List of benzodiazepines
The following table provides an overview of the pharmacological data of some benzodiazepines and marketing information.
Active ingredient | Trade name (s) | Effect type | Chemical name |
Plasma half-life (metabolite half-life ) |
Equivalent dose to 10 mg diazepam | Year of launch |
---|---|---|---|---|---|---|
Adinazolam | Deracyn (FR) | Tranquilizer, anxiolytic, antidepressant | 8-Chloro-1- (dimethylaminomethyl) -6-phenyl-4 H - [1,2,4] triazolo [4,3- a ] [1,4] benzodiazepine | 1.5-3 h | 30 mg | ? |
Alprazolam |
Tafil (D), Xanax (CH, USA), Xanax retard (CH, USA), Xanor (A), various generics (D, A) |
Tranquilizer, anxiolytic | 8-Chloro-1-methyl-6-phenyl-4 H - [1,2,4] -triazolo [4,3- a ] [1,4] benzodiazepine | 12-15 h | 1.5 mg | 1981 |
Bromazepam |
Bromazanil (D), Gityl (D), Lexostad (D), Lexotanil (D, A, CH), Bromazepam OPT (D), Normoc (D), various generics (D, A) |
Tranquilizer, anxiolytic | 7-bromo-2,3-dihydro-5- (2-pyridyl) - 1 H -1,4-benzodiazepin-2-one | 15-28 h | 6 mg | 1975 |
Camazepam | Albego (CH, ES, IT) | Anxiolytic, hypnotic | 7-chloro-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl N, N-dimethylcarbamate | 6-11 h | 10-20 mg | 1978 |
Chlordiazepoxide |
Librium (D), Librax (CH), Librocol (CH), Limbitrol (A, CH), |
Tranquilizers | 7-chloro-2-methylamino-5-phenyl-3 H -1,4-benzodiazepine-4-oxide | 5–30 h (48–96 h) | 20 mg | 1960 |
Cinolazepam | Gerodorm (BG, CZ, HU, SK, RO) | Hypnotic | 7-chloro-5- (2-fluorophenyl) -2,3-dihydro-3-hydroxy-2-oxo-1 H -1,4-benzodiazepin-1-propionitrile | 4-6 h | 40 mg | 1992 |
Clobazam |
Castilium (PT), Frisium (D, A), Noiafren (ES), Urbadan (NL), Urbanyl (CH) |
Tranquilizer, anxiolytic, anti-epileptic | 7-chloro-1-methyl-5-phenyl-1 H -1,5 -benzodiazepine-2,4 (3 H , 5 H ) -dione | 18 h (36–80–120 h) | 20 mg | 1977 |
Clonazepam |
Antelepsin (D), Rivotril (D, CH) |
Anti-epileptic | 5- (2-chlorophenyl) -2,3-dihydro-7-nitro-1 H -1,4-benzodiazepin-2-one | 30-40 h | 2 mg | 1973 |
Clonazolam | - | Anti-epileptic | 6- (2-Chlorophenyl) -1-methyl-8-nitro-4 H - s -triazolo [4,3- a ] -1,4-benzodiazepine | 16 h | 0.5 mg | Designer drug |
Cloniprazepam | - | Anxiolytic, tranquilizer | 5- (2-Chlorophenyl) -1-cyclopropylmethyl-7-nitro-1,3-dihydrobenzo [e] [1,4] diazepin-2-one | ? | 1-2 mg | Designer drug |
Clorazepate |
Tranxene (international trade name), Tranxilium (D, A, CH) |
Tranquilizers | 7-chloro-2,3-dihydro-2,2-dihydroxy-5-phenyl-1 H -1,4-benzodiazepine-3-carboxylic acid | nordazepam ( N- desmethyldiazepam)] | 2 h [approx. 30–90 h for the active metabolite20 mg | 1969 |
Cloxazolam |
Akton (BE, LU), Cloxam (PT), Elum (BE), Lubalix (CH), Olcadil (D, CH, AT), Sepazon (HK, JP) |
