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

• ChemBase ID: 1366
• Molecular Formular: C19H17ClN2O
• Molecular Mass: 324.80408
• Monoisotopic Mass: 324.10294085
• SMILES: Clc1cc2c(N(CC3CC3)C(=O)CN=C2c2ccccc2)cc1
• Canonical SMILES: Clc1ccc2c(c1)C(=NCC(=O)N2CC1CC1)c1ccccc1
• InChI: InChI=1S/C19H17ClN2O/c20-15-8-9-17-16(10-15)19(14-4-2-1-3-5-14)21-11-18(23)22(17)12-13-6-7-13/h1-5,8-10,13H,6-7,11-12H2
• InChIKey: MWQCHHACWWAQLJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-chloro-1-(cyclopropylmethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• IUPAC Traditional name: prazepam
• Brand Name: Centrax; Demetrin; Lysanxia; Prazeene; Prazene; Sedapran; Settima; Trepidan; Verstran
• Synonyms: Prazepamum [inn-latin]; Prazepam; 9-chloro-2-(cyclopropylmethyl)-6-phenyl-2,5-diazabicyclo[5.4.0]undeca-5,8,10,12-tetraen- 3-one; Prazepam

Database IDs

• CAS Number: 2955-38-6
• EC Number: 220-975-8
• MDL Number: MFCD00057905
• PubChem SID: 46505417; 24898436; 160964826
• PubChem CID: 4890
• ATC CODE: N05BA11
• CHEMBL: 969
• Chemspider ID: 4721
• DrugBank ID: DB01588
• KEGG ID: D00470
• Unique Ingredient Identifier: Q30VCC064M
• Wikipedia Title: Prazepam
• Medline Plus: a601036

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.8550754
• LogD (pH = 7.4): 3.856644
• Log P: 3.856664
• Molar Refractivity: 91.7539 cm^3
• Polarizability: 35.11395 Å^3
• Polar Surface Area: 32.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.68
• LOG S: -4.91
• Solubility (Water): 3.99e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.73 [HANSCH,C ET AL. (1995)]

Safety Information

• RTECS: DF2368000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Renal
• Half Life: 36-200 hours
• Metabolism: Hepatic
• Legal Status: Schedule IV (US)

Product Information

• Empirical Formula (Hill Notation): C19H17ClN2O

DETAILS

DrugBank - DB01588

• Drug Groups: illicit; approved
• Description: Prazepam is a benzodiazepine that is used in the treatment of anxiety disorders. It is a schedule IV drug in the U.S.
• Indication: For the treatment of anxiety disorders.
• Pharmacology: Prazepam is a benzodiazepine derivative drug. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Benzodiazepines may be habit-forming (causing mental or physical dependence), especially when taken for a long time or in high doses.
• Toxicity: Symptoms of overdose include somnolence, confusion, coma, and diminished reflexes. Respiration, pulse and blood pressure should be monitored.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 36-200 hours
• External Links: Wikipedia

Sigma Aldrich - P3654

Biochem/physiol Actions
Anxiolytic