26171-23-3

• 常用中文名：托麦汀
• 常用英文名：1-Methyl-5-p-toluoylpyrrole-2-acetic acid
• CAS号：26171-23-3
• 分子式：C₁₅H₁₅NO₃
• 分子量：257.284
• 相关类别： 信号通路 免疫及炎症 COX
• 发布时间：2018-03-29 08:00:00
• 更新时间：2024-01-02 14:03:05
• Tolmetin 是一种具有口服活性的,有效的 COX 抑制剂,对人 COX-1 和 COX-2 的 IC50 值分别为 0.35 µM 和 0.82 µM。Tolmetin 属于非甾体类物质,具有强效的抗炎活性。

名称

• 中文名: 托麦汀
• 英文名: tolmetin
• 中文别名: 2-[1-甲基-5-(4-甲基苯甲酰)吡咯-2-基]乙酸; 托美汀
• 英文别名: [3H]-Tolmetin; [1-Methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid; EINECS 247-497-2; Tolmetino; 1H-Pyrrole-2-acetic acid, 1-methyl-5-(4-methylbenzoyl)-; Tolmetine; Tolmetina; TOLMETIN; Tolmetinum; 2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetic acid; Tolectin; 5-(p-toluoyl)-1-methylpyrrole-2-acetic acid; 5-(4-methylbenzoyl)-1-methyl-pyrrol-2-ylacetic acid; 1-Methyl-5-p-toluoylpyrrole-2-acetic acid; Tolmetine [INN-French]; 2-(1-Methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl)acetic acid; 1-methyl-5-(4-methylbenzoyl)pyrrol-2-acetic acid; 1-Methyl-5-(p-toluoyl)-2-pyrroleacetic acid; Tolmetina [DCIT]; 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetic acid; 1-METHYL-5-P-TOLUOYL-PYRROLE-2-ACETIC ACID

物化性质

• 密度: 1.2±0.1 g/cm3
• 沸点: 483.2±40.0 °C at 760 mmHg
• 熔点: 156ºC
• 分子式: C₁₅H₁₅NO₃
• 分子量: 257.284
• 闪点: 246.0±27.3 °C
• 精确质量: 257.105194
• PSA: 59.30000
• LogP: 1.55
• 外观性状: 灰白色结晶粉末
• 蒸汽压: 0.0±1.3 mmHg at 25°C
• 折射率: 1.582
• 储存条件: 存放于惰性气体之中;避免空气
• 水溶解性: 222 mg/L

生物活性

• 描述: Tolmetin 是一种具有口服活性的,有效的 COX 抑制剂,对人 COX-1 和 COX-2 的 IC50 值分别为 0.35 µM 和 0.82 µM。Tolmetin 属于非甾体类物质,具有强效的抗炎活性。
• 相关类别:
  研究领域 >> 癌症
  研究领域 >> 炎症/免疫
  信号通路 >> 免疫及炎症 >> COX
• 靶点:

  Human COX-1:0.35 μM (IC50)

  Human COX-2:0.82 μM (IC50)

• 体外研究: 托美汀(0.25mm)对大鼠脑匀浆脂质过氧化无明显影响。托美汀(0.25,0.5,0.75,1mm)在大鼠脑匀浆中显示自由基清除特性,但不产生超氧阴离子[3]。托美汀(0.001-100μM)对HT-29结肠癌细胞具有一定的抗癌活性,且呈剂量依赖性[4]。托美汀(0-100μM)对成骨细胞生长无影响[5]。
• 体内研究: 托美汀(30100mg/kg；灌胃；单次给药或每日两次,持续3天和14天)在单次给药后4h显示出最大的溃疡形成作用,而在体重180-200g的雄性Wistar大鼠中,重复给药3天和14天后,其溃疡作用显著降低。托美汀在100 mg/kg时引起胃损伤[2]。托美汀(5 mg/kg,每天两次,共5天)预处理可显著减轻喹啉酸(QA)诱导的神经毒性[3]。
• 参考文献:

  [1]. T D Warner, et al. Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis. Proc Natl Acad Sci U S A. 1999 Jun 22;96(13):7563-8.

  [2]. DADAŞ, Yakup, et al. Synthesis and anticancer activity of some novel tolmetin thiosemicarbazides. Marmara Pharmaceutical Journal 19(3) • April 2015

  [3]. Etcheverry SB, et al. Three new vanadyl(IV) complexes with non-steroidal anti-inflammatory drugs (Ibuprofen, Naproxen and Tolmetin). Bioactivity on osteoblast-like cells in culture. J Inorg Biochem. 2002 Jan 1;88(1):94-100.

  [4]. Etcheverry SB, et al. Three new vanadyl(IV) complexes with non-steroidal anti-inflammatory drugs (Ibuprofen, Naproxen and Tolmetin). Bioactivity on osteoblast-like cells in culture. J Inorg Biochem. 2002 Jan 1;88(1):94-100.

  [5]. Etcheverry SB, et al. Three new vanadyl(IV) complexes with non-steroidal anti-inflammatory drugs (Ibuprofen, Naproxen and Tolmetin). Bioactivity on osteoblast-like cells in culture. J Inorg Biochem. 2002 Jan 1;88(1):94-100.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : UX9287000 CHEMICAL NAME : Pyrrole-2-acetic acid, 1-methyl-5-p-toluoyl- CAS REGISTRY NUMBER : 26171-23-3 BEILSTEIN REFERENCE NO. : 0485305 LAST UPDATED : 199612 DATA ITEMS CITED : 10 MOLECULAR FORMULA : C15-H15-N-O3 MOLECULAR WEIGHT : 257.31 WISWESSER LINE NOTATION : T5NJ A1 BVR D1& E1VQ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 293 mg/kg TOXIC EFFECTS : Gastrointestinal - ulceration or bleeding from stomach REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 25,1526,1975 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Rectal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 744 mg/kg TOXIC EFFECTS : Biochemical - Metabolism (Intermediary) - effect on inflammation or mediation of inflammation REFERENCE : AFTOD7 Archivos de Farmacologia y Toxicologia. (Universidad Complutense, Facultad de Medicina, Departamento Coordinado de Farmacologia, Ciudad Universitaria, Madrid 3, Spain) V.1- 1975- Volume(issue)/page/year: 5,257,1979 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 914 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 38,90,1983 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 600 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 38,90,1983 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 680 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 8,45,1977 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Unreported SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1107 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 19,460,1984 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - species unspecified DOSE/DURATION : 300 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : IJMRAQ Indian Journal of Medical Research. (Indian Council of Medical Research, Ansari Nagar, New Delhi 110 029, India) V.1- 1913- Volume(issue)/page/year: 81,621,1985 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 200 mg/kg/4D-I TOXIC EFFECTS : Gastrointestinal - ulceration or bleeding from stomach REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 52,454,1980 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 1680 mg/kg/8W-I TOXIC EFFECTS : Brain and Coverings - other degenerative changes Liver - other changes Nutritional and Gross Metabolic - changes in metals, not otherwise specified REFERENCE : TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: (Suppl),245,1992 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 20600 ug/kg SEX/DURATION : female 21 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 30(1),25A,1984

安全

• 危害码 (欧洲): Xi
• 海关编码: 2933990090

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海关

海关编码	2933990090
中文概述	2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%
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Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%