Tranquilizers | 10-Chloro-11b- (2-chlorophenyl) -2,3,7,11b-tetrahydro [1,3] oxazolo [3,2- d ] [1,4] benzodiazepin-6-one | delorazepam (chlordesmethyldiazepam)] | 55-75 h [approx. 80–115 h for the active metabolite4 mg | 1974 |
Delorazepam |
Briantum (CH), Dadumir (IT), EN (IT), various generics (IT) |
Anxiolytic, premedication | 7-chloro-5- (2-chlorophenyl) -1,3-dihydro-1,4-benzodiazepin-2 (2 H ) -one | 80-115 h | 1 mg | |
Diazepam |
Diazep-CT (D), Faustan (D), Gewacalm (A), Paceum (CH), Psychopax (A, CH), Stesolid (D, A, CH), Valiquid (D), Valium (D, A, CH , L), Valocordin-Diazepam (D), various generics (D, CH) |
Tranquilizer, anti-epileptic, anxiolytic | 7-chloro-2,3-dihydro-1-methyl-5-phenyl-1 H -1,4-benzodiazepin-2-one | nordazepam (N-desmethyldiazepam)] | 24–48 h [approx. 30–90 h for the active metabolite10 mg | 1963 |
Diclazepam | - | Tranquilizer, anxiolytic, muscle relaxant | 7-chloro-1-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one | 42 h | 1 mg | Designer drug |
Doxefazepam | Doxans (IT) | Hypnotic | 7-chloro-5- (2-fluorophenyl) -3-hydroxy-1- (2-hydroxyethyl) -2,3-dihydro-1 H -1,4-benzodiazepin-2-one | 3-4 h | 10 mg | 1984 |
Estazolam |
Domnamid (DK), Eszo (TW), Esilgan (IT) Eurodin (JP), Nuctalon (FR), ProSom (USA), Sedarest (PE), |
Hypnotic | 8-Chloro-6-phenyl-4 H - s -triazolo- [4,3a] [1,4] benzodiazepine | 10–24 h | 1-2 mg | 1975 |
Ethyl loflazepat |
Meilax (JP), Victan (FR, BE), |
Tranquilizers | 7-Chloro-5- (2-fluorophenyl) -2-oxo-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylic acid ethyl ester | 51-103 h | 2 mg | 1982 |
Flualprazolam | - | Hypnotic | 6- (2-Fluorophenyl) -1-methyl-8-chloro-4H- [1,2,4] triazolo [4,3-a] [1,4] benzodiazepine | 20 h | 0.25 mg | Designer drug |
Flubromazepam | - | Hypnotic, anxiolytic, tranquilizer, muscle relaxant, anti-epileptic | 7-Bromo-5- (2-fluorophenyl) -1,3-dihydro-1,4-benzodiazepin-2-one | 106 h | 4 mg | Designer drug |
Flubromazolam | - | Hypnotic | 8-Bromo-6- (2-fluorophenyl) -1-methyl-4 H - [1,2,4] triazolo [4,3- a ] [1,4] benzodiazepine | 20 h | 0.25 mg | Designer drug |
Fludiazepam |
Erispan (JP, TW), Sedepam (TW) |
Tranquilizer, hypnotic | 7-chloro-5- (2-fluorophenyl) -1-methyl-1,3-dihydro-2 H -1,4-benzodiazepin-2-one | 10-30 h | 1 mg | 1981 |
Flunitrazepam |
Fluninoc (D), Rohypnol (D, A, CH), some generics (D) |
Hypnotic | 5- (2-fluorophenyl) -2,3-dihydro-1-methyl-7-nitro-1 H -1,4-benzodiazepin-2-one | 16-35 h | 0.5-1 mg | 1976 |
Flunitrazolam | - | Hypnotic | 6- (2-Fluorophenyl) -1-methyl-8-nitro-4 H -benzo [ f ] [1,2,4] triazolo [4,3- a ] [1,4] diazepine | ? | 0.5 mg | Designer drug |
Flurazepam |
