DISUFENTON SODIUM

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H13NO7S2.2Na
Molecular Weight	381.333
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0
Stereo Comments	MM2 minimum energy of Z and E are 288.5886 and 451.3651 kcal/mol respectively (for free acid).

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[Na+].CC(C)(C)[N+](\[O-])=C\C1=C(C=C(C=C1)S([O-])(=O)=O)S([O-])(=O)=O

InChI

InChIKey=XLZOVRYBVCMCGL-BPNVQINPSA-L

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/b12-7-;;

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16467546 | https://www.ncbi.nlm.nih.gov/pubmed/28832600 | https://www.ncbi.nlm.nih.gov/pubmed/29673616

AstraZeneca developed disufenton (NXY-059), a free radical trapping agent, for the treatment of ischaemic stroke and other brain injuries. Nevertheless, large clinical trial (3306 versus 1722 patients) was neutral, providing no evidence for the efficacy of disufenton sodium in patients with stroke. One study using rat cortical brain slices concluded that NXY-059 improved neuronal survival. However, another study in mouse neuroblastoma cells reported no effect. Another study reported that NXY-059 restored endothelial blood-brain. Histological analyses revealed several therapeutic advantages associated with disufenton sodium treatment following acute acoustic trauma, including reductions in inner and outer hair cell loss; reductions in acute acoustic trauma-induced loss of calretinin-positive afferent nerve fibers in the spiral lamina; and reductions in fibrocyte loss within the spiral ligament. However, AstraZeneca terminated the development program.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Free radical 2 Target ID: Free radical Sources: https://www.ncbi.nlm.nih.gov/pubmed/29673616	Chelating Agent 139

PubMed

Title	Date	PubMed
NXY-059, a Failed Stroke Neuroprotectant, Offers No Protection to Stem Cell-Derived Human Neurons.	2018-08	29673616
HPN-07, a free radical spin trapping agent, protects against functional, cellular and electrophysiological changes in the cochlea induced by acute acoustic trauma.	2017	28832600
Commentary : Hypothesis Focused Ultrasound and NXY-059 in Experimental Cerebral Ischemia: A New Therapeutic Opportunity?	2016	27680203
Neuroprotection for ischaemic stroke: translation from the bench to the bedside.	2012-07	22394615
Potential implication of the chemical properties and bioactivity of nitrone spin traps for therapeutics.	2012-06	22709256
Neuroprotection for stroke: current status and future perspectives.	2012	23109881
NXY-059 does not significantly interact with furosemide in healthy volunteers.	2006-12	17101741

Name

Type

Language

DISUFENTON SODIUM SALT

Preferred Name

English

DISUFENTON SODIUM

Official Name

English

DISODIUM 4-((TERT-BUTYLIMINO)METHYL)BENZENE-1,3-DISULFONATE N-OXIDE

Common Name

English

disufenton sodium [INN]

Common Name

English

OKN-007

Code

English

HPN-07

Code

English

1,3-BENZENEDISULFONIC ACID, 4-(((1,1-DIMETHYLETHYL)OXIDOIMINO)METHYL), DISODIUM SALT

Common Name

English

DISUFENTON SODIUM [MART.]

Common Name

English

DISUFENTON SODIUM [USAN]

Common Name

English

CEROVIVE

Common Name

English

DISODIUM 4-(((1,1-DIMETHYLETHYL)IMINO)METHYL)BENZENE-1,3-DISULPHONATE N-OXIDE

Common Name

English

DISUFENTON SODIUM SALT [MI]

Common Name

English

DISODIUM 4-(((1,1-DIMETHYLETHYL)IMINO)METHYL)BENZENE-1,3-DISULFONATE N-OXIDE

Common Name

English

Disufenton sodium [WHO-DD]

Common Name

English

DISODIUM 4-((TERT-BUTYLIMINO)METHYL)BENZENE-1,3-DISULPHONATE N-OXIDE

Common Name

English

NXY-059

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

531616