7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

• ChemBase ID: 680
• Molecular Formular: C17H12ClF3N2O
• Molecular Mass: 352.7381896
• Monoisotopic Mass: 352.05902535
• SMILES: Clc1cc2c(N(CC(F)(F)F)C(=O)CN=C2c2ccccc2)cc1
• Canonical SMILES: Clc1ccc2c(c1)C(=NCC(=O)N2CC(F)(F)F)c1ccccc1
• InChI: InChI=1S/C17H12ClF3N2O/c18-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)22-9-15(24)23(14)10-17(19,20)21/h1-8H,9-10H2
• InChIKey: WYCLKVQLVUQKNZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• IUPAC Traditional name: halazepam
• Brand Name: Pacinone; Paxipam
• Synonyms: Halazepamum [INN-Latin]; Halazepam; 7-Chloro-1,3-dihydro-5-phenyl-1-(2,2,2-trifluoroethyl)-2H-1,4-benzodiazepin-2-one; 7-Chloro-1-(2,2,2-trifluoroethyl)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one; 7-Chloro-1-(2,2,2-trifluoroethyl)-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one; Paxipam; Sch 12041; Schering 12041; 9-chloro- 6-phenyl- 2-(2,2,2-trifluoroethyl)- 2,5-diazabicyclo[5.4.0] undeca- 5,8,10,12-tetraen -3-one

Database IDs

• CAS Number: 23092-17-3
• PubChem SID: 46508415; 160964143
• PubChem CID: 31640
• ATC CODE: N05BA13
• CHEMBL: 970
• Chemspider ID: 29343
• DrugBank ID: DB00801
• KEGG ID: D00338
• Unique Ingredient Identifier: 320YC168LF
• Wikipedia Title: Halazepam
• Medline Plus: a684001

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.878328
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.030893
• LogD (pH = 7.4): 4.031179
• Log P: 4.031183
• Molar Refractivity: 85.262 cm^3
• Polarizability: 31.457148 Å^3
• Polar Surface Area: 32.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.52
• LOG S: -5.32
• Solubility (Water): 1.70e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 4.3

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Renal
• Metabolism: Hepatic
• Legal Status: Schedule IV (US)

DETAILS

DrugBank - DB00801

• Drug Groups: illicit; approved
• Description: Halazepam is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. It is a trifluoromethyl derivative of nordazepam. While its structure may be similar to chlordiazepoxide and diazepam, it has both less toxicity and less tendency to cause paradoxical hostility and aggression than either of them. [Wikipedia]
• Indication: Used to relieve anxiety, nervousness, and tension associated with anxiety disorders.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• References: Fann WE, Pitts WM, Wheless JC: Pharmacology, efficacy, and adverse effects of halazepam, a new benzodiazepine. Pharmacotherapy. 1982 Mar-Apr;2(2):72-9. [Pubmed]
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - H101500

A benzodiazepine derivative that possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. It is a precursor to Desmethyldiazepam (D291595) and is equal to or more effective than Diazepam (D416855) with a lower frequency of s

REFERENCES

• Fann WE, Pitts WM, Wheless JC: Pharmacology, efficacy, and adverse effects of halazepam, a new benzodiazepine. Pharmacotherapy. 1982 Mar-Apr;2(2):72-9. Pubmed
• Fann, W.E. et al.: Pharmacother., 2, 72 (1982)
• Greenblatt, D.J. et al.: Lancet, 1, 1358 (1982)