| Identification | More | [Name]
Racecadotril | [CAS]
81110-73-8 | [Synonyms]
ACETORPHAN
n-[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]-glycine phenylmethyl ester
RACECADOTRIL
tiorfan
(+-)-n-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)glycinephenylmethyleste
n-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-,phenylmethylester,(+-)-glycin
n-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-glycinphenylmethylester
RACECADORTRIL
RACECADOTRIL: ACETORPHAN
Glycine, N-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-, phenylmethyl ester | [EINECS(EC#)]
688-010-7 | [Molecular Formula]
C21H23NO4S | [MDL Number]
MFCD00865520 | [Molecular Weight]
385.48 | [MOL File]
81110-73-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
89°C | [Boiling point ]
574.5±50.0 °C(Predicted) | [density ]
1.206 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
DMSO: ≥44mg/mL | [form ]
powder | [pka]
13.63±0.46(Predicted) | [color ]
white to tan | [Merck ]
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 | [SMILES]
C(OCC1=CC=CC=C1)(=O)CNC(=O)C(CSC(C)=O)CC1=CC=CC=C1 | [CAS DataBase Reference]
81110-73-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Racecadotril(81110-73-8), also known as acetorphan, is a kind of antidiarrheal drug acting as a peripherally acting enkephalinase inhibitor. 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.
| [Chemical Properties]
White Solid | [Originator]
Bioprojet (France) | [Uses]
Racecadotril(81110-73-8) 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. | [Definition]
ChEBI: Racecadotril is a N-acyl-amino acid. It is a pro-drug that is metabolized in vivo into the active compound, thiorphan. It has been investigated for the basic science and treatment of Diarrhea, Acute Diarrhea, and Acute Gastroenteritis. | [Brand name]
Tiorfan | [Mechanism of action]
When Racecadotril enters the body, Racecadotril will be rapidly converted into Thiorphan which interacts specifically with the active site of the enzyme enkephalinase (a cell membrane peptidase enzyme found most commonly on the epithelium of the small intestine), blocking the effect of the enzyme and preventing the loss of the effect of endogenous peptides. | [Clinical Use]
Acetorphan is an orally-active enkephalinase inhibitor introduced in 1993 for the treatment of acute diarrhea in adults.It displays antidiarrheal activity via a purely antisecretory mechanism without inhibiting intestinal transit. | [Side effects]
Racecadotril may cause headache, drowsiness, fever, nausea and vomiting. Besides, in special cases, there may be rare side effects such as rash, erythema, acne skin, urticaria, erythema multiforme, tongue edema, face edema, eyelid edema, angioedema. | [Synthesis]
Benzaldehyde and diethyl malonate were combined, reduced, and hydrolyzed
to form benzyl malonic acid. This acid was then reacted with
paraformaldehyde and diethylamine to produce benzyl acrylic acid.
Thioacetic acid was then added to this compound, and it was condensed
with benzyl glycinate p-toluenesulphonate to obtain racecadotril. Overall, the process had a yield of 66%. | [Drug interactions]
Potentially hazardous interactions with other drugs
None known | [Metabolism]
Quickly metabolised by hydrolysis to active metabolite,
thiorphan. Racecadotril is eliminated as active and
inactive metabolites. Elimination is mainly via the renal
route, and to a much lesser extent via the faecal route
(around 8%). The pulmonary route is not significant (less
than 1% of the dose). | [storage]
Store at -20°C | [Mode of action]
Acetorphan acts as rapidly as loperamide, a classical muopiate receptor agonist that exhibits its antidiarrheal effect via an antitransit mechanism, without producing constipation or other side effects. The novel mechanism of action may render acetorphan potentially useful in the management of infectious diarrhea. | [References]
https://en.wikipedia.org/wiki/Racecadotril
https://patient.info/medicine/racecadotril-for-acute-diarrhoea-hidrasec |
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