ContaminantDB: Estazolam

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (21)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:39 UTC

Update Date

2026-05-14 16:58:48 UTC

Accession Number

CHEM002379

Identification

Common Name

Estazolam

Class

Small Molecule

Description

Estazolam 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 (GABA_A) 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.

Contaminant Sources

HMDB Contaminants - Urine
IARC Carcinogens Group 3
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Anti-Anxiety Agent
Anticonvulsant
Drug
GABA Modulator
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
8-Chloro-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepine	ChEBI
Estazolamum	ChEBI
ProSom	Kegg
D40TA	HMDB
Hormona brand OF estazolam	HMDB
Abbott brand OF estazolam	HMDB
Nuctalon	HMDB
D-40TA	HMDB
Takeda brand OF estazolam	HMDB
Tasedan	HMDB

Chemical Formula

C₁₆H₁₁ClN₄

Average Molecular Mass

294.738 g/mol

Monoisotopic Mass

294.067 g/mol

CAS Registry Number

29975-16-4

IUPAC Name

12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaene

Traditional Name

estazolam

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 Key

CDCHDCWJMGXXRH-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,2,4-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

triazoles (CHEBI:4858 )
triazolobenzodiazepine (CHEBI:4858 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Kidney
Liver

Pathways

Not Available

Applications

Biological Roles

GABA modulator

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	228-229°C
Boiling Point	Not Available
Solubility	Practically insoluble (1.5 mg/L)

Predicted Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	1.72	ALOGPS
logP	2.09	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.4	ChemAxon
pKa (Strongest Basic)	4.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.44 m³·mol⁻¹	ChemAxon
Polarizability	29.83 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-2190000000-7bceaaf0dfe0270e210a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-8b0f7d04b982deb5a038	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-6608de192721b2ce8c75	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03xu-8690000000-2b0a33869a0469e8d7b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-3bf04c7178bea5e8dea2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0090000000-4b4a11f4e7a928221cff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5c-1090000000-7609bb7b371102913ae0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-7f5d232a357b1b41cae8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-7f5d232a357b1b41cae8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-0090000000-b88d0c4f35949ad6a7ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-1901824a83af80ea7083	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0090000000-1901824a83af80ea7083	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0090000000-f5fb876690ac80360a52	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4u-4590000000-dbd088d66293b3b539c3	Spectrum

Toxicity Profile

Route of Exposure

Tablets have been found to be equivalent in absorption to an orally administered solution of estazolam. In healthy subjects who received up to three times the recommended dose, peak estazolam plasma concentrations occurred within two hours after dosing (range 0.5 to 6.0 hours) and were proportional to the administered dose, suggesting linear pharmacokinetics over the dosage range tested.

Mechanism of Toxicity

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 (GABA_A) 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.

Metabolism

Extensively metabolized in the liver. In vitro studies with human liver microsomes indicate that the biotransformation of estazolam to the major circulating metabolite 4-hydroxy-estazolam is mediated by cytochrome P450 3A (CYP3A). Route of Elimination: Estazolam is extensively metabolized. The elimination of the parent drug takes place via hepatic metabolism of estazolam to hydroxylated and other metabolites that are eliminated largely in the urine both free and conjugated. Less than 5% of a 2 mg dose of estazolam was excreted unchanged in the urine, with only 4% of the dose appearing in the feces. Radiolabel mass balance studies indicate that the main route of excretion is via the kidneys. After 5 days, 87% of the administered radioactivity was excreted in human urine. Less than 4% of the dose was excreted unchanged. Half Life: The range of estimates for the mean elimination half-life of estazolam varies from 10 to 24 hours.

Toxicity Values

LD50: 740 mg/kg (oral, male mice) (6) LD50: 3200 mg/kg (oral, rat) (6) LD50 300 mg/kg (oral, rabbit) (6)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (4)

Uses/Sources

For the short-term management of insomnia characterized by difficulty in falling asleep, frequent nocturnal awakenings, and/or early morning awakenings.

Minimum Risk Level

Not Available

Health Effects

May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

Symptoms

Symptoms of overdose include confusion, depressed breathing, drowsiness and eventually coma, lack of coordination, and slurred speech.

Treatment

Gastric evacuation, either by the induction of emesis, lavage, or both, should be performed immediately. Maintenance of adequate ventilation is essential. General supportive care, including frequent monitoring of the vital signs and close observation of the patient, is indicated. Fluids should be administered intravenously to maintain blood pressure and encourage diuresis. The value of dialysis in treatment of benzodiazepine overdose has not been determined. The physician may wish to consider contacting a Poison Control Center for up-to-date information on the management of hypnotic drug product overdose. Flumazenil, a specific benzodiazepine receptor antagonist, is indicated for the complete or partial reversal of the sedative effects of benzodiazepines and may be used in situations when an overdose with a benzodiazepine is known or suspected. (5)

Concentrations

Not Available

External Links

DrugBank ID

DB01215

HMDB ID

HMDB0015346

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID