ETIZOLAM

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H15ClN4S
Molecular Weight	342.846
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=CC2=C(S1)N3C(C)=NN=C3CN=C2C4=CC=CC=C4Cl

InChI

InChIKey=VMZUTJCNQWMAGF-UHFFFAOYSA-N

InChI=1S/C17H15ClN4S/c1-3-11-8-13-16(12-6-4-5-7-14(12)18)19-9-15-21-20-10(2)22(15)17(13)23-11/h4-8H,3,9H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C17H15ClN4S
Molecular Weight	342.846
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.who.int/medicines/access/controlled-substances/5.7_Etizolam_PreRev.pdf
Curator's Comment: description was created based on several sources, including, www.ncbi.nlm.nih.gov/pubmed/25538342

Etizolam is an analogue of benzodiazepine that contains thienotriazolodiazepine group. The drug was developed and approved in Japan and now is used in Japan, Italy and India for the treatment of anxiety disorders. Etizolam exerts its action through activation of GABA A receptors, moreover, the agonistic behavior was shown on isolated neurons. There are several cases when etizolam dependence was reported. In many countries the drug is recognized as a psychoactive substance and its distribution is illegal there.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor 3 Target ID: CHEMBL2364024 Sources: http://www.who.int/medicines/access/controlled-substances/5.7_Etizolam_PreRev.pdf	Agonist 2752		92.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety disorder with depressive symptoms 1 Sources: http://www.who.int/medicines/access/controlled-substances/5.7_Etizolam_PreRev.pdf	Primary		Approved 8583	DEPAS Approved Use Unknown

C_max

Value	Dose	Analyte	Population
35.25 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400061_1179025F1352_1_902_1F.pdf#page=22	0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
40.39 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400061_1179025F1352_1_902_1F.pdf#page=23	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
17.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
20.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
20.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
15.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
18.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
20.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2065698/	0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
9.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2065698/	0.5 mg 2 times / day multiple, oral dose: 0.5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
266.66 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400061_1179025F1352_1_902_1F.pdf#page=22	0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
277.07 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400061_1179025F1352_1_902_1F.pdf#page=23	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
105 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
158 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
158 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
59.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
138 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
158 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
46.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2065698/	0.5 mg 2 times / day multiple, oral dose: 0.5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
12.24 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400061_1179025F1352_1_902_1F.pdf#page=22	0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
13.26 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400061_1179025F1352_1_902_1F.pdf#page=23	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
10.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
14.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
14.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
14.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16261363/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2065698/	0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2065698/	0.5 mg 2 times / day multiple, oral dose: 0.5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ETIZOLAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
7% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400061_1179025F1352_1_902_1F.pdf#page=24			ETIZOLAM plasma	Homo sapiens

Doses

Dose	Population	Adverse events
0.5 mg 2 times / day multiple, oral Recommended Dose: 0.5 mg, 2 times / day Route: oral Route: multiple Dose: 0.5 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1981698/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1981698/	Disc. AE: Drowsiness, Gastralgia... AEs leading to discontinuation/dose reduction: Drowsiness (8.3%) Gastralgia (8.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/1981698/
1 mg 3 times / day multiple, oral Recommended Dose: 1 mg, 3 times / day Route: oral Route: multiple Dose: 1 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11952667/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11952667/	Disc. AE: Erythema annulare centrifugum... AEs leading to discontinuation/dose reduction: Erythema annulare centrifugum Sources: https://pubmed.ncbi.nlm.nih.gov/11952667/
0.5 mg single, oral Accidental dose Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17666930/	healthy, CHILD Health Status: healthy Age Group: CHILD Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17666930/	Other AEs: Excitation, muscle weaknes... Other AEs: Excitation muscle weaknes Drowsiness Hypotonia Sources: https://pubmed.ncbi.nlm.nih.gov/17666930/

AEs

AE	Significance	Dose	Population
Drowsiness	8.3% Disc. AE	0.5 mg 2 times / day multiple, oral Recommended Dose: 0.5 mg, 2 times / day Route: oral Route: multiple Dose: 0.5 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1981698/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1981698/
Gastralgia	8.3% Disc. AE	0.5 mg 2 times / day multiple, oral Recommended Dose: 0.5 mg, 2 times / day Route: oral Route: multiple Dose: 0.5 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1981698/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1981698/
Erythema annulare centrifugum	Disc. AE	1 mg 3 times / day multiple, oral Recommended Dose: 1 mg, 3 times / day Route: oral Route: multiple Dose: 1 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11952667/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11952667/
Drowsiness		0.5 mg single, oral Accidental dose Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17666930/	healthy, CHILD Health Status: healthy Age Group: CHILD Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17666930/
Excitation		0.5 mg single, oral Accidental dose Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17666930/	healthy, CHILD Health Status: healthy Age Group: CHILD Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17666930/
Hypotonia		0.5 mg single, oral Accidental dose Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17666930/	healthy, CHILD Health Status: healthy Age Group: CHILD Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17666930/
muscle weaknes		0.5 mg single, oral Accidental dose Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17666930/	healthy, CHILD Health Status: healthy Age Group: CHILD Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17666930/

