275:
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24:
33:
538:
42:
392:
1288:
1286:, 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
710:
501:
Preliminary studies demonstrate that
Ebselen exhibits promising inhibitory activity against SARS-CoV-2 in cell-based assays. The effect was attributed to irreversible inhibition of the
405:
489:
Ebselen is a potent scavenger of hydrogen peroxide as well as hydroperoxides including membrane bound phospholipid and cholesterylester hydroperoxides. Several ebselen
738:
Kil J, Pierce C, Tran H, Gu R, Lynch ED (April 2007). "Ebselen treatment reduces noise induced hearing loss via the mimicry and induction of glutathione peroxidase".
513:
Generally, synthesis of the characteristic scaffold of ebselen, the benzoisoselenazolone ring system, can be achieved either through reaction of primary amines (RNH
1327:
1312:
324:
1248:
Balkrishna SJ, Bhakuni BS, Chopra D, Kumar S (December 2010). "Cu-catalyzed efficient synthetic methodology for ebselen and related Se-N heterocycles".
781:
Kil, Jonathan; Harruff, E. Emily; Longenecker, Ryan J. (2022). "Development of ebselen for the treatment of sensorineural hearing loss and tinnitus".
711:"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"
110:
475:
439:), is a synthetic organoselenium drug molecule with anti-inflammatory, anti-oxidant and cytoprotective activity. It acts as a mimic of
1307:
289:
32:
529:), or through the efficient Cu-catalyzed selenation / heterocyclization of o-halobenzamides, a methodology developed by Kumar
1322:
1317:
889:
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412:
232:
23:
253:
918:
1076:"Identification of ebselen and its analogues as potent covalent inhibitors of papain-like protease from SARS-CoV-2"
117:
456:
987:
Satheeshkumar K, Mugesh G (April 2011). "Synthesis and antioxidant activity of peptide-based ebselen analogues".
715:
688:
195:
644:"Ebselen in acute ischemic stroke: a placebo-controlled, double-blind clinical trial. Ebselen Study Group"
440:
482:
157:
1087:
1038:
894:
845:
54:
932:
Marshall AC, Kidd SE, Lamont-Friedrich SJ, Arentz G, Hoffmann P, Coad BR, Bruning JB (March 2019).
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76:
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The first patent for 2-Phenyl-1,2-benzoselenazol-3(2H)-one was filed in 1980 and granted in 1982.
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via a covalent bond formation with the thiol group of the active center's cysteine (Cys-145).
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Weglarz-Tomczak E, Tomczak JM, Talma M, Burda-Grabowska M, Giurg M, Brul S (February 2021).
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853:
790:
747:
655:
608:
573:
502:
468:
352:
1213:
Engman L, Hallberg A (1989-06-01). "Expedient synthesis of ebselen and related compounds".
642:
Yamaguchi T, Sano K, Takakura K, Saito I, Shinohara Y, Asano T, Yasuhara H (January 1998).
241:
86:
564:
Schewe T (October 1995). "Molecular actions of ebselen--an antiinflammatory antioxidant".
177:
274:
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1042:
849:
832:
Singh N, Halliday AC, Thomas JM, Kuznetsova OV, Baldwin R, Woon EC, et al. (2013).
137:
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1108:
1075:
964:
933:
866:
833:
599:
Parnham M, Sies H (March 2000). "Ebselen: prospective therapy for cerebral ischaemia".
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383:
1301:
818:
577:
521:-lithiation of benzanilides followed by oxidative cyclization (Route II) mediated by
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188:
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221:
919:"Drug disarms deadly C. difficile bacteria without destroying healthy gut flora"
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1133:"Recent advances in developing small-molecule inhibitors against SARS-CoV-2"
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have been shown to scavenge hydrogen peroxide in the presence of thiols.
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InChI=1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H
1226:
308:
InChI=1/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H
857:
208:
1261:
1182:"Photochemical Reaction of 2-Aryl-1, 2-benzisoselenazol-3 (2 H)-ones"
1131:
Xiang R, Yu Z, Wang Y, Wang L, Huo S, Li Y, et al. (July 2021).
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148:
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Except where otherwise noted, data are given for materials in their
1025:
Jin Z, Du X, Xu Y, Deng Y, Liu M, Zhao Y, et al. (June 2020).
480:
infections and has been shown to have antifungal activity against
128:
116:
109:
99:
1027:"Structure of M from SARS-CoV-2 and discovery of its inhibitors"
890:"New drug for bipolar disorder may offer fewer side effects"
258:
1180:
Kamigata N, Iizuka H, Izuoka A, Kobayashi M (July 1986).
