Disufenton sodium (NXY-059) 168021-79-2_Reactive Oxygen Species_Immunology / Inflammation_Signaling Pathways_Products

NXY-059 (also known as Cerovive, OKN007, Disufenton Sodium) is a disulfonyl derivative that has shown a significant differences in arterial Po2 and pH between the experimental groups before ischemia in BBB permeability study with Po2 value of 112.9±9.7mm Hg and pH value of 7.443±0.01. In addition, in rats, NXY-059 has been reported to significantly improve neurologic deficits at 24 hours when given at 6 hours of reperfusion. Besides, treatment with NXY-059 has been revealed to significantly ameliorate the brain damage. Thereby, the mean volumes of infarct and total damage are reduced to 9.2±14.8%（P<0.05） and 10.9±15.8%(P<0.01), respectively.

Physicochemical Properties

Molecular Formula

C11H13NNA2O7S2

Molecular Weight

381.33

Exact Mass

380.992

CAS #

168021-79-2

Related CAS #

168021-77-0;168021-79-2 (sodium);

PubChem CID

6440181

Appearance

White to off-white solid powder

LogP

2.907

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

Rotatable Bond Count

Heavy Atom Count

Complexity

578

Defined Atom Stereocenter Count

SMILES

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

InChi Key

XLZOVRYBVCMCGL-BPNVQINPSA-L

InChi Code

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-;;

Chemical Name

disodium;4-[(Z)-[tert-butyl(oxido)azaniumylidene]methyl]benzene-1,3-disulfonate

Synonyms

Cerovive, Disufenton Sodium;NXY059; NXY 059; NXY-059; CXY 059; CXY059; CXY-059; OKN007; OKN-007; OKN 007; ARL 16556; ARL16556; ARL-16556; CPI-22; CPI22; CPI 22

HS Tariff Code

2934.99.9001

Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro

In vitro activity: NXY-059 is more soluble than the spin trapping agent α-phenyl-N-tert-butyl nitrone (PBN). In an in vitro blood-brain barrier (BBB) model, 250 mM of NXY-059 administered at the onset or up to 4 h after oxygen glucose deprivation (OGD) produces a significant reduction in the increased BBB permeability caused by OGD. Furthermore, OGD produces a huge influx of tissue plasminogen activator across the BBB, which is substantially reduced by NXY-059.

ln Vivo

NXY-059 reduces infarct volume in rats subjected to 2 hours of middle cerebral artery occlusion in a dose-dependent manner. At equimolar doses (3.0 mg/kg for NXY-059 and 1.4 mg/kg for PBN), NXY-059 is more efficacious than PBN. Similar results are obtained when a recovery period of 7 days is allowed. The window of therapeutic opportunity for NXY-059 is 3 to 6 hours after the start of recirculation. NXY-059, a free radical-trapping agent, has a substantial protective effect, lessening the disability caused by an experimentally induced stroke in a primate species. NXY-059 treatment reduces the overall amount of brain damage by >50% of saline-treatment values, with similar levels of protection afforded to both white and gray matter. Treatment with NXY-059 (50 mg/kg subcutaneous plus 8.8 mg/kg/h for 3 days subcutaneous delivered via implanted osmotic pumps) significantly decreases neurological impairment following intracerebral hemorrhage in rat, and reduces the neutrophil infiltrate observed 48 hours post-hemorrhage in the vicinity of the hematoma, and the number of TUNEL-positive cells 48 hours post-hemorrhage at the hematoma margin.

Animal Protocol

Dissolved in physiological saline; 0.3, 3.0 or 30 mg/kg; Injected via the right jugular vein

Monofilament fishing line is used to produce occlusion and neurologic deficit in male Wistar rats

References

[1]. Neuroprotective effects of a novel nitrone, NXY-059, after transient focal cerebral ischemia in the rat. J Cereb Blood Flow Metab, 1999, 19(7), 778-787.

[2]. NXY-059, a free radical--trapping agent, substantially lessens the functional disability resulting from cerebral ischemia in a primate species. Stroke, 2001, 32(1), 190-198.

[3]. Cerebrovascular protection as a possible mechanism for the protective effects of NXY-059 in preclinical models: an in vitro study. Brain Res, 2009, 19(1294), 144-152.

Additional Infomation

Disufenton Sodium is a disulfonyl derivative of phenyl-tert-butyl nitrone (PBN), with potential anti-glioma activity. Although the exact mechanism(s) of action of OKN007 are still largely unknown, this agent appears to inhibit cancer cell proliferation and migration. This agent appears to inhibit the activity of sulfatase 2 (SULF2), a highly specific endoglucosamine-6-sulfatase that is overexpressed in the extracellular matrix of cancer cells and catalyzes the removal of sulfate from the 6-O-sulfate esters of heparin. In addition, OKN007 may induce changes in tumor metabolism and scavenge free radicals.

Solubility Data

Solubility (In Vitro)

DMSO:76 mg/mL (199.3 mM)

Water:76 mg/mL (199.3 mM)

Ethanol:<1 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: 100 mg/mL (262.24 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

Solubility in Formulation 2: Saline: 30 mg/mL

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.6224 mL	13.1120 mL	26.2240 mL
	5 mM	0.5245 mL	2.6224 mL	5.2448 mL
	10 mM	0.2622 mL	1.3112 mL	2.6224 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

PeptideDB

Disufenton sodium (NXY-059) 168021-79-2

CAS No.: 168021-79-2

Physicochemical Properties

Biological Activity

Solubility Data