Dalmadorm (D, CH), Staurodorm (D), Flurazepam Real (D), |
Hypnotic | 7-chloro-1- (2-diethylaminoethyl) -5- (2-fluorophenyl) -2,3-dihydro-1 H -1,4-benzodiazepin-2-one | nordazepam (N-desmethyldiazepam)] | 1.5 h [approx. 30–90 h for the active metabolite15-30 mg | 1970 |
Flutazolam | Coreminal (JP) | Tranquilizers | 10-Chloro-11b- (2-fluorophenyl) -7- (2-hydroxyethyl) -2,3,7,11b-tetrahydro [1,3] oxazolo [3,2-d] [1,4] benzodiazepine-6 -on | 3-4 h | 30 mg | 1984 |
Flutoprazepam | Restas (JP) | Tranquilizers | 7-chloro-1- (cyclopropylmethyl) -5- (2-fluorophenyl) -3 H -1,4-benzodiazepin-2-one | (60–90 h) | 3-4 mg | 1986 |
Halazepam |
Alapryl (ES), Pacinone (BE, NL), Paxipam (IT, USA) |
Tranquilizers | 7-chloro-2,3-dihydro-5-phenyl-1- (2,2,2-trifluoroethyl) -1 H -1,4-benzodiazepin-2-one | (30-100 h) | 20 mg | 1981 |
Haloxazolam | Somelin (JP) | Hypnotic | 10-Bromo-11b- (2-fluorophenyl) -2,3,7,11b-tetrahydro [1,3] oxazolo [3,2-d] [1,4] benzodiazepin-6-one | 42-123 h | 10 mg | ? |
Loprazolam |
Avlane (FR), Dormonoct (GB), Sonin (D) |
Tranquilizers | 6- (2-Chlorophenyl) -2,4-dihydro-2 - [(4-methyl-1-piperazinyl) methylene] -8-nitro-1 H -imidazo [1,2- a ] [1,4] benzodiazepine -1-on | 8-9 h | 1-1.5 mg | 1987 |
Lorazepam |
Ativan (USA, GB), Lorazepam dura (D), Merlit (A), Tavor (D), Temesta (CH, A, L, B), Tolid (D), various generics |
Tranquilizer, hypnotic, anti-epileptic | ( RS ) -7-chloro-5- (2-chlorophenyl) -2,3-dihydro-3-hydroxy-1 H -1,4-benzodiazepin-2-one | 12.9-16.2 hours | 2 mg | 1963 |
Lormetazepam |
Ergocalm (D), Loramet (CH), Loretam (D), Noctamid (A, D, CH), Sedalam (D), various generics (D) |
Hypnotic | ( RS ) -7-Chloro-5- (2-chlorophenyl) -2,3-dihydro-3-hydroxy-1-methyl-1 H -1,4-benzodiazepin-2-one | 10-14 h | 1 mg | 1980 |
Ketazolam |
Anxon (GB), Contamex (D), Solatran (D, CH), Unakalm (FR), |
Tranquilizer, anti-epileptic, anxiolytic | 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4 H - [1,3] oxazino [3,2- d ] [1,4] benzodiazepine-4,7 (6 H ) -dion | Northazepam ) | 50 h (36–200 h,15-20 mg | 1980 |
Meclonazepam | - | Hypnotic | (3 S ) -5- (2-Chlorophenyl) -3-methyl-7-nitro-1,3-dihydro-2 H -1,4-benzodiazepin-2-one | ? | 1 mg | Designer drug |
Medazepam |
Rudotel (D), Nobrium (D) |
Tranquilizers | 7-chloro-2,3-dihydro-1-methyl-5-phenyl-1 H -1,4-benzodiazepine | nordazepam (N-desmethyldiazepam)] | 2–5 h [approx. 30–90 h for the active metabolite20 mg | 1969 |
Metaclazepam | Talis (D, AT) | Anxiolytic | 7-Bromo-5- (2-chlorophenyl) -2-methoxymethyl-1-methyl-2,3-dihydro-1 H -1,4-benzodiazepine | 16 h | 10 mg | 1988 |
Mexazolam |
Melex (JP), Sedoxil (PT) |
