EBSELEN

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 Search

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

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT03013400 | https://www.ncbi.nlm.nih.gov/pubmed/26593266 | https://www.ncbi.nlm.nih.gov/pubmed/29405440 | https://www.ncbi.nlm.nih.gov/pubmed/28716314 | https://www.ncbi.nlm.nih.gov/pubmed/29447264

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
Bifunctional epoxide hydrolase 2 1 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	Inhibitor 8297		550.0 nM [Ki]
Acetylcholinesterase 207 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	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Bipolar disorder 34 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23299882	Palliative	Phase II 1132	Unknown Approved Use Unknown
Meniere's disease 16 Sources: https://clinicaltrials.gov/ct2/show/NCT02603081	Palliative	Phase II 1132	Unknown Approved Use Unknown
Hearing loss 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28716314	Preventing	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
30.3 ng/mL EXPERIMENT https://www.sto.nato.int/publications/STO Meeting Proceedings/RTO-MP-AVT-158/MP-AVT-158-23.pdf	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 EXPERIMENT https://www.sto.nato.int/publications/STO Meeting Proceedings/RTO-MP-AVT-158/MP-AVT-158-23.pdf	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 EXPERIMENT https://www.sto.nato.int/publications/STO Meeting Proceedings/RTO-MP-AVT-158/MP-AVT-158-23.pdf	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 EXPERIMENT https://www.sto.nato.int/publications/STO Meeting Proceedings/RTO-MP-AVT-158/MP-AVT-158-23.pdf	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	Analyte	Population
546.31 ng × h/mL EXPERIMENT https://www.sto.nato.int/publications/STO Meeting Proceedings/RTO-MP-AVT-158/MP-AVT-158-23.pdf	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 EXPERIMENT https://www.sto.nato.int/publications/STO Meeting Proceedings/RTO-MP-AVT-158/MP-AVT-158-23.pdf	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 EXPERIMENT https://www.sto.nato.int/publications/STO Meeting Proceedings/RTO-MP-AVT-158/MP-AVT-158-23.pdf	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 EXPERIMENT https://www.sto.nato.int/publications/STO Meeting Proceedings/RTO-MP-AVT-158/MP-AVT-158-23.pdf	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

T_1/2

Value	Dose	Analyte	Population
6.42 h EXPERIMENT https://www.sto.nato.int/publications/STO Meeting Proceedings/RTO-MP-AVT-158/MP-AVT-158-23.pdf	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 EXPERIMENT https://www.sto.nato.int/publications/STO Meeting Proceedings/RTO-MP-AVT-158/MP-AVT-158-23.pdf	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 EXPERIMENT https://www.sto.nato.int/publications/STO Meeting Proceedings/RTO-MP-AVT-158/MP-AVT-158-23.pdf	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 EXPERIMENT https://www.sto.nato.int/publications/STO Meeting Proceedings/RTO-MP-AVT-158/MP-AVT-158-23.pdf	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

