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
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
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 Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P34913|||Q9HBJ2 Gene ID: 2053.0 Gene Symbol: EPHX2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23219563 |
550.0 nM [Ki] | ||
Target ID: P22303|||Q53F46 Gene ID: 43.0 Gene Symbol: ACHE Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29405440 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30.3 ng/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBSELEN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED |
|
70.3 ng/mL |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBSELEN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED |
|
67.5 ng/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBSELEN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED |
|
83.4 ng/mL |
1600 mg single, oral dose: 1600 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBSELEN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
546.31 ng × h/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBSELEN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED |
|
710.1 ng × h/mL |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBSELEN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED |
|
883.15 ng × h/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBSELEN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED |
|
992.64 ng × h/mL |
1600 mg single, oral dose: 1600 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBSELEN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.42 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBSELEN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED |
|
14.4 h |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBSELEN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED |
|
12.1 h |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBSELEN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED |
|
16.7 h |
1600 mg single, oral dose: 1600 mg route of administration: Oral experiment type: SINGLE co-administered: |
EBSELEN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED |
PubMed
Title | Date | PubMed |
---|---|---|
Inhibition of ebselen on aflatoxin B(1)-induced hepatocarcinogenesis in Fischer 344 rats. | 2000 Dec |
|
The protective mechanism of antioxidants in cadmium-induced ototoxicity in vitro and in vivo. | 2008 Jul |
|
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle. | 2010 Feb 23 |
|
Ebselen reduces hyperglycemia temporarily-induced by diazinon: a compound with insulin-mimetic properties. | 2012 May 30 |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29405440
ebselen at concentrations equal or higher than 10 µM inhibited the activity of cortical and hippocampal G4/acethylcholinesterase (AChE), but not G1/AChE isoform.
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NCI_THESAURUS |
C1323
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NCI_THESAURUS |
C275
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C65503
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100000080483
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77543
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60940-34-3
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DTXSID7045150
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757883
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C042986
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5475
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EBSELEN
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DB12610
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SUB06439MIG
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m4803
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3194
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ACTIVE MOIETY