NS-398
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MedKoo CAT#: 522677

CAS#: 123653-11-2

Description: NS-398 is a selective inhibitor of cyclooxygenase-2 (COX-2). NS-398 Inhibits Choroidal Neovascularization and Subretinal Fibrosis. NS-398 enhances the efficacy of bortezomib against RPMI8226 human multiple myeloma cells. NS-398 inhibits proliferation and induces apoptosis in human osteosarcoma cells via downregulation of the survivin pathway. NS-398-enhanced apoptosis of esophageal carcinoma cell EC9706 by adjusting expression of survivin and caspase-3.


Chemical Structure

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NS-398
CAS# 123653-11-2

Theoretical Analysis

MedKoo Cat#: 522677
Name: NS-398
CAS#: 123653-11-2
Chemical Formula: C13H18N2O5S
Exact Mass: 314.0936
Molecular Weight: 314.36
Elemental Analysis: C, 49.67; H, 5.77; N, 8.91; O, 25.45; S, 10.20

Price and Availability

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10.0mg USD 90.0 Same Day
25.0mg USD 150.0 Same Day
50.0mg USD 250.0 Same Day
100.0mg USD 350.0 Same Day
200.0mg USD 550.0 Same Day
500.0mg USD 850.0 Same Day
1.0g USD 1450.0 Same Day
2.0g USD 2450.0 Same Day
5.0g USD 3950.0 Same Day
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Synonym: NS-398; NS 398; NS398.

IUPAC/Chemical Name: N-[2-(cyclohexyloxy)-4-nitrophenyl]-methanesulfonamide

InChi Key: KTDZCOWXCWUPEO-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H18N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h7-9,11,14H,2-6H2,1H3

SMILES Code: CS(=O)(NC1=CC=C([N+]([O-])=O)C=C1OC2CCCCC2)=O

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, not in water

Shelf Life: >2 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

Biological target: NS-398 is a non-steroidal an-inflammatory agent with analgesic and antipyretic effects, and selectively inhibits prostaglandin G/H synthase 2/cyclooxygenase 2 (COX-2) activity, with an IC50 of 3.8 μM, and has no effect on COX-1 at 100 μM.
In vitro activity: The aim of this study was to investigate the growth inhibitory mechanism of NS-398, a selective cyclooxygenase-2 (COX-2) inhibitor, in two hepatocellular carcinoma (HCC) cell lines (HepG2 and Huh7). The hepatoma cell lines were first characterized by their expression of COX-2. Samples containing 50 μg of extracted protein were loaded onto the gel. Immunoblot analysis revealed that both cell lines expressed COX-2 protein. The expression of COX-2 was inhibited by NS-398. Immunoblot analysis also demonstrated different COX-2 expressions after treatment with 100 μmol/L NS-398 for different periods of time (Figure11). To determine the effect of the selective COX-2 inhibitor NS-398 on HepG2 and Huh7 cells, cell viability was determined by WST-1 assay. Growth-inhibitory experiments were performed by treating cells with various doses of NS-398 for different periods of time. As shown in Figure2,2, NS398 reduced cell viability in a time- and dose-dependent manner on both cell lines. NS-398 did not induce apoptosis in HepG2 and Huh7 cells. Both cell lines showed a down-regulation of PCNA expression after treatment with 100 μmol/L of NS-398 in a time dependent manner. In particular, NS-398 treatments significantly suppressed the cellular proliferation in Huh7 cells. In conclusion, selective COX-2 inhibitor, NS-398, inhibits the growth of HepG2 and Huh7 cells by inducing cell cycle arrest and is a potential candidate as an effective chemopreventive tool against human HCC. Reference: World J Gastroenterol. 2007 Feb 28; 13(8): 1175–1181. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4146990/
In vivo activity: The aim of this study was to further investigate the effects of NS-398 on the changes in expression and/or activity of COX-2, cytochrome P450 4A1 (CYP4A1), inducible NO synthase (iNOS), and peroxynitrite formation in serum, renal, cardiac, and/or vascular tissues of lipopolysaccharide (LPS)-treated rats. LPS (10mg/kg, i.p.)-induced decrease in blood pressure was associated with increased protein levels of COX-2, iNOS, and nitrotyrosine in kidney, heart, thoracic aorta, and superior mesenteric artery. The activities of COX-2 and iNOS as well as levels of PGI2, PGE2, and nitrotyrosine were also increased in the systemic circulation and renal, cardiac, and vascular tissues of LPS-treated rats. In contrast, renal, cardiac, and vascular CYP4A1 protein expression as well as systemic and tissue levels of 20-HETE were decreased in endotoxemic rats. These effects of LPS, except COX-2 protein expression, were prevented by NS-398 (10 mg/kg, i.p.), given 1h after injection of LPS. These data suggest that COX-2-derived vasodilator prostanoids, PGI2 and PGE2, produced during endotoxemia increase iNOS protein expression and activity as well as peroxynitrite formation resulting in decreased CYP4A1 protein expression and 20-HETE synthesis. Taken together, we concluded that an increase in 20-HETE levels associated with a decrease in the production of vasodilator prostanoids and NO participates in the effect of NS-398 to prevent hypotension in the rat model of septic shock. Reference: Prostaglandins Other Lipid Mediat. Jul-Aug 2013;104-105:93-108. https://pubmed.ncbi.nlm.nih.gov/22975359/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 5.0 15.9

