Racecadotril

Racecadotril

Clinical data
Trade names	Hidrasec, Tiorfan
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	A07XA04 (WHO)
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Protein binding	90% (active thiorphan metabolite)
Metabolism	Liver-mediated
Biological half-life	3 hours
Excretion	Urine (81.4%), feces (8%)
Identifiers
IUPAC name (RS)-Benzyl N-[3-(acetylthio)-2-benzylpropanoyl]glycinate
Synonyms	Benzyl 2-[3-(acetylthio)-2-benzylpropanamido]acetate
CAS Number	81110-73-8 Y
PubChem CID	107751
ChemSpider	96913 N
UNII	76K53XP4TO
ChEMBL	CHEMBL2103772 N
ECHA InfoCard	100.214.352
Chemical and physical data
Formula	C21H23NO4S
Molar mass	385.47662 g/mol
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
SMILES CC(=O)SCC(CC1=CC=CC=C1)C(=O)NCC(=O)OCC2=CC=CC=C2
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) N Key:ODUOJXZPIYUATO-UHFFFAOYSA-N N
NY (what is this?)

Racecadotril, also known as acetorphan, is an antidiarrheal drug which acts as a peripherally acting enkephalinase inhibitor. Unlike other opioid medications used to treat diarrhea, which reduce intestinal motility, racecadotril has an effect—it reduces the secretion of water and electrolytes into the intestine. It is available in France (where it was first introduced in ~1990) and other European countries (including Germany, Italy, the UK, Spain and the Czech Republic) as well as most of South America and some South East Asian countries (including China, India and Thailand), but not in the United States. It is sold under the tradenames Hidrasec or, in France, Tiorfan. In Italy it is sold under the tradename Tiorfix.

Thiorphan is the active metabolite of racecadotril, which exerts the bulk of its inhibitory actions on enkephalinase.