Nimesulide

Base Information

• Chemical Name: Nimesulide
• CAS No.: 51803-78-2
• Molecular Formula: C13H12N2O5S
• Molecular Weight: 308.315
• European Community (EC) Number: 257-431-4
• NSC Number: 758412
• UNII: V4TKW1454M
• DSSTox Substance ID: DTXSID3037250
• Nikkaji Number: J12.917H
• Wikipedia: Nimesulide
• Wikidata: Q20994
• NCI Thesaurus Code: C29842
• Pharos Ligand ID: 8S5C11D5RX6Z,8SRPZB8H6YD1
• Metabolomics Workbench ID: 52381
• ChEMBL ID: CHEMBL56367
• Mol file: 51803-78-2.mol

Synonyms:4-nitro-2-phenoxymethanesulfonanilide;Antifloxil;Aulin;Eskaflam;Guaxan;lizepat;Mesulid;Nexen;Nimesil;nimesulide;R 805;R-805;Redaflam

Chemical Property of Nimesulide

Chemical Property:

• Appearance/Colour: Yellow Needle-Like Crystals
• Melting Point: 140-146 °C
• Boiling Point: 442 °C at 760 mmHg
• PKA: pKa 6.56± 0.03(H2O,t =25,I=0.02)(Approximate)
• Flash Point: 221.1 °C
• PSA: 109.60000
• Density: 1.451 g/cm³
• LogP: 4.43560
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, freely soluble in acetone, slightly soluble in anhydrous ethanol.
• Water Solubility.: Soluble in water (<50 &#181;g/ml), 1:10 DMSO:PBS (pH 7.2) (<200 &#181;g/ml), ethanol (1 mg/ml), DMSO (15 mg/ml), D
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 308.04669266
• Heavy Atom Count: 21
• Complexity: 450

Purity/Quality:

99%min , ^*data from raw suppliers

Nimesulide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Nonsteroidal Antiinflammatory Drugs
• Canonical SMILES: CS(=O)(=O)NC1=C(C=C(C=C1)[N+](=O)[O-])OC2=CC=CC=C2
• Recent ClinicalTrials: Comparative Analysis of the Effectiveness of the Use of Nimesulide and CBD Oil in Patients With Pain in the Preauricular Region Due to the Pain-dysfunctional Syndrome of the Temporomandibular Joint.
• Recent EU Clinical Trials: EFFICACY AND TOLERABILITY OF NIMESULIDE FOR THE TREATMENT OF MIGRAINE TTACKS: A RANDOMISED, MULTICOUNTRY, DOUBLE BLIND, PLACEBO CONTROLLED, CROSS-OVER TRIAL
• Recent NIPH Clinical Trials: THE ROLE OF LIFE STYLE AND DIET MODIFICATIONS ON TREATMENT OF CHRONIC PELVIC PAIN SYNDROME
• Description: Nimesulide is a relatively COX-2 selective, non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. It is indicated for the treatment of acute pain, symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults. However, due to the risk of causing hepatotoxicity, it should not be taken long-term. It has also been withdrawn from the markets in many countries. It mechanism of action is through targeting on various key mediators in the inflammatory process such as COX-2 mediated prostaglandins, free radicals, proteolytic enzymes and histamine. Nimesulide is a non-steroidal anti-inflammatory drug (NSAID) and COX-2 inhibitor (IC50s = 1.27 and 0.03 μM for the human and ovine enzymes, respectively). It is selective for COX-2 over COX-1 (IC50s = 70 and 22 μM for the human and ovine enzymes, respectively). Nimesulide also inhibits sodium-dependent neutral amino acid transporter (B0AT1) with an IC50 value of 23 μM for the rat kidney transporter. It inhibits infection-induced increases in brain prostaglandin E2 (PGE2; ) levels, as well as reduces pyresis (ED50 = 0.3 mg/kg), in yeast-infected rats. Nimesulide (2.9 mg/kg) inhibits formalin-induced hindpaw thermal hyperalgesia in rats.
• Uses: Antiinflammatory agent. Preferentially inhibits COX-2 over COX-1. Suppresses chemical-induced carcinogenesis in mice and rats. Inhibits LPS-induced TNF-alpha production Labelled Nimesulide (N477500). Antiinflammatory agent. Preferentially inhibits COX-2 over COX-1. Suppresses chemical-induced carcinogenesis in mice and rats. Inhibits LPS-induced TNF-α production. Antiinflammatory;'Cyclooxygenase 2 inhibitor For the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old. Labelled Nimesulide . Antiinflammatory agent. Preferentially inhibits COX-2 over COX-1. Suppresses chemical-induced carcinogenesis in mice and rats. Inhibits LPS-induced TNF-α production.;Labeled Nimesulide, intended for use as an internal standard for th Nimesulide is a selective inhibitor of COX-2. The IC50 values are 70 and 1.27 μM for human recombinant COX-1 and -2 (at 20 μM arachidonic acid), respectively, and 22 and 0.03 μM for ovine COX-1 and -2 (at 100 μM arachidonic acid), respectively.[Cayman Chemical]
• Clinical Use: Nimesulide is a nonsteroidal antiinflammatory/analgesic agent useful in the treatment of rheumatoid arthritis, as well as acute inflammation such as that induced by periodontal surgery or urinary tract infections.

