73121-56-9

• 常用中文名：恩前列素
• 常用英文名：Enprostil
• CAS号：73121-56-9
• 分子式：C₂₃H₂₈O₆
• 分子量：400.46
• 相关类别： 原料药 激素及调节内分泌功能类药 前列腺素类药
• 发布时间：2018-03-29 08:00:00
• 更新时间：2024-01-09 11:16:54

• 为合成的去氢PGE2，能抑制动物和人体的基础胃酸和由组胺、五肽胃泌素、食物等引起的胃酸分泌。用于胃炎、胃溃疡及十二指肠溃疡。

名称

• 中文名: 恩前列素
• 英文名: methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate
• 中文别名: 恩前列腺素; [1Α,2Β(1E,3R^^),3Α]-7-[-3-羟基-2-(-3-羟基-4-苯氧基-1-丁烯基)-5-氧环戊基]-4,5-庚二烯酸甲酯
• 英文别名: Enprostil (JAN/USAN/INN); 4,5-Heptadienoic acid, 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5-oxocyclopentyl]-, methyl ester; Syngard; Enprostil; (dl)-9-Keto-11a,15a-dihydroxy-16-phenoxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic Acid Methyl Ester; Camleed (TN); methyl (4,5,6S)-7-<(1R,2R,3R)-3-hydroxy-2-<(E)-(3R)-3-hydroxy-4-phenoxy-1-butenyl>-5-oxocyclopentyl>-4,5-heptadienoate; Gardrine; Methyl 7-{(1R,2R,3R)-3-hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5-oxocyclopentyl}-4,5-heptadienoate; [1a,2b(1E,3R*),3a]-7-[3-Hydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)-5-oxocyclopentyl]-4,5-heptadienoic Acid Methyl Ester; methyl (4,5,6R)-7-<(1R,2R,3R)-3-hydroxy-2-<(E)-(3R)-3-hydroxy-4-phenoxy-1-butenyl>-5-oxocyclopentyl>-4,5-heptadienoate; Camleed; Gardrin; Methyl 7-{(1R,2R,3R)-3-hydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxybut-1-en-1-yl]-5-oxocyclopentyl}hepta-4,5-dienoate

物化性质

• 密度: 1.2±0.1 g/cm3
• 沸点: 552.9±50.0 °C at 760 mmHg
• 分子式: C₂₃H₂₈O₆
• 分子量: 400.46
• 闪点: 185.7±23.6 °C
• 精确质量: 400.188599
• PSA: 93.06000
• LogP: 1.45
• 蒸汽压: 0.0±1.6 mmHg at 25°C
• 折射率: 1.586
• 分子结构:

  1、 摩尔折射率：111.84

  2、 摩尔体积（cm³/mol）：333.2

  3、 等张比容（90.2K）：868.5

  4、 表面张力（dyne/cm）：46.1

  5、 极化率（10-24cm3）：44.33

• 计算化学:

  1.疏水参数计算参考值（XlogP）:1.3

  2.氢键供体数量:2

  3.氢键受体数量:6

  4.可旋转化学键数量:11

  5.互变异构体数量:3

  6.拓扑分子极性表面积93.1

  7.重原子数量:29

  8.表面电荷:0

  9.复杂度:613

  10.同位素原子数量:0

  11.确定原子立构中心数量:4

  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:1

  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.性状：白色或类白色蜡状固体，在30℃软化，46℃液化。

  2.溶解度：极易溶于水，溶于乙醇或丙二醇或碳酸丙烯酯。

  3.UV最大吸收(甲醇)：220，265，271，277nm(ε10200，1380，1740，1450)。

生物活性

• 描述: 恩前列素(RS 84135)是一种前列腺素E2衍生物。恩前列素能抑制阿莫胃泌素刺激的胃酸分泌,并能减少胃蛋白酶的分泌。Enprostil也可以作为抗溃疡剂,用于十二指肠或胃溃疡的研究[1][2]。
• 相关类别:
  研究领域 >> 内分泌
  信号通路 >> 其他 >> 其他
• 参考文献:

  [1]. Kohli Y, et al. Antisecretory effect of a PGE2 derivative, enprostil (TA/RS-84135): inhibitory action of amogastrin-stimulated secretion. Drugs Exp Clin Res. 1988;14(11):673-8.

  [2]. Goa K L, et al. Enprostil: a preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in the treatment of peptic ulcer disease[J]. Drugs, 1987, 34(5): 539-559.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : MI5433000 CHEMICAL NAME : 4,5-Heptadienoic acid, 7-(3-hydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)-5-oxoc yclopentyl)-, methyl ester, (1-alpha,2-beta(1E,3R*),3-alpha)- CAS REGISTRY NUMBER : 73121-56-9 LAST UPDATED : 199504 DATA ITEMS CITED : 5 MOLECULAR FORMULA : C23-H28-O6 MOLECULAR WEIGHT : 400.51 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 : >1600 ug/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - cyanosis Musculoskeletal - other changes Nutritional and Gross Metabolic - body temperature decrease REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 23,2327,1989 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >160 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 23,2327,1989 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1600 ug/kg TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Gastrointestinal - changes in structure or function of salivary glands REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 23,2327,1989 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 80 ug/kg TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - ptosis Behavioral - tremor Nutritional and Gross Metabolic - body temperature decrease REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 23,2327,1989 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Primate - monkey DOSE/DURATION : >320 ug/kg TOXIC EFFECTS : Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 23,2327,1989

合成路线

157543-66-3 ~67% 73121-56-9

文献：Gooding, Owen W.; Beard, Colin C.; Cooper, Gary F.; Jackson, David Y. Journal of Organic Chemistry, 1993 , vol. 58, # 14 p. 3681 - 3686

286840-19-5 ~% 73121-56-9

文献：Synthesis, , # 8 p. 792 - 794

54347-99-8 ~% 73121-56-9

文献：Synthesis, , # 8 p. 792 - 794

286840-20-8 ~% 73121-56-9

文献：Synthesis, , # 8 p. 792 - 794

117253-98-2 ~% 73121-56-9

文献：Journal of the Chemical Society, Chemical Communications, , # 10 p. 1251 - 1252

149862-37-3 ~% 73121-56-9

文献：Journal of the Chemical Society, Chemical Communications, , # 10 p. 1251 - 1252

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制备

化合物(Ⅰ)先经硅烷化，再氧化，然后脱硅烷基，得到恩前列素。