81110-73-8

Usage

Uses

Used in Pharmaceutical Industry:
Racecadotril is used as an antidiarrheal agent for reducing hypersecretion of water and electrolytes into the intestinal lumen, providing relief from diarrhea without causing constipation or other side effects.
It is also used as an enkephalinase inhibitor for its antisecretory mechanism, which helps manage acute diarrhea in adults by preventing the degradation of endogenous opioids and reducing the amount of secreted water produced by the intestines.

References

https://en.wikipedia.org/wiki/Racecadotril https://patient.info/medicine/racecadotril-for-acute-diarrhoea-hidrasec

Originator

Bioprojet (France)

Clinical Use

Treatment of acute diarrhoea

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).

InChI:InChI=1/C20H21NO5S/c22-18(26-13-16-9-5-2-6-10-16)12-21-19(23)17(14-27-20(24)25)11-15-7-3-1-4-8-15/h1-10,17H,11-14H2,(H,21,23)(H,24,25)

Upstream product

• 1738-68-7 Gly-OBz 
• 65444-05-5 2-acetylthiomethyl-3-phenyl-propionyl chloride 
• 5669-19-2 2-Benzyl-2-propenoic acid 
• 91702-98-6 3-acetylthio-2-benzylpropanoic acid 
• 607-81-8 diethyl 2-benzylmalonate 
• 616-75-1 2-benzylmalonic acid 
• 100-51-6 benzyl alcohol 
• 27019-47-2 β-alanine benzyl ester p-toluenesulfonate 
• 10147-11-2 propargyl benzene 
• 20593-63-9 2-Benzylacrylic acid ethyl ester 
• 1738-76-7 glycine benzyl ester p-toluenesulfonic acid salt 
• 124815-67-4 (S)-2-acetylthiomethyl-3-phenylpropanoic acid 
• 2612-30-8 2-benzyl-1,3-propanediol 
• 49769-78-0 2-benzyl-malonic acid dimethyl ester 

Relevant academic research and scientific papers

Enantioseparation of racecadotril using polysaccharide-type chiral stationary phases in polar organic mode

Enantioseparation of the antidiarrheal drug, racecadotril, was investigated by liquid chromatography using polysaccharide-type chiral stationary phases in polar organic mode. The enantiodiscrimininating properties of 4 different chiral columns (Chiralpak

A by 3 - phenyl -1 - methylacetylene preparation quickly disintegrating process method (by machine translation)

A by 3 - phenyl - 1 - propyne preparation quickly disintegrating process method, which belongs to the technical field of pharmaceutical intermediates. In the preparation quickly disintegrating in the process, intermediate benzyl acrylic acid yield and purity of the most important, this method first using 3 - phenyl - 1 - propyne as the raw material, in the palladium catalyst Pd2 (Dba)3 And the ligand dppp with ethyl carbonate under the catalysis of the reaction to the one-step synthesis of benzyl acrylic acid, its advantage lies in atmospheric pressure to complete the addition reaction, functional group tolerance is good, high efficiency, high purity, the production process is greatly simplified, and to obtain the target product preparation process of yield and purity than the traditional process much higher. The method has the advantages of greatly improve the productivity, reduce the cost, improve the safety, energy saving and the like, in accordance with the green reaction of modern chemical production requirement. (by machine translation)

Method for synthesizing racecadotril

The invention provides a method for synthesizing racecadotril. The method comprises the following steps: I, enabling a compound (II) to react with an acylation reagent so as to obtain a compound (III); II, enabling he compound (III) to react with benzyl g

Method for preparing racecadotril through one-pot process

The invention belongs to the technical field of drug synthesis, and particularly relates to a method for preparing racecadotril through a one-pot process. The method comprises the followings steps: firstly, adding 2-benzyl-3-ethanethioyl crylic acid, orga

Preparation method and detection method for ecadotril

The invention provides a preparation method and detection method for ecadotril. 2-benzyl-3-hydroxypropionic acid is used as a raw material, and a four-step method is employed for preparing an intermediate and ecadotril, so more options are provided for acquisition of the bulk drug ecadotril. At the same time, based on the fact that (R)-phenylethylamine has slightly different abilities in elution of ecadotril and ecadotril enantiomers, a liquid-phase detection method for racecadotril in European Pharmacopoeia is employed for separation and detection in a liquid-phase system of an achiral column. The detection method is simple to operate and easy to implement.

"A PROCESS FOR THE PREPARATION OF N-[2-[(ACETYLTHIO) METHYL]-1-OXO-3-PHENYLPROPYL] GLYCINE PHENYL METHYL ESTER AND INTERMEDIATES THEREOF"

The present invention provides a process for the preparation of N-[2-[(acetylthio) methyl]-1-oxo-3-phenylpropyl] glycine phenyl methyl ester and intermediates thereof.

Structural studies of racecadotril and its process impurities by NMR and mass spectroscopy

Three unknown impurities in racecadotril bulk drug at levels below 0.5% were detected by simple reverse phase isocratic high performance liquid chromatography (HPLC). Structures for these impurities were proposed by molecular ion information and their fragmentation pattern obtained by LC-MS and these impurities were confirmed by NMR spectroscopy. The impurities I, II and III were characterized as benzyl 2-methyl carboximido acetate, benzyl 2-phenyl ethyl carboximido acetate, and benzyl 2-(1-benzyl vinyl carboximido) acetate. These structures were further confirmed by co-injecting of synthetic standards of impurities with racecadotril. The mechanism of the formation of these process related impurities is discussed.

Method for producing optically active phenylpropionic acid derivative

Optically active N-(S-2-acetylthiomethyl-1-oxo-3-phenylpropyl)-glycine benzyl ester useful as an enkephalin inhibitory agent or ACE inhibitory agent can be produced at low cost in an industrial manner, by a method comprising subjecting optically active 2-hydroxymethyl-3-phenylpropionic acid and glycine benzyl ester to condensation to subsequently convert the hydroxyl group into an elimination group, and substituting the elimination group with an acetylthio group.

New asymmetric synthesis of dexecadotril and ecadotril starting from a single precursor

We describe herein a method providing access to both enantiomers of 3-acetylthio-2-benzylpropionic acid via enzymatic desymmetrization of 2-benzyl-1,3-propanediol. These compounds are respectively the starting materials for the synthesis of ecadotril, and dexecadotril, which are powerful inhibitors of NEP (EC 3.4.24.11) and have been developed as therapeutic agents.

PROCESS FOR THE ASYMMETRIC SYNTHESIS OF S-ACYL DERIVATIVES OF 2-MERCAPTOMETHYL -3- PHENYL PROPANOIC ACID, APPLICATION TO THE SYNTHESIS OF N-(MERCAPTOACYL) AMINO ACID DERIVATIVES

Process for the asymmetric synthesis of S-acyl derivatives of 2-mercaptomethyl-3-phenylpropanoic acid of formula (I): characterized in that it comprises the steps consisting in:a) preparing the diol (VI) by reduction of a malonic ester (V) in the presence of a hydride; b) preparing the monoacetates (VII R) or (VII S) respectively; c) subjecting these monoacetates to an oxidation in order to form the acids (IX S) or (IX R);d) saponifying the compounds (IX S) or (IX R) in order to form the hydroxy acids (X S) or (X R);e) thioacylating the hydroxy acids (X S) or (X R) with a mercapto acid R. sub.1 SH (XI), according to a Mitsunobu-type reaction, in order to lead to the desired acids (I R) (I S) respectively and application to the synthesis of N-(mercaptoacyl)amino acid derivatives (II). STR1