Racecadotril

Structural formula
	1: 1 mixture of ( R ) -form (left) and ( S ) -form (right)
General
Non-proprietary name	Racecadotril
other names	( RS ) - (2-Acetylsulfanylmethyl-3-phenylpropionylamino) acetic acid benzyl ester ( IUPAC ) ; (±) - (2-Acetylsulfanylmethyl-3-phenylpropionylamino) acetic acid benzyl ester;
Molecular formula	C 21 H 23 NO 4 S
External identifiers / databases
EC number	688-010-7
ECHA InfoCard	100.214.352
PubChem	107751
ChemSpider	96913
DrugBank	DB11696
Wikidata	Q416677
Drug information
ATC code	A07 XA04
Drug class	Antidiarrheal
properties
Molar mass	385.48 g · mol -1
Physical state	firmly
Melting point	89 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 302-400
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Racecadotril is a medicine that is used to treat the symptoms of diarrhea . Racecadotril works by inhibiting the enzyme enkephalinase . Racecadotril has been on the market in Germany since April 2007.

pharmacology

application areas

Racecadotril is approved for the symptomatic treatment of diarrhea in adults and for supplementary use as an antidiarrheal for infants from 3 months of age and children together with oral fluid and electrolyte intake. In 2013, Racecadotril was released from the prescription requirement for use against diarrhea in adults over the age of 18.

Mechanism of action

Racecadotril is what is called a prodrug . After oral administration, it is only activated in the body by enzymes from the esterase group through hydrolytic cleavage to the metabolite thiorphan. This metabolite is an enkephalinase inhibitor and inhibits the breakdown of endogenous enkephalins . Enkephalins inhibit the secretion of water and electrolytes into the intestinal lumen via δ- opiate receptors .

Side effects

Vomiting and fever have been observed frequently during treatment of infants with racecadotril. However, these side effects can also be considered symptoms of the underlying disease. In addition, occasional hypokalaemia , intestinal obstruction and bronchospasm and isolated skin rashes were observed. In clinical studies with adults, in addition to non-specific side effects such as headache , nausea , constipation and dizziness , abdominal pain , flatulence , loss of appetite , thirst and fever also occurred.

Interactions

There are currently no known interactions with other drugs.

Stereoisomerism

Racecadotril is chiral , so it contains a stereocenter . There are thus two enantiomers , the ( R ) form and the ( S ) form. The commercial preparations contain the drug as a racemate (1: 1 mixture of enantiomers).

Drug market

Monopreparations

Tiorfan (D), Vaprino (D), DiaVerde (D), Hidrasec (A)

Individual evidence

^ The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1392, ISBN 978-0-911910-00-1 .
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of (RS) -Benzyl N- [3- (acetylthio) -2-benzylpropanoyl] glycinate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 5, 2020, is reproduced from a self-classification by distributors .
^ Information from the Drugs Commission of German Pharmacists, announcement in the PZ of March 7, 2013.

[1] The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1392, ISBN 978-0-911910-00-1 .

[2] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of (RS) -Benzyl N- [3- (acetylthio) -2-benzylpropanoyl] glycinate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 5, 2020, is reproduced from a self-classification by distributors .

[3] Information from the Drugs Commission of German Pharmacists, announcement in the PZ of March 7, 2013.