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C5174

Sigma-Aldrich

4′-Chlorodiazepam

≥98% (TLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H12Cl2N2O
CAS Number:
14439-61-3
Molecular Weight:
319.19
Beilstein/REAXYS Number:
685202
MDL number:
MFCD00043406
UNSPSC Code:
12352200
PubChem Substance ID:
24892765
NACRES:
NA.77

Quality Level

200

assay

≥98% (TLC)

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

solubility

2-hydroxypropyl-β-cyclodextrin: insoluble
H2O: insoluble

SMILES string

O=C1CN=C(C2=CC=C(Cl)C=C2)C3=CC(Cl)=CC=C3N1C

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

InChI key

PUMYFTJOWAJIKF-UHFFFAOYSA-N

Gene Information

rat ... Tspo(24230)

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Application

4′-Chlorodiazepam has been used as a translocator protein ligand in mitochondrial functional studies. It has also been used to investigate its protective effects on glucose deprived T98G astrocyte cell lines.

Biochem/physiol Actions

4′-Chlorodiazepam (Ro5-4864) is a potent selective ligand for 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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A TSPO ligand prevents mitochondrial sterol accumulation and dysfunction during myocardial ischemia-reperfusion in hypercholesterolemic rats
Musman J, et al.
Biochemical Pharmacology, 142, 87-95 (2017)
4?-Chlorodiazepam protects mitochondria in T98G astrocyte cell line from glucose deprivation
Baez E, et al.
Neurotoxicity Research, 32(2), 163-171 (2017)
Federico Da Settimo et al.
Journal of medicinal chemistry, 51(18), 5798-5806 (2008-08-30)
Novel N,N-disubstituted indol-3-ylglyoxylamides (1-56), bearing different combinations of substituents R 1-R 5, were synthesized and evaluated as ligands of the translocator protein (TSPO), the 18 kDa protein representing the minimal functional unit of the "peripheral-type benzodiazepine receptor" (PBR). Most of
Lauren H Fairley et al.
Journal of neuroinflammation, 18(1), 76-76 (2021-03-21)
The translocator protein (TSPO) has been identified as a positron emission tomography (PET)-visible biomarker of inflammation and promising immunotherapeutic target for the treatment of Alzheimer's disease (AD). While TSPO ligands have been shown to reduce the accumulation of the toxic
Judy Choi et al.
Glia, 59(2), 219-230 (2010-12-03)
In the brain, translocator protein (18 kDa) (TSPO), previously called peripheral benzodiazepine receptor (PBR), is a glial protein that has been extensively used as a biomarker of brain injury and inflammation. However, the functional role of TSPO in glial cells
View All Related Papers

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