Disufenton sodium

{{Drugbox

| Verifiedfields = changed

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| verifiedrevid = 405853279

| IUPAC_name = Disodium 4-[(Z)-(tert-butyl-oxidoazaniumylidene)methyl]benzene-1,3-disulfonate

| image = Disufenton sodium.png

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 168021-79-2

| ATC_prefix = none

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| PubChem = 6440181

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1627056

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 7M1J3HN9VO

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D03875

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 28530805

| C=11 | H=13 | N=1 | Na=2 | O=7 | S=2

| smiles = CC(C)(C)[N+]([O-])=Cc1ccc(cc1S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+]

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C11H15NO7S2.2Na/c1-11(2,3)12(13)7-8-4-5-9(20(14,15)16)6-10(8)21(17,18)19;;/h4-7H,1-3H3,(H,14,15,16)(H,17,18,19);;/q;2*+1/p-2

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = XLZOVRYBVCMCGL-UHFFFAOYSA-L

}}

Disufenton sodium (Cerovive, OKN-007, NXY-059, HPN-07){{cite journal | vauthors = Varela-Nieto I, Murillo-Cuesta S, Rodríguez-de la Rosa L, Oset-Gasque MJ, Marco-Contelles J | title = Use of Radical Oxygen Species Scavenger Nitrones to Treat Oxidative Stress-Mediated Hearing Loss: State of the Art and Challenges | journal = Frontiers in Cellular Neuroscience | volume = 15 | pages = 711269 | date = September 1, 2021 | pmid = 34539349 | pmc = 8440819 | doi = 10.3389/fncel.2021.711269 | publisher = Frontiers Media SA | doi-access = free }} is a free radical trapping nitrone-based antioxidant compound that has been under development for several medical conditions.{{cite journal | vauthors = Zhao Z, Cheng M, Maples KR, Ma JY, Buchan AM | title = NXY-059, a novel free radical trapping compound, reduces cortical infarction after permanent focal cerebral ischemia in the rat | journal = Brain Research | volume = 909 | issue = 1–2 | pages = 46–50 | date = August 2001 | pmid = 11478919 | doi = 10.1016/s0006-8993(01)02618-x | publisher = Elsevier BV | s2cid = 36633423 }}{{cite journal | vauthors = Choi SH, Choi CH | title = Noise-Induced Neural Degeneration and Therapeutic Effect of Antioxidant Drugs | journal = Journal of Audiology & Otology | volume = 19 | issue = 3 | pages = 111–119 | date = December 2015 | pmid = 26771008 | pmc = 4704551 | doi = 10.7874/jao.2015.19.3.111 | publisher = The Korean Audiological Society }}

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{{cite journal | vauthors = Lees KR, Zivin JA, Ashwood T, Davalos A, Davis SM, Diener HC, Grotta J, Lyden P, Shuaib A, Hårdemark HG, Wasiewski WW | display-authors = 6 | title = NXY-059 for acute ischemic stroke | journal = The New England Journal of Medicine | volume = 354 | issue = 6 | pages = 588–600 | date = February 2006 | pmid = 16467546 | doi = 10.1056/NEJMoa052980 | doi-access = free }}{{cite journal | vauthors = Lees KR, Davalos A, Davis SM, Diener HC, Grotta J, Lyden P, Shuaib A, Ashwood T, Hardemark HG, Wasiewski W, Emeribe U, Zivin JA | display-authors = 6 | title = Additional outcomes and subgroup analyses of NXY-059 for acute ischemic stroke in the SAINT I trial | journal = Stroke | volume = 37 | issue = 12 | pages = 2970–2978 | date = December 2006 | pmid = 17068304 | doi = 10.1161/01.STR.0000249410.91473.44 | doi-access = free }} 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". AstraZeneca then terminated the development programme.{{cite web | url = http://investors.renovis.com/phoenix.zhtml?c=148297&p=irol-newsArticle&t=Regular&id=921678& | title = Renovis: Press Release| archive-url = https://web.archive.org/web/20061028094321/http://investors.renovis.com/phoenix.zhtml?c=148297&p=irol-newsArticle&t=Regular&id=921678& | archive-date=October 28, 2006 }}

