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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:41 UTC
HMDB IDHMDB0014618
Secondary Accession Numbers
  • HMDB14618
Metabolite Identification
Common NameChlordiazepoxide
DescriptionChlordiazepoxide is only found in individuals that have used or taken this drug. It is an anxiolytic benzodiazepine derivative with anticonvulsant, sedative, and amnesic properties. It has also been used in the symptomatic treatment of alcohol withdrawal. [PubChem]Chlordiazepoxide binds to stereospecific benzodiazepine (BZD) binding sites on GABA (A) receptor complexes at several sites within the central nervous system, including the limbic system and reticular formation. This results in an increased binding of the inhibitory neurotransmitter GABA to the GABA(A) receptor.BZDs, therefore, enhance GABA-mediated chloride influx through GABA receptor channels, causing membrane hyperpolarization. The net neuro-inhibitory effects result in the observed sedative, hypnotic, anxiolytic, and muscle relaxant properties.
Structure
Data?1582753199
Synonyms
ValueSource
7-Chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepin-4-oxideChEBI
CDPChEBI
Chlordiazepoxide baseChEBI
ChlordiazepoxidumChEBI
ClopoxideChEBI
HelogaphenChEBI
LibritabsChEBI
MethaminodiazepoxideChEBI
MultumChEBI
RisolidChEBI
SilibrinChEBI
TropiumChEBI
Chemical FormulaC16H14ClN3O
Average Molecular Weight299.755
Monoisotopic Molecular Weight299.082539792
IUPAC Name7-chloro-2-(methylamino)-5-phenyl-3H-1,4λ⁵-benzodiazepin-4-one
Traditional Namemultum
CAS Registry Number58-25-3
SMILES
CNC1=NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)=N(=O)C1
InChI Identifier
InChI=1S/C16H14ClN3O/c1-18-15-10-20(21)16(11-5-3-2-4-6-11)13-9-12(17)7-8-14(13)19-15/h2-9H,10H2,1H3,(H,18,19)
InChI KeyANTSCNMPPGJYLG-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
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Imidolactam
  • Nitrone
  • Azacycle
  • Carboxylic acid amidine
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Amidine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Organic zwitterion
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point236.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.02 g/LNot Available
LogP1.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM170.430932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP2.01ALOGPS
logP3.05ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.52ChemAxon
pKa (Strongest Basic)6.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity87.34 m³·mol⁻¹ChemAxon
Polarizability30.97 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+168.27330932474
DeepCCS[M-H]-165.91530932474
DeepCCS[M-2H]-199.63330932474
DeepCCS[M+Na]+174.8730932474
AllCCS[M+H]+166.632859911
AllCCS[M+H-H2O]+162.932859911
AllCCS[M+NH4]+170.032859911
AllCCS[M+Na]+170.932859911
AllCCS[M-H]-169.932859911
AllCCS[M+Na-2H]-169.332859911
AllCCS[M+HCOO]-168.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChlordiazepoxideCNC1=NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)=N(=O)C13842.9Standard polar33892256
ChlordiazepoxideCNC1=NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)=N(=O)C12883.2Standard non polar33892256
ChlordiazepoxideCNC1=NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)=N(=O)C12807.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chlordiazepoxide,1TMS,isomer #1CN(C1=NC2=CC=C(Cl)C=C2C(C2=CC=CC=C2)=[N+]([O-])C1)[Si](C)(C)C2639.0Semi standard non polar33892256
Chlordiazepoxide,1TMS,isomer #1CN(C1=NC2=CC=C(Cl)C=C2C(C2=CC=CC=C2)=[N+]([O-])C1)[Si](C)(C)C2642.7Standard non polar33892256
Chlordiazepoxide,1TMS,isomer #1CN(C1=NC2=CC=C(Cl)C=C2C(C2=CC=CC=C2)=[N+]([O-])C1)[Si](C)(C)C3604.9Standard polar33892256
Chlordiazepoxide,1TBDMS,isomer #1CN(C1=NC2=CC=C(Cl)C=C2C(C2=CC=CC=C2)=[N+]([O-])C1)[Si](C)(C)C(C)(C)C2822.4Semi standard non polar33892256
Chlordiazepoxide,1TBDMS,isomer #1CN(C1=NC2=CC=C(Cl)C=C2C(C2=CC=CC=C2)=[N+]([O-])C1)[Si](C)(C)C(C)(C)C2862.5Standard non polar33892256
Chlordiazepoxide,1TBDMS,isomer #1CN(C1=NC2=CC=C(Cl)C=C2C(C2=CC=CC=C2)=[N+]([O-])C1)[Si](C)(C)C(C)(C)C3669.