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY100752	https://www.001chemical.com/chem/60940-34-3
3B Scientific (Wuhan) Corp	3B3-064910	http://www.3bsc.com/index/pro_info.php?id=104100
AA Blocks	AA003HSE	https://www.aablocks.com/goods/Goods/detail?id=AA003HSE
AK Scientific, Inc. (AKSCI)	V1941	http://www.aksci.com/item_detail.php?cat=V1941
Aaron Chemicals	AR003IK6	http://www.aaronchem.com/60940-34-3
AbMole Bioscience	M9794	http://www.abmole.com/products/ebselen.html
Acadechem	ACDS-029115	http://www.acadechemical.com/product/103814
Achemtek	0102-012702	http://www.achemtek.com/60940-34-3
Acros Organics	AC300572500	https://www.fishersci.com/shop/products/ebselen-99-acros-organics/AC300572500
Alfa Chemistry	AP60940343	https://reagents.alfa-chemistry.com/product/ebselen-cas-60940-34-3-13992.html
Alfa Chemistry	ACM60940343	https://www.alfa-chemistry.com/ebselen-cas-60940-34-3-item-284902.htm
Ambeed	A121080	https://www.ambeed.com/products/60940-34-3.html
Ambinter	Amb19930433	http://www.ambinter.com/reference/19930433
Angel Pharmatech	AG-11889	http://www.angelpharmatech.com/60940-34-3.html
Ark Pharm	AK115695	http://www.arkpharminc.com/products/60940-34-3.html
Aurora Fine Chemicals LLC	A13.111.938	http://online.aurorafinechemicals.com/info?ID=A13.111.938
AvaChem Scientific	6301	https://www.avachem.com/productSearch.asp?6301
BLD Pharm	BD127093	http://www.bldpharm.com/products/60940-34-3.html
BOC Sciences	60940-34-3	https://www.bocsci.com/ebselen-cas-60940-34-3-item-84-72972.html
BioChemPartner	BCP17134	http://www.biochempartner.com/60940-34-3-BCP17134
Boerchem	BC224294	http://www.boerchem.com/?product_37800.html
CSNpharm	CSN10885	https://www.csnpharm.com/products/ebselen.html
Calbiochem	324483	http://www.emdbiosciences.com/product/324483
Chem Scene	CS-5534	http://www.chemscene.com/60940-34-3.html
ChemMol	30108733	http://www.chemmol.com/chemmol/30108733.html
ChemMol	44007169	http://www.chemmol.com/chemmol/44007169.html
ChemMol	49409019	http://www.chemmol.com/chemmol/49409019.html
ChemMol	99119666	http://www.chemmol.com/chemmol/99119666.html
Chemspace	CSSB00016999338	https://chem-space.com/CSSB00016999338
DC Chemicals	DC9848	http://www.dcchemicals.com/product_show-Ebselen.html
Debye Scientific	DB-072873	http://www.debyesci.com/cas_60940-34-3.html
EMD Millipore	324483	http://www.emdbiosciences.com/product/324483
Excenen	EX-A1447	http://www.excenen.com/searchresultlist.php?id=60940-34-3
Finetech	FT-0759332	http://www.finetechnology-ind.com/prod/detail/pub/60940-34-3.html
Glentham Life Sciences	GP4285	http://www.glentham.com/products/product/GP4285/
Hairui	HR128557	http://www.hairuichem.com/en/product/60940-34-3.html
Hello Bio	HB0270	http://www.hellobio.com/ebselen.html
Lab Network	LN00198236	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00198236
Matrix Scientific	99432	https://www.matrixscientific.com/099432.html
MedChem Express	HY-13750	https://www.medchemexpress.com/Ebselen.html
MolPort	MolPort-003-666-383	https://www.molport.com/shop/molecule-link/MolPort-003-666-383
Molcore	MC100752	https://www.molcore.com/product/60940-34-3
MuseChem	I004298	https://www.musechem.com/product/I004298.html
OChem	2642	http://www.ocheminc.com/index.php?act=psearch&pid=940E343
Selleck Chemicals	S6676	http://www.selleckchem.com/products/ebselen.html
Sigma-Aldrich	E3520_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/e3520?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S013458	http://www.sinfoobiotech.com/product/1016856
Smolecule	S526823	http://www.smolecule.com/products/s526823
TCI (Tokyo Chemical Industry)	E0946	http://www.tcichemicals.com/eshop/en/us/commodity/E0946/index.html
THE BioTek	bt-266938	https://www.thebiotek.com/product/inhibitors/bt-266938
Tocris	5245	https://www.tocris.com/products/ebselen_5245
Yuhao Chemical	RT8353	http://www.chemyuhao.com/60940-34-3.html
abcr GmbH	AB348737	http://www.abcr.com/shop/en/AB348737
eNovation Chemicals	D375990	https://www.enovationchem.com/ProductDetails.asp?ProductID=D375990
eNovation Chemicals	D633211	https://www.enovationchem.com/ProductDetails.asp?ProductID=D633211
eNovation Chemicals	D672529	https://www.enovationchem.com/ProductDetails.asp?ProductID=D672529
eNovation Chemicals	D766334	https://www.enovationchem.com/ProductDetails.asp?ProductID=D766334
eNovation Chemicals	D972699	https://www.enovationchem.com/ProductDetails.asp?ProductID=D972699
iChemical	EBD7144	http://www.ichemical.com/products/60940-34-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Effects of the seleno-organic substance Ebselen in two different models of acute pancreatitis.	1991 May	1713672
PZ-51 (Ebselen) in vivo protection against adriamycin-induced mouse cardiac and hepatic lipid peroxidation and toxicity.	1992 Aug 18	1510734
Interaction of ebselen with glutathione S-transferase and papain in vitro.	1994 Mar 15	8147899
Molecular actions of ebselen--an antiinflammatory antioxidant.	1995 Oct	7590103
Cellular factors as alternative targets for inhibition of HIV-1.	1997 Feb	9037371
Inhibition of ebselen on aflatoxin B(1)-induced hepatocarcinogenesis in Fischer 344 rats.	2000 Dec	11133813
Transcriptional and posttranscriptional regulation of endothelial nitric oxide synthase expression by hydrogen peroxide.	2000 Feb 18	10679488
