Metaclazepam

Structural formula
General
Non-proprietary name	Metaclazepam
other names	7-Bromo-5- (2-chlorophenyl) -2- (methoxymethyl) -1-methyl-2,3-dihydro-1 H -1,4-benzodiazepine
Molecular formula	C 18 H 18 BrCIN 2 O
Brief description	Yellow-red krist. Powder, practically odorless with a slightly bitter taste
External identifiers / databases
PubChem	71272
ChemSpider	64398
Wikidata	Q6822419
Drug information
ATC code	N05 BA
Drug class	Benzodiazepine; Anxiolytic;
properties
Molar mass	393.71 g · mol -1
Physical state	firmly
Melting point	193-196 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	1578 mg kg −1 ( LD 50 , mouse , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Metaclazepam is a drug from the group of benzodiazepines and has amnestic , anxiolytic , anticonvulsant , hypnotic , sedative and muscle relaxing potential. The sedating and muscle relaxing properties are only very weak, the anxiolytic properties are particularly pronounced. This was the reason why it was used in medicine as an anxiolytic .

Metaclazepam was launched in 1988 by Kali Chemie under the finished drug name Talis . It is no longer in trade worldwide today.

Pharmacokinetics

After oral administration of metaclazepam, maximum plasma concentrations are reached within 0.33–1.33 hours. The bioavailability is only 40–75%. This is probably due to a particularly high first pass effect or incomplete absorption . The half-life of metaclazepam itself is 12 hours, that of its active metabolite N- desmethylmetaclazepam 12-16 hours. The equivalent dose to 10 mg diazepam is 15 mg.

Side effects

Dizziness, tiredness or incoordination may occur, especially in higher doses or at the beginning of treatment. In rare cases, a paradoxical (opposing) effect with excitement (fear, aggressiveness, agitated state of confusion) can occur, which must never be answered by increasing the dose. Like all drugs from the benzodiazepine class, metaclazepam has a high potential for addiction and abuse.

Trade names

Monopreparations

Talis (D, AT no longer available in stores)

Individual evidence

^ W. Althaus, J. Block, A. Förster, M. Kühnhold, D. Meister, M. Wischniewski: Analytical profile of metaclazepam. . In: drug research . 36, No. 9, 1986, pp. 1302-1306. PMID 3790179 .
↑ ^a ^b Jürgen Falbe, Manfred Regitz (Ed.): RÖMPP Lexikon Chemie . Metaclazepam. Thieme, 2014, ISBN 978-3-13-200031-5 ( limited preview in Google book search).
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ DE Patent 2221558A1
↑ G. Buschmann, UG Kühl, O. Rohte: General pharmacology of the anxiolytic compound metaclazepam in comparison to other benzodiazepines . In: drug research . 35, No. 11, 1985, pp. 1643-1655. PMID 2868732 .
↑ P. Marano, F. Patti, F. Nicoletti: Controlled study on the anxiolytic activity of a newly-developed benzodiazepine, metaclazepam . In: Current Medical Research and Opinion . 11, No. 1, 1988, pp. 41-44. PMID 2898320 .
↑ Peter Riederer, Gerd Laux (Ed.): Neuro-Psychopharmaka: A Therapy Manual Volume 1 . General principles of pharmacopsychiatry. Springer, 2013, ISBN 978-3-7091-7377-0 ( limited preview in Google book search).
^ W. Gielsdorf, KH Molz, HJ Hausleiter, G. Achtert, P. Philipp: Pharmacokinetic profile of metaclazepam (Talis), a new 1.4-benzodiazepine. Influence of different dosage regimens on the pharmacokinetic profile of metaclazepam and its main metabolite under steady-state conditions . In: European Journal of Drug Metabolism and Pharmacokinetics 21 . 11, No. 3, 1986, pp. 205-210. PMID 3816876 .
↑ Peter Riederer, Gerd Laux (Ed.): Neuro-Psychopharmaka: A Therapy Manual Volume 2 . Tranquilizers and hypnotics. Springer, 2013, ISBN 978-3-7091-6593-5 ( limited preview in Google book search).

[Analytical_profile_of_metaclazepam-1] W. Althaus, J. Block, A. Förster, M. Kühnhold, D. Meister, M. Wischniewski: Analytical profile of metaclazepam. . In: drug research . 36, No. 9, 1986, pp. 1302-1306. PMID 3790179 .

[RÖMPP-2] Jürgen Falbe, Manfred Regitz (Ed.): RÖMPP Lexikon Chemie . Metaclazepam. Thieme, 2014, ISBN 978-3-13-200031-5 ( limited preview in Google book search).

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[4] DE Patent 2221558A1

[5] G. Buschmann, UG Kühl, O. Rohte: General pharmacology of the anxiolytic compound metaclazepam in comparison to other benzodiazepines . In: drug research . 35, No. 11, 1985, pp. 1643-1655. PMID 2868732 .

[6] P. Marano, F. Patti, F. Nicoletti: Controlled study on the anxiolytic activity of a newly-developed benzodiazepine, metaclazepam . In: Current Medical Research and Opinion . 11, No. 1, 1988, pp. 41-44. PMID 2898320 .

[7] Peter Riederer, Gerd Laux (Ed.): Neuro-Psychopharmaka: A Therapy Manual Volume 1 . General principles of pharmacopsychiatry. Springer, 2013, ISBN 978-3-7091-7377-0 ( limited preview in Google book search).

[Talis-8] W. Gielsdorf, KH Molz, HJ Hausleiter, G. Achtert, P. Philipp: Pharmacokinetic profile of metaclazepam (Talis), a new 1.4-benzodiazepine. Influence of different dosage regimens on the pharmacokinetic profile of metaclazepam and its main metabolite under steady-state conditions . In: European Journal of Drug Metabolism and Pharmacokinetics 21 . 11, No. 3, 1986, pp. 205-210. PMID 3816876 .

[9] Peter Riederer, Gerd Laux (Ed.): Neuro-Psychopharmaka: A Therapy Manual Volume 2 . Tranquilizers and hypnotics. Springer, 2013, ISBN 978-3-7091-6593-5 ( limited preview in Google book search).