Ebselen
{{chembox
| Verifiedfields = changed
| verifiedrevid = 437141678
| ImageFile = Ebselen-2D-skeletal.png
| ImageSize = 200px
| ImageName = Skeletal formula of ebselen
| ImageFile1 = Ebselen-3D-balls.png
| ImageSize1 = 200px
| ImageFile2 = Ebselen-3D-vdW.png
| ImageSize2 = 200px
| ImageName1 = Ball-and-stick model of the ebselen molecule
| PIN = 2-Phenyl-1,2-benzoselenazol-3(2H)-one
| OtherNames=
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3082
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 40X2P7DPGH
| InChI = 1/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H
| InChIKey = DYEFUKCXAQOFHX-UHFFFAOYAZ
| SMILES1 = O=C1c3ccccc3[Se]N1c2ccccc2
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 77543
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 51085
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DYEFUKCXAQOFHX-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo= 60940-34-3
| PubChem=3194
| SMILES=C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C3[Se]2
}}
|Section2={{Chembox Properties
| Formula=C13H9NOSe
| MolarMass=274.17666
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
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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.{{cite web |title=Ebselen |url=https://go.drugbank.com/drugs/DB12610 |publisher=DrugBank |access-date=4 February 2025 |date=29 January 2025}} 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.
Ebselen has been entered into clinical trials as a lead compound intended for the potential treatment of various diseases.{{cite web |title=Ebselen pipeline |url=https://soundpharma.com/pipeline/ |publisher=Sound Pharmaceuticals, Inc. |access-date=4 February 2025 |date=2025}} Its most advanced clinical trial is a Phase III study in people with Meniere's disease, completed in July 2024.{{cite web |title=SPI-1005 for the Treatment of Meniere's Disease (STOPMD-3) |url=https://clinicaltrials.gov/study/NCT04677972 |publisher=ClinicalTrials.gov, US National Library of Medicine |access-date=4 February 2025 |date=1 August 2024}}
In vitro, ebselen is a mimic of glutathione peroxidase and reacts with peroxynitrite.{{cite journal | vauthors = Schewe T | title = Molecular actions of ebselen - an antiinflammatory antioxidant | journal = General Pharmacology | volume = 26 | issue = 6 | pages = 1153–69 | date = October 1995 | pmid = 7590103 | doi = 10.1016/0306-3623(95)00003-J }} It is purported to have antioxidant and anti-inflammatory properties.
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),{{cite journal | vauthors = Kamigata N, Iizuka H, Izuoka A, Kobayashi M | title = Photochemical Reaction of 2-Aryl-1, 2-benzisoselenazol-3 (2 H)-ones. | journal = Bulletin of the Chemical Society of Japan | date = July 1986 | volume = 59 | issue = 7 | pages = 2179–83 | doi = 10.1246/bcsj.59.2179 | doi-access = free }} by ortho-lithiation of benzanilides followed by oxidative cyclization (Route II) mediated by cupric bromide (CuBr2),{{Cite journal| vauthors = Engman L, Hallberg A |date=1989-06-01|title=Expedient synthesis of ebselen and related compounds|journal=The Journal of Organic Chemistry|volume=54|issue=12|pages=2964–2966|doi=10.1021/jo00273a035|issn=0022-3263}} or through the efficient Cu-catalyzed selenation / heterocyclization of o-halobenzamides, a methodology developed by Kumar et al.{{cite journal | vauthors = Balkrishna SJ, Bhakuni BS, Chopra D, Kumar S | title = Cu-catalyzed efficient synthetic methodology for ebselen and related Se-N heterocycles | journal = Organic Letters | volume = 12 | issue = 23 | pages = 5394–7 | date = December 2010 | pmid = 21053969 | doi = 10.1021/ol102027j }} (Route III).
History
The first patent for 2-phenyl-1,2-benzoselenazol-3(2H)-one was filed in 1980 and granted in 1982.{{Cite patent|number=DE3027073A1|title=2-phenyl-1,2-benzisoselenazol-3(2h)-on enthaltende pharmazeutische praeparate und ihre verwendung|gdate=1982-02-18|invent1=Etschenberg|invent2=Renson|invent3=Winkelmann|inventor1-first=Eugen Dr|inventor2-first=Marcel Prof Dipl-Chem Jupille|inventor3-first=Johannes Dr 5000 Köln|url=https://patents.google.com/patent/DE3027073A1/en?q=(ebselen)&oq=ebselen&sort=old}}
Research
Ebselen is in preliminary clinical development for the potential treatment of hearing loss and depression, among other medical indications.{{cite web |title=Ebselen search: list of clinical trials sponsored by Sound Pharmaceuticals |url=https://clinicaltrials.gov/search?term=%22Sound%20Pharmaceuticals%22 |publisher=ClinicalTrials.gov, US National Library of Medicine |access-date=4 February 2025 |date=2025}}
References
{{reflist}}
External links
- [https://soundpharma.com/ Sound Pharmaceuticals, Inc., corporate website]
Category:Organoselenium compounds
Category:Selenium heterocycles