Technology Process of Nimesulide

There total 8 articles about Nimesulide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

sodium N-(methylsulfonyl)-N-(4-nitro-2-phenoxyphenyl)sulfamate → nimesulide (51803-78-2)

Guidance literature:

With hydrogenchloride; In water; pH=~ 2;

Reference yield: 74.3%

1-amino-2-phenoxy-4-nitrobenzene (5422-92-4) + methanesulfonyl chloride (124-63-0) → nimesulide (51803-78-2)

Guidance literature:

1-amino-2-phenoxy-4-nitrobenzene; methanesulfonyl chloride; With triethylamine; In dichloromethane; at 20 ℃; for 23h; Cooling with ice;

With sodium hydroxide; In water; for 16h; Reflux;

DOI:10.1016/j.bmc.2015.10.007

Reference yield:

5-Nitro-2-aminophenol (121-88-0) → nimesulide (51803-78-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic acid / Reflux

2.1: copper diacetate; pyridine N-oxide; pyridine; oxygen / dichloromethane / 72 h / 20 °C / Molecular sieve

3.1: hydrazine hydrate / methanol / 6 h / Reflux

4.1: triethylamine / dichloromethane / 23 h / 20 °C / Cooling with ice

4.2: 16 h / Reflux

With pyridine; pyridine N-oxide; oxygen; copper diacetate; hydrazine hydrate; acetic acid; triethylamine; In methanol; dichloromethane;

DOI:10.1016/j.bmc.2015.10.007

upstream raw materials:

N-(2-Phenoxyphenyl)-methansulfonamid

5-Nitro-2-aminophenol

2-(2-hydroxy-4-nitrophenyl)isoindoline-1,3-dione

1-amino-2-phenoxy-4-nitrobenzene

Downstream raw materials:

N-(4-amino-2-phenoxy phenyl) methanesulfonamide

4-Hydroxy-Nimesulide

4-hydroxylamine nimesulide

N-Methyl-N-(4-nitro-2-phenoxy-phenyl)-methanesulfonamide

Refernces

1,2,3-Triazole-nimesulide hybrid: Their design, synthesis and evaluation as potential anticancer agents

10.1016/j.bmcl.2016.12.030

This research explores the creation of a new hybrid template that integrates the structural features of nimesulide and the 1,2,3-triazole moiety, eliminating the problematic nitro group of nimesulide. The compounds were synthesized using a mild and greener CuAAC approach in water, resulting in a library of molecules with potential anticancer properties. The synthesized compounds were tested against various cancer cell lines, including A549 (lung cancer), HepG2 (liver cancer), HeLa (cervical cancer), and DU145 (prostate cancer), with three compounds (3f, 3g, and 3i) showing promising growth inhibition (IC50 ~ 6-10 μM) and selective activity towards cancer cells. These compounds also inhibited PDE4B in vitro (60-70% at 10 μM), supported by docking studies with PLP scores ranging from 87 to 94. The study concludes that the new hybrid template could be useful for identifying novel anticancer agents, and the described methodology offers an eco-friendly approach for synthesizing such compounds.

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