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
Nightmares and panic disorder associated with carvedilol overdose.	2002 Nov	12398570
[Practical analysis of toxic substances useful for clinical toxicology--10--benzodiazepine].	2004 Apr	15266852
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
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
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
Benzodiazepine metabolism: an analytical perspective.	2008 Oct	18855614

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