Preparing Stock Solutions

The following data is based on the product molecular weight 314.36 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. Shen W, Li Y, Tang Y, Cummins J, Huard J. NS-398, a cyclooxygenase-2-specific inhibitor, delays skeletal muscle healing by decreasing regeneration and promoting fibrosis. Am J Pathol. 2005 Oct;167(4):1105-17. doi: 10.1016/S0002-9440(10)61199-6. PMID: 16192645; PMCID: PMC1603662. 2. Baek JY, Hur W, Wang JS, Bae SH, Yoon SK. Selective COX-2 inhibitor, NS-398, suppresses cellular proliferation in human hepatocellular carcinoma cell lines via cell cycle arrest. World J Gastroenterol. 2007 Feb 28;13(8):1175-81. doi: 10.3748/wjg.v13.i8.1175. PMID: 17451196; PMCID: PMC4146990. 3. Tunctan B, Sari AN, Kacan M, Unsal D, Buharalioglu CK, Sahan-Firat S, Korkmaz B, Falck JR, Malik KU. NS-398 reverses hypotension in endotoxemic rats: contribution of eicosanoids, NO, and peroxynitrite. Prostaglandins Other Lipid Mediat. 2013 JulAug;104-105:93-108. doi: 10.1016/j.prostaglandins.2012.08.007. Epub 2012 Sep 5. PMID: 22975359; PMCID: PMC3774147.
In vitro protocol: 1. Shen W, Li Y, Tang Y, Cummins J, Huard J. NS-398, a cyclooxygenase-2-specific inhibitor, delays skeletal muscle healing by decreasing regeneration and promoting fibrosis. Am J Pathol. 2005 Oct;167(4):1105-17. doi: 10.1016/S0002-9440(10)61199-6. PMID: 16192645; PMCID: PMC1603662. 2. Baek JY, Hur W, Wang JS, Bae SH, Yoon SK. Selective COX-2 inhibitor, NS-398, suppresses cellular proliferation in human hepatocellular carcinoma cell lines via cell cycle arrest. World J Gastroenterol. 2007 Feb 28;13(8):1175-81. doi: 10.3748/wjg.v13.i8.1175. PMID: 17451196; PMCID: PMC4146990.
In vivo protocol: 1. Shen W, Li Y, Tang Y, Cummins J, Huard J. NS-398, a cyclooxygenase-2-specific inhibitor, delays skeletal muscle healing by decreasing regeneration and promoting fibrosis. Am J Pathol. 2005 Oct;167(4):1105-17. doi: 10.1016/S0002-9440(10)61199-6. PMID: 16192645; PMCID: PMC1603662. 2. Tunctan B, Sari AN, Kacan M, Unsal D, Buharalioglu CK, Sahan-Firat S, Korkmaz B, Falck JR, Malik KU. NS-398 reverses hypotension in endotoxemic rats: contribution of eicosanoids, NO, and peroxynitrite. Prostaglandins Other Lipid Mediat. 2013 JulAug;104-105:93-108. doi: 10.1016/j.prostaglandins.2012.08.007. Epub 2012 Sep 5. PMID: 22975359; PMCID: PMC3774147.

