Disufenton

Title: Disufenton
CAS Registry Number: 168021-77-0
CAS Name: 4-[[(1,1-Dimethylethyl)oxidoimino]methyl]-1,3-benzenedisulfonic acid
Additional Names: 2,4-disulfonyl-a-phenyl-tert-butylnitrone
Molecular Formula: C11H15NO7S2
Molecular Weight: 337.37
Percent Composition: C 39.16%, H 4.48%, N 4.15%, O 33.20%, S 19.01%
Literature References: Nitrone-based spin trapping agent; derivative of PBN, q.v. Prepn: J. M. Carney, WO 9517876; idem, US 5488145 (1995, 1996 both to Oklahoma Med. Res. Found.). Pharmacology: S. Kuroda et al., J. Cereb. Blood Flow Metab. 19, 778 (1999). Comparative radical trapping study: K. R. Maples et al., Free Radical Res. 34, 417 (2001). Clinical pharmacokinetics: K. R. Lees et al., Stroke 32, 675 (2001). Clinical trial in acute ischemic stroke: idem et al., N. Engl. J. Med. 354, 588 (2006). Reviews of pharmacology and therapeutic potential: P. A. Lapchak, Curr. Opin. Invest. Drugs 3, 1758-1762 (2002); P. A. Lapchak, D. M. Araujo, CNS Drug Rev. 9, 253-262 (2003).
Properties: White powder. Soly (g/ml): water >1.
Derivative Type: Sodium salt
CAS Registry Number: 168021-79-2
Additional Names: Disodium 4-[(tert-butylimino)methyl]benzene-1,3-disulfonate N-oxide
Manufacturers' Codes: ARL-16556; CPI-22; CXY-059; NXY-059
Trademarks: Cerovive (AstraZeneca)
Molecular Formula: C11H13NNa2O7S2
Molecular Weight: 381.33
Percent Composition: C 34.65%, H 3.44%, N 3.67%, Na 12.06%, O 29.37%, S 16.82%
Therap-Cat: Neuroprotective.
Keywords: Neuroprotective.
Disulfamide Disulfoton Disul-sodium Dita Bark Ditazol

Disufenton sodium
Disufenton sodium.png
Systematic (IUPAC) name
Disodium 4-[(Z)-(tert-butyl-oxidoazaniumylidene)methyl]benzene-1,3-disulfonate
Clinical data
Legal status  ?
Identifiers
ATC code None
PubChem CID 6440181
UNII 7M1J3HN9VO N
KEGG D03875 YesY
ChEMBL CHEMBL1627056 N
Chemical data
Formula C11H13NNa2O7S2 
Mol. mass 381.33 g/mol
 N (what is this?)  (verify)

Disufenton sodium (NXY-059, Cerovive) is the disulfonyl derivative of the neuroprotective spin trap phenylbutynitrone 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.