Skip to Content
Merck
CN

E3520

Ebselen

powder, ≥98% (TLC)

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

Looking for similar products? Visit Product Comparison Guide

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).

signalword

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000453960
0000453960
0000384459
0000334537
0000384459

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Andrew C Terentis et al.
Biochemistry, 49(3), 591-600 (2009-12-17)
The heme enzyme indoleamine 2,3-dioxygenase (IDO) plays an important immune regulatory role by catalyzing the oxidative degradation of l-tryptophan. Here we show that the selenezal drug ebselen is a potent IDO inhibitor. Exposure of human macrophages to ebselen inhibited IDO
N Noguchi et al.
Biochimica et biophysica acta, 1213(2), 176-182 (1994-07-14)
The oxidative modification of low density lipoprotein (LDL) is accepted to be an important early event of atherosclerosis, but it has not yet been well understood. The preventive effects of two antioxidants with different functions, ebselen and probucol, against the
Selcuk Yatmaz et al.
American journal of respiratory cell and molecular biology, 48(1), 17-26 (2012-09-25)
Oxidative stress caused by excessive reactive oxygen species production is implicated in influenza A virus-induced lung disease. Glutathione peroxidase (GPx)-1 is an antioxidant enzyme that may protect lungs from such damage. The objective of this study was to determine if
Ebselen, a glutathione peroxidase mimetic seleno-organic compound, as a multifunctional antioxidant implication for inflammation-associated carcinogenesis
Nakamura Y, et al.
The Journal of Biological Chemistry, 277(4), 2687-2694 (2002)
Diana Islam et al.
American journal of respiratory and critical care medicine, 199(10), 1214-1224 (2018-12-07)
Rationale: There are controversial reports on applications of mesenchymal stromal cells (MSCs) in patients with acute respiratory distress syndrome (ARDS). Objectives: We hypothesized that lung microenvironment was the main determinant of beneficial versus detrimental effects of MSCs during ARDS. Methods:
View All Related Papers

Articles

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.

Papain, Cysteine Protease, Properties & Products

Uncover properties and applications of the cysteine protease papain and find inhibitors, substrates, and other papain products.

膳食抗氧化剂

抗氧化剂可保护生物系统免受含氧自由基和氧化还原过渡金属离子（如铁、铜和镉）引起的氧化损伤。

半胱氨酸蛋白酶——木瓜蛋白酶的特性和产品

木瓜蛋白酶是肽酶C1家族的一种半胱氨酸蛋白酶。它由单一多肽链组成，含有三个二硫键和一个酶活性所必需的巯基。

Global Trade Item Number

SKUGTIN
E3520-100MG04061833603314
E3520-25MG04061833603321

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service