benzyl 2-{2-[(acetylsulfanyl)methyl]-3-phenylpropanamido}acetate

• ChemBase编号: 73050
• 分子式: C21H23NO4S
• 平均质量: 385.47662
• 单一同位素质量: 385.13477922
• SMILES: c1ccc(cc1)COC(=O)CNC(=O)C(CSC(=O)C)Cc1ccccc1
• Canonical SMILES: O=C(CNC(=O)C(Cc1ccccc1)CSC(=O)C)OCc1ccccc1
• InChI: InChI=1S/C21H23NO4S/c1-16(23)27-15-19(12-17-8-4-2-5-9-17)21(25)22-13-20(24)26-14-18-10-6-3-7-11-18/h2-11,19H,12-15H2,1H3,(H,22,25)
• InChIKey: ODUOJXZPIYUATO-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: benzyl 2-{2-[(acetylsulfanyl)methyl]-3-phenylpropanamido}acetate
• IUPAC传统名: racecadotril; benzyl 2-{2-[(acetylsulfanyl)methyl]-3-phenylpropanamido}acetate
• 别名: (±)-Acetorphan; (RS)-Benzyl N-[3-(acetylthio)-2-benzylpropanoyl]glycinate; Cadotril; Redotil; Tiorfan; Zedott; Racecadotril; Acetorphan; Racecadotril; N-[2-[(Acetylthio)methyl]-1-oxo-3-phenylpropyl]glycine Phenylmethyl Ester; (+/-)-Racecadotril

登记号

• CAS号: 81110-73-8
• MDL号: MFCD00865520
• PubChem SID: 162037970
• PubChem CID: 107751

理论计算性质

• Acid pKa: 12.602205
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 3.1748388
• LogD (pH = 7.4): 3.1748364
• Log P: 3.1748388
• 摩尔折射率: 105.9974 cm^3
• 极化性: 41.64099 Å^3
• 极化表面积: 72.47 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; DMSO: ≥44 mg/mL; Methanol
• 外观: White Solid; white to tan powder
• 熔点: 72-74°C

安全信息

• 保存条件: -20°C; Refrigerator
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-50/53
• 安全公开号: 60-61
• GHS危险品标识: GHS07; GHS09
• GHS警示词: Warning
• GHS危险声明: H302-H400
• GHS警示性声明: P273
• 保存温度: room temp

产品相关信息

• 纯度: ≥98% (HPLC); 95+%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C21H23NO4 S

详细说明

Selleck Chemicals - S2503

Research Area: Metabolic Disease
Biological Activity:
Racecadotril is a peripherally acting enkephalinase inhibitor with an IC50 of 4.5 µM.Unlike other medications used to treat diarrhea, which reduce intestinal motility, racecadotril has an antisecretory effect—it reduces the secretion of water and electrolytes into the intestine. A small randomized controlled trial found racecadotril to significantly reduce the duration and volume of watery diarrhea in children when given as an adjunct to oral rehydration therapy. [1][2]References on Racecadotril (Acetorphan)[1] Int J Antimicrob Agents., 2000 Feb, 14(1):75-9.[2] http://en.wikipedia.org/wiki/Racecadotril, ,

Sigma Aldrich - SML0043

Biochem/physiol Actions
Racecadotril is a neutral endopeptidase inhibitor, an antidiarrheal drug which acts as a peripherally acting enkephalinase inhibitor.

Toronto Research Chemicals - R070600

Antidiarrheal; enkephalinase inhibitor, reducing the amount of water and electrolytes into the intestine.

参考文献

• Schwartz JC et al. Int J Antimicrob Agents. 2000
• Cezard, J., et al.: Gastroenterol., 120, 799 (2001)
• Sato, T., et al.: J. Med. Chem., 51, 7705 (2001)
• Lakshmana, P., et al.: J. Pharm. Res., 8, 39 (2001)