Hmdb loader
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
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-11-09 23:29:27 UTC
HMDB IDHMDB0014967
Secondary Accession Numbers
  • HMDB14967
Metabolite Identification
Common NameDiazepam
DescriptionDiazepam is a benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of gamma-aminobutyric acid activity. It is used in the treatment of severe anxiety disorders, as a hypnotic in the short-term management of insomnia, as a sedative and premedicant, as an anticonvulsant, and in the management of alcohol withdrawal syndrome. (From Martindale, The Extra Pharmacopoeia, 30th ed, p589).
Structure
Data?1582753243
Synonyms
ValueSource
7-Chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-oneChEBI
Methyl diazepinoneChEBI
ValiumChEBI
DiastatKegg
MethyldiazepinoneHMDB
ApaurinMeSH, HMDB
FaustanMeSH, HMDB
RelaniumMeSH, HMDB
SeduxenMeSH, HMDB
DiazemulsMeSH, HMDB
SibazonMeSH, HMDB
StesolidMeSH, HMDB
Chemical FormulaC16H13ClN2O
Average Molecular Weight284.74
Monoisotopic Molecular Weight284.071640755
IUPAC Name7-chloro-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
Traditional Namediazepam
CAS Registry Number439-14-5
SMILES
CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
InChI KeyAAOVKJBEBIDNHE-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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point125 - 126 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogP2.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM164.230932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP10(2.63) g/LALOGPS
logP10(3.08) g/LChemAxon
logS10(-4.4) g/LALOGPS
pKa (Strongest Basic)2.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity79.81 m³·mol⁻¹ChemAxon
Polarizability29.39 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DiazepamCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C13713.2Standard polar33892256
DiazepamCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C12408.4Standard non polar33892256
DiazepamCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C12449.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Diazepam CI-B (Non-derivatized)splash10-000i-0090000000-413ec5151b3a9fd41c472017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diazepam EI-B (Non-derivatized)splash10-0a4i-3690000000-3c601fed832ff090653a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diazepam EI-B (Non-derivatized)splash10-0a59-1290000000-da27f63bddb3263e00632017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diazepam CI-B (Non-derivatized)splash10-000i-0090000000-413ec5151b3a9fd41c472018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diazepam EI-B (Non-derivatized)splash10-0a4i-3690000000-3c601fed832ff090653a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diazepam EI-B (Non-derivatized)splash10-0a59-1290000000-da27f63bddb3263e00632018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diazepam GC-MS (Non-derivatized) - 70eV, Positivesplash10-05r0-1290000000-3f7c85c012a85c7146de2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diazepam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a59-2490000000-41352db33c43d0b968762014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-QTOF , positive-QTOFsplash10-000i-0090000000-bece36773a183e23bfff2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-QTOF , positive-QTOFsplash10-000i-0490000000-fbdfb84836374f27ffc72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-QTOF , positive-QTOFsplash10-0006-0950000000-75d9ab376c968b83f2552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-QTOF , positive-QTOFsplash10-0006-0940000000-c585bcb21e1b3008adc12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0590000000-2c33d4fd40c36c20a4a62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-000i-0090000000-695f91d3d5f2e1902be32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-000i-0090000000-15d8ced2d42d3e292bb12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-000i-0290000000-dfdaecb8b27bc1ad2c9e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-0fdx-0890000000-b77eb07ad61e288eeb192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-0006-0940000000-fb79dac6c46f730fb4652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-0006-1930000000-a6412a876983038340342017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-000i-0090000000-31830c983339c0e0d9182017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-000i-0090000000-1028986b8e3b82b4bf962017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-000i-0290000000-0c2338f41998da54e8c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-0fdx-0890000000-48e88a1c67f0fc25384f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-0f6x-0940000000-ce56b132903858bd3b6b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-0006-1930000000-b61e92cac5094920cf322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0590000000-e26e1398541d17b6632e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diazepam LC-ESI-ITFT , positive-QTOFsplash10-0f7c-0590000000-541488ae806b0dbd97cb2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diazepam 10V, Positive-QTOFsplash10-000i-0090000000-a82533f29e9cb01fa7fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diazepam 20V, Positive-QTOFsplash10-000i-0090000000-79bbd4209063f20101f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diazepam 40V, Positive-QTOFsplash10-0006-8970000000-5c77f50a4816eecfef042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diazepam 10V, Negative-QTOFsplash10-001i-0090000000-5a624d4584e17376f63c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diazepam 20V, Negative-QTOFsplash10-001i-0090000000-31d6bb00202f2493ec8d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diazepam 40V, Negative-QTOFsplash10-0pb9-9070000000-364b9c313a672f6532072016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00829 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00829 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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 IDDB00829
Phenol Explorer Compound IDNot Available
FooDB IDFDB007103
KNApSAcK IDNot Available
Chemspider ID2908
KEGG Compound IDC06948
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiazepam
METLIN IDNot Available
PubChem Compound3016
PDB IDDZP
ChEBI ID49575
Food Biomarker OntologyNot Available
VMH IDC06948
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mant A, Whicker SD, McManus P, Birkett DJ, Edmonds D, Dumbrell D: Benzodiazepine utilisation in Australia: report from a new pharmacoepidemiological database. Aust J Public Health. 1993 Dec;17(4):345-9. [PubMed:7911332 ]
  2. McLean MJ, Macdonald RL: Benzodiazepines, but not beta carbolines, limit high frequency repetitive firing of action potentials of spinal cord neurons in cell culture. J Pharmacol Exp Ther. 1988 Feb;244(2):789-95. [PubMed:2450203 ]
  3. Earley JV, Fryer RI, Ning RY: Quinazolines and 1,4-benzodiazepines. LXXXIX: Haptens useful in benzodiazepine immunoassay development. J Pharm Sci. 1979 Jul;68(7):845-50. [PubMed:458601 ]
  4. Oishi R, Nishibori M, Itoh Y, Saeki K: Diazepam-induced decrease in histamine turnover in mouse brain. Eur J Pharmacol. 1986 May 27;124(3):337-42. [PubMed:3089825 ]
  5. Usami N, Yamamoto T, Shintani S, Ishikura S, Higaki Y, Katagiri Y, Hara A: Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5. [PubMed:11995921 ]