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Nimesulide

Nimesulide structure

CAS No:
51803-78-2
Formula:
C13H12N2O5S
Chemical 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
Categories:
Active Pharmaceutical Ingredients > Antipyretic Analgesics

Description

Nimesulide is a selective COX-2 inhibitor, with IC50s of 70 nM-70 μM in a time-dependent manner, but it shows no effect on COX-1 (IC50 >100 μM). Nimesulide has potent anti-inflammatory, analgesic and antipyretic properties.

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 It has also been withdrawn from the markets in many countries.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 IC50value 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.

Yellow Needle-Like Crystals

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.

Nimesulide Basic Attributes

Molecular Weight：

308.31

Exact Mass：

308.31

EC Number：

257-431-4

Color/Form：

Light orange to Yellow to Green

HScode：

2935.90.9500

Characteristics

λmax：

391nm(H2O)(lit.)

PSA：

110

XLogP3：

2.6

Appearance：

Yellow Needle-Like Crystals

Density：

1.451±0.06 g/cm3(Predicted)

Melting Point：

140-146°C

Boiling Point：

442.0±55.0 °C(Predicted)

Flash Point：

221.1±31.5 °C

Refractive Index：

1.638

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.

Storage Conditions：

2-8°C

Toxicity：

LD50 orally in rats: 324 mg/kg (Swingle, Moore)

PKA：

pKa 6.56± 0.03(H2O,t =25,I=0.02)(Approximate)

Critical Temperature & Pressure：

2-8°C

Safety Information

Packing level：

III

Hazard category：

6.1

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

Xn,Xi

safety instructions：

36-26

RTECS Number：

PB0970000

Marks：

Xn,Xi

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P301 + P310

Hazard Statements：

22-36/37/38

RIDADR：

UN 2811 6.1/PG 3

Nimesulide Use and Manufacturing

Methods of Manufacturing

Nitrification of brominated benzene produces o-nitrobromobenzene, and undergoes nucleophilic substitution reaction with sodium phenolate to form diphenyl ether derivatives. After catalyzed hydrogenation of Raney nickel to reduce nitro to amino, methanesulfonyl chloride at 85℃ and organic base In the presence of sulfonylation, the final nitration is Nimesulide. The final nitration reaction can proceed as follows. 17.3g (0.675m01) of the sulfonylated product was dissolved in 175ml of hot glacial acetic acid, and with stirring, 5.92g (0.0675mol) 70% nitric acid was added dropwise within 15min. After heating on the steam bath for 4h, pour into water. The precipitate precipitated was filtered and recrystallized with ethanol to obtain a light brown nimesulide, melting point 143-144.5°C.

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]

Antiinflammatory agent. Preferentially inhibits COX-2 over COX-1. Suppresses chemical-induced carcinogenesis in mice and rats. Inhibits LPS-induced TNF-alpha 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.

Drug Function and Efficacy

This product is a non-steroidal anti-inflammatory drug with anti-inflammatory, analgesic and antipyretic effects. Its mechanism of action is not yet fully understood, but it may be mainly related to the inhibition of prostaglandin synthesis, mediator release of leukocytes and oxidative reactions of polymorphonuclear leukocytes.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Nimesulide Granules
Ingredients	The main ingredient of this product is nimesulide, and its chemical name is: N-[4-nitro-2-phenoxyphenyl] methanesulfonamide.
Indication	Due to the high plasma protein binding rate of this product, it may displace other protein-bound drugs. Furosemide affects the absorption of nimesulide, causing the AUC value of nimesulide to decrease by about 25%; fenofibrate, tolbutamide, and salicylic acid can displace nimesulide from plasma proteins, while furosemide, glibenclamide, and therapeutic doses of warfarin have no effect on the binding rate of nimesulide to proteins.
Specifications	50mg
Manufacturer	Suzhou Yushi Pharmaceutical Co., Ltd.

Nimesulide Dispersible Tablets
Ingredients	The main ingredient of this product is nimesulide, and its chemical name is: N-[4-nitro-2-phenoxyphenyl] methanesulfonamide.
Indication	Due to the high plasma protein binding rate of this product, it may displace other protein-bound drugs. Furosemide affects the absorption of nimesulide, causing the AUC value of nimesulide to decrease by about 25%; fenofibrate, tolbutamide, and salicylic acid can displace nimesulide from plasma proteins, while furosemide, glibenclamide, and therapeutic doses of warfarin have no effect on the binding rate of nimesulide to proteins.
Specifications	0.1g
Manufacturer	Guizhou Jisheng Pharmaceutical Co., Ltd.

Nimesulide Capsules
Ingredients	The main ingredient of this product is nimesulide, and its chemical name is: N-[4-nitro-2-phenoxyphenyl] methanesulfonamide.
Indication	Due to the high plasma protein binding rate of this product, it may displace other protein-bound drugs. Furosemide affects the absorption of nimesulide, causing the AUC value of nimesulide to decrease by about 25%; fenofibrate, tolbutamide, and salicylic acid can displace nimesulide from plasma proteins, while furosemide, glibenclamide, and therapeutic doses of warfarin have no effect on the binding rate of nimesulide to proteins.
Specifications	0.1 g
Manufacturer	Hengcheng Pharmaceutical Group Huainan Co., Ltd.

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Registered Holders

Guangzhou Winsun Pharmaceutical Co., Ltd.

China
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