Racecadotril
Grundinformationen
- CAS
81110-73-8- Standard-SMILES
CC(=O)SCC(Cc1ccccc1)C(=O)NCC(=O)OCc1ccccc1- InChIKey
ODUOJXZPIYUATO-UHFFFAOYSA-N- Summenformel
- C21H23NO4S
- Durchschnittliche Molmasse
- 385,5 g/mol
- Monoisotopische Masse
- 385,13477939
Überblick
2-[[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]acetic acid (phenylmethyl) ester is a N-acyl-amino acid.
Namen und Bezeichner
- Bevorzugter Name
- Racecadotril
- IUPAC
- benzyl 2-[[2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetate
- Englischer Name
- Racecadotril
- Summenformel
- C21H23NO4S
- Molmasse
- 385.48
Namen und Synonyme
Racecadotril81110-73-8AcetorphanHidrasecTiorfanTiorfixracecadotriloNSC-75982876K53XP4TObenzyl 2-[[2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetateGlycine, N-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-, phenylmethyl ester, (+-)-DTXSID8045513
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- CAS
81110-73-8- PubChem CID
- 107751
- DTXSID
DTXSID8045513- ChEMBL
CHEMBL2103772
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,3
- Polarare Oberfläche (TPSA)
- 97,8 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 11
- Schwere Atome
- 27
- Formalladung
- 0
- Komplexität
- 485
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals
Human DrugsBreast Feeding; Lactation; Milk, Human; Antidiarrheals
Physikochemische Eigenschaften
- Schmelzpunkt
- 89 °C · 89°C
- Siedepunkt
- 574.5 · 574.5±50.0 °C(Predicted)
- Dichte
- 1.206 · 1.206
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Löslichkeit
- 44 mg/mL · DMSO: ≥44mg/mL
- pka
- 13.63 · 13.63±0.46(Predicted)
- Aggregatzustand
- powder
- Farbe
- 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
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (93%)
Toxikologische Informationen
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
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 3077 9 / PGIII
- hs_code
- 29309090
- RTECS-Nr.
- MB7606872
- risk_code
- 22-50/53
- hazard_code
- Xn,N
- safety_code
- 60-61
- Speicherklasse
Chemie und Industrie
Pharmakologische Informationen
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).
Verwendung und Herstellung
UsesUse (kg; approx.) in Germany (2009): >100
Anwendungen
BeschreibungRacecadotril, 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.
VerwendenRacecadotril 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.
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