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Revision as of 00:09, 1 July 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified fields - updated 'KEGG_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit Latest revision as of 11:12, 10 October 2023 edit undo128.176.164.35 (talk)No edit summary 
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{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
⚫ | verifiedrevid = 437141678
⚫ | UNII_Ref = {{fdacite|changed|FDA}}
⚫ | UNII = 40X2P7DPGH
⚫ | verifiedrevid = 408415096
| ImageFile = Ebselen-2D-skeletal.png | ImageFile = Ebselen-2D-skeletal.png
| ImageSize = 200px | ImageSize = 200px
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| ImageSize2 = 200px | ImageSize2 = 200px
| ImageName1 = Ball-and-stick model of the ebselen molecule | ImageName1 = Ball-and-stick model of the ebselen molecule
|IUPACName = 2-Phenyl-1,2-benzoselenazol-3-one | PIN = 2-Phenyl-1,2-benzoselenazol-3(2''H'')-one
|OtherNames= | OtherNames=
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3082 | 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 | 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 | InChIKey = DYEFUKCXAQOFHX-UHFFFAOYAZ
| SMILES1 = O=C1c3ccccc3N1c2ccccc2 | SMILES1 = O=C1c3ccccc3N1c2ccccc2
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| ChEBI = 77543
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 51085 | ChEMBL = 51085
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| StdInChIKey = DYEFUKCXAQOFHX-UHFFFAOYSA-N | StdInChIKey = DYEFUKCXAQOFHX-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo= 60940-34-3 | CASNo= 60940-34-3
| PubChem=3194 | PubChem=3194
| SMILES=C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C32 | SMILES=C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C32
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|Section2= {{Chembox Properties |Section2={{Chembox Properties
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| MolarMass=274.17666 | MolarMass=274.17666
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''Ebselen''' or '''2-phenyl-1, 2-benzisoselenazol-3(2H)-one''' (also called '''PZ 51''' or '''DR3305'''), is a mimic of ] and can also react with ].<ref>{{cite journal |author=Schewe T |title=Molecular actions of ebselen--an antiinflammatory antioxidant |journal=Gen Pharmacol |volume=26 |issue=6 |pages=1153–69 |year=1995 |pmid=7590103}}</ref> It is being investigated as a possible treatment for ] and ],<ref>{{cite journal |author=Parnham M, Sies H |title=Ebselen: prospective therapy for cerebral ischaemia |journal=Expert Opin Investig Drugs |volume=9 |issue=3 |pages=607–19 |year=2000 |pmid=11060699 |doi=10.1517/13543784.9.3.607}}</ref><ref>{{cite journal |author=Yamaguchi T, Sano K, Takakura K, Saito I, Shinohara Y, Asano T, Yasuhara H |title=Ebselen in acute ischemic stroke: a placebo-controlled, double-blind clinical trial. Ebselen Study Group |url=http://stroke.ahajournals.org/cgi/content/full/29/1/12 |journal=Stroke |volume=29 |issue=1 |pages=12–7 |date=1 January 1998|pmid=9445321 }}</ref> as well as ].