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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:27 UTC
HMDB IDHMDB0015346
Secondary Accession Numbers
  • HMDB15346
Metabolite Identification
Common NameEstazolam
DescriptionEstazolam is only found in individuals that have used or taken this drug. It is a benzodiazepine with anticonvulsant, hypnotic, and muscle relaxant properties. It has been shown in some cases to be more potent than diazepam or nitrazepam. [PubChem]Benzodiazepines bind nonspecifically to benzodiazepine receptors, which affects 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 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?1582753287
Synonyms
ValueSource
8-Chloro-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepineChEBI
EstazolamumChEBI
ProSomKegg
D40TAHMDB
Hormona brand OF estazolamHMDB
Abbott brand OF estazolamHMDB
NuctalonHMDB
D-40TAHMDB
Takeda brand OF estazolamHMDB
TasedanHMDB
Chemical FormulaC16H11ClN4
Average Molecular Weight294.738
Monoisotopic Molecular Weight294.067224079
IUPAC Name12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene
Traditional Nameestazolam
CAS Registry Number29975-16-4
SMILES
ClC1=CC2=C(C=C1)N1C=NN=C1CN=C2C1=CC=CC=C1
InChI Identifier
InChI=1S/C16H11ClN4/c17-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)18-9-15-20-19-10-21(14)15/h1-8,10H,9H2
InChI KeyCDCHDCWJMGXXRH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2,4-triazolo[4,3-a][1,4]benzodiazepines. These are aromatic compounds containing a 1,4-benzodiazepine fused to and sharing a nitrogen atom with a 1,2,4-triazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,2,4-triazolo[4,3-a][1,4]benzodiazepines
Alternative Parents
Substituents
  • 1,2,4-triazolo[4,3-a][1,4]benzodiazepine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • 1,2,4-triazole
  • Heteroaromatic compound
  • Ketimine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Imine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point228.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.042 g/LNot Available
LogP4.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP1.72ALOGPS
logP2.09ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)18.4ChemAxon
pKa (Strongest Basic)4.97ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.44 m³·mol⁻¹ChemAxon
Polarizability29.83 ųChemAxon
Number of Rings4ChemAxon
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]+164.04930932474
DeepCCS[M-H]-161.69130932474
DeepCCS[M-2H]-194.84430932474
DeepCCS[M+Na]+170.14230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EstazolamClC1=CC2=C(C=C1)N1C=NN=C1CN=C2C1=CC=CC=C13928.0Standard polar33892256
EstazolamClC1=CC2=C(C=C1)N1C=NN=C1CN=C2C1=CC=CC=C12808.4Standard non polar33892256
EstazolamClC1=CC2=C(C=C1)N1C=NN=C1CN=C2C1=CC=CC=C12898.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Estazolam GC-MS (Non-derivatized) - 70eV, Positivesplash10-016r-2190000000-7bceaaf0dfe0270e210a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estazolam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Estazolam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4u-4590000000-dbd088d66293b3b539c32014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estazolam 10V, Positive-QTOFsplash10-0002-0090000000-8b0f7d04b982deb5a0382016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estazolam 20V, Positive-QTOFsplash10-0002-0090000000-6608de192721b2ce8c752016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estazolam 40V, Positive-QTOFsplash10-03xu-8690000000-2b0a33869a0469e8d7b52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estazolam 10V, Negative-QTOFsplash10-0006-0090000000-3bf04c7178bea5e8dea22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estazolam 20V, Negative-QTOFsplash10-0006-0090000000-4b4a11f4e7a928221cff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estazolam 40V, Negative-QTOFsplash10-0a5c-1090000000-7609bb7b371102913ae02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estazolam 10V, Positive-QTOFsplash10-0002-0090000000-7f5d232a357b1b41cae82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estazolam 20V, Positive-QTOFsplash10-0002-0090000000-7f5d232a357b1b41cae82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estazolam 40V, Positive-QTOFsplash10-014j-0090000000-b88d0c4f35949ad6a7ab2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estazolam 10V, Negative-QTOFsplash10-0006-0090000000-1901824a83af80ea70832021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estazolam 20V, Negative-QTOFsplash10-0006-0090000000-1901824a83af80ea70832021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Estazolam 40V, Negative-QTOFsplash10-0006-0090000000-f5fb876690ac80360a522021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 DB01215 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01215 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 IDDB01215
