5-(2-chlorophenyl)-7-ethyl-1-methyl-1H,2H,3H-thieno[2,3-e][1,4]diazepin-2-one

• ChemBase ID: 1343
• Molecular Formular: C16H15ClN2OS
• Molecular Mass: 318.8211
• Monoisotopic Mass: 318.05936179
• SMILES: Clc1c(C2=NCC(=O)N(c3sc(cc23)CC)C)cccc1
• Canonical SMILES: CCc1sc2c(c1)C(=NCC(=O)N2C)c1ccccc1Cl
• 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
• InChIKey: CHBRHODLKOZEPZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(2-chlorophenyl)-7-ethyl-1-methyl-1H,2H,3H-thieno[2,3-e][1,4]diazepin-2-one
• IUPAC Traditional name: rize; 5-(2-chlorophenyl)-7-ethyl-1-methyl-3H-thieno[2,3-e][1,4]diazepin-2-one
• Brand Name: Veratran, Rize, Clozan; Rize; Rizen; Tienor; Trecalmo; Veratran; Distensan; Clozan
• Synonyms: Clotiazepamum [inn-latin]; Clotiazepam; 5-(o-Chlorophenyl)-7-ethyl-1,3-dihydro-1-methyl-2H-thieno[2,3-e]-1,4-diazepin-2-one; 1-Methyl-5-o-chlorophenyl-7-ethyl-1,2-dihydro-3H-thieno[2,3-e][1,4]diazepin-2-one; 5-(o-Chlorophenyl)-7-ethyl-1-methyl-1,2-dihydro-3H-thieno[2,3-e][1,4]diazepin-2-one; Clotiazepam; Clozan; Rize; Rizen; Tienor; Trecalmo; Veratran; Y 6047

Database IDs

• CAS Number: 33671-46-4
• PubChem SID: 160964803; 46508776
• PubChem CID: 2811
• ATC CODE: N05BA21
• Chemspider ID: 2709
• DrugBank ID: DB01559
• KEGG ID: D01328
• Unique Ingredient Identifier: ZCN055599V
• Wikipedia Title: Clotiazepam

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.1126184
• LogD (pH = 7.4): 4.11295
• Log P: 4.112954
• Molar Refractivity: 85.6579 cm^3
• Polarizability: 32.618286 Å^3
• Polar Surface Area: 32.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.58
• LOG S: -4.77
• Solubility (Water): 5.37e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.18 [MARUYAMA,T ET AL. (1992)]

Pharmacology Properties

• Admin Routes: Oral, sublingual, liquid drops
• Bioavailability: ~90%
• Excretion: Renal
• Half Life: 6-18 hr
• Metabolism: Hepatic
• Legal Status: Schedule IV (US)

DETAILS

DrugBank - DB01559

• Drug Groups: illicit; approved
• Description: Clotiazepam is a benzodiazepine derivative, not approved for sale in the U.S. or Canada, but has been approved in the U.K. It is a schedule IV drug in Canada.
• Indication: For the treatment of anxiety disorders.
• Pharmacology: Clotiazepam is a benzodiazepine derivative possessing anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Stage 2 NREM sleep is significantly increased by clotiazepam.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 4 hours
• Protein Binding: 99% bound to plasma proteins.
• References: Nakazawa Y, Kotorii M, Oshima M, Horikawa S, Tachibana H: Effects of thienodiazepine derivatives on human sleep as compared to those of benzodiazepine derivatives. Psychopharmacologia. 1975 Oct 31;44(2):165-71. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - C587410

A thienodiazepine derivative that possesses anxiolytic, skeletal muscle relaxant anticonvulsant, sedative properties as well as contributing to siginificant increase stage 2 NREM sleep. It binds to benzodiazepine site of the GABAA receptor where it acts a

REFERENCES

• Nakazawa Y, Kotorii M, Oshima M, Horikawa S, Tachibana H: Effects of thienodiazepine derivatives on human sleep as compared to those of benzodiazepine derivatives. Psychopharmacologia. 1975 Oct 31;44(2):165-71. Pubmed
• Mandrioli, R. et al.: Curr.Drug Metab., 8, 827 (2008)
• Nakazawa, Y. et al.: Psychopharmacol., 44, 165 (2008)
• Yakushiji, T. et al.: Br. J. Pharmacol., 98, 735 (2008)