Anxiolytic | 10-Chloro-11b- (2-chlorophenyl) -3-methyl-2,3,7,11b-tetrahydrooxazolo [3,2- d ] [1,4] benzodiazepin-6-one | (74 h) | 10 mg | 1984 |
Midazolam |
Buccolam (D, CH), Dormicum (D, CH), various generics (CH) |
Short hypnotic | 8-chloro-6- (2-fluorophenyl) -1-methyl-4 H -imidazo [1,5- a ] [1,4] benzodiazepine | 1.5-2.5 h | 7.5 mg orally (1 mg i.v.) | 1982 |
Nifoxipam | - | Hypnotic, tranquilizer | 5- (2-fluorophenyl) -3-hydroxy-7-nitro-1,3-dihydro-2 H -1,4-benzodiazepin-2-one | ? | ? | Designer drug |
Nimetazepam | Erimin (JP) | Hypnotic | 2,3-Dihydro-7-nitro-5-phenyl-1-methyl-1 H -1,4-benzodiazepin-2-one | 18-30 h | 5 mg | 1977 |
Nitrazepam |
Dormo-Puren (D), Imeson (D), Mogadan (D), Mogadon (A, CH), Novanox (D), Radedorm (D) |
Hypnotic, anti-epileptic | 2,3-Dihydro-7-nitro-5-phenyl-1 H -1,4-benzodiazepin-2-one | 18-30 h | 5 mg | 1965 |
North Azepam |
Calmday (BE, NL), Madar (IT), Nordaz (FR), Stilny (AT, BE), Tranxilium N (D), Vegesan (D, CH) |
Tranquilizers | 7-chloro-2,3-dihydro-5-phenyl-1 H -1,4-benzodiazepin-2-one | 50–90 h (8 h) | 20 mg | 1973 |
Oxazepam |
Adumbran (D, A), Anxiolit (A, CH), Durazepam (D), Praxiten (D, A), Seresta (CH), various generics (D) |
Tranquilizers | ( RS ) -7-chloro-2,3-dihydro-3-hydroxy-5-phenyl-1 H -1,4-benzodiazepin-2-one | 5-15 h | 30 mg | 1965 |
Oxazolam |
Hializan (SP), Sera (TH), Serebon (HK), Serenal (JP), Tranquit (D), Quiadon (D) |
Tranquilizers | (2 RS , 11b SR ) -10-Chloro-2-methyl-11b-phenyl-2,3,7,11b-tetrahydro [1,3] oxazolo [3,2-d] [1,4] benzodiazepine-6 (5 H ) -one | nordazepam ( N- desmethyldiazepam)] | 1.5 h [approx. 30–90 h for the active metabolite40 mg | 1970 |
Phenazepam |
Elzepam (RU), fenazepam (GE), fenazepams (LT), phenzepine (GE), phenorelaxane (RU) |
Tranquilizers | 7-Bromo-5- (2-chlorophenyl) -1,3-dihydro-1,4-benzodiazepin-2-one | (60 h) | 1 mg | 1974 |
Pinazepam |
Domar (IT), Duna (ES, IT) |
Anxiolytic | 7-chloro-5-phenyl-1- (prop-2-in-1-yl) -1,3-dihydro-2 H -1,4-benzodiazepin-2-one | nordazepam ( N- desmethyldiazepam)] | 10-15 h [approx. 30–90 h for the active metabolite20 mg | 1975 |
Prazepam |
Demetrin (D, CH), Centrax (GB, US), Lysanxia (FR), Reapam (D) |
Tranquilizers | 7-chloro-1- (cyclopropylmethyl) -2,3-dihydro-5-phenyl-1 H -1,4-benzodiazepin-2-one | nordazepam (N-desmethyldiazepam)] | 1.5 h [approx. 30–90 h for the active metabolite20 mg | 1973 |
Pyrazolam | - | Anxiolytic | 8-Bromo-1-methyl-6- (pyridin-2-yl) -4 H - [1,2,4] triazolo [4,3- a ] [1,4] benzodiazepine | 16-18 h | 1 mg | Designer drug |
Quazepam |
Doral (US, JP), Quiedorm (ES) |
Hypnotic | 7-chloro-5- (2-fluorophenyl) -2,3-dihydro-1- (2,2,2-trifluoroethyl) -1 H -1,4-benzodiazepine-2-thione | (25–41 h) | 20 mg | 1985 |
Temazepam |
