Article · Wikipedia archive · Last revised Jul 30, 2026

Ebselen

Ebselen, is a synthetic organoselenium molecule under preliminary investigation as a drug candidate. It belongs to the class of compounds related to benzene and its derivatives. It is being developed by the Seattle biotechnology company, Sound Pharmaceuticals, Inc. It has also been reported to target tubulin, blocking its polymerization.

Last revised
Jul 30, 2026
Read time
≈ 2 min
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Citations
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Source
Wikipedia ↗
Ebselen
Skeletal formula of ebselen
Skeletal formula of ebselen source ↗
Ball-and-stick model of the ebselen molecule
Ball-and-stick model of the ebselen molecule source ↗
source ↗
Names
Preferred IUPAC name
2-Phenyl-1,2-benzoselenazol-3(2H)-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.132.190
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 checkY
    Key: DYEFUKCXAQOFHX-UHFFFAOYSA-N checkY
  • 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).
☒N verify (what is checkY☒N ?)

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

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.15

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.310

See also

See also

References

References

  1. "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 (2025). "NanoDSF Screening for Anti-tubulin Agents Uncovers New Structure–Activity Insights". Journal of Medicinal Chemistry. doi:10.1021/acs.jmedchem.5c01008.
  3. "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. 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.
External links