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

• ChemBase编号: 4292
• 分子式: C13H12N2O5S
• 平均质量: 308.30978
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: N-(4-nitro-2-phenoxyphenyl)methanesulfonamide
• IUPAC传统名: nimesulide
• 别名: 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

登记号

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

理论计算性质

JChem

• Acid pKa: 6.855871
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 1.7701044
• LogD (pH = 7.4): 1.2792746
• Log P: 1.7866564
• 摩尔折射率: 76.3067 cm^3
• 极化性: 29.74128 Å^3
• 极化表面积: 101.22 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.56
• LOG S: -4.23
• 溶解度: 1.82e-02 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: Pale Yellow Solid
• 熔点: 145-147°C

安全信息

• 保存条件: -20°C; -20°C Freezer; 2-8°C
• RTECS编号: PB0970000
• 欧盟危险性物质标志: 有毒(Toxic) (T); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3; III
• 澳大利亚Hazchem: 2X
• 危险公开号: 22; R:25
• 安全公开号: 36; S:28-29-36/37/39-45
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P301 + P310
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... ALB(213), PTGS1(5742), PTGS2(5743)

产品相关信息

• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C13H12N2O5S

详细说明

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 Due to concerns about the risk of hepatotoxicity, nimesulide has been withdrawn from market in many countries.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.

参考文献

• 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)