Normison (CH), Planum (D), Remestan (D), Temazep (D), various generics |
Hypnotic | ( RS ) -7-chloro-3-hydroxy-1-methyl-5-phenyl-1 H -1,4-benzodiazepin-2 (3 H ) -one | 5-13 h | 20 mg | 1970 |
Tetrazepam |
Musaril (D), Myolastan (A, FR), Rilex (D), various generics (D, A) |
Myotonolytic (muscle relaxant) | 7-chloro-5- (1-cyclohexenyl) -1-methyl-1 H -1,4-benzodiazepin-2 (3 H ) -one | 18 h | 20 mg | 1981 |
Triazolam |
Halcion (D, A, CH), Songar (IT) |
Hypnotic | 8-chloro-6- (2-chlorophenyl) -1-methyl-4 H -1,2,4-triazolo [4,3- a ] [1,4] benzodiazepine | 1.4-4.6 h | 0.5 mg | 1978 |
Individual evidence
- ↑ Frank Schneider, Sabrina Weber (eds.): Clinic Manual - Psychiatry, Psychosomatics and Psychotherapy. Springer, Heidelberg 2008, ISBN 978-3-540-78466-1 , p. 209.
- ↑ GW Peng: Assay of adinazolam in plasma by liquid chromatography. In: Journal of pharmaceutical sciences . No. 73 , August 1984, p. 1173-1175 , PMID 6491930 .
- ↑ David Nutt, James C Ballenger, Jean-Pierre Lepine: Panic Disorders: Clinical Diagnosis, Management and Mechanisms . 1st edition. Martin Dunitz Ltd, London 1998, ISBN 1-85317-518-8 , pp. 152 (English, limited preview in Google Book search).
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- ^ A b P. Riederer, G. Laux, W. Pöldinger: Neuro-Psychopharmaka A Therapy Manual . Volume 2: Tranquilizers and Hypnotics . 1st edition. Springer, 2013, ISBN 978-3-7091-7357-2 , pp. 384 , doi : 10.1007 / 978-3-7091-6593-5 .
- ↑ Janos Fischer, C. Robin Ganellin: Analogue-based Drug Discovery . 1st edition. Wiley-VCH, 2006, ISBN 3-527-31257-9 , pp. 539 (English).
- ↑ a b Peter Riederer, Gerd Laux: Neuro-Psychopharmaka: A therapy manual . tape 1 . Springer-Verlag, 2013, ISBN 978-3-7091-6674-1 , chap. Historical outline: History of psychotropic drugs , p. 63 ( limited preview in the Google book search): "Sales data of synthetic psychotropic drugs on the German market"
- ↑ a b c W. Forth, D. Henschler, W. Rummel, K. Starke (eds.): General and special pharmacology and toxicology. 6th edition. BI-Wissenschaftsverlag, 1992, ISBN 3-411-15026-2 , pp. 292-293.
- ↑ P. Riederer, G. Laux, W. Pöldinger (Eds.): Neuro-Psychopharmaka: A therapy manual . Volume 1: General principles of pharmacopsychiatry . Springer, Vienna 1992, ISBN 3-7091-7377-9 , 3.3 Pharmako-EEG, p. 97 , doi : 10.1007 / 978-3-7091-6674-l : "[...] that the dose of the test substance cloxazolam equipotent to 5 mg diazepam was 2 mg [...]"
- ↑ Bjoern Moosmann, Philippe Bisel, Volker Auwärter: Characterization of the designer benzodiazepine diclazepam and preliminary data on its metabolism and pharmacokinetics. In: Drug Testing and Analysis. 2014, doi: 10.1002 / dta.1628 .
