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E3520

Ebselen

powder, ≥98% (TLC)

Synonym(s):

2-Phenyl-1,2-benzisoselenazol-3(2H)-one

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About This Item

Empirical Formula (Hill Notation):
C13H9NOSe
CAS Number:
60940-34-3
Molecular Weight:
274.18
UNSPSC Code:
12352202
PubChem Substance ID:
24278417
NACRES:
NA.77
MDL number:
MFCD00210937
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Product Name

Ebselen, cysteine modifier

Quality Level

200

assay

≥98% (TLC)

form

powder

mp

176-182  °C

solubility

chloroform: 19.60-20.40 mg/mL, clear, yellow

storage temp.

2-8°C

SMILES string

O=C1N([Se]c2ccccc12)c3ccccc3

InChI

1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H

InChI key

DYEFUKCXAQOFHX-UHFFFAOYSA-N

General description

Ebselen is a sympathomimetic amine.

Application

Ebselen has been used as a:
  • voltage-dependent calcium channels (VDCCs) blocker
  • glutathione peroxidase mimetic to test its inhibitory effect on contraction-mediated deoxy glucose (2-DG) uptake in mouse

extensor digitorum longus (fast-twitch) muscle
  • glucocerebrosidase inhibitor
  • hepatitis C virus helicase inhibitor

Biochem/physiol Actions

Ebselen, a glutathione-peroxidase-mimic, elicits anti-inflammatory activity. It also has anti-atherosclerotic functionality. Ebselen displays antibacterial action on) multidrug-resistant Staphylococcus aureus (MRSA) infections and could be a potential therapeutic target for treating MRSA based skin infection. It is regarded as neuroprotective agent and elicits chemopreventive functionality in inflammation-associated carcinogenesis.
An organo-selenium compound possessing antioxidant properties. Inhibits mammalian lipoxygenases in the absence of thiol groups, and glutathione S-transferase and papain via the interaction with cysteine residues. Also inhibits indoleamine 2,3-dioxygenase by covalently modifying a cysteine residue, the effect being reversible with dithiothreitol. Inhibits oxidation of low density lipoproteins (LDL).

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Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
019M4181V
13180510
038M4170V
13171004
117M4039V

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Articles

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Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

View All Articles
Repurposing ebselen for treatment of multidrug-resistant staphylococcal infections
Thangamani S, et al.
Scientific reports, 5, 11596-11596 (2015)
Optimization and validation of two miniaturized glucocerebrosidase enzyme assays for high throughput screening
Urban DJ, et al.
Combinatorial Chemistry & High Throughput Screening, 11(10), 817-824 (2008)
Chuanjiang Dong et al.
Frontiers in microbiology, 10, 3016-3016 (2020-02-06)
As a thiol-dependent enzyme, thioredoxin reductase (TrxR) is a promising antibacterial drug target. Ebselen, an organo-selenium with well-characterized toxicology and pharmacology, was recently reported to have potent antibacterial activity against Staphylococcus aureus. In this paper, we demonstrated that ebselen has
View All Related Papers

Global Trade Item Number

SKUGTIN
E3520-100MG04061833603314
E3520-25MG04061833603321