123653-11-2

Basic information

• Product Name: NS-398
• Synonyms: NS-398;N-[2-(CYCLOHEXYLOXY)-4-NITROPHENYL]-METHANESULFONAMIDE;NS-398 98%;N-[2-(cyclohexoxy)-4-nitro-phenyl]methanesulfonamide;Taisho NS 398
• CAS NO: 123653-11-2
• Molecular Formula: C₁₃H₁₈N₂O₅S
• Molecular Weight: 314.36
• Product Categories: Lipid signaling;Signalling
• Mol File: 123653-11-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 124-126 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 490.6°Cat760mmHg
• Flash Point: 250.5°C
• Appearance: off-white/solid
• Density: 1.377g/cm³
• Vapor Pressure: 8.98E-10mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: Store at RT
• Solubility: DMSO: >5 mg/mL
• PKA: 6.33±0.10(Predicted)
• CAS DataBase Reference: NS-398(CAS DataBase Reference)
• NIST Chemistry Reference: NS-398(123653-11-2)
• EPA Substance Registry System: NS-398(123653-11-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: PB0473500
• Hazardous Substances Data: 123653-11-2(Hazardous Substances Data)

Usage

Description

NS-398 is a selective inhibitor of cyclooxygenase-2 (COX-2), a C-nitro compound that is N-methylsulfonyl-4-nitroaniline bearing an additional cyclohexyloxy substituent at position 2. It exhibits a higher affinity for COX-2 compared to COX-1, with IC50 values of 75 and 1.77 μM for human recombinant COX-1 and -2, respectively, and 220 and 0.15 μM for ovine COX-1 and -2, respectively.

Uses

Used in Pharmaceutical Industry:
NS-398 is used as a selective Cox-2 inhibitor for its neuroprotective properties. It is particularly effective in modulating the inflammatory response and has potential applications in the treatment of various conditions associated with COX-2 overexpression, such as pain, inflammation, and neurodegenerative diseases.
Used in Research Applications:
In the field of research, NS-398 is used as a valuable tool for studying the role of COX-2 in various biological processes and disease mechanisms. It helps researchers understand the molecular pathways involved in inflammation and pain, as well as the potential therapeutic targets for developing new drugs.
Used in Drug Development:
NS-398 serves as a starting point for the development of new drugs targeting COX-2, which may have improved selectivity, potency, and reduced side effects compared to existing COX-2 inhibitors. This can lead to the development of more effective treatments for conditions where COX-2 plays a significant role, such as arthritis, Alzheimer's disease, and cancer.

Biological Activity

Selective cyclooxygenase-2 inhibitor (IC 50 values are 3.8 and > 100 μ M for COX-2 and COX-1 respectively). Induces apoptosis in colorectal tumor cells and elevates COX-2 protein expression in vitro . Orally active and non-ulcerogenic analgesic and anti-inflammatory in vivo .

references

[1]. futaki n, takahashi s, yokoyama m, et al. ns-398, a new anti-inflammatory agent, selectively inhibits prostaglandin g/h synthase/cyclooxygenase (cox-2) activity in vitro. prostaglandins, 1994, 47(1): 55-59.[2]. elder dj, halton de, crew te, et al. apoptosis induction and cyclooxygenase-2 regulation in human colorectal adenoma and carcinoma cell lines by the cyclooxygenase-2-selective non-steroidal anti-inflammatory drug ns-398. int j cancer, 2000, 86(4): 553-560.[3]. mack strong ve, mackrell pj, concannon em, et al. ns-398 treatment after trauma modifies nf-kappab activation and improves survival. j surg res, 2001, 98(1): 40-46.

InChI:InChI=1/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

Upstream product

• 121-88-0 5-Nitro-2-aminophenol 
• 626-62-0 Cyclohexyl iodide 
• 183110-93-2 2-cyclohexyloxy-4-nitroaniline 
• 124-63-0 methanesulfonyl chloride 

Relevant articles and documents

Synthesis of carbon-11 labeled sulfonanilide analogues as new potential PET agents for imaging of aromatase in breast cancer

Aromatase is a particularly good target in the treatment of estrogen receptor positive breast cancer. Novel carbon-11 labeled sulfonanilide analogues, N-[11C]methyl-N-(2-alkyloxy-4-nitrophenyl)-methanesulfonamide s ([11C]3a-f, alkyl

Novel sulfonanilide analogues suppress aromatase expression and activity in breast cancer cells independent of COX-2 inhibition

Aromatase is a particularly attractive target in the treatment of estrogen receptor positive breast cancer. Aromatase levels in breast cancer cells are enhanced by prostaglandins and reduced by COX inhibitors. The synthesis and biological evaluation of a

Antiangiogenic combination therapy for the treatment of cancer

The present invention provides combinations of a DNA topoisomerase I inhibiting agent and a selective COX-2 inhibiting agent for preventing, treating, and/or reducing the risk of developing a neoplasia disorder in a mammal.