Basic information
- CAS
81110-73-8- Standard SMILES
CC(=O)SCC(Cc1ccccc1)C(=O)NCC(=O)OCc1ccccc1- InChIKey
ODUOJXZPIYUATO-UHFFFAOYSA-N- Molecular formula
- C21H23NO4S
- Average molar mass
- 385.5 g/mol
- Monoisotopic mass
- 385.13477939
Overview
2-[[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]acetic acid (phenylmethyl) ester is a N-acyl-amino acid.
Names & identifiers
- Preferred name
- Racecadotril
- IUPAC
- benzyl 2-[[2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetate
- English name
- Racecadotril
- Molecular formula
- C21H23NO4S
- Molecular weight
- 385.48
Names & synonyms
Racecadotril81110-73-8AcetorphanHidrasecTiorfanTiorfixracecadotriloNSC-75982876K53XP4TObenzyl 2-[[2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetateGlycine, N-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-, phenylmethyl ester, (+-)-DTXSID8045513
Show more names
ZedottRedotilCadotrilRacecadoRACECADORTRILRacemic CardoRacecadotril>
racecadotrilumbenzyl 2-((2-(acetylsulfanylmethyl)-3-phenylpropanoyl)amino)acetateRefChem:178501A07XA04DTXCID00209955N-(3-acetylmercapto-2-benzylpropanoyl)glycine benzyl esterbenzyl 2-(2-((acetylsulfanyl)methyl)-3-phenylpropanamido)acetateBenzyl 2-(3-(acetylthio)-2-benzylpropanamido)acetate
Database identifiers
- CAS
81110-73-8- PubChem CID
- 107751
- DTXSID
DTXSID8045513- ChEMBL
CHEMBL2103772
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 97.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 11
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 485
Experimental & physicochemical properties
DrugsPharmaceuticals
Human DrugsBreast Feeding; Lactation; Milk, Human; Antidiarrheals
Physicochemical properties
- Melting point
- 89 °C · 89°C
- Boiling point
- 574.5 · 574.5±50.0 °C(Predicted)
- Density
- 1.206 · 1.206
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- 44 mg/mL · DMSO: ≥44mg/mL
- pka
- 13.63 · 13.63±0.46(Predicted)
- form
- powder
- color
- white to tan
- Merck
- 14 · 14,8090
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2.3% (1 of 43) of reports.
Warning
H302 (93%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (93%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Acetorphan
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- 3
- rtecs
- MB7606872
- ridadr
- UN 3077 9 / PGIII
- hs_code
- 29309090
- risk_code
- 22-50/53
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- Xn,N
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
MeSH Pharmacological Classification
Miscellaneous agents found useful in the symptomatic treatment of diarrhea. They have no effect on the agent(s) that cause diarrhea, but merely alleviate the condition.
Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES).
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >100
Applications
DescriptionRacecadotril, also known as acetorphan, is a kind of antidiarrheal drug acting as a peripherally acting enkephalinase inhibitor. It belongs to the group of gastrointestinal drugs and is also a lipophilic derivative of Thiorphan. Racecadotril is a dipeptide in which there is a single amide bond. It has an antisecretory effect, reducing the secretion of water and electrolytes into the intestine. Racecadotril is a pro-drug that is metabolized in vivo into the active compound, thiorphan. Thiorphan exerts its inhibitory effect on enkephalinase, reducing the amount of secreted water produced by the intestines. In this case, the body loses less fluid, and the symptoms of diarrhea can be alleviated.
UsesRacecadotril is an enkephalinase inhibitor that prevents the degradation of endogenous opioids. It demonstrates antidiarrheal activity by reducing hypersecretion of water and electrolytes into the intestinal lumen. It is an effective and safe treatment for acute diarrhea in adults and children.
Upstream & downstream products
Upstream raw materials
Related reactions
1 records
Compound notes
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