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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:15 UTC
HMDB IDHMDB15528
Secondary Accession NumbersNone
Metabolite Identification
Common NameQuazepam
DescriptionQuazepam is only found in individuals that have used or taken this drug. It is a drug which is a benzodiazepine derivative. It induces impairment of motor function and has hypnotic properties. Quazepam is used to treat insomnia.Benzodiazepines bind nonspecifically to benzodiazepine receptors, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Structure
Thumb
Synonyms
ValueSource
DoralKegg
Chemical FormulaC17H11ClF4N2S
Average Molecular Weight386.794
Monoisotopic Molecular Weight386.026759579
IUPAC Name7-chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine-2-thione
Traditional Namequazepam
CAS Registry Number36735-22-5
SMILES
FC1=CC=CC=C1C1=NCC(=S)N(CC(F)(F)F)C2=C1C=C(Cl)C=C2
InChI Identifier
InChI=1S/C17H11ClF4N2S/c18-10-5-6-14-12(7-10)16(11-3-1-2-4-13(11)19)23-8-15(25)24(14)9-17(20,21)22/h1-7H,8-9H2
InChI KeyInChIKey=IKMPWMZBZSAONZ-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
  • Halobenzene
  • Fluorobenzene
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Aryl chloride
  • Thiolactam
  • Tertiary amine
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Imine
  • Amine
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-anxiety Agents
  • Benzodiazepines
  • GABA Modulators
  • Hypnotics and Sedatives
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point137.5 - 139 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.31e-03 g/LNot Available
LogP4.03SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0023 mg/mLALOGPS
logP4.76ALOGPS
logP5.06ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)18.93ChemAxon
pKa (Strongest Basic)2.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area15.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity93.47 m3·mol-1ChemAxon
Polarizability33.99 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-05aa-3988000000-ca1cf29da979ef46dd6cView 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 DB01589
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01589
  • 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
Blood0-0.1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01589
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4825
KEGG Compound IDC07336
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuazepam
NuGOwiki LinkHMDB15528
Metagene LinkHMDB15528
METLIN IDNot Available
PubChem Compound4999
PDB IDNot Available
ChEBI ID774423
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 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
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 monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  4. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
  5. 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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]
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. Meldrum BS, Chapman AG: Benzodiazepine receptors and their relationship to the treatment of epilepsy. Epilepsia. 1986;27 Suppl 1:S3-13. [3017690 ]
  2. Billard W, Crosby G, Iorio L, Chipkin R, Barnett A: Selective affinity of the benzodiazepines quazepam and 2-oxo-quazepam for BZ1 binding site and demonstration of 3H-2-oxo-quazepam as a BZ1 selective radioligand. Life Sci. 1988;42(2):179-87. [2892106 ]