WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 205872
CAS#: 60940-34-3
Description: Ebselen, also known as SPI-1005, is an organoselenium compound with potential anti-oxidant, anti-inflammatory and cytoprotective activity. Upon oral administration of SPI-1005, this agent mimics the activity of glutathione peroxidase (GPx) and can utilize glutathione to reduce other unstable molecules, thus preventing the formation of reactive oxygen species (ROS) and reducing oxidative stress on the cell. In the cochlea, this agent may prevent drug-induced injury to the auditory hair cells thereby preventing hearing loss. GPx is the main antioxidant enzyme in the cochlea and protects the inner ear from loud sounds and biochemical damage. In addition, ebselen is able to inhibit the activity of many enzymes involved in inflammation.
MedKoo Cat#: 205872
Name: Ebselen
CAS#: 60940-34-3
Chemical Formula: C13H9NOSe
Exact Mass: 274.98494
Molecular Weight: 274.17666
Elemental Analysis: C, 56.95; H, 3.31; N, 5.11; O, 5.84; Se, 28.80
Synonym: SPI-1005; SPI1005; SPI 1005; Ebselen; PZ 51; PZ51; PZ-51; DR3305; DR 3305; DR-3305
IUPAC/Chemical Name: 2-phenylbenzo[d][1,2]selenazol-3(2H)-one
InChi Key: DYEFUKCXAQOFHX-UHFFFAOYSA-N
InChi Code: InChI=1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H
SMILES Code: O=C1N(C2=CC=CC=C2)[Se]C3=CC=CC=C13
Appearance: White solid powder.
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2931.90.6000
The following data is based on the product molecular weight 274.17666 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Ren X, Zou L, Lu J, Holmgren A. Selenocysteine in mammalian thioredoxin reductase and application of ebselen as a therapeutic. Free Radic Biol Med. 2018 Nov 1;127:238-247. doi: 10.1016/j.freeradbiomed.2018.05.081. Epub 2018 May 25. Review. PubMed PMID: 29807162.
2: May HC, Yu JJ, Guentzel MN, Chambers JP, Cap AP, Arulanandam BP. Repurposing Auranofin, Ebselen, and PX-12 as Antimicrobial Agents Targeting the Thioredoxin System. Front Microbiol. 2018 Mar 5;9:336. doi: 10.3389/fmicb.2018.00336. eCollection 2018. Review. PubMed PMID: 29556223; PubMed Central PMCID: PMC5844926.
3: Noguchi N. Ebselen, a useful tool for understanding cellular redox biology and a promising drug candidate for use in human diseases. Arch Biochem Biophys. 2016 Apr 1;595:109-12. doi: 10.1016/j.abb.2015.10.024. Review. PubMed PMID: 27095225.
4: Martini F, Bruning CA, Soares SM, Nogueira CW, Zeni G. Inhibitory effect of ebselen on cerebral acetylcholinesterase activity in vitro: kinetics and reversibility of inhibition. Curr Pharm Des. 2015;21(7):920-4. Review. PubMed PMID: 25312723.
5: Azad GK, Tomar RS. Ebselen, a promising antioxidant drug: mechanisms of action and targets of biological pathways. Mol Biol Rep. 2014 Aug;41(8):4865-79. doi: 10.1007/s11033-014-3417-x. Review. PubMed PMID: 24867080.
6: Fang J, Zhong L, Zhao R, Holmgren A. Ebselen: a thioredoxin reductase-dependent catalyst for alpha-tocopherol quinone reduction. Toxicol Appl Pharmacol. 2005 Sep 1;207(2 Suppl):103-9. Review. PubMed PMID: 15979675.
7: Parnham M, Sies H. Ebselen: prospective therapy for cerebral ischaemia. Expert Opin Investig Drugs. 2000 Mar;9(3):607-19. Review. PubMed PMID: 11060699.
8: Sies H, Masumoto H. Ebselen as a glutathione peroxidase mimic and as a scavenger of peroxynitrite. Adv Pharmacol. 1997;38:229-46. Review. PubMed PMID: 8895811.
9: Schewe T. Molecular actions of ebselen--an antiinflammatory antioxidant. Gen Pharmacol. 1995 Oct;26(6):1153-69. Review. PubMed PMID: 7590103.
10: Sies H. Ebselen. Methods Enzymol. 1995;252:341-2. Review. PubMed PMID: 7476371.
11: Sies H. Ebselen: a glutathione peroxidase mimic. Methods Enzymol. 1994;234:476-82. Review. PubMed PMID: 7808321.
12: Sies H. Ebselen, a selenoorganic compound as glutathione peroxidase mimic. Free Radic Biol Med. 1993 Mar;14(3):313-23. Review. PubMed PMID: 8458589.
13: Parnham MJ, Leyck S, Graf E, Dowling EJ, Blake DR. The pharmacology of ebselen. Agents Actions. 1991 Jan;32(1-2):4-9. Review. PubMed PMID: 2058468.
14: Parnham MJ. Biological activities and clinical potential of Ebselen. Adv Exp Med Biol. 1990;264:193-7. Review. PubMed PMID: 2244495.
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. It is being investigated as a possible treatment for reperfusion injury and stroke, as well as tinnitus. Ebselen is a potent scavenger of hydrogen peroxide as well as hydroperoxides including membrane bound phospholipid and cholesterylester hydroperoxides. (source: http://en.wikipedia.org/wiki/Ebselen).
