110690-43-2

• 常用中文名：乙嘧替氟
• 常用英文名：emitefur
• CAS号：110690-43-2
• 分子式：C₂₈H₁₉FN₄O₈
• 分子量：558.47100
• 相关类别： 原料药 抗肿瘤药 抗代谢类抗肿瘤药
• 发布时间：2018-03-14 08:00:00
• 更新时间：2024-01-16 20:17:18
• Emitefur 是一种有口服活性的,有效的抗癌药物。Emitefur 可用于晚期胃癌患者。

名称

• 中文名: 乙嘧替氟
• 英文名: (6-benzoyloxy-3-cyanopyridin-2-yl) 3-[3-(ethoxymethyl)-5-fluoro-2,6-dioxopyrimidine-1-carbonyl]benzoate
• 中文别名: 依米替氟:BOF-A2; 3-[[3-(乙氧基甲基)-5-氟-3,6-二氢-2,6-二氧-L(2H)-嘧啶基]羧基]苯甲酸

物化性质

• 密度: 1.52 g/cm3
• 沸点: 755.1ºC at 760 mmHg
• 熔点: 162-164°
• 分子式: C₂₈H₁₉FN₄O₈
• 分子量: 558.47100
• 闪点: 410.5ºC
• 精确质量: 558.11900
• PSA: 159.58000
• LogP: 2.53668
• 蒸汽压: 1.09E-22mmHg at 25°C
• 折射率: 1.663
• 分子结构:

  1、 摩尔折射率：136.16

  2、 摩尔体积（cm³/mol）：367.3

  3、 等张比容（90.2K）：1094.6

  4、 表面张力（dyne/cm）：78.8

  5、 极化率（10-24cm3）：53.97

• 计算化学:

  1.疏水参数计算参考值（XlogP）:3.6

  2.氢键供体数量:0

  3.氢键受体数量:11

  4.可旋转化学键数量:10

  5.互变异构体数量:无

  6.拓扑分子极性表面积156

  7.重原子数量:41

  8.表面电荷:0

  9.复杂度:1110

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1.熔点：162～164℃。

生物活性

• 描述: Emitefur 是一种有口服活性的,有效的抗癌药物。Emitefur 可用于晚期胃癌患者。
• 相关类别:
  研究领域 >> 癌症
  信号通路 >> 其他 >> 其他
• 参考文献:

  [1]. Sugimachi K, et al. A phase II trial of a new 5-fluorouracil derivative, BOF-A2 (Emitefur), for patients with advanced gastric cancer. Surg Today. 2000;30(12):1067-72.

毒性和生态

毒理学数据: 急性毒性LD50小鼠，雄大鼠，雌大鼠(mg/kg)：＞5000，1850，1934 口服。 CHEMICAL IDENTIFICATION RTECS NUMBER : DG9895000 CHEMICAL NAME : Benzoic acid, 3-((3-(ethoxymethyl)-5-fluoro-3,6-dihydro-2,6-dioxo-1 (2H)-pyrimidinyl) carbonyl)-, 6-(benzoyloxy)-3-cyano-2-pyridinyl ester CAS REGISTRY NUMBER : 110690-43-2 LAST UPDATED : 199503 DATA ITEMS CITED : 13 MOLECULAR FORMULA : C28-H19-F-N4-O8 MOLECULAR WEIGHT : 558.51 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 : 1850 mg/kg TOXIC EFFECTS : Blood - changes in spleen Skin and Appendages - hair Nutritional and Gross Metabolic - body temperature decrease TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 250 mg/kg TOXIC EFFECTS : Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >5 gm/kg TOXIC EFFECTS : Gastrointestinal - other changes Blood - changes in spleen Nutritional and Gross Metabolic - body temperature decrease TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Primate - monkey DOSE/DURATION : 250 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Gastrointestinal - hypermotility, diarrhea Blood - changes in spleen TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 3640 mg/kg/13W-I TOXIC EFFECTS : Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 3640 mg/kg/1Y-I TOXIC EFFECTS : Behavioral - food intake (animal) Blood - changes in spleen Blood - other changes TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Primate - monkey DOSE/DURATION : 7280 mg/kg/1Y-I TOXIC EFFECTS : Nutritional and Gross Metabolic - changes in chlorine Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - dehydrogenases TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Primate - monkey DOSE/DURATION : 2730 mg/kg/13W-I TOXIC EFFECTS : Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 520 mg/kg SEX/DURATION : female 17-21 day(s) after conception lactating female 21 day(s) post-birth TOXIC EFFECTS : Reproductive - Effects on Newborn - behavioral TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 65 mg/kg SEX/DURATION : female 6-18 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system TYPE OF TEST : Micronucleus test MUTATION DATA TYPE OF TEST : Cytogenetic analysis TEST SYSTEM : Rodent - hamster Ovary DOSE/DURATION : 60 mg/L REFERENCE : JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 18(Suppl 3),11,1993

制备

间苯二甲酰氯(Ⅰ)和化合物(Ⅱ)在三乙胺作用下，在二氧六环中回流，缩合得到化合物(Ⅲ)。再和化合物(Ⅳ)在三乙胺及乙腈中回流，即得乙嘧替氟。
上述合成中用到的化合物(Ⅳ)可由苯甲酰氯和3-氰基-2，6-二羟基吡啶，在三乙胺及二甲基甲酰胺中缩合而得。