Activation of matrix metalloproteinase-2 by overexpression of manganese superoxide dismutase in human breast cancer MCF-7 cells involves reactive oxygen species.	2002 Jun 7	11929863
Functionalized alkyl and aryl diselenides as antimicrobial and antiviral agents: synthesis and properties.	2003 Dec	14630233
An inducible nitric oxide synthase-luciferase reporter system for in vivo testing of anti-inflammatory compounds in transgenic mice.	2003 Jun 15	12794164
Hypoxia and stretch regulate intercellular communication in vascular smooth muscle cells through reactive oxygen species formation.	2003 Oct 1	12958040
Interaction of selenium compounds with zinc finger proteins involved in DNA repair.	2004 Aug	15265038
Renal and hepatic ALA-D activity and selected oxidative stress parameters of rats exposed to inorganic mercury and organoselenium compounds.	2004 Jan	14630126
Azaanalogues of ebselen as antimicrobial and antiviral agents: synthesis and properties.	2004 Nov	15544790
Dimethyl sulfoxide and ebselen prevent convulsions induced by 5-aminolevulinic acid.	2004 Oct	15532533
Cardioprotective effects of subcutaneous ebselen against daunorubicin-induced cardiomyopathy in rats.	2006 Dec	17169121
Oral pretreatment with ebselen enhances heat shock protein 72 expression and reduces myocardial infarct size.	2006 Nov	17345791
Oxidative stress induces ADAM9 protein expression in human prostate cancer cells.	2006 Oct 1	17018608
Small-molecule screening identifies the selanazal drug ebselen as a potent inhibitor of DMT1-mediated iron uptake.	2006 Sep	16984886
Functional involvement of PHOSPHO1 in matrix vesicle-mediated skeletal mineralization.	2007 Apr	17227223
The protective mechanism of antioxidants in cadmium-induced ototoxicity in vitro and in vivo.	2008 Jul	18629305
Effects of poly(ADP-ribose) polymerase inhibition in bladder damage caused by cyclophosphamide in rats.	2008 Mar	18296739
Mitochondria-derived reactive oxygen species mediate heme oxygenase-1 expression in sheared endothelial cells.	2009 Apr	19131585
The redox state of glutathione regulates the hypoxic induction of HIF-1.	2009 Mar 15	19374849
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle.	2010 Feb 23	20142494
Reactive oxygen species, Ki-Ras, and mitochondrial superoxide dismutase cooperate in nerve growth factor-induced differentiation of PC12 cells.	2010 Jul 30	20495008
Selenoprotein-dependent up-regulation of hematopoietic prostaglandin D2 synthase in macrophages is mediated through the activation of peroxisome proliferator-activated receptor (PPAR) gamma.	2011 Aug 5	21669866
3-(2,6-dimethylphenyl)-2-selenoxo-1,3-thiazolidin-4-one suppresses hydrogen peroxide-induced cytotoxicity on PC12 cells via activation of MAPK.	2011 Dec	21960664
A superoxide anion-scavenger, 1,3-selenazolidin-4-one suppresses serum deprivation-induced apoptosis in PC12 cells by activating MAP kinase.	2011 Dec 15	22001386
TGF-β regulates Nox4, MnSOD and catalase expression, and IL-6 release in airway smooth muscle cells.	2011 Feb	21131394
Methylmercury-induced alterations in astrocyte functions are attenuated by ebselen.	2011 Jun	21300091
The monoamine oxidase A inhibitor clorgyline is a broad-spectrum inhibitor of fungal ABC and MFS transporter efflux pump activities which reverses the azole resistance of Candida albicans and Candida glabrata clinical isolates.	2012 Mar	22203607
Ebselen reduces hyperglycemia temporarily-induced by diazinon: a compound with insulin-mimetic properties.	2012 May 30	22484362
Interrogating a hexokinase-selected small-molecule library for inhibitors of Plasmodium falciparum hexokinase.	2013 Aug	23716053
Mitochondrial electron transfer chain complexes inhibition by different organochalcogens.	2013 Feb	23103426
Ebselen reduces the toxicity of mechlorethamine in A-431 cells via inhibition of apoptosis.	2013 Jun	23649643
Development of an HTS assay for EPHX2 phosphatase activity and screening of nontargeted libraries.	2013 Mar 1	23219563
Antimalarial screening via large-scale purification of Plasmodium falciparum Ca2+-ATPase 6 and in vitro studies.	2013 Nov	23497141
In vitro glutathione peroxidase mimicry of ebselen is linked to its oxidation of critical thiols on key cerebral suphydryl proteins - A novel component of its GPx-mimic antioxidant mechanism emerging from its thiol-modulated toxicology and pharmacology.	2013 Oct 25	23933410
Glutathione peroxidase mimic ebselen improves glucose-stimulated insulin secretion in murine islets.	2014 Jan 10	23795780
The seleno-organic compound ebselen impairs mitochondrial physiology and induces cell death in AR42J cells.	2014 Sep 17	25068500

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.

Name

Type

Language

EBSELEN

Official Name

English

NSC-639762

Code

English

2-PHENYL-1,2-BENZISOSELENAZOL-3(2H)-ONE

Systematic Name

English

SPI-1005

Code

English

ebselen [INN]

Common Name

English

EBSELEN [JAN]

Common Name

English

EBSELEN [MI]

Common Name

English

DR-3305

Code

English

EBSELEN [MART.]

Common Name

English

NSC-757883

Code

English

DR3305

Code

English

Ebselen [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1323