Ebselen

Ebselen (also called PZ 51, DR3305, and SPI-1005), is a synthetic organoselenium molecule under preliminary investigation as a drug candidate.^[1] It belongs to the class of compounds related to benzene and its derivatives.^[1] It is being developed by the Seattle biotechnology company, Sound Pharmaceuticals, Inc.^[1]

Ebselen

Skeletal formula of ebselen
Ball-and-stick model of the ebselen molecule
Names
Preferred IUPAC name 2-Phenyl-1,2-benzoselenazol-3(2H)-one
Identifiers
CAS Number	60940-34-3 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:77543 N
ChEMBL	ChEMBL51085 Y
ChemSpider	3082 Y
ECHA InfoCard	100.132.190
PubChem CID	3194
UNII	40X2P7DPGH Y
CompTox Dashboard (EPA)	DTXSID7045150
InChI InChI=1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H Y Key: DYEFUKCXAQOFHX-UHFFFAOYSA-N Y InChI=1/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H Key: DYEFUKCXAQOFHX-UHFFFAOYAZ
SMILES C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C3[Se]2 O=C1c3ccccc3[Se]N1c2ccccc2
Properties
Chemical formula	C13H9NOSe
Molar mass	274.17666
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Ebselen has been entered into clinical trials as a lead compound intended for the potential treatment of various diseases.^[2] Its most advanced clinical trial is a Phase III study in people with Meniere's disease, completed in July 2024.^[3]

In vitro, ebselen is a mimic of glutathione peroxidase and reacts with peroxynitrite.^[4] It is purported to have antioxidant and anti-inflammatory properties.^[1][4]

Synthesis

Generally, synthesis of the characteristic scaffold of ebselen, the benzoisoselenazolone ring system, can be achieved either through reaction of primary amines (RNH₂) with 2-(chloroseleno)benzoyl chloride (Route I),^[5] by ortho-lithiation of benzanilides followed by oxidative cyclization (Route II) mediated by cupric bromide (CuBr₂),^[6] or through the efficient Cu-catalyzed selenation / heterocyclization of o-halobenzamides, a methodology developed by Kumar et al.^[7] (Route III).

History

The first patent for 2-phenyl-1,2-benzoselenazol-3(2H)-one was filed in 1980 and granted in 1982.^[8]

Research

Ebselen is in preliminary clinical development for the potential treatment of hearing loss and depression, among other medical indications.^[2][9]