2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid

• ChemBase编号: 383
• 分子式: C15H15NO3
• 平均质量: 257.2845
• 单一同位素质量: 257.10519335
• SMILES: O=C(c1n(c(cc1)CC(=O)O)C)c1ccc(cc1)C
• Canonical SMILES: OC(=O)Cc1ccc(n1C)C(=O)c1ccc(cc1)C
• InChI: InChI=1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18)
• InChIKey: UPSPUYADGBWSHF-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid
• IUPAC传统名: [1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetic acid; tolmetin
• 商标名: Tolectin; Tolectin DS
• 别名: 1-Methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetic Acid Sodium Dihydrate; 1-Methyl-5-p-toluoylpyrrole-2-acetic Acid Sodium Dihydrate; 5-[(p-Tolyl)carbonyl]-1-methylpyrrole-2-acetic Acid Sodium Dihydrate; McN 2559-21-98; Tolectin; Tolmene; Tolmetin Sodium Salt Dihydrate; Tolmetine [INN-French]; Tolmetino [INN-Spanish]; Tolmetinum [INN-Latin]; Tolmetina [DCIT]; Tolmetin Sodium; Tolmetin; 1-Methyl-5-p-toluoylpyrrole-2-acetic acid; 2-(1-Methyl-5-(4-Methylbenzoyl)-1H-pyrrol-2-yl)acetic acid

登记号

• CAS号: 26171-23-3; 64490-92-2
• MDL号: MFCD00599595
• PubChem SID: 46507060; 160963846
• PubChem CID: 5509
• ATC码: M02AA21; M01AB03
• CHEMBL: 1020
• Chemspider ID: 5308
• DrugBank ID: DB00500
• KEGG ID: D02355
• 美国药典/FDA物质标识码: D8K2JPN18B
• 维基百科标题: Tolmetin
• Medline Plus: a681033

理论计算性质

JChem

• Acid pKa: 3.9581683
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 1.1776481
• LogD (pH = 7.4): -0.4552389
• Log P: 2.727331
• 摩尔折射率: 72.3928 cm^3
• 极化性: 27.405663 Å^3
• 极化表面积: 59.3 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: 2.81
• LOG S: -3.29
• 溶解度: 1.31e-01 g/l

分子性质

理化性质

• 溶解度: 222 mg/L; Water
• 外观: White Solid
• 熔点: >288°C (dec.)
• 疏水性(logP): 2.6

安全信息

• 保存条件: -20°C Freezer
• 保存注意事项: IRRITANT
• TSCA收录: false

药理学性质

• 给药途径: oral
• 半衰期: 1-2 hours, next phase up to 5 hours

产品相关信息

• 纯度: 95+%; 97%

详细说明

DrugBank - DB00500

• Drug Groups: approved
• Description: A non-steroidal anti-inflammatory agent (anti-inflammatory agents, NON-steroidal) similar in mode of action to indomethacin. [PubChem]
• Indication: For the relief of signs and symptoms of rheumatoid arthritis and osteoarthritis, including the treatment of acute flares long-term management. Also for treatment of juvenile rheumatoid arthritis.
• Pharmacology: Tolmetin is a nonsteroidal anti-inflammatory agent. Studies in animals have shown tolmetin to possess anti-inflammatory, analgesic and antipyretic activity. In the rat, tolmetin prevents the development of experimentally induced polyarthritis and also decreases established inflammation. In patients with either rheumatoid arthritis or osteaoarthritis, tolmetin is as effective as aspirin and indomethacin in controlling disease activity, but the frequency of the milder gastrointestinal adverse effects and tinnitus was less than in aspirin-treated patients, and the incidence of central nervous system adverse effects was less than in indomethacin-treated patients. In patients with juvenile rheumatoid arthritis, tolmetin is as effective as aspirin in controlling disease activity, with a similar incidence of adverse reactions. tolmetin has produced additional therapeutic benefit when added to a regimen of gold salts and, to a lesser extent, with corticosteroids. Tolmetin should not be used in conjunction with salicylates since greater benefit from the combination is not likely, but the potential for adverse reactions is increased.
• Toxicity: Symptoms of overdose include lethargy, drowsiness, nausea, vomiting, and epigastric pain.
• Affected Organisms: Humans and other mammals
• Biotransformation: Essentially all of the administered dose is recovered in the urine in 24 hours either as an inactive oxidative metabolite or as conjugates of tolmetin.
• Absorption: Rapidly and almost completely absorbed with peak plasma levels being reached within 30-60 minutes after an oral therapeutic dose.
• Half Life: Biphasic elimination from the plasma consisting of a rapid phase with a half-life of one to 2 hours followed by a slower phase with a half-life of about 5 hours.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - T535350

Anti-inflammatory.

参考文献

• Carson, et al.: J. Med. Chem., 14, 646 (1971)
• Wong, S., et al.: J. Pharmacol. Exp. Ther., 185, 127 (1971)
• Brogden, R.N., et al.: Drugs, 15, 429 (1971)