<ref>{{cite journal|title=Ebselen treatment reduces noise induced hearing loss via the mimicry and induction of glutathione peroxidase|journal=Hearing Research|volume=226|issue=1–2|pages=44–51|last1=Kil|first1=Jonathan|year=2007|last2=Pierce|first2=Carol|last3=Tran|pmid=17030476|first3=Huy|last4=Gu|first4=Rende|last5=Lynch|first5=Eric D|doi=10.1016/j.heares.2006.08.006}}</ref> '''Ebselen''' (also called '''PZ 51''', '''DR3305''', and '''SPI-1005'''), is a synthetic organoselenium drug molecule with anti-inflammatory, anti-oxidant and cytoprotective activity. It acts as a mimic of ] and can also react with ].<ref>{{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 }}</ref> It is being investigated as a possible treatment for ] and ],<ref>{{cite journal | vauthors = Parnham M, Sies H | title = Ebselen: prospective therapy for cerebral ischaemia | journal = Expert Opinion on Investigational Drugs | volume = 9 | issue = 3 | pages = 607–19 | date = March 2000 | pmid = 11060699 | doi = 10.1517/13543784.9.3.607 | s2cid = 42599736 }}</ref><ref>{{cite journal | vauthors = Yamaguchi T, Sano K, Takakura K, Saito I, Shinohara Y, Asano T, Yasuhara H | title = Ebselen in acute ischemic stroke: a placebo-controlled, double-blind clinical trial. Ebselen Study Group | journal = Stroke | volume = 29 | issue = 1 | pages = 12–7 | date = January 1998 | pmid = 9445321 | doi = 10.1161/01.STR.29.1.12 | doi-access = free }}</ref> ],<ref>{{cite web |url=https://clinicaltrials.gov/ct2/show/NCT04677972 |title=SPI-1005 for the Treatment of Meniere's Disease |work=] |access-date=7 November 2022}}</ref><ref>{{cite web |url=https://www.prnewswire.com/news-releases/sound-pharma-initiates-enrollment-in-pivotal-phase-3-clinical-trial-of-spi-1005-for-the-treatment-of-hearing-loss-and-tinnitus-in-menieres-disease-301595208.html |title=Sound Pharma initiates enrollment in pivotal Phase 3 clinical trial of SPI-1005 for the treatment of hearing loss and tinnitus in Meniere's disease |date=2022-07-28 |work=] |access-date=7 November 2022}}</ref> ] and ],<ref>{{cite journal | vauthors = Kil J, Pierce C, Tran H, Gu R, Lynch ED | title = Ebselen treatment reduces noise induced hearing loss via the mimicry and induction of glutathione peroxidase | journal = Hearing Research | volume = 226 | issue = 1–2 | pages = 44–51 | date = April 2007 | pmid = 17030476 | doi = 10.1016/j.heares.2006.08.006 | s2cid = 39896274 }}</ref><ref name="Kil 2022 p=108209">{{cite journal |last1=Kil |first1=Jonathan |last2=Harruff |first2=E. Emily |last3=Longenecker |first3=Ryan J. |title=Development of ebselen for the treatment of sensorineural hearing loss and tinnitus |journal=Hearing Research |publisher=Elsevier BV |volume=413 |year=2022 |page=108209 |issn=0378-5955 |pmid=33678494 |doi=10.1016/j.heares.2021.108209|s2cid=231956488 }}</ref> and ].<ref>{{cite journal | vauthors = Singh N, Halliday AC, Thomas JM, Kuznetsova OV, Baldwin R, Woon EC, Aley PK, Antoniadou I, Sharp T, Vasudevan SR, Churchill GC | display-authors = 6 | title = A safe lithium mimetic for bipolar disorder | journal = Nature Communications | volume = 4 | pages = 1332 | year = 2013 | pmid = 23299882 | pmc = 3605789 | doi = 10.1038/ncomms2320 | bibcode = 2013NatCo...4.1332S }}</ref><ref>{{cite web |url=http://www.ox.ac.uk/news/2013-01-08-new-drug-bipolar-disorder-may-offer-fewer-side-effects |title=New drug for bipolar disorder may offer fewer side effects |author=<!--Staff writer(s); no by-line.--> |date=2013-01-08 |work=] Latest News |access-date=12 January 2013}}</ref>


