Ebselen

Ebselen

Names
IUPAC name 2-Phenyl-1,2-benzoselenazol-3-one
Identifiers
CAS Registry Number	60940-34-3 Y
ChEBI	CHEBI:77543 N
ChEMBL	ChEMBL51085 Y
ChemSpider	3082 Y
InChI InChI=1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H Y Key: DYEFUKCXAQOFHX-UHFFFAOYSA-N Y 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
Jmol-3D images	Image Image
PubChem	3194
SMILES C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C3[Se]2 O=C1c3ccccc3[Se]N1c2ccccc2
UNII	40X2P7DPGH Y
Properties
Chemical formula	C13H9NOSe
Molar mass	274.17666
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Ebselen or 2-phenyl-1, 2-benzisoselenazol-3(2H)-one (also called PZ 51 or DR3305), is a mimic of glutathione peroxidase and can also react with peroxynitrite.^[1] It is being investigated as a possible treatment for reperfusion injury and stroke,^[2][3] hearing loss and tinnitus,^[4] and bipolar disorder.^[5][6]

Ebselen is a potent scavenger of hydrogen peroxide as well as hydroperoxides including membrane bound phospholipid and cholesterylester hydroperoxides. Several ebselen analogues have been shown to scavenge hydrogen peroxide in the presence of thiols.^[7]

References

1. ↑ Schewe T (1995). "Molecular actions of ebselen--an antiinflammatory antioxidant". Gen Pharmacol 26 (6): 1153–69. doi:10.1016/0306-3623(95)00003-J. PMID 7590103. 
2. ↑ Parnham M, Sies H (2000). "Ebselen: prospective therapy for cerebral ischaemia". Expert Opin Investig Drugs 9 (3): 607–19. doi:10.1517/13543784.9.3.607. PMID 11060699. 
3. ↑ Yamaguchi T, Sano K, Takakura K, Saito I, Shinohara Y, Asano T, Yasuhara H (1 January 1998). "Ebselen in acute ischemic stroke: a placebo-controlled, double-blind clinical trial. Ebselen Study Group". Stroke 29 (1): 12–7. doi:10.1161/01.STR.29.1.12. PMID 9445321. 
4. ↑ Kil, Jonathan; Pierce, Carol; Tran, Huy; Gu, Rende; Lynch, Eric D (2007). "Ebselen treatment reduces noise induced hearing loss via the mimicry and induction of glutathione peroxidase". Hearing Research 226 (1–2): 44–51. doi:10.1016/j.heares.2006.08.006. PMID 17030476. 
5. ↑ Singh, N.; Halliday, A. C.; Thomas, J. M.; Kuznetsova, O. V.; Baldwin, R.; Woon, E. C. Y.; Aley, P. K.; Antoniadou, I.; Sharp, T.; Vasudevan, S. R.; Churchill, G. C. (2013). "A safe lithium mimetic for bipolar disorder". Nature Communications 4: 1332. doi:10.1038/ncomms2320. PMC 3605789. PMID 23299882. 
6. ↑ "New drug for bipolar disorder may offer fewer side effects". University of Oxford Latest News. 2013-01-08. Retrieved 12 January 2013. 
7. ↑ Satheeshkumar K, Mugesh G (2011). "Synthesis and Antioxidant Activity of Peptide-Based Ebselen Analogues.". Chem. Eur. J. 17 (17): 4849–57. doi:10.1002/chem.201003417.