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Nimesulide

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  • Nimesulide
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  • $30.00 / 25mg
  • 2026-02-01
  • CAS:51803-78-2
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  • Purity: 98.00%
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Nimesulide Basic information
Product Name:Nimesulide
Synonyms:nimed;4-NITRO-2-PHENOXYMETHANE SULPHONANILIDE;CETIRIZINE DIHYDROCHLORIDE EPC(CRM STANDARD);CETIRIZINE DIHYDROCHLORIDE IMP. E (EP):(RS)-2-[2-[2-[4-[(4-CHLOROPHENYL)-PHENYLMETHYL]PIPERAZIN-1-YL]ETHOXY]ETHOXY]ACETIC ACID MM(CRM STANDARD);CETIRIZINE DIHYDROCHLORIDE MM(CRM STANDARD);4-Nitro-2-phenoxymethanesulfonamide;Nide;Nidol
CAS:51803-78-2
MF:C13H12N2O5S
MW:308.31
EINECS:257-431-4
Product Categories:All Inhibitors;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Active Pharmaceutical Ingredients;Aromatics;Isotope Labelled Compounds;Sulfur & Selenium Compounds;Other APIs;51803-78-2
Mol File:51803-78-2.mol
Nimesulide Structure
Nimesulide Chemical Properties
Melting point 140-146°C
Boiling point 442.0±55.0 °C(Predicted)
density 1.451±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility Practically insoluble in water, freely soluble in acetone, slightly soluble in anhydrous ethanol.
pkapKa 6.56± 0.03(H2O,t =25,I=0.02)(Approximate)
form Solid
color Light orange to Yellow to Green
biological sourcesynthetic (organic)
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), DMF (15 mg/ml), chloroform, dichloromethane, acetone (freely soluble), and 1N NaOH.
λmax391nm(H2O)(lit.)
Merck 14,6548
Stability:Stable. Incompatible with strong oxidizing agents.
Major Applicationpharmaceutical (small molecule)
InChI1S/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3
InChIKeyHYWYRSMBCFDLJT-UHFFFAOYSA-N
SMILESCS(NC1=C(OC2=CC=CC=C2)C=C([N+]([O-])=O)C=C1)(=O)=O
CAS DataBase Reference51803-78-2(CAS DataBase Reference)
EPA Substance Registry SystemMethanesulfonamide, N-(4-nitro-2-phenoxyphenyl)- (51803-78-2)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 36-26
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS PB0970000
HS Code 2935.90.9500
HazardClass 6.1
PackingGroup III
Storage Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsAcute Tox. 3 Oral
ToxicityLD50 orally in rats: 324 mg/kg (Swingle, Moore)
MSDS Information
ProviderLanguage
Nimesulide English
SigmaAldrich English
Nimesulide Usage And Synthesis
DescriptionNimesulide 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.
DescriptionNimesulide 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.
Chemical PropertiesYellow Needle-Like Crystals
OriginatorRiker (USA)
UsesAntiinflammatory agent. Preferentially inhibits COX-2 over COX-1. Suppresses chemical-induced carcinogenesis in mice and rats. Inhibits LPS-induced TNF-alpha production
UsesLabelled 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.
UsesAntiinflammatory;'Cyclooxygenase 2 inhibitor
UsesFor the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old.
UsesLabelled 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
UsesNimesulide 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]
DefinitionChEBI: Nimesulide is an aromatic ether having phenyl and 2-methylsulfonamido-5-nitrophenyl as the two aryl groups. It has a role as a cyclooxygenase 2 inhibitor and a non-steroidal anti-inflammatory drug. It is a C-nitro compound, a sulfonamide and an aromatic ether. It is functionally related to a nitrobenzene.
Brand nameNimulid.
General DescriptionNimesulide, a nonsteroidal anti-inflammatory drug (NSAID) belongs to the sulfonanilide class.
Biological ActivitySelective, orally active cyclooxygenase-2 (COX-2) inhibitor. Produces potent analgesic, anti-inflammatory and antipyretic activities in vivo . Reported to produce fewer gastrointestinal side effects than standard NSAIDs.
Biochem/physiol ActionsHighly selective cyclooxygenase-2 inhibitor.
Clinical UseNimesulide 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.
Synthesis
4-Nitro-2-phenoxyaniline

5422-92-4

Methanesulfonyl chloride

124-63-0

Nimesulide

51803-78-2

General procedure for the synthesis of N-(4-nitro-2-phenoxyphenyl)methanesulfonamide from 4-nitro-2-phenoxyaniline and methanesulfonyl chloride: 4-nitro-2-phenoxyaniline (500 mg, 2.2 mmol) was dissolved in anhydrous methylene chloride (2.2 mL), anhydrous triethylamine (484 μL, 3.5 mmol) was added, and the reaction was stirred for 1 min at room temperature. Methanesulfonyl chloride (840 μL, 10.9 mmol) was added dropwise to the reaction mixture under cooling in an ice bath. The reaction mixture was stirred for 23 hours and then the reaction was quenched with distilled water. The reaction was extracted with chloroform and the organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent. To the residue was added 3M aqueous sodium hydroxide solution (10 mL) and stirred at 80-90 °C for 16 hours. After completion of the reaction, it was acidified by adding 5 M hydrochloric acid and extracted again with chloroform. The organic phases were combined, dried over anhydrous sodium sulfate and filtered, and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with the eluent of chloroform/hexane/acetone (1:8:1) to afford N-(4-nitro-2-phenoxyphenyl)methanesulfonamide (497.4 mg, 74.3% yield) as a light yellow solid with a melting point of 142-144 °C (literature value: 143-144.5 °C). The product was confirmed by 1H NMR (600 MHz, DMSO-d6), FTIR (KBr) and mass spectrometry (EI-MS, HR-MS).

Referenceshttps://en.wikipedia.org/wiki/Nimesulide
https://www.drugbank.ca/drugs/DB04743
Tag:Nimesulide(51803-78-2) Related Product Information
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