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
Show more names
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
- Formal charge
- 0
- Complexity
- 450
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)
- form
- Solid
- color
- Light orange to Yellow to Green
- 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.
- λmax
- 391 nm · 391nm(H2O)(lit.)
- Merck
- 14 · 14,6548
- Stability
- Stable. Incompatible with strong oxidizing agents.
- Major Application
- pharmaceutical (small molecule)
- InChI
- 1S/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
- InChIKey
- HYWYRSMBCFDLJT-UHFFFAOYSA-N
- SMILES
- CS(NC1=C(OC2=CC=CC=C2)C=C([N+]([O-])=O)C=C1)(=O)=O
- CAS DataBase Reference
- 51803 · 51803-78-2(CAS DataBase Reference)
- FDA UNII
- 4 TKW1454M · V4TKW1454M
- ATC code
- 1 AX17,M02AA26 · M01AX17,M02AA26
- EPA Substance Registry System
- Methanesulfonamide, N-(4-nitro-2-phenoxyphenyl)- (51803-78-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301
- Precautionary statements
- 301 · P301+P310+P330
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 36 · 36-26
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 970000 · PB0970000
- HS Code
- 2935.9 · 2935.90.9500
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 Oral · Acute Tox. 3 Oral
- Toxicity
- 50 orally · LD50 orally in rats: 324 mg/kg (Swingle, Moore)
- Limited Quantities
- 5 kg · 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
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
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn,Xi
- safety_code
- 36-26
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301
- Limited Quantities
- 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P301+P310+P330
Chemistry & industry
Applications
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.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
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
Linked notes
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