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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:31 UTC
HMDB IDHMDB0014376
Secondary Accession Numbers
  • HMDB14376
Metabolite Identification
Common NameTemazepam
DescriptionTemazepam is only found in individuals that have used or taken this drug. It is a benzodiazepine that acts as a gamma-aminobutyric acid modulator and anti-anxiety agent. [PubChem]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
Data?1582753171
Synonyms
ValueSource
RestorilKegg
HydroxydiazepamHMDB
MethyloxazepamHMDB
N-MethyloxazepamHMDB
OxydiazepamHMDB
Apotex brand OF temazepamHMDB
Katwijk brand OF temazepamHMDB
Knoll brand OF temazepamHMDB
NocturneHMDB
NormitabHMDB
Novopharm brand OF temazepamHMDB
Nu pharm brand OF temazepamHMDB
Nu temazepamHMDB
Nu-pharm brand OF temazepamHMDB
PMS TemazepamHMDB
PMS-TemazepamHMDB
RemestanHMDB
Sigma brand OF temazepamHMDB
3 HydroxydiazepamHMDB
3-HydroxydiazepamHMDB
AHP brand OF temazepamHMDB
Apo-temazepamHMDB
Genopharm brand OF temazepamHMDB
Genpharm brand OF temazepamHMDB
Mallinckrodt brand OF temazepamHMDB
NortemHMDB
Novo temazepamHMDB
Nu-temazepamHMDB
Orion brand OF temazepamHMDB
PlanumHMDB
TenoxHMDB
Wyeth brand OF temazepamHMDB
CT-Arzneimittel brand OF temazepamHMDB
Apo temazepamHMDB
EuhypnosHMDB
ICN brand OF temazepamHMDB
NormisonHMDB
Norton brand OF temazepamHMDB
Novartis brand OF temazepamHMDB
Pfizer brand 1 OF temazepamHMDB
Pfizer brand 2 OF temazepamHMDB
Pharmascience brand OF temazepamHMDB
Scheffler brand OF temazepamHMDB
SignopamHMDB
Tema, norkotralHMDB
TemazeHMDB
TemtabsHMDB
CT Arzneimittel brand OF temazepamHMDB
Alphapharm brand OF temazepamHMDB
DasuenHMDB
Desitin brand OF temazepamHMDB
Gen temazepamHMDB
Gen-temazepamHMDB
LevanxolHMDB
Norkotral temaHMDB
Novo-temazepamHMDB
Pronervon THMDB
Temazep von CTHMDB
Von CT, temazepMeSH
Chemical FormulaC16H13ClN2O2
Average Molecular Weight300.74
Monoisotopic Molecular Weight300.066555377
IUPAC Name7-chloro-3-hydroxy-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
Traditional Nametemazepam
CAS Registry Number846-50-4
SMILES
CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C16H13ClN2O2/c1-19-13-8-7-11(17)9-12(13)14(18-15(20)16(19)21)10-5-3-2-4-6-10/h2-9,15,20H,1H3
InChI KeySEQDDYPDSLOBDC-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
  • Alkanolamine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organohalogen compound
  • Organochloride
  • Imine
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point119 - 121 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.053 g/LNot Available
LogP3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.053 g/LALOGPS
logP2.16ALOGPS
logP2.79ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)10.68ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.9 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity81.01 m³·mol⁻¹ChemAxon
Polarizability30.32 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0076-1290000000-b5520ec3d2305756be73Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0kmr-9437000000-0244d11da064e8c0d1e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0019000000-f9c9fe92391b593143ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0091000000-b26b004678460e39d9dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0090000000-d71ab75b6d551af5cf29Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0390000000-43e671827e9519f8cbd7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a6r-0980000000-6fcab627ec42157d1ed9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0092000000-36017deb260bb70b05cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-7d9e12c41cdc37869173Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0339000000-d65623eab9da4e6e0a8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-3930000000-e6777c2ed8db44e9e193Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-7fc31b3910bb0c20262cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-0190000000-f5990016db4cbf3432daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9340000000-37b87e4eed991dce5a03Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-4391000000-eba55d0cdbd09c877424Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00231 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00231 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 IDDB00231
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5198
