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MedKoo Cat#: 205872 | Name: Ebselen
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Ebselen
Ebselen
CAS#60940-34-3

Theoretical Analysis

MedKoo Cat#: 205872

Name: Ebselen

CAS#: 60940-34-3

Chemical Formula: C13H9NOSe

Exact Mass: 274.9849

Molecular Weight: 274.18

Elemental Analysis: C, 56.95; H, 3.31; N, 5.11; O, 5.84; Se, 28.80

Price and Availability

Size Price Availability Quantity
100mg USD 150.00 Ready to ship
200mg USD 250.00 Ready to ship
500mg USD 550.00 Ready to ship
1g USD 750.00 Ready to ship
2g USD 1,350.00 Ready to ship
5g USD 2,450.00 Ready to ship
10g USD 3,950.00 Ready to ship
20g USD 6,950.00 Ready to ship
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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
More Info
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).    
Biological target:
Ebselen (SPI-1005) is a voltage-dependent calcium channel (VDCC) blocker and an inhibitor of HIV-1 capsid CTD dimerization.
In vitro activity:
Thus, in the present study, it was also found that Ebselen treatment resulted in decreased oxidative PPP flux, leading to increasing intracellular 6-PG levels and decreasing Ru-5-P levels and NADPH/NADP+ ratio. While the lactate production and ROS level were upward in the K562 and H1299 cells (Figure 3A–F). In the normal lung BEAS-2B cells, Ebselen treatment also resulted in decreased NADPH/NADP+ ratio but did not have an effect on lactate level (Supplementary Figure 2A and B), while the effect of Ebselen on ROS level was partially abolished by knocking down 6PGD in H1299 and BEAS-2B cells (Supplementary Figure 2C–E). The elimination of 6PGD is not complete by shRNA and this also could explain the effects of Ebselen on ROS are very moderate. These results suggested that Ebselen regulates cell metabolism by targeting 6PGD. Reference: Cancer Manag Res. 2020; 12: 6921–6934. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7415460/
In vivo activity:
Ebselen-treated mice had a markedly diminished bacterial burden compared to the negative control, with few scattered aggregates in the deep dermis (Fig 3E, arrows) and normal collagen fiber architecture. Inflammation was similarly markedly decreased and present only at the deep tissue margin, indicating tissue clearing and signs of wound healing (Fig 3E, dashed boxes). On higher view, bacteria were sparse and markedly decreased compared to the negative control, with few colonies in between collagen fibers and occasionally forming clusters (Fig 3F, arrows). Scale bars represent 1 mm in 2× view images (Fig 3A, 3C and 3E) and 100 μm in 20× view images, respectively (Fig 3B, 3D and 3F). Reference: PLoS One. 2021; 16(2): e0247508. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7899319/
Solvent mg/mL mM
Solubility
DMSO 36.6 133.51
Acetone 8.5 30.93
Acetonitrile 3.2 11.63
Ethanol 5.2 19.04
Methanol 5.6 20.42
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 274.18 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Amporndanai K, Meng X, Shang W, Jin Z, Rogers M, Zhao Y, Rao Z, Liu ZJ, Yang H, Zhang L, O'Neill PM, Samar Hasnain S. Inhibition mechanism of SARS-CoV-2 main protease by ebselen and its derivatives. Nat Commun. 2021 May 24;12(1):3061. doi: 10.1038/s41467-021-23313-7. PMID: 34031399. 2. Feng Q, Li X, Sun W, Li Y, Yuan Y, Guan B, Zhang S. Discovery of Ebselen as an Inhibitor of 6PGD for Suppressing Tumor Growth. Cancer Manag Res. 2020 Aug 5;12:6921-6934. doi: 10.2147/CMAR.S254853. PMID: 32801914; PMCID: PMC7415460. 3. Mohammad H, Abutaleb NS, Dieterly AM, Lyle LT, Seleem MN. Evaluation of ebselen in resolving a methicillin-resistant Staphylococcus aureus infection of pressure ulcers in obese and diabetic mice. PLoS One. 2021 Feb 22;16(2):e0247508. doi: 10.1371/journal.pone.0247508. PMID: 33617589; PMCID: PMC7899319. 4. Brassington K, Chan SMH, Seow HJ, Dobric A, Bozinovski S, Selemidis S, Vlahos R. Ebselen reduces cigarette smoke-induced endothelial dysfunction in mice. Br J Pharmacol. 2021 Apr;178(8):1805-1818. doi: 10.1111/bph.15400. Epub 2021 Feb 27. PMID: 33523477; PMCID: PMC8074626.
In vitro protocol:
1. Amporndanai K, Meng X, Shang W, Jin Z, Rogers M, Zhao Y, Rao Z, Liu ZJ, Yang H, Zhang L, O'Neill PM, Samar Hasnain S. Inhibition mechanism of SARS-CoV-2 main protease by ebselen and its derivatives. Nat Commun. 2021 May 24;12(1):3061. doi: 10.1038/s41467-021-23313-7. PMID: 34031399. 2. Feng Q, Li X, Sun W, Li Y, Yuan Y, Guan B, Zhang S. Discovery of Ebselen as an Inhibitor of 6PGD for Suppressing Tumor Growth. Cancer Manag Res. 2020 Aug 5;12:6921-6934. doi: 10.2147/CMAR.S254853. PMID: 32801914; PMCID: PMC7415460.
