Disufenton sodium (Cerovive)
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MedKoo CAT#: 200721

CAS#: 168021-79-2 (sodium)

Description: Disufenton sodium, also known as Cerovive, OKN007, NXY-059, 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.


Chemical Structure

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Disufenton sodium (Cerovive)
CAS# 168021-79-2 (sodium)

Theoretical Analysis

MedKoo Cat#: 200721
Name: Disufenton sodium (Cerovive)
CAS#: 168021-79-2 (sodium)
Chemical Formula: C11H13NNa2O7S2
Exact Mass: 0.00
Molecular Weight: 381.330
Elemental Analysis: C, 34.65; H, 3.44; N, 3.67; Na, 12.06; O, 29.37; S, 16.82

Price and Availability

Size Price Availability Quantity
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 350 Ready to ship
200mg USD 550 Ready to ship
500mg USD 950 Ready to ship
1g USD 1650 Ready to ship
2g USD 2650 2 Weeks
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Related CAS #: 168021-77-0 (free base)   168021-79-2 (sodium)  

Synonym: 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; Cerovive; Disufenton sodium

IUPAC/Chemical Name: sodium (Z)-4-((tert-butyloxidoazanylidene)methyl)benzene-1,3-disulfonate

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-;;

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

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, DMF, PBS, and EtOH

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:  

Biological target: Disufenton sodium (NXY-059) is the disulfonyl derivative of the neuroprotective spin trap phenylbutynitrone (PBN) and is a very powerful scavenger of free radicals.
In vitro activity: To determine the specific molecular mechanisms of the antitumor effect of OKN-007 on HCC cells, this study measured the effect of OKN-007 on the activity of two well-known oncogenic signaling pathways in HCC, including TGFB1/ SMAD2 signaling and Hedgehog/GLI1 signaling. First, luciferase expression was measured in SULF2-positive Huh7 cells transfected with luciferase reporter constructs responsive to activated TGFB1 pathway SMAD transcription factors or to the Hh pathway GLI transcription factors. OKN-007 treatment significantly suppressed SMAD-responsive luciferase activity (Fig. 4A; P = 0.03), as well as GLI-responsive luciferase activity (Fig. 4B; P = 0.03). Immunoblotting confirmed the concomitant suppression of the activated transcription factors pSMAD2 (Fig. 4A) and GLI1 (Fig. 4B). These data support the hypothesis that OKN-007 treatment suppresses the activation of signaling pathways and mediators that we have previously shown to be responsive to SULF2 expression, including TGFB1/SMAD2 and Hedgehog/GLI1. Reference: Genes Chromosomes Cancer. 2013 Mar;52(3):225-36. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3889201/
In vivo activity: Remarkably, this study observed that OHC (outer hair cell) loss was not only significantly reduced in HPN-07 (Disufenton sodium) treated animals in tonotopic regions corresponding to the initial insult, but its subsequent apical migration was also blocked in the treated animals.In contrast to OHC loss, which plateaued at about 10d post-insult, IHC (inner hair cell) loss continued longitudinally, with most of the loss occurring between 21 and 180d in the untreated animals. In contrast, less than 1% IHC loss was observed at all tonotopic positions in HPN-07-treated animals during the 180d study period. The progressive IHC loss observed in untreated, noise-exposed chinchilla may be attributable to ongoing inflammation or oxidative stress post-injury, both of which have been shown to be attenuated by HPN-07 treatment in other tissue injuries. The observed protection of afferent nerve fibers in the treatment group may, thus, be an indirect effect of HC protection or a direct antioxidant effect on the nerve fibers themselves. Reference: PLoS One. 2017; 12(8): e0183089. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5568441/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 44.7 117.25
DMF 20.0 52.45
Ethanol 2.0 5.24
PBS (pH 7.2) 10.0 26.22
Water 54.7 143.47

Preparing Stock Solutions

The following data is based on the product molecular weight 381.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Zheng X, Gai X, Han S, Moser CD, Hu C, Shire AM, Floyd RA, Roberts LR. The human sulfatase 2 inhibitor 2,4-disulfonylphenyl-tert-butylnitrone (OKN-007) has an antitumor effect in hepatocellular carcinoma mediated via suppression of TGFB1/SMAD2 and Hedgehog/GLI1 signaling. Genes Chromosomes Cancer. 2013 Mar;52(3):225-36. doi: 10.1002/gcc.22022. Epub 2012 Oct 29. PMID: 23109092; PMCID: PMC3889201. 2. Mutch NJ, Moore NR, Mattsson C, Jonasson H, Green AR, Booth NA. The use of the Chandler loop to examine the interaction potential of NXY-059 on the thrombolytic properties of rtPA on human thrombi in vitro. Br J Pharmacol. 2008 Jan;153(1):124-31. doi: 10.1038/sj.bjp.0707543. Epub 2007 Nov 5. PMID: 17982476; PMCID: PMC2199381. 3. Ewert D, Hu N, Du X, Li W, West MB, Choi CH, Floyd R, Kopke RD. HPN-07, a free radical spin trapping agent, protects against functional, cellular and electrophysiological changes in the cochlea induced by acute acoustic trauma. PLoS One. 2017 Aug 23;12(8):e0183089. doi: 10.1371/journal.pone.0183089. PMID: 28832600; PMCID: PMC5568441. 4. Floyd RA, Chandru HK, He T, Towner R. Anti-cancer activity of nitrones and observations on mechanism of action. Anticancer Agents Med Chem. 2011 May 1;11(4):373-9. doi: 10.2174/187152011795677517. PMID: 21651461; PMCID: PMC3246679.
In vitro protocol: 1. Zheng X, Gai X, Han S, Moser CD, Hu C, Shire AM, Floyd RA, Roberts LR. The human sulfatase 2 inhibitor 2,4-disulfonylphenyl-tert-butylnitrone (OKN-007) has an antitumor effect in hepatocellular carcinoma mediated via suppression of TGFB1/SMAD2 and Hedgehog/GLI1 signaling. Genes Chromosomes Cancer. 2013 Mar;52(3):225-36. doi: 10.1002/gcc.22022. Epub 2012 Oct 29. PMID: 23109092; PMCID: PMC3889201. 2. Mutch NJ, Moore NR, Mattsson C, Jonasson H, Green AR, Booth NA. The use of the Chandler loop to examine the interaction potential of NXY-059 on the thrombolytic properties of rtPA on human thrombi in vitro. Br J Pharmacol. 2008 Jan;153(1):124-31. doi: 10.1038/sj.bjp.0707543. Epub 2007 Nov 5. PMID: 17982476; PMCID: PMC2199381.
In vivo protocol: 1. Ewert D, Hu N, Du X, Li W, West MB, Choi CH, Floyd R, Kopke RD. HPN-07, a free radical spin trapping agent, protects against functional, cellular and electrophysiological changes in the cochlea induced by acute acoustic trauma. PLoS One. 2017 Aug 23;12(8):e0183089. doi: 10.1371/journal.pone.0183089. PMID: 28832600; PMCID: PMC5568441. 2. Floyd RA, Chandru HK, He T, Towner R. Anti-cancer activity of nitrones and observations on mechanism of action. Anticancer Agents Med Chem. 2011 May 1;11(4):373-9. doi: 10.2174/187152011795677517. PMID: 21651461; PMCID: PMC3246679.

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