TETRAZEPAM

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H17ClN2O
Molecular Weight	288.772
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C2=CC=C(Cl)C=C2C(=NCC1=O)C3=CCCCC3

InChI

InChIKey=IQWYAQCHYZHJOS-UHFFFAOYSA-N

InChI=1S/C16H17ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h5,7-9H,2-4,6,10H2,1H3

HIDE SMILES / InChI

Molecular Formula	C16H17ClN2O
Molecular Weight	288.772
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24845943 | https://www.ncbi.nlm.nih.gov/pubmed/26012498

Tetrazepam was the most widely prescribed muscle relaxant in Germany. After a series of studies, which have shown, that tetrazepam caused cutaneous adverse effects and toxic epidermal necrolysis, the drug was withdrawn from the market.

Approval Year

PubMed

Title	Date	PubMed
An updated overview of clinical guidelines for the management of non-specific low back pain in primary care.	2010-12	20602122
Analysis of six benzodiazepines in vitreous humor by high-performance liquid chromatography-photodiode-array detection.	2010-11	21073805
[Multimodal treatment of chronic unspecific low back pain].	2010-09-14	20831016
Solubilization of poorly water-soluble drugs by mixed micelles based on hydrogenated phosphatidylcholine.	2010-08-16	20580793
Development and validation of an EI-GC-MS method for the determination of benzodiazepine drugs and their metabolites in blood: applications in clinical and forensic toxicology.	2010-08-01	20172681
Assessment of abuse potential of benzodiazepines from a prescription database using 'doctor shopping' as an indicator.	2010-07	20527997
The impact of perfectionism and anxiety traits on action monitoring in major depressive disorder.	2010-07	20473695
Patient-reported-outcomes in subjects with painful lumbar or cervical radiculopathy treated with pregabalin: evidence from medical practice in primary care settings.	2010-06	19798503
Occupational allergic contact dermatitis from tetrazepam in nurses.	2010-05	20536478
Experimental design for optimization of microwave-assisted extraction of benzodiazepines in human plasma.	2010-05	20204329
Benzodiazepines medazepam and midazolam are activators of pregnane X receptor and weak inducers of CYP3A4: investigation in primary cultures of human hepatocytes and hepatocarcinoma cell lines.	2010-03-15	20080160
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009-10-02	19798416
Occupational airborne contact allergy to tetrazepam in a geriatric nurse.	2009-10	19453384
No cross-reactions between tetrazepam and other benzodiazepines: a possible chemical explanation.	2009-07	19659970
Lumbar spondylosis: clinical presentation and treatment approaches.	2009-06	19468872
Metabolic studies of tetrazepam based on electrochemical simulation in comparison to in vivo and in vitro methods.	2009-04-10	19233363
Unraveling the metabolic transformation of tetrazepam to diazepam with mass spectrometric methods.	2008-12	18949465
[Current differential diagnosis of hypereosinophilic syndrome].	2008-08-01	18666600
Probable drug rash with eosinophilia and systemic symptoms syndrome related to tetrazepam.	2008-07	18031497
Patch testing in non-immediate drug eruptions.	2008-06-15	20525127
Systemic dermatitis due to tetrazepam.	2008	18973107
Acute generalized exanthematous pustulosis due to tetrazepam.	2008	18447141
Detection of diazepam in urine, hair and preserved oral fluid samples with LC-MS-MS after single and repeated administration of Myolastan and Valium.	2007-08	17468852
[Comparative study on Chinese medicine and western medicine for treatment of prolapse of lumbar intervertebral disc].	2007-05	17645261
Medicolegal aspects of tetrazepam metabolism.	2007-05	17021899
Development of in situ ion selective sensors for dissolution.	2007-01-02	17386443
Erythema multiforme to tetrazepam.	2007	17583114
Toxic epidermal necrolysis caused by tetrazepam.	2006-10	17040464
Toxic epidermal necrolysis caused by tetrazepam.	2006-04	16650186
Determination of ibuprofen and tetrazepam in human urine by micellar electrokinetic capillary chromatography.	2006-01	16328252
Screening method for benzodiazepines and hypnotics in hair at pg/mg level by liquid chromatography-mass spectrometry/mass spectrometry.	2005-10-15	16154525
Windows of detection of tetrazepam in urine, oral fluid, beard, and hair, with a special focus on drug-facilitated crimes.	2005-10	16175127
Screening and confirmatory method for benzodiazepines and hypnotics in oral fluid by LC-MS/MS.	2005-06-10	15944062
Medicinal and injection therapies for mechanical neck disorders.	2005-04-18	15846603
Occupational airborne contact dermatitis from sporadic exposure to tetrazepam during machine maintenance.	2005-03	15811045
[Drug Safety. Preventing medication errors].	2004-09-17	15369443
Screening, library-assisted identification and validated quantification of 23 benzodiazepines, flumazenil, zaleplone, zolpidem and zopiclone in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization.	2004-08	15329838
Sex-dependent modulation of treatment response.	2004-03	22034399
Possible mechanism(s) for relaxant effect of aqueous and macerated extracts from Nigella sativa on tracheal chains of guinea pig.	2004-02-25	15070429
Occupational airborne contact allergy to tetrazepam.	2003-11	14996051
Major bleeding during combined treatment with indomethacin and low doses of acenocoumarol in a homozygous patient for 2C9*3 variant of cytochrome p-450 CYP2C9.	2003-07	12876643
[Medical treatment of spasticity].	2003-05	12746699
[Determination of benzodiazepine derivatives mixture by high performance liquid chromatography].	2003	14617855
Direct injection micellar liquid chromatographic determination of benzodiazepines in serum.	2002-11-25	12401349
Formulating and stability of benzodiazepines in a new lipid emulsion formulation.	2002-11	12611276
Tetrazepam drug sensitivity -- usefulness of the patch test.	2002-09	12492544
[Analysis of benzodiazepine derivative mixture by gas-liquid chromatography].	2002	12474705
Guidelines for performing skin tests with drugs in the investigation of cutaneous adverse drug reactions.	2001-12	11846746
Development of a novel parenteral formulation for tetrazepam using a lipid emulsion.	2001-11	11794814
Adverse reaction to tetrazepam.	2001	11642573

Patents

Sample Use Guides

In Vivo Use Guide

Tetrazepam was given orally as a single dose of 50 mg and repeated administration for 5 consecutive days of 50 mg at 12-h intervals, in tablet form

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:19 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:19 GMT 2025`
Record UNII	FO92091VP8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRAZEPAM

Official Name

English

MYOLASTAN

Preferred Name

English

Tetrazepam [WHO-DD]

Common Name

English

CB 4261

Code

English

tetrazepam [INN]

Common Name

English

TETRAZEPAM [EP MONOGRAPH]

Common Name

English

TETRAZEPAM [MART.]

Common Name

English

CB-4261

Code

English

TETRAZEPAM [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QM03BX07