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Showing metabocard for Estazolam (HMDB0015346)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (17) Show 17 proteinsXML
enzymes (17) Show 17 proteins
Record Information
Version4.0
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
MOLSDFPDBSMILESInChI
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point228.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.042 g/LNot Available
LogP4.7Not Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-016r-2190000000-7bceaaf0dfe0270e210aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-8b0f7d04b982deb5a038Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-6608de192721b2ce8c75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xu-8690000000-2b0a33869a0469e8d7b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-3bf04c7178bea5e8dea2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-4b4a11f4e7a928221cffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-1090000000-7609bb7b371102913ae0Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4u-4590000000-dbd088d66293b3b539c3Spectrum
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 ID
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. 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 ]
  3. 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 ]

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

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
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 ]
Enzyme Details
2. Gamma-aminobutyric acid receptor subunit gamma-2
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 ]
Enzyme Details
3. Gamma-aminobutyric acid receptor subunit alpha-1
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 ]
Enzyme Details
4. Gamma-aminobutyric acid receptor subunit alpha-2
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 ]
Enzyme Details
5. Gamma-aminobutyric acid receptor subunit alpha-3
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 ]
Enzyme Details
6. Gamma-aminobutyric acid receptor subunit alpha-5
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 ]
Enzyme Details
7. Gamma-aminobutyric acid receptor subunit beta-1
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 ]
Enzyme Details
8. Gamma-aminobutyric acid receptor subunit beta-2
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 ]
Enzyme Details
9. Gamma-aminobutyric acid receptor subunit beta-3
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 ]
Enzyme Details
10. Gamma-aminobutyric acid receptor subunit delta
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.

Show all enzymes and transporters