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3146
KEGG Compound IDC06981
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEstazolam
METLIN IDNot Available
PubChem Compound3261
PDB IDNot Available
ChEBI ID4858
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. 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 ]
  2. 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 ]
  3. Watanabe S, Ohta H, Sakurai Y, Takao K, Ueki S: [Electroencephalographic effects of 450191-S and its metabolites in rabbits with chronic electrode implants]. Nihon Yakurigaku Zasshi. 1986 Jul;88(1):19-32. [PubMed:3758874 ]

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. Braestrup C, Squires RF: Pharmacological characterization of benzodiazepine receptors in the brain. Eur J Pharmacol. 1978 Apr 1;48(3):263-70. [PubMed:639854 ]
  2. Miller LG, Greenblatt DJ, Barnhill JG, Deutsch SI, Shader RI, Paul SM: Benzodiazepine receptor binding of triazolobenzodiazepines in vivo: increased receptor number with low-dose alprazolam. J Neurochem. 1987 Nov;49(5):1595-601. [PubMed:2889803 ]
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. Braestrup C, Squires RF: Pharmacological characterization of benzodiazepine receptors in the brain. Eur J Pharmacol. 1978 Apr 1;48(3):263-70. [PubMed:639854 ]
  2. Miller LG, Greenblatt DJ, Barnhill JG, Deutsch SI, Shader RI, Paul SM: Benzodiazepine receptor binding of triazolobenzodiazepines in vivo: increased receptor number with low-dose alprazolam. J Neurochem. 1987 Nov;49(5):1595-601. [PubMed:2889803 ]
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. Braestrup C, Squires RF: Pharmacological characterization of benzodiazepine receptors in the brain. Eur J Pharmacol. 1978 Apr 1;48(3):263-70. [PubMed:639854 ]
  2. Miller LG, Greenblatt DJ, Barnhill JG, Deutsch SI, Shader RI, Paul SM: Benzodiazepine receptor binding of triazolobenzodiazepines in vivo: increased receptor number with low-dose alprazolam. J Neurochem. 1987 Nov;49(5):1595-601. [PubMed:2889803 ]
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. Braestrup C, Squires RF: Pharmacological characterization of benzodiazepine receptors in the brain. Eur J Pharmacol. 1978 Apr 1;48(3):263-70. [PubMed:639854 ]
  2. Miller LG, Greenblatt DJ, Barnhill JG, Deutsch SI, Shader RI, Paul SM: Benzodiazepine receptor binding of triazolobenzodiazepines in vivo: increased receptor number with low-dose alprazolam. J Neurochem. 1987 Nov;49(5):1595-601. [PubMed:2889803 ]
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. Braestrup C, Squires RF: Pharmacological characterization of benzodiazepine receptors in the brain. Eur J Pharmacol. 1978 Apr 1;48(3):263-70. [PubMed:639854 ]
  2. Miller LG, Greenblatt DJ, Barnhill JG, Deutsch SI, Shader RI, Paul SM: Benzodiazepine receptor binding of triazolobenzodiazepines in vivo: increased receptor number with low-dose alprazolam. J Neurochem. 1987 Nov;49(5):1595-601. [PubMed:2889803 ]
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. Braestrup C, Squires RF: Pharmacological characterization of benzodiazepine receptors in the brain. Eur J Pharmacol. 1978 Apr 1;48(3):263-70. [PubMed:639854 ]
  2. Miller LG, Greenblatt DJ, Barnhill JG, Deutsch SI, Shader RI, Paul SM: Benzodiazepine receptor binding of triazolobenzodiazepines in vivo: increased receptor number with low-dose alprazolam. J Neurochem. 1987 Nov;49(5):1595-601. [PubMed:2889803 ]
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. Braestrup C, Squires RF: Pharmacological characterization of benzodiazepine receptors in the brain. Eur J Pharmacol. 1978 Apr 1;48(3):263-70. [PubMed:639854 ]
  2. Miller LG, Greenblatt DJ, Barnhill JG, Deutsch SI, Shader RI, Paul SM: Benzodiazepine receptor binding of triazolobenzodiazepines in vivo: increased receptor number with low-dose alprazolam. J Neurochem. 1987 Nov;49(5):1595-601. [PubMed:2889803 ]
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. Braestrup C, Squires RF: Pharmacological characterization of benzodiazepine receptors in the brain. Eur J Pharmacol. 1978 Apr 1;48(3):263-70. [PubMed:639854 ]
  2. Miller LG, Greenblatt DJ, Barnhill JG, Deutsch SI, Shader RI, Paul SM: Benzodiazepine receptor binding of triazolobenzodiazepines in vivo: increased receptor number with low-dose alprazolam. J Neurochem. 1987 Nov;49(5):1595-601. [PubMed:2889803 ]
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. Braestrup C, Squires RF: Pharmacological characterization of benzodiazepine receptors in the brain. Eur J Pharmacol. 1978 Apr 1;48(3):263-70. [PubMed:639854 ]
  2. Miller LG, Greenblatt DJ, Barnhill JG, Deutsch SI, Shader RI, Paul SM: Benzodiazepine receptor binding of triazolobenzodiazepines in vivo: increased receptor number with low-dose alprazolam. J Neurochem. 1987 Nov;49(5):1595-601. [PubMed:2889803 ]

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