7-chloro-5-(4-chlorophenyl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

• ChemBase ID: 129289
• Molecular Formular: C16H12Cl2N2O
• Molecular Mass: 319.18528
• Monoisotopic Mass: 318.03266837
• SMILES: Clc1ccc(cc1)C1=NCC(=O)N(c2c1cc(Cl)cc2)C
• Canonical SMILES: Clc1ccc(cc1)C1=NCC(=O)N(c2c1cc(Cl)cc2)C
• InChI: InChI=1S/C16H12Cl2N2O/c1-20-14-7-6-12(18)8-13(14)16(19-9-15(20)21)10-2-4-11(17)5-3-10/h2-8H,9H2,1H3
• InChIKey: PUMYFTJOWAJIKF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-chloro-5-(4-chlorophenyl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• IUPAC Traditional name: 4-chlorodiazepam
• Synonyms: Ro5-4864; 7-Chloro-5-(4-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one; Ro 5-4864; Ro5-4864; 4′-Chlorodiazepam

Database IDs

• CAS Number: 14439-61-3
• MDL Number: MFCD00043406
• Beilstein Number: 685202
• PubChem SID: 162223583; 24892765
• PubChem CID: 1688
• Wikipedia Title: Ro5-4864

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.6797466
• LogD (pH = 7.4): 3.6801264
• Log P: 3.6801312
• Molar Refractivity: 84.6167 cm^3
• Polarizability: 32.202152 Å^3
• Polar Surface Area: 32.67 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 2-hydroxypropyl-β-cyclodextrin: insoluble; H2O: insoluble
• Melting Point: 160-163 °C

Safety Information

• RTECS: DF0500000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 22-24/25
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Gene Information: rat ... Tspo(24230)

Product Information

• Purity: ≥98% (TLC); ≥98.0% (CHN)
• Empirical Formula (Hill Notation): C16H12Cl2N2O

DETAILS

Sigma Aldrich - C5174

Application
Peripheral benzodiazepine ligand useful in distinguishing central-type from peripheral-type benzodiazepine receptors.
Biochem/physiol Actions
4′-Chlorodiazepam (Ro5-4864) is a potent selective antagonist of the mitochondrial translocator protein 18kDa (TSPO), formerly known as the peripheral benzodiazepine receptor (PBR). Ro5-4864 does not bind to GABA(A) receptors and lacks typical benzodiazepine effects, but has been found to be neuroprotective in several studies.

Sigma Aldrich - 24104

Other Notes
Diazepam analog which binds very strongly to peripheral benzodiazepine receptors, but has negligible affinity for central receptors1.