Disufenton sodium

Disufenton sodium

Systematic (IUPAC) name
Disodium 4-[(Z)-(tert-butyl-oxidoazaniumylidene)methyl]benzene-1,3-disulfonate
Identifiers
ATC code	none
PubChem	CID 6440181
ChemSpider	28530805
UNII	7M1J3HN9VO
KEGG	D03875
ChEMBL	CHEMBL1627056
Chemical data
Formula	C11H13NNa2O7S2
Molar mass	381.33 g/mol
SMILES CC(C)(C)[N+](=Cc1ccc(cc1S(=O)(=O)[O-])S(=O)(=O)[O-])[O-].[Na+].[Na+]
InChI InChI=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 Key:XLZOVRYBVCMCGL-UHFFFAOYSA-L
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Disufenton sodium (NXY-059, Cerovive) is the disulfonyl derivative of the neuroprotective spin trap phenylbutylnitrone or "PBN". It was under development at the drug company AstraZeneca. A 2005 phase-3 clinical trial^[1][2] 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".^[1] AstraZeneca then terminated the development programme.^[3] PBN and its derivatives hydrolyze and oxidize in vitro to form respectively MNP-OH (AKA, NtBHA) and its parent spin-trap MNP.

References

1. Lees, Kennedy R.; Zivin, Justin A.; Ashwood, Tim; Davalos, Antonio; Davis, Stephen M.; Diener, Hans-Christoph; Grotta, James; Lyden, Patrick; et al. (2006). "NXY-059 for Acute Ischemic Stroke". New England Journal of Medicine 354 (6): 588–600. doi:10.1056/NEJMoa052980. PMID 16467546.
2. Lees, KR; Davalos, A; Davis, SM; Diener, HC; Grotta, J; Lyden, P; Shuaib, A; Ashwood, T; et al. (2006). "Additional outcomes and subgroup analyses of NXY-059 for acute ischemic stroke in the SAINT I trial". Stroke; a journal of cerebral circulation 37 (12): 2970–8. doi:10.1161/01.STR.0000249410.91473.44. PMID 17068304.
3. Renovis: Press Release

External links

• Oxidants, antioxidants and the ischemic brain
• NXY-059: Review of Neuroprotective Potential for Acute Stroke