Ebselen

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Ebselen
Skeletal formula of ebselen Ebselen-2D-skeletal.png
Skeletal formula of ebselen
Ball-and-stick model of the ebselen molecule Ebselen-3D-balls.png
Ball-and-stick model of the ebselen molecule
Ebselen-3D-vdW.png
Names
Preferred IUPAC name
2-Phenyl-1,2-benzoselenazol-3(2H)-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.132.190 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H Yes check.svgY
    Key: DYEFUKCXAQOFHX-UHFFFAOYSA-N Yes check.svgY
  • 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
  • C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C3[Se]2
  • O=C1c3ccccc3[Se]N1c2ccccc2
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] It has also been reported to target tubulin, blocking its polymerization. [2]

Contents


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).

Ebselen Routes.png

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]

References

  1. 1 2 3 4 "Ebselen". DrugBank. 29 January 2025. Retrieved 4 February 2025.
  2. ↑ Baksheeva VE, La Rocca R, Allegro D, Derviaux C, Pasquier E, Roche P, Morelli X, Devred F, Golovin AV, Tsvetkov PO (2015). "NanoDSF Screening for Anti-tubulin Agents Uncovers New Structure–Activity Insights". Journal of Medicinal Chemistry. doi:10.1021/acs.jmedchem.5c01008.
  3. 1 2 "Ebselen pipeline". Sound Pharmaceuticals, Inc. 2025. Retrieved 4 February 2025.
  4. ↑ "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.
  5. 1 2 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.
  6. ↑ 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 .
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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
  10. ↑ "Ebselen search: list of clinical trials sponsored by Sound Pharmaceuticals". ClinicalTrials.gov, US National Library of Medicine. 2025. Retrieved 4 February 2025.
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