ETIZOLAM

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=C(Cl)C=CC=C4

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

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 2678		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 8429	DEPAS Approved Use Unknown

PubMed

Title	Date	PubMed
[A patient with Parkinson's disease complicated by hypothyroidism who developed malignant syndrome after discontinuation of etizolam].	2002 Feb	12424963
Etizolam, an anti-anxiety agent, attenuates recurrence of chronic subdural hematoma--evaluation by computed tomography.	2002 Feb	11944589
Etizolam-induced superficial erythema annulare centrifugum.	2002 Jan	11952667
Nightmares and panic disorder associated with carvedilol overdose.	2002 Nov	12398570
[Case of prolonged recovery from serotonin syndrome caused by paroxetine].	2003	15027311
[Practical analysis of toxic substances useful for clinical toxicology--10--benzodiazepine].	2004 Apr	15266852
Inhibition of the metabolism of etizolam by itraconazole in humans: evidence for the involvement of CYP3A4 in etizolam metabolism.	2004 Aug	15232663
Effects of concomitant fluvoxamine on the plasma concentration of etizolam in Japanese psychiatric patients: wide interindividual variation in the drug interaction.	2004 Dec	15570188
Etizolam and benzodiazepine induced blepharospasm.	2004 Mar	14966178
[Case report of pentazocine dependence from a standpoint of the cognitive therapy].	2004 Oct	15573677
Delirium induced by abrupt discontinuation of paroxetine.	2004 Winter	14990771
Effect of platelet-activating factor receptor antagonist, etizolam, on resolution of chronic subdural hematoma--a prospective study to investigate use as conservative therapy.	2005 Dec	16377949
Pharmacokinetics and pharmacodynamics of etizolam are influenced by polymorphic CYP2C19 activity.	2005 Dec	16261363
Pharmacokinetic interactions between Japanese traditional Kampo medicine and modern medicine (IV). Effect of Kamisyoyosan and Tokisyakuyakusan on the pharmacokinetics of etizolam in rats.	2005 Feb	15684484
Inhibitory effects of psychotropic drugs on mexiletine metabolism in human liver microsomes: prediction of in vivo drug interactions.	2005 Jun	16192107
Induction of the metabolism of etizolam by carbamazepine in humans.	2005 May	15776275
Contribution of human hepatic cytochrome p450 isoforms to the metabolism of psychotropic drugs.	2005 Sep	16141545
Low tolerance and dependence liabilities of etizolam: molecular, functional, and pharmacological correlates.	2005 Sep 5	16107249
Chronic pain induces anxiety with concomitant changes in opioidergic function in the amygdala.	2006 Apr	16123756
Multi-center randomized control trial of etizolam plus NSAID combination for tension-type headache.	2007	17443036
Effects of genetic polymorphism of cytochrome P450 enzymes on the pharmacokinetics of benzodiazepines.	2007 Aug	17635335
Serotonin syndrome in a case of depression with various somatic symptoms: the difficulty in differential diagnosis.	2007 Jan 30	16916568
Accidental etizolam ingestion in a child.	2007 Jul	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 May	17454433
Absence status associated with focal activity and polydipsia-induced hyponatremia.	2008 Apr	18728738
Rebound insomnia induced by abrupt withdrawal of hypnotics in sleep-disturbed rats.	2008 Nov 12	18789918
Case report: Etizolam and its major metabolites in two unnatural death cases.	2008 Nov 20	18976871
Benzodiazepine metabolism: an analytical perspective.	2008 Oct	18855614
[A case of serotonin syndrome following minimum doses of sertraline].	2009	19999561
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 Dec	20110024
Fluvoxamine monotherapy for psychotic depression: the potential role of sigma-1 receptors.	2009 Dec 21	20025739
Inclusion of thienodiazepines in prescription rate of anxiolytics.	2009 Jun	19566784
Benzodiazepine prescription and length of hospital stay at a Japanese university hospital.	2009 Oct 9	19818119
Fluvoxamine for blonanserin-associated akathisia in patients with schizophrenia: report of five cases.	2010 Apr 24	20416096
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
Medication use as a risk factor for inpatient falls in an acute care hospital: a case-crossover study.	2010 May	20573090
Effects of etizolam and ethyl loflazepate on the P300 event-related potential in healthy subjects.	2010 Nov 3	21047414

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.

Name

Type

Language

ETIZOLAM

Official Name

English

etizolam [INN]

Common Name

English

SEDEKOPAN

Brand 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

Classification Tree Code System Code

NCI_THESAURUS

C1012