PubMed

Title	Date	PubMed
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Effects of etizolam and ethyl loflazepate on the P300 event-related potential in healthy subjects.	2010-11-03	21047414
Medication use as a risk factor for inpatient falls in an acute care hospital: a case-crossover study.	2010-05	20573090
Fluvoxamine for blonanserin-associated akathisia in patients with schizophrenia: report of five cases.	2010-04-24	20416096
Fluvoxamine monotherapy for psychotic depression: the potential role of sigma-1 receptors.	2009-12-21	20025739
Effects of treatment with etizolam 0.5 mg BID on cognitive performance: a 3-week, multicenter, randomized, double-blind, placebo-controlled, two-treatment, three-period, noninferiority crossover study in patients with anxiety disorder.	2009-12	20110024
Benzodiazepine prescription and length of hospital stay at a Japanese university hospital.	2009-10-09	19818119
Inclusion of thienodiazepines in prescription rate of anxiolytics.	2009-06	19566784
[A case of serotonin syndrome following minimum doses of sertraline].	2009	19999561
Case report: Etizolam and its major metabolites in two unnatural death cases.	2008-11-20	18976871
Rebound insomnia induced by abrupt withdrawal of hypnotics in sleep-disturbed rats.	2008-11-12	18789918
Benzodiazepine metabolism: an analytical perspective.	2008-10	18855614
Absence status associated with focal activity and polydipsia-induced hyponatremia.	2008-04	18728738
Effects of genetic polymorphism of cytochrome P450 enzymes on the pharmacokinetics of benzodiazepines.	2007-08	17635335
Accidental etizolam ingestion in a child.	2007-07	17666930
Effects of different cyclodextrins on the morphology, loading and release properties of poly (DL-lactide-co-glycolide)-microparticles containing the hypnotic agent etizolam.	2007-05	17454433
Serotonin syndrome in a case of depression with various somatic symptoms: the difficulty in differential diagnosis.	2007-01-30	16916568
Multi-center randomized control trial of etizolam plus NSAID combination for tension-type headache.	2007	17443036
Chronic pain induces anxiety with concomitant changes in opioidergic function in the amygdala.	2006-04	16123756
Effect of platelet-activating factor receptor antagonist, etizolam, on resolution of chronic subdural hematoma--a prospective study to investigate use as conservative therapy.	2005-12	16377949
Pharmacokinetics and pharmacodynamics of etizolam are influenced by polymorphic CYP2C19 activity.	2005-12	16261363
Low tolerance and dependence liabilities of etizolam: molecular, functional, and pharmacological correlates.	2005-09-05	16107249
Contribution of human hepatic cytochrome p450 isoforms to the metabolism of psychotropic drugs.	2005-09	16141545
Inhibitory effects of psychotropic drugs on mexiletine metabolism in human liver microsomes: prediction of in vivo drug interactions.	2005-06	16192107
Induction of the metabolism of etizolam by carbamazepine in humans.	2005-05	15776275
Pharmacokinetic interactions between Japanese traditional Kampo medicine and modern medicine (IV). Effect of Kamisyoyosan and Tokisyakuyakusan on the pharmacokinetics of etizolam in rats.	2005-02	15684484
Effects of concomitant fluvoxamine on the plasma concentration of etizolam in Japanese psychiatric patients: wide interindividual variation in the drug interaction.	2004-12	15570188
[Case report of pentazocine dependence from a standpoint of the cognitive therapy].	2004-10	15573677
Inhibition of the metabolism of etizolam by itraconazole in humans: evidence for the involvement of CYP3A4 in etizolam metabolism.	2004-08	15232663
[Practical analysis of toxic substances useful for clinical toxicology--10--benzodiazepine].	2004-04	15266852
Etizolam and benzodiazepine induced blepharospasm.	2004-03	14966178
Delirium induced by abrupt discontinuation of paroxetine.	2004	14990771
[Case of prolonged recovery from serotonin syndrome caused by paroxetine].	2003	15027311
Nightmares and panic disorder associated with carvedilol overdose.	2002-11	12398570
[A patient with Parkinson's disease complicated by hypothyroidism who developed malignant syndrome after discontinuation of etizolam].	2002-02	12424963
Etizolam, an anti-anxiety agent, attenuates recurrence of chronic subdural hematoma--evaluation by computed tomography.	2002-02	11944589
Etizolam-induced superficial erythema annulare centrifugum.	2002-01	11952667

Sample Use Guides

In Vivo Use Guide

0.5 mg twice daily

Route of Administration: Oral

In Vitro Use Guide

Exposure of rat hippocampal neurons in culture to 10 microM etizolam for 5 days reduced the amounts of alpha5 and gamma2S receptor subunit mRNAs.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:28:27 GMT 2025` Edited by `admin` on `Mon Mar 31 18:28:27 GMT 2025`
Record UNII	A76XI0HL37
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ETIZOLAM

Official Name

English

SEDEKOPAN

Preferred Name

English

etizolam [INN]

Common Name

English

4-(2-Chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine

Systematic Name

English

ETIZOLAM [MART.]

Common Name

English

Etizolam [WHO-DD]

Common Name

English

ETIZOLAM [MI]

Common Name

English

ETIZOLAM [JAN]

Common Name

English

4-(O-CHLOROPHENYL)-2-ETHYL-9-METHYL-6H-THIENO(3,2-F)-S-TRIAZOLO(4,3-A)(1,4)DIAZEPINE

Common Name

English

DEA NO. 2780

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1012