Nimesulide

HCID 4495CAS 51803-78-2

Basic information

Standard SMILES
CS(=O)(=O)Nc1ccc([N+](=O)[O-])cc1Oc1ccccc1
InChIKey
HYWYRSMBCFDLJT-UHFFFAOYSA-N
Molecular formula
C13H12N2O5S
Average molar mass
308.31 g/mol
Monoisotopic mass
308.04669266

Names & identifiers

Preferred name
Nimesulide
IUPAC
N-(4-nitro-2-phenoxyphenyl)methanesulfonamide
English name
Nimesulide
Molecular formula
C13H12N2O5S
Molecular weight
308.31

Names & synonyms

nimesulide51803-78-2N-(4-Nitro-2-phenoxyphenyl)methanesulfonamideAulinR-805Nimesulida4-NITRO-2-PHENOXYMETHANESULFONANILIDEMethanesulfonamide, N-(4-nitro-2-phenoxyphenyl)-NimesulidumR 8054'-Nitro-2'-phenoxymethanesulfonanilideDTXSID3037250
Show more names
Nimesulide-d5Nimesulide for peak identificationNideNidolnimedAufinNisuli
NSC-758412V4TKW1454MDTXCID1017250CHEBI:44445N-(4-nitro-2-(phenoxy)phenyl)methanesulfonamideN-[4-nitro-2-(phenoxy)phenyl]methanesulfonamideRefChem:6063M01AX17

Database identifiers

CAS
51803-78-2
PubChem CID
4495
DTXSID
DTXSID3037250
ChEMBL
CHEMBL56367
ChEBI
CHEBI:44445
UNII
V4TKW1454M
EC Number
257-431-4
Nikkaji
J12.917H

Properties

Computed structural properties

XLogP
2.6
Topological polar surface area
110 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
6
Rotatable bonds
4
Heavy atoms
21

Physicochemical properties

Melting point
140 · 140-146°C
Boiling point
442 · 442.0±55.0 °C(Predicted)
Density
1.451 · 1.451±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
Practically insoluble in water, freely soluble in acetone, slightly soluble in anhydrous ethanol.
pka
6.56 · pKa 6.56± 0.03(H2O,t =25,I=0.02)(Approximate)

Safety & regulation

Safety data

wgk
3
rtecs
PB0970000
ridadr
UN 2811 6.1/PG 3
hs_code
2935.90.9500
Toxicity
LD50 orally in rats: 324 mg/kg (Swingle, Moore)
risk_code
22-36/37/38

Chemistry & industry

Applications · 9 items

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.

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.

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]

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

General DescriptionNimesulide, a nonsteroidal anti-inflammatory drug (NSAID) belongs to the sulfonanilide class.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海策嵘生物科技有限公司[email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
Additional notes · 1 item

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.

Related reactions

3 records

Linked notes

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