| Identification | More | [Name]
Nimesulide | [CAS]
51803-78-2 | [Synonyms]
4-NITRO-2-PHENOXYMETHANE SULPHONANILIDE
AULIN
FANSIDOL
MESULID
N-(4-NITRO-2-PHENOXY)METHANESULFONANILIDE
N-(4-NITRO-2-PHENOXYPHENYL)METHANESULFONAMIDE
NIMESULIDE
R-805
4’-nitro-2’-phenoxy-methanesulfonanilid
4-nitro-2-phenoxy-methanesulfonanilide
flogovital
n-(4-nitro-2-phenoxyphenyl)-methanesulfonamid
nimed
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
Nisuli | [EINECS(EC#)]
257-431-4 | [Molecular Formula]
C13H12N2O5S | [MDL Number]
MFCD00079470 | [Molecular Weight]
308.31 | [MOL File]
51803-78-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow Needle-Like Crystals | [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. | [form ]
neat | [pka]
pKa 6.56± 0.03(H2O,t =25,I=0.02)(Approximate) | [color ]
Light orange to Yellow to Green | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [biological source]
synthetic (organic) | [Water Solubility ]
Soluble in water (<50 µg/ml), 1:10 DMSO:PBS (pH 7.2) (<200 µg/ml), ethanol (1 mg/ml), DMSO (15 mg/ml), DMF (15 mg/ml), chloroform, dichloromethane, acetone (freely soluble), and 1N NaOH. | [Usage]
Antiinflammatory agent. Preferentially inhibits COX-2 over COX-1. Suppresses chemical-induced carcinogenesis in mice and rats. Inhibits LPS-induced TNF-alpha production | [λmax]
391nm(H2O)(lit.) | [Merck ]
14,6548 | [InChIKey]
HYWYRSMBCFDLJT-UHFFFAOYSA-N | [CAS DataBase Reference]
51803-78-2(CAS DataBase Reference) | [EPA Substance Registry System]
Methanesulfonamide, N-(4-nitro-2-phenoxyphenyl)- (51803-78-2) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
PB0970000
| [HS Code ]
2935.90.9500 | [HazardClass ]
6.1 | [PackingGroup ]
III | [Toxicity]
LD50 orally in rats: 324 mg/kg (Swingle, Moore) |
| Questions and Answers (Q&A) | Back Directory | [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.
| [References]
https://en.wikipedia.org/wiki/Nimesulide
https://www.drugbank.ca/drugs/DB04743
|
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Needle-Like Crystals | [Originator]
Riker (USA) | [Uses]
Antiinflammatory agent. Preferentially inhibits COX-2 over COX-1. Suppresses chemical-induced carcinogenesis in mice and rats. Inhibits LPS-induced TNF-alpha production | [Uses]
Antiinflammatory;'Cyclooxygenase 2 inhibitor | [Uses]
For the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old. | [Uses]
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. | [Uses]
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 | [Uses]
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] | [Definition]
ChEBI: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 name]
Nimulid. | [General Description]
Nimesulide, a nonsteroidal anti-inflammatory drug (NSAID) belongs to the sulfonanilide class. | [Biological Activity]
Selective, 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.牋. | [Biochem/physiol Actions]
Highly selective cyclooxygenase-2 inhibitor. | [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. | [Synthesis]
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). | [storage]
Store at 2-8°C |
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