1)N(CC1CC1)C(=O)CN=C2C1=CC=CC=C12773.0Standard non polar33892256
PrazepamClC1=CC2=C(C=C1)N(CC1CC1)C(=O)CN=C2C1=CC=CC=C12639.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prazepam GC-MS (Non-derivatized) - 70eV, Positivesplash10-002e-3090000000-85ecde8de7c9923c1afc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prazepam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prazepam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00r5-3391000000-0113e86cca51d223d4122014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Prazepam 35V, Positive-QTOFsplash10-00b9-0098000000-121cdb4df09299b2a55f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prazepam 10V, Positive-QTOFsplash10-056r-5009000000-0f619abd238690bf909e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prazepam 20V, Positive-QTOFsplash10-0a4i-9022000000-7d0f4b34a0dc683c936a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prazepam 40V, Positive-QTOFsplash10-0a4i-9000000000-7386d4be3880cf54c8942016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prazepam 10V, Negative-QTOFsplash10-00di-0029000000-d01af5072c81e6d914562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prazepam 20V, Negative-QTOFsplash10-00xr-1097000000-243b0ed20eedd8c76c722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prazepam 40V, Negative-QTOFsplash10-0006-9460000000-91a4eb6554df563a38982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prazepam 10V, Positive-QTOFsplash10-004i-0009000000-db9fa6607403d494beac2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prazepam 20V, Positive-QTOFsplash10-0032-0094000000-cc4f8e8cd825513296242021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prazepam 40V, Positive-QTOFsplash10-05n3-4190000000-fa9f154eaa14bdf4214a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prazepam 10V, Negative-QTOFsplash10-00di-0009000000-33c2d52f8e6510237ee42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prazepam 20V, Negative-QTOFsplash10-00yi-3095000000-d45edb96f10dbdf7642e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prazepam 40V, Negative-QTOFsplash10-001i-9070000000-47517480edb6242ad95f2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01588 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01588 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01588
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4721
KEGG Compound IDC07366
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPrazepam
METLIN IDNot Available
PubChem Compound4890
PDB IDNot Available
ChEBI ID195969
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 17 proteins in total.

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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed: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. [PubMed: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. [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 ]
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:7773620 ]

Only showing the first 10 proteins. There are 17 proteins in total.