447:. It is being investigated as a possible treatment for
400:
517:) with 2-(chloroseleno)benzoyl chloride (Route I), by
684:"SPI-1005 for the Treatment of Meniere's Disease"
220:
474:Additionally, ebselen may be effective against
85:
834:"A safe lithium mimetic for bipolar disorder"
8:
1020:
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1186:Bulletin of the Chemical Society of Japan
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934:"Structure, Mechanism, and Inhibition of
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601:Expert Opinion on Investigational Drugs
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942:Antimicrobial Agents and Chemotherapy
301:Key: DYEFUKCXAQOFHX-UHFFFAOYSA-N
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136:
7:
1328:Heterocyclic compounds with 2 rings
1313:SARS-CoV-2 main protease inhibitors
311:Key: DYEFUKCXAQOFHX-UHFFFAOYAZ
211:
14:
497:Possible anti-SARS-CoV-2 activity
1215:The Journal of Organic Chemistry
390:
332:C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C32
40:
31:
22:
386:(at 25 °C , 100 kPa).
59:2-Phenyl-1,2-benzoselenazol-3(2
1:
989:Chemistry: A European Journal
795:10.1016/j.heares.2021.108209
752:10.1016/j.heares.2006.08.006
578:10.1016/0306-3623(95)00003-J
1137:Acta Pharmaceutica Sinica B
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1149:10.1016/j.apsb.2021.06.016
1100:10.1038/s41598-021-83229-6
1052:10.1038/s41586-020-2223-y
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1308:Organoselenium compounds
613:10.1517/13543784.9.3.607
477:Clostridioides difficile
443:and can also react with
789:. Elsevier BV: 108209.
376:274.17666
1001:10.1002/chem.201003417
938:Thioredoxin Reductase"
661:10.1161/01.STR.29.1.12
441:glutathione peroxidase
337:O=C1c3ccccc3N1c2ccccc2
1323:Nitrogen heterocycles
1318:Selenium heterocycles
936:Aspergillus fumigatus
838:Nature Communications
716:Sound Pharmaceuticals
689:Sound Pharmaceuticals
483:Aspergillus fumigatus
1199:10.1246/bcsj.59.2179
955:10.1128/AAC.02281-18
895:University of Oxford
566:General Pharmacology
55:Preferred IUPAC name
1227:10.1021/jo00273a035
1092:2021NatSR..11.3640W
1043:2020Natur.582..289J
850:2013NatCo...4.1332S
18:
1080:Scientific Reports
921:. Medical Express.
858:10.1038/ncomms2320
449:reperfusion injury
413:Infobox references
16:
1262:10.1021/ol102027j
1221:(12): 2964–2966.
1037:(7811): 289–293.
457:Ménière's disease
421:Chemical compound
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254:CompTox Dashboard
118:Interactive image
111:Interactive image
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533:(Route III).
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503:main protease
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901:. Retrieved
899:. 2013-01-08
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721:. Retrieved
719:. 2022-07-28
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461:hearing loss
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423:
70:Identifiers
60:
1284:DE3027073A1
1086:(1): 3640.
897:Latest News
654:(1): 12–7.
366:NOSe
346:Properties
196:100.132.190
158:ChEMBL51085
138:CHEBI:77543
1302:Categories
903:12 January
723:7 November
695:7 November
552:References
372:Molar mass
242:40X2P7DPGH
169:ChemSpider
98:3D model (
87:60940-34-3
77:CAS Number
1235:0022-3263
819:231956488
803:0378-5955
509:Synthesis
1270:21053969
1167:34249607
1118:33574416
1061:32272481
1009:21400619
974:30642940
876:23299882
844:: 1332.
811:33678494
768:39896274
760:17030476
629:42599736
621:11060699
465:tinnitus
437:SPI-1005
17:Ebselen
1158:8260826
1109:7878891
1088:Bibcode
1039:Bibcode
965:6395915
867:3605789
846:Bibcode
670:9445321
586:7590103
544:History
491:analogs
425:Ebselen
406:what is
404: (
209:PubChem
1290:
1268:
1233:
1165:
1155:
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1106:
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1031:Nature
1007:
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766:
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648:Stroke
627:
619:
584:
531:et al.
467:, and
453:stroke
435:, and
433:DR3305
401:verify
398:
325:SMILES
149:ChEMBL
49:Names
815:S2CID
764:S2CID
625:S2CID
525:(CuBr
519:ortho
429:PZ 51
290:InChI
129:ChEBI
100:JSmol
63:)-one
1266:PMID
1231:ISSN
1163:PMID
1114:PMID
1057:PMID
1005:PMID
970:PMID
905:2013
872:PMID
807:PMID
799:ISSN
756:PMID
725:2022
697:2022
666:PMID
617:PMID
582:PMID
463:and
451:and
233:UNII
222:3194
178:3082
1258:doi
1223:doi
1194:doi
1153:PMC
1145:doi
1104:PMC
1096:doi
1047:doi
1035:582
997:doi
960:PMC
950:doi
862:PMC
854:doi
791:doi
787:413
748:doi
744:226
656:doi
609:doi
574:doi
259:EPA
212:CID
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358:C
261:)
257:(
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61:H
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
