Brotizolam

Brotizolam
Clinical data
Trade names	Lendormin
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	N05CD09 (WHO) ;
Legal status
Legal status	BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: Prescription only (Anlage III for higher doses); UK: Class C; US: Unscheduled; UN: Schedule IV;
Pharmacokinetic data
Bioavailability	48–95%
Metabolism	Hepatic
Elimination half-life	4.4 hours (range, 2.6–6.9 h)
Excretion	Renal
Identifiers
	IUPAC name 2-Bromo-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine;
CAS Number	57801-81-7 ;
PubChem CID	2451;
DrugBank	DB09017 ;
ChemSpider	2357 ;
UNII	5XZM1R3DKF;
KEGG	D01744 ;
ChEMBL	ChEMBL32479 ;
CompTox Dashboard (EPA)	DTXSID0022692 ;
ECHA InfoCard	100.055.404
Chemical and physical data
Formula	C15H10BrClN4S
Molar mass	393.69 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES ClC1=CC=CC=C1C2=NCC3=NN=C(C)N3C4=C2C=C(Br)S4;
	InChI InChI=1S/C15H10BrClN4S/c1-8-19-20-13-7-18-14(9-4-2-3-5-11(9)17)10-6-12(16)22-15(10)21(8)13/h2-6H,7H2,1H3 ; Key:UMSGKTJDUHERQW-UHFFFAOYSA-N ;
	(what is this?) (verify)

Brotizolam^[3] (marketed under brand name Lendormin) is a sedative-hypnotic^[4] thienotriazolodiazepine^[5] drug which is a benzodiazepine analog.^[6] It possesses anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties, and is considered to be similar in effect to other short-acting hypnotic benzodiazepines such as triazolam or midazolam.^[7] It is used in the short-term treatment of severe insomnia. Brotizolam is a highly potent and short-acting hypnotic, with a typical dose ranging from 0.125 to 0.25 milligrams, which is rapidly eliminated with an average half-life of 4.4 hours (range 3.6–7.9 hours).^[8]

It was patented in 1974^[9] and came into medical use in 1984.^[10] Brotizolam is not approved for sale in the UK, United States or Canada. It is approved for sale in the Netherlands, Germany, Spain, Belgium, Luxembourg, Austria, Portugal, Israel, Italy, Taiwan and Japan.

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ "DEA Diversion Control Division" (PDF). Archived from the original (PDF) on 2019-10-17. Retrieved 2015-12-10.
^ US 4094984 6-Phenyl-8-bromo-4H-s-triazolo-[3,4C]-thieno-[2,3E]-1,4-diazepines and salts thereof
^ Fink M, Irwin P (September 1981). "Pharmacoelectroencephalographic study of brotizolam, a novel hypnotic". Clinical Pharmacology and Therapeutics. 30 (3): 336–42. doi:10.1038/clpt.1981.169. PMID 7273596. S2CID 30788171.
^ Catabay A, Taniguchi M, Jinno K, Pesek JJ, Williamsen E (1 March 1998). "Separation of 1,4-Benzodiazepines and Analogues Using Cholesteryl-10-Undecenoate Bonded Phase in Microcolumn Liquid Chromatography". Journal of Chromatographic Science. 36 (3): 113. doi:10.1093/chromsci/36.3.111.
^ Jochemsen R, Wesselman JG, van Boxtel CJ, Hermans J, Breimer DD (1983). "Comparative pharmacokinetics of brotizolam and triazolam in healthy subjects". British Journal of Clinical Pharmacology. 16 (Suppl 2): 291S–297S. doi:10.1111/j.1365-2125.1983.tb02303.x. PMC 1428224. PMID 6140948.
^ Mandrioli R, Mercolini L, Raggi MA (October 2008). "Benzodiazepine metabolism: an analytical perspective". Current Drug Metabolism. 9 (8): 827–44. doi:10.2174/138920008786049258. PMID 18855614.
^ Langley MS, Clissold SP (February 1988). "Brotizolam. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy as an hypnotic". Drugs. 35 (2): 104–22. doi:10.2165/00003495-198835020-00002. PMID 3281819. S2CID 243228878.
^ US4094984 6-Phenyl-8-bromo-4H-s-triazolo-[3,4C]-thieno-[2,3E]-1,4-diazepines and salts thereof
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 539. ISBN 9783527607495.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[2] "DEA Diversion Control Division" (PDF). Archived from the original (PDF) on 2019-10-17. Retrieved 2015-12-10.

[3] US 4094984 6-Phenyl-8-bromo-4H-s-triazolo-[3,4C]-thieno-[2,3E]-1,4-diazepines and salts thereof

[4] Fink M, Irwin P (September 1981). "Pharmacoelectroencephalographic study of brotizolam, a novel hypnotic". Clinical Pharmacology and Therapeutics. 30 (3): 336–42. doi:10.1038/clpt.1981.169. PMID 7273596. S2CID 30788171.

[5] Catabay A, Taniguchi M, Jinno K, Pesek JJ, Williamsen E (1 March 1998). "Separation of 1,4-Benzodiazepines and Analogues Using Cholesteryl-10-Undecenoate Bonded Phase in Microcolumn Liquid Chromatography". Journal of Chromatographic Science. 36 (3): 113. doi:10.1093/chromsci/36.3.111.

[pmid6140948-6] Jochemsen R, Wesselman JG, van Boxtel CJ, Hermans J, Breimer DD (1983). "Comparative pharmacokinetics of brotizolam and triazolam in healthy subjects". British Journal of Clinical Pharmacology. 16 (Suppl 2): 291S–297S. doi:10.1111/j.1365-2125.1983.tb02303.x. PMC 1428224. PMID 6140948.

[7] Mandrioli R, Mercolini L, Raggi MA (October 2008). "Benzodiazepine metabolism: an analytical perspective". Current Drug Metabolism. 9 (8): 827–44. doi:10.2174/138920008786049258. PMID 18855614.

[pmid3281819-8] Langley MS, Clissold SP (February 1988). "Brotizolam. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy as an hypnotic". Drugs. 35 (2): 104–22. doi:10.2165/00003495-198835020-00002. PMID 3281819. S2CID 243228878.

[9] US4094984 6-Phenyl-8-bromo-4H-s-triazolo-[3,4C]-thieno-[2,3E]-1,4-diazepines and salts thereof

[Fis2006-10] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 539. ISBN 9783527607495.

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