Chemistry:Disufenton sodium

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Short description: Chemical compound
Disufenton sodium
Disufenton sodium.png
Clinical data
ATC code
  • none
Identifiers
CAS Number
PubChem CID
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UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC11H13NNa2O7S2
Molar mass381.32 g·mol−1
3D model (JSmol)
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Disufenton sodium (Cerovive, OKN-007, NXY-059, HPN-07)[1] is a free radical trapping nitrone-based antioxidant compound that has been under development for several medical conditions.[2][3]

Chemistry

Disufenton sodium is the disulfonyl derivative of the neuroprotective nitrone spin trap phenylbutylnitrone or "PBN". PBN and its derivatives hydrolyze and oxidize in vitro to form respectively MNP-OH (AKA, NtBHA) and its parent spin-trap MNP.

Research

Disufenton sodium was under development at the drug company AstraZeneca. A 2005 phase-3 clinical trial[4][5] called "SAINT-1" reported some efficacy in the acute treatment of ischemia injury due to stroke. However, a 2006 attempt to repeat this trial indicated no significant activity. After ruling out other causes, the authors tentatively attributed the positive results in the first trial to "chance".[4] AstraZeneca then terminated the development programme.[6]

Disufenton sodium has been researched as a potential treatment for use in brain tumors and cancers, including diffuse intrinsic pontine glioma (DIPG)[7][8] and glioblastoma.[9][10]

A compound (NHPN-1010) containing a combination of disufenton sodium and acetylcysteine has been researched as a potential treatment for tinnitus and hearing loss.[11][12][13][14]

References

  1. ↑ "Use of Radical Oxygen Species Scavenger Nitrones to Treat Oxidative Stress-Mediated Hearing Loss: State of the Art and Challenges". Frontiers in Cellular Neuroscience (Frontiers Media SA) 15: 711269. September 1, 2021. doi:10.3389/fncel.2021.711269. PMID 34539349. 
  2. ↑ "NXY-059, a novel free radical trapping compound, reduces cortical infarction after permanent focal cerebral ischemia in the rat". Brain Research (Elsevier BV) 909 (1–2): 46–50. August 2001. doi:10.1016/s0006-8993(01)02618-x. PMID 11478919. 
  3. ↑ "Noise-Induced Neural Degeneration and Therapeutic Effect of Antioxidant Drugs". Journal of Audiology & Otology (The Korean Audiological Society) 19 (3): 111–119. December 2015. doi:10.7874/jao.2015.19.3.111. PMID 26771008. 
  4. ↑ 4.0 4.1 "NXY-059 for acute ischemic stroke". The New England Journal of Medicine 354 (6): 588–600. February 2006. doi:10.1056/NEJMoa052980. PMID 16467546. 
  5. ↑ "Additional outcomes and subgroup analyses of NXY-059 for acute ischemic stroke in the SAINT I trial". Stroke 37 (12): 2970–2978. December 2006. doi:10.1161/01.STR.0000249410.91473.44. PMID 17068304. 
  6. ↑ "Renovis: Press Release". http://investors.renovis.com/phoenix.zhtml?c=148297&p=irol-newsArticle&t=Regular&id=921678&. 
  7. ↑ "OKlahoma Nitrone-007: novel treatment for diffuse intrinsic pontine glioma". Journal of Translational Medicine (Springer Science and Business Media LLC) 18 (1): 424. November 2020. doi:10.1186/s12967-020-02593-5. PMID 33168005. 
  8. ↑ "FDA grants fast track status to OKN-007 for diffuse intrinsic pontine glioma". March 3, 2021. https://www.healio.com/news/hematology-oncology/20210303/fda-grants-fast-track-status-to-okn007-for-diffuse-intrinsic-pontine-glioma. 
  9. ↑ "Phase Ib clinical trial of OKN-007 in recurrent malignant glioma.". Journal of Clinical Oncology (American Society of Clinical Oncology (ASCO)) 38 (15_suppl): 2538. May 20, 2020. doi:10.1200/jco.2020.38.15_suppl.2538. ISSN 0732-183X. 
  10. ↑ "A tale of two multi-focal therapies for glioblastoma: An antibody targeting ELTD1 and nitrone-based OKN-007". Journal of Cellular and Molecular Medicine (Wiley) 26 (2): 570–582. January 2022. doi:10.1111/jcmm.17133. PMID 34910361. 
  11. ↑ "Electrophysiological assessment and pharmacological treatment of blast-induced tinnitus". PLOS ONE (Public Library of Science (PLoS)\) 16 (1): e0243903. January 7, 2021. doi:10.1371/journal.pone.0243903. PMID 33411811. Bibcode: 2021PLoSO..1643903L. 
  12. ↑ "Blast-induced tinnitus: Animal models". The Journal of the Acoustical Society of America (Acoustical Society of America (ASA)) 146 (5): 3811–3831. November 2019. doi:10.1121/1.5132551. PMID 31795642. Bibcode: 2019ASAJ..146.3811Z. 
  13. ↑ "Congressionally Directed Medical Research Programs (CDMRP) Search Awards". https://cdmrp.army.mil/search.aspx?LOG_NO=DM120099. 
  14. ↑ "Hough Ear Institute receives $300K grant to support research treatments for hearing loss". July 27, 2020. https://okcfox.com/news/local/hough-ear-institute-receives-300k-grant-to-support-research-treatments-for-hearing-loss. 

Further reading

  • "NXY-059: review of neuroprotective potential for acute stroke". The Annals of Pharmacotherapy 40 (3): 461–471. March 2006. doi:10.1345/aph.1E636. PMID 16507608. 
  • "Oxidants, antioxidants and the ischemic brain". The Journal of Experimental Biology 207 (Pt 18): 3221–3231. August 2004. doi:10.1242/jeb.01022. PMID 15299043. 



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