BENTAZEPAM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H16N2OS
Molecular Weight	296.387
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1CN=C(C2=C(N1)SC3=C2CCCC3)C4=CC=CC=C4

InChI

InChIKey=AIZFEOPQVZBNGH-UHFFFAOYSA-N

InChI=1S/C17H16N2OS/c20-14-10-18-16(11-6-2-1-3-7-11)15-12-8-4-5-9-13(12)21-17(15)19-14/h1-3,6-7H,4-5,8-10H2,(H,19,20)

HIDE SMILES / InChI

Molecular Formula	C17H16N2OS
Molecular Weight	296.387
Charge	0
Count

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

Description
Sources: http://www.unav.edu/publicaciones/revistas/index.php/revista-de-medicina/article/viewFile/7295/6402
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/bentazepam.html | https://www.ncbi.nlm.nih.gov/pubmed/1983365 | https://www.ncbi.nlm.nih.gov/pubmed/7008536 | http://www.sciencedirect.com/science/article/pii/S0011393X0580178X | https://www.ncbi.nlm.nih.gov/pubmed/9451703

Bentazepam (also known as Thiadipone, Tiadipona) is a benzodiazepine analog, used as a short-action anxiolytic. Bentazepam a thienodiazepine with the same main mechanism of action as the classic 1,4-benzodiazepines, is a short-action anxiolytic, with an elimination-half-life of 3 to 5 hours in healthy volunteers. Bentazepam possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. A severe benzodiazepine overdose with bentazepam may result in coma and respiratory failure. Adverse effects include dry mouth, somnolence, asthenia, dyspepsia, constipation, nausea and drug-induced lymphocytic colitis has been associated with bentazepam. Severe liver damage and hepatitis has also been associated with bentazepam. Whilst liver failure from bentazepam is considered to be rare, liver function monitoring has been recommended for all patients taking bentazepam.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; agonist GABA site 13 Target ID: CHEMBL2109244 Sources: http://www.unav.edu/publicaciones/revistas/index.php/revista-de-medicina/article/viewFile/7295/6402	Positive Allosteric Modulator 186

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 275 Sources: http://www.sciencedirect.com/science/article/pii/S0011393X0580178X	Primary		Approved 8583	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
313.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2893777/	25 mg 1 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		BENTAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
386 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2877954/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		BENTAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.34 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2877954/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		BENTAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/135412795#section=BioAssay-Results Page: 103.0

PubMed

Title	Date	PubMed
Outcome of acute idiosyncratic drug-induced liver injury: Long-term follow-up in a hepatotoxicity registry.	2006-12	17133470
An online misadventure with haloperidol.	2003-10	14519026
[Acute hepatitis due to bentazepam].	2003-05-10	12747823
Collagenous and lymphocytic colitis. evaluation of clinical and histological features, response to treatment, and long-term follow-up.	2003-02	12591052

Patents

Sample Use Guides

In Vivo Use Guide

bentazepam, administered orally at a dose of 25 mg with dosage intervals of 8, 12 and 24 h over 5 days of treatment.

Route of Administration: Oral

In Vitro Use Guide

To examine the mitotic profiles of the Wg3h and CHE-3N cultures in the presence or absence of the Bentazepam the cells were seeded on sterile glass slides in petri dishes. Cells undergoing logarithmic phase growth, were treated with the Bentazepam for 18 (Don:Wg3h cells) and 22 h (CHE-3N cells) (a time corresponding to 1 cell cycle, allowing for mitotic delay) and harvested in 3:1 methanol/ acetic acid fixative, supplemented with Ca 2+ and Mg 2+ ions. Following a perchloric acid treatment to remove RNA, the cells were stained simultaneously with Brilliant blue R (to stain the spindle fibres blue) and Safranin O (to stain the chromosomes red).

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:03:35 GMT 2025` Edited by `admin` on `Wed Apr 02 09:03:35 GMT 2025`
Record UNII	66JKK43S1Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENTAZEPAM

Official Name

English

CI-718

Preferred Name

English

Bentazepam [WHO-DD]

Common Name

English

BENTAZEPAM [USAN]

Common Name

English

bentazepam [INN]

Common Name

English

1,3,6,7,8,9-Hexahydro-5-phenyl-2H-[1]benzothieno[2,3-E]-1,4-diazepin-2-one

Systematic Name

English

2H-(1)BENZOTHIENO(2,3-E)-1,4-DIAZEPIN-2-ONE, 1,3,6,7,8,9-HEXAHYDRO-5-PHENYL-

Systematic Name

English

BENTAZEPAM [MART.]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N05BA24