N-(4-nitro-2-phenoxyphenyl)methanesulfonamide

• ChemBase ID: 4292
• Molecular Formular: C13H12N2O5S
• Molecular Mass: 308.30978
• Monoisotopic Mass: 308.04669249
• SMILES: [O-][N+](=O)c1ccc(NS(=O)(=O)C)c(c1)Oc1ccccc1
• Canonical SMILES: [O-][N+](=O)c1ccc(c(c1)Oc1ccccc1)NS(=O)(=O)C
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-nitro-2-phenoxyphenyl)methanesulfonamide
• IUPAC Traditional name: nimesulide
• Synonyms: 4-Nitro-2-phenoxymethane-sulfonamide; 4'-Nitro-2'-phenoxymethanesulfonanilide; Aulin; Flogovital; Lizepat; Mesulid; Nimed; Nimepast; Nimsulid; Nimulid; Nise*Gel; Nisulid; Nizer; Orthobid; R 805; Sulide; Sulidene; Nimesulide; N-[4-Nitro-2-phenoxyphenyl]-methanesulfonamide; N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide; Nimesulide

Database IDs

• CAS Number: 51803-78-2
• EC Number: 257-431-4
• MDL Number: MFCD00079470
• PubChem SID: 24278583; 160967724
• PubChem CID: 4495

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.855871
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.7701044
• LogD (pH = 7.4): 1.2792746
• Log P: 1.7866564
• Molar Refractivity: 76.3067 cm^3
• Polarizability: 29.74128 Å^3
• Polar Surface Area: 101.22 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.56
• LOG S: -4.23
• Solubility (Water): 1.82e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 145-147°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer; 2-8°C
• RTECS: PB0970000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 22; R:25
• Safety Statements: 36; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ALB(213), PTGS1(5742), PTGS2(5743)

Product Information

• Salt Data: Free Base
• Empirical Formula (Hill Notation): C13H12N2O5S

DETAILS

MP Biomedicals - 02155838

(N-[4-Nitro-2-phenoxyphenyl]-methanesulfonamide)

DrugBank - DB04743

• Drug Groups: experimental
• Description: Nimesulide is a relatively COX-2 selective, non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Its approved indications are the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old. Due to concerns about the risk of hepatotoxicity, nimesulide has been withdrawn from market in many countries.
• Indication: For the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old.
• Pharmacology: Food, gender and advanced age have negligible effects on nimesulide pharmacokinetics.
• Toxicity: Oral TDLO (human): 1.429 mg/kg; Oral TDLO (woman): 2 mg/kg; Oral LD50 (rat): 200 mg/kg; Oral LD50 (mouse): 392 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Extensive biotransformation, mainly to 4-hydroxynimesulide (which also appears to be biologically active).
• Absorption: Rapidly absorbed following oral administration.
• Half Life: 1.8–4.7 hours
• Protein Binding: >97.5%
• Elimination: Renal (50%), fecal (29%)
• External Links: Wikipedia; Drugs.com

Selleck Chemicals - S2040

Research Area: Inflammation
Biological Activity:

Sigma Aldrich - N1016

Biochem/physiol Actions
Highly selective cyclooxygenase-2 inhibitor.

Toronto Research Chemicals - N477500

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

REFERENCES

• Pairet, M., et al.: Inflamm. Res., 47, S93 (1998)
• Fukutake, M., et al.: Carcinogenesis, 19, 1939 (1998)
• Okajima., E., et al.: Cancer Res., 58, 3028 (1998)
• Azab, A., et al.: Life Sci., 63, 323 (1998)