Racecadotril

Bezeichnung:Racecadotril

CAS-Nr81110-73-8

Englisch Name:Racecadotril

CBNumberCB3378722

SummenformelC21H23NO4S

Molgewicht385.48

MOL-Datei81110-73-8.mol

Racecadotril physikalisch-chemischer Eigenschaften

Schmelzpunkt	89°C
Siedepunkt	574.5±50.0 °C(Predicted)
Dichte	1.206
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	DMSO: ≥44mg/mL
pka	13.63±0.46(Predicted)
Aggregatzustand	powder
Farbe	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 Datenbank	81110-73-8(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,N
R-Sätze:	22-50/53
S-Sätze:	60-61
RIDADR	UN 3077 9 / PGIII
WGK Germany	3
RTECS-Nr.	MB7606872
HS Code	29309090

Gefahreninformationscode (GHS)

Racecadotril Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Racecadotril, 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.
Chemische Eigenschaften
White Solid
Originator
Bioprojet (France)
Verwenden
Racecadotril 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.
Trademarks
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
Racecadotril(Acetorphan, 81110-73-8) is an anti-secretory drug that has been used for acute diarrhoea in children as an adjunct to oral rehydration therapy. It displays antidiarrheal activity via a purely antisecretory mechanism without inhibiting intestinal transit.
Nebenwirkungen
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.
Synthese
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%.
Stoffwechsel
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).
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.
Einzelnachweise
[1] https://en.wikipedia.org/wiki/Racecadotril
[2] https://patient.info/medicine/racecadotril-for-acute-diarrhoea-hidrasec
[3] LIANGYI. Racecadotril for acute diarrhoea in children.[J]. Cochrane Database of Systematic Reviews, 2019. DOI:10.1002/14651858.CD009359.pub2.
[4] WUH T. Increase of plasma insulin by racecadotril, an inhibitor of enkephalinase, in Wistar rats.[J]. Hormone and Metabolic Research, 2010. DOI:10.1055/s-0029-1246190.
[5] ASADIMEHDI. Design, synthesis, and evaluation of novel racecadotril-tetrazole-amino acid derivatives as new potent analgesic agents.[J]. Research in Pharmaceutical Sciences, 2021. DOI:10.4103/1735-5362.319573.

Racecadotril Upstream-Materialien And Downstream Produkte

Racecadotril Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

81110-73-8, Racecadotril Verwandte Suche:

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