U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C13H9NOSe
Molecular Weight 274.18
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EBSELEN

SMILES

O=C1N([Se]C2=CC=CC=C12)C3=CC=CC=C3

InChI

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

HIDE SMILES / InChI

Molecular Formula C13H9NOSe
Molecular Weight 274.18
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Ebselen is a small molecule mimic and inducer of glutathione peroxidase activity and possesses antioxidant and anti-inflammatory properties. This drug has been investigated in phase II clinical trials for the treatment of Meniere's disease, bipolar disorder and in the prevention of hearing loss. Besides, experiments on mice have shown that ZIKV infection could be on the list for potential use of ebselen. It alleviates testicular pathology in mice with Zika virus infection and prevents its sexual transmission. Ebselen has various mechanisms of action. It binds to the N-terminal domain of soluble epoxide hydrolase and chemically reacts with the enzyme to quickly and irreversibly inhibit one of the enzymes' activity: phosphatase (Nterm-phos). Besides, ebselen inhibits inositol monophosphatase and thus exhibits lithium-like on human central nervous system (CNS) function. In addition, ebselen inhibits the G4 isoform of acetylcholinesterase. It is a well-known relationship between the cholinergic system and learning, memory and other common cognitive processes, thus ebselen can be studied for the treatment of memory impairment diseases.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
550.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown
Palliative
Unknown
Preventing
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
30.3 ng/mL
200 mg single, oral
EBSELEN plasma
Homo sapiens
67.5 ng/mL
400 mg single, oral
EBSELEN plasma
Homo sapiens
70.3 ng/mL
800 mg single, oral
EBSELEN plasma
Homo sapiens
83.4 ng/mL
1600 mg single, oral
EBSELEN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
546.31 ng × h/mL
200 mg single, oral
EBSELEN plasma
Homo sapiens
883.15 ng × h/mL
400 mg single, oral
EBSELEN plasma
Homo sapiens
710.1 ng × h/mL
800 mg single, oral
EBSELEN plasma
Homo sapiens
992.64 ng × h/mL
1600 mg single, oral
EBSELEN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
6.42 h
200 mg single, oral
EBSELEN plasma
Homo sapiens
12.1 h
400 mg single, oral
EBSELEN plasma
Homo sapiens
14.4 h
800 mg single, oral
EBSELEN plasma
Homo sapiens
16.7 h
1600 mg single, oral
EBSELEN plasma
Homo sapiens

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Bipolar Disorder: ebselen capsules each containing 200mg taken orally twice a day for 3 weeks Meniere's Disease: 200, 400 or 600 mg of drug bid po x 21d hearing loss: 400 mg twice daily
Route of Administration: Oral
In Vitro Use Guide
ebselen at concentrations equal or higher than 10 µM inhibited the activity of cortical and hippocampal G4/acethylcholinesterase (AChE), but not G1/AChE isoform.
Substance Class Chemical
Record UNII
40X2P7DPGH
Record Status Validated (UNII)
Record Version