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

• ChemBase ID: 73050
• Molecular Formular: C21H23NO4S
• Molecular Mass: 385.47662
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 2-{2-[(acetylsulfanyl)methyl]-3-phenylpropanamido}acetate
• IUPAC Traditional name: racecadotril; benzyl 2-{2-[(acetylsulfanyl)methyl]-3-phenylpropanamido}acetate
• Synonyms: (±)-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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 12.602205
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.1748388
• LogD (pH = 7.4): 3.1748364
• Log P: 3.1748388
• Molar Refractivity: 105.9974 cm^3
• Polarizability: 41.64099 Å^3
• Polar Surface Area: 72.47 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: ≥44 mg/mL; Methanol
• Apperance: White Solid; white to tan powder
• Melting Point: 72-74°C

Safety Information

• Storage Condition: -20°C; Refrigerator
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H400
• GHS Precautionary statements: P273
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC); 95+%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C21H23NO4 S

DETAILS

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.

REFERENCES

• 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)