KEGG Compound IDC07125
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTemazepam
METLIN IDNot Available
PubChem Compound5391
PDB IDNot Available
ChEBI ID195909
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rooke KC: The use of flurazepam (dalmane) as a substitute for barbiturates and methaqualone/diphenhydramine (mandrax) in general practice. J Int Med Res. 1976;4(5):355-9. [PubMed:18375 ]
  2. Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines]. Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [PubMed:2570451 ]
  3. Rickels K: The clinical use of hypnotics: indications for use and the need for a variety of hypnotics. Acta Psychiatr Scand Suppl. 1986;332:132-41. [PubMed:2883820 ]
  4. Vozeh S: [Pharmacokinetic of benzodiazepines in old age]. Schweiz Med Wochenschr. 1981 Nov 21;111(47):1789-93. [PubMed:6118950 ]
  5. Shats V, Kozacov S: [Falls in the geriatric department: responsibility of the care-giver and the hospital]. Harefuah. 1995 Jun 1;128(11):690-3, 743. [PubMed:7557666 ]

Only showing the first 10 proteins. There are 25 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. Shou M, Mei Q, Ettore MW Jr, Dai R, Baillie TA, Rushmore TH: Sigmoidal kinetic model for two co-operative substrate-binding sites in a cytochrome P450 3A4 active site: an example of the metabolism of diazepam and its derivatives. Biochem J. 1999 Jun 15;340 ( Pt 3):845-53. [PubMed:10359672 ]
  2. 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:
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed: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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed: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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
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:
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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
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. 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 ]
  2. Giersch A, Boucart M, Elliott M, Vidailhet P: Atypical behavioural effects of lorazepam: clues to the design of novel therapies? Pharmacol Ther. 2010 Apr;126(1):94-108. doi: 10.1016/j.pharmthera.2010.01.004. Epub 2010 Feb 4. [PubMed:20138190 ]
General function:
Signal transduction mechanisms
Specific function:
Responsible for the manifestation of peripheral-type benzodiazepine recognition sites and is most likely to comprise binding domains for benzodiazepines and isoquinoline carboxamides. May play a role in the transport of porphyrins and heme. Plays a role in the transport of cholesterol across mitochondrial membranes in steroidogenic cells
Gene Name:
TSPO
Uniprot ID:
P30536
Molecular weight:
18778.7
References
  1. Dobbin M, Martyres RF, Clode D, Champion De Crespigny FE: Association of benzodiazepine injection with the prescription of temazepam capsules. Drug Alcohol Rev. 2003 Jun;22(2):153-7. [PubMed:12850901 ]
  2. Miller EI, Wylie FM, Oliver JS: Detection of benzodiazepines in hair using ELISA and LC-ESI-MS-MS. J Anal Toxicol. 2006 Sep;30(7):441-8. [PubMed:16959136 ]
  3. 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 ]
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. 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 ]
  2. Giersch A, Boucart M, Elliott M, Vidailhet P: Atypical behavioural effects of lorazepam: clues to the design of novel therapies? Pharmacol Ther. 2010 Apr;126(1):94-108. doi: 10.1016/j.pharmthera.2010.01.004. Epub 2010 Feb 4. [PubMed:20138190 ]
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. 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 ]
  2. Giersch A, Boucart M, Elliott M, Vidailhet P: Atypical behavioural effects of lorazepam: clues to the design of novel therapies? Pharmacol Ther. 2010 Apr;126(1):94-108. doi: 10.1016/j.pharmthera.2010.01.004. Epub 2010 Feb 4. [PubMed:20138190 ]
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. 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 ]
  2. Giersch A, Boucart M, Elliott M, Vidailhet P: Atypical behavioural effects of lorazepam: clues to the design of novel therapies? Pharmacol Ther. 2010 Apr;126(1):94-108. doi: 10.1016/j.pharmthera.2010.01.004. Epub 2010 Feb 4. [PubMed:20138190 ]

Only showing the first 10 proteins. There are 25 proteins in total.