U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C16H11ClN4
Molecular Weight 294.738
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTAZOLAM

SMILES

ClC1=CC=C2N3C=NN=C3CN=C(C4=CC=CC=C4)C2=C1

InChI

InChIKey=CDCHDCWJMGXXRH-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C16H11ClN4
Molecular Weight 294.738
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Estazolam, a triazolobenzodiazepine derivative, is an oral hypnotic agent with anticonvulsant, hypnotic, and muscle relaxant properties. It has been shown in some cases to be more potent than diazepam or nitrazepam. 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. Used for the short-term management of insomnia characterized by difficulty in falling asleep, frequent nocturnal awakenings, and/or early morning awakenings. Marketed under the brand names ProSom, Eurodin.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.8 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Estazolam

Cmax

ValueDoseCo-administeredAnalytePopulation
54.7 ng/mL
1 mg single, oral
ESTAZOLAM plasma
Homo sapiens
98.6 ng/mL
2 mg single, oral
ESTAZOLAM plasma
Homo sapiens
194 ng/mL
4 mg single, oral
ESTAZOLAM plasma
Homo sapiens
180 ng/mL
2 mg 2 times / day steady-state, oral
ESTAZOLAM plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1050 ng × h/mL
1 mg single, oral
ESTAZOLAM plasma
Homo sapiens
2060 ng × h/mL
2 mg single, oral
ESTAZOLAM plasma
Homo sapiens
4343 ng × h/mL
4 mg single, oral
ESTAZOLAM plasma
Homo sapiens
5517 ng × h/mL
2 mg 2 times / day steady-state, oral
ESTAZOLAM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
14.9 h
1 mg single, oral
ESTAZOLAM plasma
Homo sapiens
14.3 h
2 mg single, oral
ESTAZOLAM plasma
Homo sapiens
19 h
4 mg single, oral
ESTAZOLAM plasma
Homo sapiens
17 h
2 mg 2 times / day steady-state, oral
ESTAZOLAM plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Insomnia 1 to 2 mg orally at bedtime
Route of Administration: Oral
In Vitro Use Guide
Incubation of rabbit PRP with etizolam for 2 min before administration of aggregating agents inhibited aggregation induced by PAF (190 nM) with an IC50 of 3.8 uM. Etizolam at a higher concentration (300 uM) only slightly in hibited ADP (15 uM) and arachidonic acid-induced aggregation
Substance Class Chemical
Record UNII
36S3EQV54C
Record Status Validated (UNII)
Record Version