Additionally, ebselen may be effective against ] infections<ref>{{cite web | url = http://medicalxpress.com/news/2015-09-drug-deadly-difficile-bacteria-healthy.html | title = Drug disarms deadly C. difficile bacteria without destroying healthy gut flora | publisher = Medical Express}}</ref> and has been shown to have antifungal activity against '']''.<ref>{{cite journal | vauthors = Marshall AC, Kidd SE, Lamont-Friedrich SJ, Arentz G, Hoffmann P, Coad BR, Bruning JB | title = Structure, Mechanism, and Inhibition of ''Aspergillus fumigatus'' Thioredoxin Reductase | journal = Antimicrobial Agents and Chemotherapy | volume = 63 | issue = 3 | pages = e02281-18 | date = March 2019 | pmid = 30642940 | pmc = 6395915 | doi = 10.1128/AAC.02281-18 | doi-access = free }}</ref>
Ebselen is a potent scavenger of hydrogen peroxide as well as hydroperoxides including membrane bound phospholipid and cholesterylester hydroperoxides.


Ebselen is a potent scavenger of hydrogen peroxide as well as hydroperoxides including membrane bound phospholipid and cholesterylester hydroperoxides. Several ebselen ] have been shown to scavenge hydrogen peroxide in the presence of thiols.<ref>{{cite journal | vauthors = Satheeshkumar K, Mugesh G | title = Synthesis and antioxidant activity of peptide-based ebselen analogues | journal = Chemistry: A European Journal | volume = 17 | issue = 17 | pages = 4849–57 | date = April 2011 | pmid = 21400619 | doi = 10.1002/chem.201003417 }}</ref>
⚫ ==References==
<references/>


== Possible anti-SARS-CoV-2 activity ==
⚫ ]
Preliminary studies demonstrate that Ebselen exhibits promising inhibitory activity against SARS-CoV-2 in cell-based assays.<ref name="Jin2020">{{cite journal | vauthors = Jin Z, Du X, Xu Y, Deng Y, Liu M, Zhao Y, Zhang B, Li X, Zhang L, Peng C, Duan Y, Yu J, Wang L, Yang K, Liu F, Jiang R, Yang X, You T, Liu X, Yang X, Bai F, Liu H, Liu X, Guddat LW, Xu W, Xiao G, Qin C, Shi Z, Jiang H, Rao Z, Yang H | display-authors = 6 | title = Structure of M<sup>pro</sup> from SARS-CoV-2 and discovery of its inhibitors | journal = Nature | volume = 582 | issue = 7811 | pages = 289–293 | date = June 2020 | pmid = 32272481 | doi = 10.1038/s41586-020-2223-y | bibcode = 2020Natur.582..289J | doi-access = free }}</ref><ref name="Weglarz-Tomczak2021">{{cite journal | vauthors = Weglarz-Tomczak E, Tomczak JM, Talma M, Burda-Grabowska M, Giurg M, Brul S | title = Identification of ebselen and its analogues as potent covalent inhibitors of papain-like protease from SARS-CoV-2 | journal = Scientific Reports | volume = 11 | issue = 1 | pages = 3640 | date = February 2021 | pmid = 33574416 | pmc = 7878891 | doi = 10.1038/s41598-021-83229-6 | bibcode = 2021NatSR..11.3640W }}</ref><ref name="pmid34249607">{{cite journal | vauthors = Xiang R, Yu Z, Wang Y, Wang L, Huo S, Li Y, Liang R, Hao Q, Ying T, Gao Y, Yu F, Jiang S | display-authors = 6 | title = Recent advances in developing small-molecule inhibitors against SARS-CoV-2 | journal = Acta Pharmaceutica Sinica B | volume = 12| issue = 4| date = July 2021 | pages = 1591–1623 | pmid = 34249607 | pmc = 8260826 | doi = 10.1016/j.apsb.2021.06.016 }}</ref> The effect was attributed to irreversible inhibition of the ] via a covalent bond formation with the thiol group of the active center's cysteine (Cys-145).<ref name="Jin2020"/>


== Synthesis ==
Generally, synthesis of the characteristic scaffold of ebselen, the benzoisoselenazolone ring system, can be achieved either through reaction of primary amines (RNH<sub>2</sub>) with 2-(chloroseleno)benzoyl chloride (Route I),<ref>{{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 }}</ref> by ''ortho''-lithiation of benzanilides followed by oxidative cyclization (Route II) mediated by ] (CuBr<sub>2</sub>),<ref>{{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}}</ref> or through the efficient Cu-catalyzed selenation / heterocyclization of o-halobenzamides, a methodology developed by Kumar ''et al.''<ref>{{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 }}</ref> (Route III).


]
{{pharmacology-stub}}

== History ==
The first patent for 2-Phenyl-1,2-benzoselenazol-3(2H)-one was filed in 1980 and granted in 1982.<ref>{{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}}</ref>

⚫ == References ==
{{reflist|2}}

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