CAS 14439-61-3|4-chlorodiazepam|7-chloro-5-(4-chlorophenyl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one|Ro5-4864|Ro 5-4864|4′-Chlorodiazepam|Ro5-4864|7-Chloro-5-(4-chlorophenyl)-1,3-dihydro-1-m...

General Information

Structure

Molecular Formula

C₁₆H₁₂Cl₂N₂O

Molecular Mass

319.18528

Exact Mass

318.03266837

Charge

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

Canonic Smiles

Clc1ccc(cc1)C1=NCC(=O)N(c2c1cc(Cl)cc2)C

Isomeric Smiles

Clc1ccc(cc1)C1=NCC(=O)N(c2c1cc(Cl)cc2)C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

3.6797466

LogD (pH = 7.4)

3.6801264

Log P

3.6801312

Molar Refractivity

84.6167

Polarizability

32.202152

Polar Surface Area

32.67

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC Traditional name

4-chlorodiazepam

IUPAC name

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

Synonyms

Ro5-4864Ro 5-4864Ro5-48644′-Chlorodiazepam7-Chloro-5-(4-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

Names and Identifiers

Registration numbers

CAS Number

Wikipedia Title

PubChem CID

PubChem SID

Beilstein Number

MDL Number

Registration numbers

Properties

Product Information

Empirical Formula (Hill Notation)

C16H12Cl2N2O

Purity

≥98% (TLC)

≥98.0% (CHN)

Physical Property

Solubility

H2O: insoluble

2-hydroxypropyl-β-cyclodextrin: insoluble

Melting Point

160-163 °C

Pharmacology Properties

Gene Information

rat ... Tspo(24230)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

Ro5-4864

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.

24104

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

Molecule Details

References

PubChem Literature

No Data Available

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References

Bioactivity

PubChem BioAssay

Bioactivity