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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:
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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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)
Sabrina Taliani et al.
Journal of medicinal chemistry, 50(2), 404-407 (2007-01-19)
Fluorescent ligands for the peripheral-type benzodiazepine receptor (PBR) featuring the 7-nitrobenz-2-oxa-1,3-diazol-4-yl moiety were synthesized, based on N,N-dialkyl-2-phenylindol-3-ylglyoxylamides, a potent, selective class of PBR ligands previously described by us. All the new ligands are moderately to highly potent at the PBR
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
Anna M Barron et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(20), 8891-8897 (2013-05-17)
Ligands of the translocator protein (TSPO) elicit pleiotropic neuroprotective effects that represent emerging treatment strategies for several neurodegenerative conditions. To investigate the potential of TSPO as a therapeutic target for Alzheimer's disease (AD), the current study assessed the effects of
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