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Chlordiazepoxide CI-B (Non-derivatized)splash10-0udi-0079000000-a3045f81d776a5127fe92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chlordiazepoxide EI-B (Non-derivatized)splash10-001i-5590000000-a20477457b7e9f8a22ea2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chlordiazepoxide CI-B (Non-derivatized)splash10-0udi-0079000000-a3045f81d776a5127fe92018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chlordiazepoxide EI-B (Non-derivatized)splash10-001i-5590000000-a20477457b7e9f8a22ea2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlordiazepoxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ce9-3190000000-fd85fc0a63c0f6fa743a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlordiazepoxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlordiazepoxide LC-ESI-QTOF , positive-QTOFsplash10-001i-0090000000-a293b353926a16c4d11a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlordiazepoxide , positive-QTOFsplash10-004i-2590000000-965415c5fb9e79098c6d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlordiazepoxide -1V, Positive-QTOFsplash10-001i-0090000000-c7b6568f60df163a90452021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordiazepoxide 10V, Positive-QTOFsplash10-0udi-0009000000-145539550957c8a47ff22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordiazepoxide 20V, Positive-QTOFsplash10-0udi-2039000000-5d3fa4444adf37869d3a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordiazepoxide 40V, Positive-QTOFsplash10-0a4i-9000000000-23b22bc4629e93465c342016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordiazepoxide 10V, Negative-QTOFsplash10-0002-0090000000-cae96ea0a93acd325b0a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordiazepoxide 20V, Negative-QTOFsplash10-0002-1090000000-e599edf7db7a647524e42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordiazepoxide 40V, Negative-QTOFsplash10-0a6r-9030000000-ed7b2614fcfebabd55db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordiazepoxide 10V, Positive-QTOFsplash10-0udi-0009000000-20c277fa4f0e38cb48022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordiazepoxide 20V, Positive-QTOFsplash10-0udi-0029000000-72801e1fa9da3f451f422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordiazepoxide 40V, Positive-QTOFsplash10-02tc-1290000000-0b39e76350bab67085512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordiazepoxide 10V, Negative-QTOFsplash10-0002-0090000000-d48fa0574ae5210c8c302021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordiazepoxide 20V, Negative-QTOFsplash10-00kb-2090000000-459de3a61617176e7e3b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlordiazepoxide 40V, Negative-QTOFsplash10-0gc0-9010000000-5ae42ebf2246e4f7b5392021-09-22Wishart 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 DB00475 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00475 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 IDDB00475
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10248513
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlordiazepoxide
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID3611
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 References
  1. Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [PubMed:6135616 ]
  2. Vozeh S: [Pharmacokinetic of benzodiazepines in old age]. Schweiz Med Wochenschr. 1981 Nov 21;111(47):1789-93. [PubMed:6118950 ]
  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. Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine]. Arch Fr Pediatr. 1977 Jan;34(1):74-89. [PubMed:851373 ]
  5. 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 ]

Only showing the first 10 proteins. There are 21 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 monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
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. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
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. 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 ]
  2. Lee G, Gammie SC: GABAA receptor signaling in caudal periaqueductal gray regulates maternal aggression and maternal care in mice. Behav Brain Res. 2010 Dec 1;213(2):230-7. doi: 10.1016/j.bbr.2010.05.001. Epub 2010 May 8. [PubMed:20457185 ]
  3. Licata SC, Platt DM, Cook JM, Van Linn ML, Rowlett JK: Contribution of alpha1 subunit-containing gamma-aminobutyric acidA (GABAA) receptors to motor-impairing effects of benzodiazepines in squirrel monkeys. Psychopharmacology (Berl). 2009 Apr;203(3):539-46. doi: 10.1007/s00213-008-1401-7. Epub 2008 Nov 25. [PubMed:19031072 ]
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. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
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. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
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:
GABRA4
Uniprot ID:
P48169
Molecular weight:
61622.6
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
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. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
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:
GABRA6
Uniprot ID:
Q16445
Molecular weight:
51023.7
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
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. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]

Only showing the first 10 proteins. There are 21 proteins in total.