Disufenton sodium has been researched as a potential treatment for use in brain tumors and cancers, including diffuse intrinsic pontine glioma (DIPG){{cite journal | vauthors = Thomas L, Smith N, Saunders D, Zalles M, Gulej R, Lerner M, Fung KM, Carcaboso AM, Towner RA | display-authors = 6 | title = OKlahoma Nitrone-007: novel treatment for diffuse intrinsic pontine glioma | journal = Journal of Translational Medicine | volume = 18 | issue = 1 | pages = 424 | date = November 2020 | pmid = 33168005 | pmc = 7654606 | doi = 10.1186/s12967-020-02593-5 | publisher = Springer Science and Business Media LLC | doi-access = free }}{{cite web | title=FDA grants fast track status to OKN-007 for diffuse intrinsic pontine glioma | website=Healio | date=March 3, 2021 | url=https://www.healio.com/news/hematology-oncology/20210303/fda-grants-fast-track-status-to-okn007-for-diffuse-intrinsic-pontine-glioma | access-date=February 5, 2022}} and glioblastoma.{{cite journal | vauthors = Battiste JD, Ikeguchi A, Woo S, Sharan S, Zhao YD, Cohoon A, Sung S, Wright D, Teague AM, Jensen RL, Kim EH, Yang WS, Towner RA | display-authors = 6 | title=Phase Ib clinical trial of OKN-007 in recurrent malignant glioma. | journal=Journal of Clinical Oncology | publisher=American Society of Clinical Oncology (ASCO) | volume=38 | issue=15_suppl | date=May 20, 2020 | issn=0732-183X | doi=10.1200/jco.2020.38.15_suppl.2538 | pages=2538| s2cid=219772612 }}{{cite journal | vauthors = Zalles M, Smith N, Saunders D, Lerner M, Fung KM, Battiste J, Towner RA | title = A tale of two multi-focal therapies for glioblastoma: An antibody targeting ELTD1 and nitrone-based OKN-007 | journal = Journal of Cellular and Molecular Medicine | volume = 26 | issue = 2 | pages = 570–582 | date = January 2022 | pmid = 34910361 | pmc = 8743651 | doi = 10.1111/jcmm.17133 | publisher = Wiley }}

A compound (NHPN-1010) containing a combination of disufenton sodium and acetylcysteine has been researched as a potential treatment for tinnitus and hearing loss.{{cite journal | vauthors = Lu J, West MB, Du X, Cai Q, Ewert DL, Cheng W, Nakmali D, Li W, Huang X, Kopke RD | display-authors = 6 | title = Electrophysiological assessment and pharmacological treatment of blast-induced tinnitus | journal = PLOS ONE | volume = 16 | issue = 1 | pages = e0243903 | date = January 7, 2021 | pmid = 33411811 | pmc = 7790300 | doi = 10.1371/journal.pone.0243903 | publisher = Public Library of Science (PLoS)\| doi-access = free | bibcode = 2021PLoSO..1643903L | veditors = Biagini G }}{{cite journal | vauthors = Zhang J | title = Blast-induced tinnitus: Animal models | journal = The Journal of the Acoustical Society of America | volume = 146 | issue = 5 | pages = 3811–3831 | date = November 2019 | pmid = 31795642 | doi = 10.1121/1.5132551 | publisher = Acoustical Society of America (ASA) | s2cid = 208621727 | doi-access = free | bibcode = 2019ASAJ..146.3811Z }}{{cite web | title=Congressionally Directed Medical Research Programs (CDMRP) Search Awards | website=Congressionally Directed Medical Research Programs | url=https://cdmrp.army.mil/search.aspx?LOG_NO=DM120099 | archive-url=https://web.archive.org/web/20220205054218/https://cdmrp.army.mil/search.aspx?LOG_NO=DM120099 | url-status=dead | archive-date=February 5, 2022 | access-date=February 5, 2022}}{{cite web | vauthors = Martin B | title=Hough Ear Institute receives $300K grant to support research treatments for hearing loss | website=KOKH | date=July 27, 2020 | url=https://okcfox.com/news/local/hough-ear-institute-receives-300k-grant-to-support-research-treatments-for-hearing-loss | access-date=February 5, 2022}}

Disufenton sodium

Chemistry

Research

References

Further reading