- ↑ DOXEFAZEPAM . 4.1 Absorption, distribution, metabolism and excretion . In: IARC Monographs (ed.): Monographs.iarc.fr . 2018 (English, iarc.fr [PDF; accessed on March 26, 2019]).
- ↑ János Fischer, C. Robin Ganellin: Analogue-based Drug Discovery . 1st edition. John Wiley & Sons, 2006, ISBN 3-527-31257-9 , pp. 539 .
- ↑ a b c d e Jan Dreher: Benzodiazepine conversion table. In: psychiatrietogo.de. January 29, 2012, accessed March 30, 2019 .
- ↑ a b Bjoern Moosmann, Volker Auwärter: Designer benzodiazepines - Metabolism and detection. Institute of Forensic Medicine Freiburg, Forensic Toxicology, Germany. ( munich2015.com ( Memento from April 24, 2016 in the Internet Archive ), PDF file)
- ↑ a b Psychotropic dose equivalence in Japan. Table 6 Dose equivalence of anxiolytics, sedatives and hypnotics . In: The Japanese Society of Psychiatric Rating Scales. Retrieved March 11, 2019 .
- ↑ Toshiya Inada, Ataru Inagaki: Psychotropic dose equivalence in Japan . In: Psychiatry and Clinical Neurosciences . tape 69 , no. 8 , 2015, p. 445 , doi : 10.1111 / pcn.12275 , PMID 25601291 (English).
- ↑ a b Denis M. Bailey et al. a .: Annual Reports in Medicinal Chemistry . tape 20 . Elsevier, 1985, ISBN 0-12-040520-2 , pp. 318 (English, 352 pp.).
- ↑ Xin Tan, Sunao Uchida, Masato Matsuura, Kyoko Nishihara: Long-, intermediate- and short-acting benzodiazepine effects on human sleep EEG spectra . In: Psychiatry and Clinical Neurosciences . Vol. 57, No. 1 , 2003, p. 97-104 , PMID 12519461 (English).
- ↑ K. Rickels, I. Csanalosi, P. Greisman, MJ Mirman, RJ Morris, CC Weise, G. Weiss: Ketazolam and diazepam in anxiety: a controlled study. In: Journal of clinical pharmacology. Volume 20, Number 10, October 1980, pp. 581-589. PMID 6108335 .
- ↑ KETAZOLAM MAY BE AN ADVANCE OVER DIAZEPAM FOR ANXIETY. In: InPharma. 247, 1980, p. 12, doi: 10.1007 / BF03290485 .
- ↑ a b W. Forth, D. Henschler, W. Rummel (Ed.): General and special pharmacology and toxicology. 5th edition. Bibliographisches Institut & F. A. Brockhaus, 1987, ISBN 3-411-03150-6 , p. 558.
- ^ Martin Banger: Evidence-based addiction medicine. Treatment guideline substance-related disorders; with 23 tables . Ed .: Lutz G. Schmidt. 1st edition. Deutscher Ärzteverlag, Cologne 2006, ISBN 3-7691-0520-6 , p. 287 ( limited preview in Google Book search).
- ↑ 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).
- ↑ Peter Riederer, Gerd Laux, Walter Pöldinger (eds.): Neuro-Psychopharmaka A Therapy Manual . Volume 2: Tranquilizers and Hypnotics . Springer, Vienna 2013, ISBN 978-3-7091-6593-5 , pp. 107 ( limited preview in Google Book search).
- ↑ Teofarma Srl: Riassunto delle caratteristiche Product Properties: DOMAR® . Ed .: Agenzia Italiana del Farmaco. 2010 (Italian, gov.it [PDF]).
- ↑ R. Jochemsen, DD Breimer: Pharmacokinetics of benzodiazepines: metabolic pathways and plasma level profiles. In: Current Medical Research and Opinion . tape 8 , no. 4 , p. 60-79 , doi : 10.1185 / 03007998409109545 , PMID 6144464 (English).
- ↑ Janos Fischer, C. Robin Ganellin (Ed.): Analogue-based Drug Discovery . John Wiley & Sons, 2006, ISBN 3-527-60749-8 , pp. 538 .