Ebselen
Chemical compound
From Wikipedia, the free encyclopedia
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] It has also been reported to target tubulin, blocking its polymerization.[2]
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| Names | |
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| Preferred IUPAC name
2-Phenyl-1,2-benzoselenazol-3(2H)-one | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.132.190 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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).
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Ebselen has been entered into clinical trials as a lead compound intended for the potential treatment of various diseases.[3] Its most advanced clinical trial is a Phase III study in people with Meniere's disease, completed in July 2024.[4]
In vitro, ebselen is a mimic of glutathione peroxidase and reacts with peroxynitrite.[5] It is purported to have antioxidant and anti-inflammatory properties.[1][5]
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),[6] by ortho-lithiation of benzanilides followed by oxidative cyclization (Route II) mediated by cupric bromide (CuBr2),[7] or through the efficient Cu-catalyzed selenation / heterocyclization of o-halobenzamides, a methodology developed by Kumar et al.[8] (Route III).
History
The first patent for 2-phenyl-1,2-benzoselenazol-3(2H)-one was filed in 1980 and granted in 1982.[9]
Research
Ebselen is in preliminary clinical development for the potential treatment of hearing loss and depression, among other medical indications.[3][10]