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1: Zhang R, Liu Z, Zhang H, Zhang Y, Lin D. The COX-2-Selective Antagonist (NS-398) Inhibits Choroidal Neovascularization and Subretinal Fibrosis. PLoS One. 2016 Jan 13;11(1):e0146808. doi: 10.1371/journal.pone.0146808. eCollection 2016. PubMed PMID: 26760305; PubMed Central PMCID: PMC4711821.

2: Kim J, Shim M. COX-2 inhibitor NS-398 suppresses doxorubicin-induced p53 accumulation through inhibition of ROS-mediated Jnk activation. Mol Carcinog. 2016 Jan 12. doi: 10.1002/mc.22458. [Epub ahead of print] PubMed PMID: 26756900.

3: Retraction Note to: Effect of NS-398, a cyclooxygenase-2 selective inhibitor, on the cytotoxicity of cytotoxic T lymphocytes to ovarian carcinoma cells. Tumour Biol. 2015 Sep;36(9):7297. doi: 10.1007/s13277-015-3694-6. PubMed PMID: 26281984.

4: Trandafir CC, Pouliot WA, Dudek FE, Ekstrand JJ. Co-administration of subtherapeutic diazepam enhances neuroprotective effect of COX-2 inhibitor, NS-398, after lithium pilocarpine-induced status epilepticus. Neuroscience. 2015 Jan 22;284:601-10. doi: 10.1016/j.neuroscience.2014.10.021. Epub 2014 Oct 18. PubMed PMID: 25453777; PubMed Central PMCID: PMC4326254.

5: Que W, Li S, Chen J. NS-398 enhances the efficacy of bortezomib against RPMI8226 human multiple myeloma cells. Mol Med Rep. 2013 May;7(5):1641-5. doi: 10.3892/mmr.2013.1394. Epub 2013 Mar 26. PubMed PMID: 23545701.

6: Wang X, Liang Y, Wang J, Wang M. Effect of NS-398, a cyclooxygenase-2 selective inhibitor, on the cytotoxicity of cytotoxic T lymphocytes to ovarian carcinoma cells. Tumour Biol. 2013 Jun;34(3):1517-22. doi: 10.1007/s13277-013-0677-3. Epub 2013 Mar 1. Retraction in: Wang X, Liang Y, Wang J, Wang M. Tumour Biol. 2015 Aug;36(9):7297. PubMed PMID: 23456767.

7: Tunctan B, Sari AN, Kacan M, Unsal D, Buharalioglu CK, Sahan-Firat S, Korkmaz B, Falck JR, Malik KU. NS-398 reverses hypotension in endotoxemic rats: contribution of eicosanoids, NO, and peroxynitrite. Prostaglandins Other Lipid Mediat. 2013 Jul-Aug;104-105:93-108. doi: 10.1016/j.prostaglandins.2012.08.007. Epub 2012 Sep 5. PubMed PMID: 22975359; PubMed Central PMCID: PMC3774147.

8: Duan DP, Dang XQ, Wang KZ, Wang YP, Zhang H, You WL. The cyclooxygenase-2 inhibitor NS-398 inhibits proliferation and induces apoptosis in human osteosarcoma cells via downregulation of the survivin pathway. Oncol Rep. 2012 Nov;28(5):1693-700. doi: 10.3892/or.2012.1992. Epub 2012 Aug 24. PubMed PMID: 22922684.

9: Sugiyama T, Meakin LB, Galea GL, Lanyon LE, Price JS. The cyclooxygenase-2 selective inhibitor NS-398 does not influence trabecular or cortical bone gain resulting from repeated mechanical loading in female mice. Osteoporos Int. 2013 Jan;24(1):383-8. doi: 10.1007/s00198-012-1922-0. Epub 2012 Feb 14. PubMed PMID: 22349912; PubMed Central PMCID: PMC3536947.

10: Vecchio AJ, Malkowski MG. The structure of NS-398 bound to cyclooxygenase-2. J Struct Biol. 2011 Nov;176(2):254-8. doi: 10.1016/j.jsb.2011.07.019. Epub 2011 Aug 6. PubMed PMID: 21843643; PubMed Central PMCID: PMC3185125.

