Ebselen
| 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 (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 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
[edit]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
[edit]The first patent for 2-phenyl-1,2-benzoselenazol-3(2H)-one was filed in 1980 and granted in 1982.[8]
Research
[edit]Ebselen is in preliminary clinical development for the potential treatment of hearing loss and depression, among other medical indications.[2][9]
References
[edit]- ^ a b c d "Ebselen". DrugBank. 29 January 2025. Retrieved 4 February 2025.
- ^ a b "Ebselen pipeline". Sound Pharmaceuticals, Inc. 2025. Retrieved 4 February 2025.
- ^ "SPI-1005 for the Treatment of Meniere's Disease (STOPMD-3)". ClinicalTrials.gov, US National Library of Medicine. 1 August 2024. Retrieved 4 February 2025.
- ^ a b Schewe T (October 1995). "Molecular actions of ebselen - an antiinflammatory antioxidant". General Pharmacology. 26 (6): 1153–69. doi:10.1016/0306-3623(95)00003-J. PMID 7590103.
- ^ Kamigata N, Iizuka H, Izuoka A, Kobayashi M (July 1986). "Photochemical Reaction of 2-Aryl-1, 2-benzisoselenazol-3 (2 H)-ones". Bulletin of the Chemical Society of Japan. 59 (7): 2179–83. doi:10.1246/bcsj.59.2179.
- ^ Engman L, Hallberg A (1989-06-01). "Expedient synthesis of ebselen and related compounds". The Journal of Organic Chemistry. 54 (12): 2964–2966. doi:10.1021/jo00273a035. ISSN 0022-3263.
- ^ Balkrishna SJ, Bhakuni BS, Chopra D, Kumar S (December 2010). "Cu-catalyzed efficient synthetic methodology for ebselen and related Se-N heterocycles". Organic Letters. 12 (23): 5394–7. doi:10.1021/ol102027j. PMID 21053969.
- ^ DE3027073A1, Etschenberg, Eugen Dr; Renson, Marcel Prof Dipl-Chem Jupille & Winkelmann, Johannes Dr 5000 Köln, "2-phenyl-1,2-benzisoselenazol-3(2h)-on enthaltende pharmazeutische praeparate und ihre verwendung", issued 1982-02-18
- ^ "Ebselen search: list of clinical trials sponsored by Sound Pharmaceuticals". ClinicalTrials.gov, US National Library of Medicine. 2025. Retrieved 4 February 2025.