In vivo protocol:
1. Mohammad H, Abutaleb NS, Dieterly AM, Lyle LT, Seleem MN. Evaluation of ebselen in resolving a methicillin-resistant Staphylococcus aureus infection of pressure ulcers in obese and diabetic mice. PLoS One. 2021 Feb 22;16(2):e0247508. doi: 10.1371/journal.pone.0247508. PMID: 33617589; PMCID: PMC7899319. 2. Brassington K, Chan SMH, Seow HJ, Dobric A, Bozinovski S, Selemidis S, Vlahos R. Ebselen reduces cigarette smoke-induced endothelial dysfunction in mice. Br J Pharmacol. 2021 Apr;178(8):1805-1818. doi: 10.1111/bph.15400. Epub 2021 Feb 27. PMID: 33523477; PMCID: PMC8074626.
1: Wang J, Wang P, Dong C, Zhao Y, Zhou J, Yuan C, Zou L. Mechanisms of ebselen as a therapeutic and its pharmacology applications. Future Med Chem. 2020 Dec;12(23):2141-2160. doi: 10.4155/fmc-2019-0218. Epub 2020 Nov 23. PMID: 33225732. 2: Sies H. Ebselen. Methods Enzymol. 1995;252:341-2. doi: 10.1016/0076-6879(95)52037-6. PMID: 7476371. 3: Maślanka M, Mucha A. Antibacterial Activity of Ebselen. Int J Mol Sci. 2023 Jan 13;24(2):1610. doi: 10.3390/ijms24021610. PMID: 36675123; PMCID: PMC9864093. 4: Santi C, Scimmi C, Sancineto L. Ebselen and Analogues: Pharmacological Properties and Synthetic Strategies for Their Preparation. Molecules. 2021 Jul 12;26(14):4230. doi: 10.3390/molecules26144230. PMID: 34299505; PMCID: PMC8306772. 5: Kil J, Harruff EE, Longenecker RJ. Development of ebselen for the treatment of sensorineural hearing loss and tinnitus. Hear Res. 2022 Jan;413:108209. doi: 10.1016/j.heares.2021.108209. Epub 2021 Feb 19. PMID: 33678494. 6: Sies H, Parnham MJ. Potential therapeutic use of ebselen for COVID-19 and other respiratory viral infections. Free Radic Biol Med. 2020 Aug 20;156:107-112. doi: 10.1016/j.freeradbiomed.2020.06.032. Epub 2020 Jun 26. PMID: 32598985; PMCID: PMC7319625. 7: 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. PMID: 24867080. 8: 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. PMID: 27095225. 9: 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. doi: 10.1016/j.taap.2005.02.022. PMID: 15979675. 10: Gu R, Longenecker RJ, Homan J, Kil J. Ebselen attenuates tobramycin-induced ototoxicity in mice. J Cyst Fibros. 2021 Mar;20(2):271-277. doi: 10.1016/j.jcf.2020.02.014. Epub 2020 Mar 5. PMID: 32147183. 11: Parnham M, Sies H. Ebselen: prospective therapy for cerebral ischaemia. Expert Opin Investig Drugs. 2000 Mar;9(3):607-19. doi: 10.1517/13543784.9.3.607. PMID: 11060699. 12: Wu Y, Shi H, Xu Y, Pei J, Song S, Chen W, Xu S. Ebselen ameliorates renal ischemia-reperfusion injury via enhancing autophagy in rats. Mol Cell Biochem. 2022 Jun;477(6):1873-1885. doi: 10.1007/s11010-022-04413-4. Epub 2022 Mar 26. PMID: 35338455. 13: Parnham MJ, Leyck S, Graf E, Dowling EJ, Blake DR. The pharmacology of ebselen. Agents Actions. 1991 Jan;32(1-2):4-9. doi: 10.1007/BF01983300. PMID: 2058468. 14: Sies H. Ebselen: a glutathione peroxidase mimic. Methods Enzymol. 1994;234:476-82. doi: 10.1016/0076-6879(94)34118-4. PMID: 7808321. 15: Sies H, Masumoto H. Ebselen as a glutathione peroxidase mimic and as a scavenger of peroxynitrite. Adv Pharmacol. 1997;38:229-46. doi: 10.1016/s1054-3589(08)60986-2. PMID: 8895811. 16: Sies H. Ebselen, a selenoorganic compound as glutathione peroxidase mimic. Free Radic Biol Med. 1993 Mar;14(3):313-23. doi: 10.1016/0891-5849(93)90028-s. PMID: 8458589. 17: Brassington K, Chan SMH, Seow HJ, Dobric A, Bozinovski S, Selemidis S, Vlahos R. Ebselen reduces cigarette smoke-induced endothelial dysfunction in mice. Br J Pharmacol. 2021 Apr;178(8):1805-1818. doi: 10.1111/bph.15400. Epub 2021 Feb 27. PMID: 33523477; PMCID: PMC8074626. 18: Sarkar C, Abdalla M, Mondal M, Khalipha ABR, Ali N. Ebselen suitably interacts with the potential SARS-CoV-2 targets: an in-silico approach. J Biomol Struct Dyn. 2022;40(22):12286-12301. doi: 10.1080/07391102.2021.1971562. Epub 2021 Aug 30. PMID: 34459720. 19: Haritha CV, Sharun K, Jose B. Ebselen, a new candidate therapeutic against SARS-CoV-2. Int J Surg. 2020 Dec;84:53-56. doi: 10.1016/j.ijsu.2020.10.018. Epub 2020 Oct 23. PMID: 33120196; PMCID: PMC7583587. 20: Marreddy RKR, Olaitan AO, May JN, Dong M, Hurdle JG. Ebselen Not Only Inhibits Clostridioides difficile Toxins but Displays Redox-Associated Cellular Killing. Microbiol Spectr. 2021 Oct 31;9(2):e0044821. doi: 10.1128/Spectrum.00448-21. Epub 2021 Sep 1. PMID: 34468187; PMCID: PMC8557875.