11: Lee SM, Gai WW, Cheung TK, Peiris JS. Antiviral activity of a selective COX-2 inhibitor NS-398 on avian influenza H5N1 infection. Influenza Other Respir Viruses. 2011 May;5 Suppl 1:230-2. PubMed PMID: 21761591.

12: Banu NA, Daly RS, Buda A, Moorghen M, Baker J, Pignatelli M. Reduced tumour progression and angiogenesis in 1,2-dimethylhydrazine mice treated with NS-398 is associated with down-regulation of cyclooxygenase-2 and decreased beta-catenin nuclear localisation. Cell Commun Adhes. 2011 Feb;18(1-2):1-8. doi: 10.3109/15419061.2011.586754. Epub 2011 Jun 16. PubMed PMID: 21679035.

13: Li S, Tian D, Fei P, Gao Y, Chen Z, Wang Q, Tong Q. A cyclooxygase-2 inhibitor NS-398-enhanced apoptosis of esophageal carcinoma cell EC9706 by adjusting expression of survivin and caspase-3. Cancer Invest. 2011 Feb;29(2):102-6. PubMed PMID: 21329005.

14: Li N, Che CY, Hu LT, Lin J, Wang Q, Zhao GQ. Effects of COX-2 inhibitor NS-398 on IL-10 expression in rat fungal keratitis. Int J Ophthalmol. 2011;4(2):165-9. doi: 10.3980/j.issn.2222-3959.2011.02.11. Epub 2011 Apr 18. PubMed PMID: 22553634; PubMed Central PMCID: PMC3340712.

15: Tunctan B, Korkmaz B, Cuez T, Kemal Buharalioglu C, Sahan-Firat S, Falck J, Malik KU. Contribution of vasoactive eicosanoids and nitric oxide production to the effect of selective cyclooxygenase-2 inhibitor, NS-398, on endotoxin-induced hypotension in rats. Basic Clin Pharmacol Toxicol. 2010 Nov;107(5):877-82. doi: 10.1111/j.1742-7843.2010.00589.x. PubMed PMID: 22545970; PubMed Central PMCID: PMC3128812.

16: Youns M, Efferth T, Hoheisel JD. Transcript profiling identifies novel key players mediating the growth inhibitory effect of NS-398 on human pancreatic cancer cells. Eur J Pharmacol. 2011 Jan 10;650(1):170-7. doi: 10.1016/j.ejphar.2010.10.026. Epub 2010 Oct 20. PubMed PMID: 20969859.

17: Lee SY, Lee MY, Park SH, Kim TH, Moon YT, Han JH, Myung SC. NS-398 (a selective cyclooxygenase-2 inhibitor) decreases agonist-induced contraction of the human ureter via calcium channel inhibition. J Endourol. 2010 Nov;24(11):1863-8. doi: 10.1089/end.2009.0461. Epub 2010 Oct 19. PubMed PMID: 20958135.

18: Fernández-Martínez AB, Bajo AM, Valdehita A, Isabel Arenas M, Sánchez-Chapado M, Carmena MJ, Prieto JC. Multifunctional role of VIP in prostate cancer progression in a xenograft model: suppression by curcumin and COX-2 inhibitor NS-398. Peptides. 2009 Dec;30(12):2357-64. doi: 10.1016/j.peptides.2009.09.018. Epub 2009 Sep 20. PubMed PMID: 19772879.

19: Liu JF, Zhu GJ, Jamieson GG, Wu TC, Zhu TN, Shan BE, Drew PA. NS-398 induces apoptosis in human esophageal cancer cells through inhibition of NF-kappaB downstream regulation of cyclooxygenase-2. Cancer Invest. 2009 Jan;27(1):17-23. doi: 10.1080/07357900801992913. PubMed PMID: 19160097.

20: John-Aryankalayil M, Palayoor ST, Cerna D, Falduto MT, Magnuson SR, Coleman CN. NS-398, ibuprofen, and cyclooxygenase-2 RNA interference produce significantly different gene expression profiles in prostate cancer cells. Mol Cancer Ther. 2009 Jan;8(1):261-73. doi: 10.1158/1535-7163.MCT-08-0928. PubMed PMID: 19139136; PubMed Central PMCID: PMC2861287.

NS-398

10.0mg / USD 90.0