Clotiazepam

Clotiazepam
Clinical data
Trade names	Veratran, Rize, Clozan
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral, sublingual, liquid drops
ATC code	N05BA21 (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: Schedule IV;
Pharmacokinetic data
Bioavailability	~90%
Metabolism	Hepatic
Elimination half-life	4 hours
Excretion	Renal
Identifiers
	IUPAC name 5-(2-chlorophenyl)-7-ethyl-1-methyl-3H-thieno[2,3-e][1,4]diazepin-2-one;
CAS Number	33671-46-4 ;
PubChem CID	2811;
DrugBank	DB01559 ;
ChemSpider	2709 ;
UNII	ZCN055599V;
KEGG	D01328 ;
ChEMBL	ChEMBL1697737 ;
CompTox Dashboard (EPA)	DTXSID0022852 ;
ECHA InfoCard	100.046.920
Chemical and physical data
Formula	C16H15ClN2OS
Molar mass	318.82 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES ClC1=C(C2=NCC(N(C)C3=C2C=C(CC)S3)=O)C=CC=C1;
	InChI InChI=1S/C16H15ClN2OS/c1-3-10-8-12-15(11-6-4-5-7-13(11)17)18-9-14(20)19(2)16(12)21-10/h4-8H,3,9H2,1-2H3 ; Key:CHBRHODLKOZEPZ-UHFFFAOYSA-N ;
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Clotiazepam^[3] (marketed under brand name Clozan, Distensan, Trecalmo, Rize, Rizen and Veratran) is a thienodiazepine drug which is a benzodiazepine analog. The clotiazepam molecule differs from benzodiazepines in that the benzene ring has been replaced by a thiophene ring.^[4] It possesses anxiolytic,^[5] skeletal muscle relaxant,^[6] anticonvulsant, sedative properties.^[7] Stage 2 NREM sleep is significantly increased by clotiazepam.^[8]

^ 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.
^ "Clotiazépam" (PDF). HAS - Direction de l'Evaluation Médicale. Economique et de Santé Publique. 20 May 2015.
^ DE 2107356, Nakanishi M, Kazuhiko A, Tetsuya T, Shiroki M, "Thieno-(2,3-E)(1,4)diazepin-2-ones", issued 3 May 1978, assigned to Yoshitomi Pharmaceutical Industries, Ltd.
^ Niwa T, Shiraga T, Ishii I, Kagayama A, Takagi A (September 2005). "Contribution of human hepatic cytochrome p450 isoforms to the metabolism of psychotropic drugs". Biological & Pharmaceutical Bulletin. 28 (9): 1711–1716. doi:10.1248/bpb.28.1711. PMID 16141545.
^ Klicpera C, Strian F (May 1978). "Autonomic perception and responses in anxiety-inducing situations". Pharmakopsychiatrie, Neuro-Psychopharmakologie. 11 (3): 113–120. doi:10.1055/s-0028-1094569. PMID 27828.
^ Fukuda T, Tsumagari T (August 1983). "Effects of psychotropic drugs on the rage responses induced by electrical stimulation of the medial hypothalamus in cats". Japanese Journal of Pharmacology. 33 (4): 885–890. doi:10.1254/jjp.33.885. PMID 6632385.
^ Mandrioli R, Mercolini L, Raggi MA (October 2008). "Benzodiazepine metabolism: an analytical perspective". Current Drug Metabolism. 9 (8): 827–844. doi:10.2174/138920008786049258. PMID 18855614.
^ Nakazawa Y, Kotorii M, Oshima M, Horikawa S, Tachibana H (October 1975). "Effects of thienodiazepine derivatives on human sleep as compared to those of benzodiazepine derivatives". Psychopharmacologia. 44 (2): 165–171. doi:10.1007/BF00421005. PMID 709. S2CID 13365554.

[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] "Clotiazépam" (PDF). HAS - Direction de l'Evaluation Médicale. Economique et de Santé Publique. 20 May 2015.

[3] DE 2107356, Nakanishi M, Kazuhiko A, Tetsuya T, Shiroki M, "Thieno-(2,3-E)(1,4)diazepin-2-ones", issued 3 May 1978, assigned to Yoshitomi Pharmaceutical Industries, Ltd.

[4] Niwa T, Shiraga T, Ishii I, Kagayama A, Takagi A (September 2005). "Contribution of human hepatic cytochrome p450 isoforms to the metabolism of psychotropic drugs". Biological & Pharmaceutical Bulletin. 28 (9): 1711–1716. doi:10.1248/bpb.28.1711. PMID 16141545.

[Klicpera-1978-5] Klicpera C, Strian F (May 1978). "Autonomic perception and responses in anxiety-inducing situations". Pharmakopsychiatrie, Neuro-Psychopharmakologie. 11 (3): 113–120. doi:10.1055/s-0028-1094569. PMID 27828.

[Fukuda-1983-6] Fukuda T, Tsumagari T (August 1983). "Effects of psychotropic drugs on the rage responses induced by electrical stimulation of the medial hypothalamus in cats". Japanese Journal of Pharmacology. 33 (4): 885–890. doi:10.1254/jjp.33.885. PMID 6632385.

[Mandrioli-2008-7] Mandrioli R, Mercolini L, Raggi MA (October 2008). "Benzodiazepine metabolism: an analytical perspective". Current Drug Metabolism. 9 (8): 827–844. doi:10.2174/138920008786049258. PMID 18855614.

[8] Nakazawa Y, Kotorii M, Oshima M, Horikawa S, Tachibana H (October 1975). "Effects of thienodiazepine derivatives on human sleep as compared to those of benzodiazepine derivatives". Psychopharmacologia. 44 (2): 165–171. doi:10.1007/BF00421005. PMID 709. S2CID 13365554.

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