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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Agonist 2,752		92.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety disorder with depressive symptoms 1	Primary		Approved 8,583	DEPAS

C_max

Value	Dose	Analyte	Population
35.25 ng/mL	0.5 mg single, oral	ETIZOLAM plasma	Homo sapiens
40.39 ng/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
17.3 ng/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
20.7 ng/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
20.7 ng/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
15.4 ng/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
18.7 ng/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
20.7 ng/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
8.3 ng/mL	0.5 mg single, oral	ETIZOLAM plasma	Homo sapiens
9.3 ng/mL	0.5 mg 2 times / day multiple, oral	ETIZOLAM plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
266.66 ng × h/mL	0.5 mg single, oral	ETIZOLAM plasma	Homo sapiens
277.07 ng × h/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
105 ng × h/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
158 ng × h/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
158 ng × h/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
59.4 ng × h/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
138 ng × h/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
158 ng × h/mL	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
46.1 ng × h/mL	0.5 mg 2 times / day multiple, oral	ETIZOLAM plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
12.24 h	0.5 mg single, oral	ETIZOLAM plasma	Homo sapiens
13.26 h	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
10.5 h	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
14.8 h	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
14.8 h	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
8.3 h	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
12 h	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
14.8 h	1 mg single, oral	ETIZOLAM plasma	Homo sapiens
3.4 h	0.5 mg single, oral	ETIZOLAM plasma	Homo sapiens
3.5 h	0.5 mg 2 times / day multiple, oral	ETIZOLAM plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
7%			ETIZOLAM plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
0.5 mg 2 times / day multiple, oral Recommended	unhealthy, ADULT	Disc. AE: Drowsiness, Gastralgia...
1 mg 3 times / day multiple, oral Recommended	unhealthy, ADULT	Disc. AE: Erythema annulare centrifugum...
0.5 mg single, oral Accidental dose	healthy, CHILD	Other AEs: Excitation, muscle weaknes...

Showing 1 to 3 of 3 entries

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AEs

Show entries

AE	Significance	Dose	Population
Drowsiness	8.3% Disc. AE	0.5 mg 2 times / day multiple, oral Recommended	unhealthy, ADULT
Gastralgia	8.3% Disc. AE	0.5 mg 2 times / day multiple, oral Recommended	unhealthy, ADULT
Erythema annulare centrifugum	Disc. AE	1 mg 3 times / day multiple, oral Recommended	unhealthy, ADULT
Drowsiness		0.5 mg single, oral Accidental dose	healthy, CHILD
Excitation		0.5 mg single, oral Accidental dose	healthy, CHILD

Showing 1 to 5 of 7 entries

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PubMed

PubMed

Show entries

Title	Date	PubMed
[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