Racecadotril

Racecadotril
Clinical data
Trade names	Hidrasec, Tiorfan, Zedott, others
Other names	Benzyl 2-[3-(acetylthio)-2-benzylpropanamido]acetate
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth
ATC code	A07XA04 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); EU: Rx-only;
Pharmacokinetic data
Protein binding	90% (active metabolite thiorphan)
Metabolism	Liver-mediated
Onset of action	30 min
Elimination half-life	3 hours
Excretion	Urine (81.4%), feces (8%)
Identifiers
	IUPAC name (RS)-Benzyl N-[3-(acetylthio)-2-benzylpropanoyl]glycinate;
CAS Number	81110-73-8 ;
PubChem CID	107751;
DrugBank	DB11696;
ChemSpider	96913 ;
UNII	76K53XP4TO;
KEGG	D08464;
ChEMBL	ChEMBL2103772 ;
CompTox Dashboard (EPA)	DTXSID8045513 ;
ECHA InfoCard	100.214.352
Chemical and physical data
Formula	C21H23NO4S
Molar mass	385.48 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
Melting point	89 °C (192 °F)
	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) ; Key:ODUOJXZPIYUATO-UHFFFAOYSA-N ;
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Racecadotril, also known as acetorphan, is an antidiarrheal medication which acts as a peripheral enkephalinase inhibitor.^[3] Unlike other opioid medications used to treat diarrhea, which reduce intestinal motility, racecadotril has an antisecretory effect — it reduces the secretion of water and electrolytes into the intestine.^[3] It is available in France (where it was first introduced in ~1990) and other European countries (including Germany, Italy, the United Kingdom, Spain, Portugal, Poland, Finland, Russia 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 tradename Hidrasec, among others.^[4] Thiorphan is the active metabolite of racecadotril, which exerts the bulk of its inhibitory actions on enkephalinases.^[5]

^ "Active substance: racecadotril" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 26 November 2020.
^ ^a ^b ^c ^d "SPC-DOC_PL 39418-0003.PDF" (PDF). Medicines and Healthcare Products Regulatory Agency. Bioprojet Europe Ltd. 26 December 2012. Retrieved 7 May 2014.^{[permanent dead link]}
^ ^a ^b Matheson AJ, Noble S (April 2000). "Racecadotril". Drugs. 59 (4): 829–35, discussion 836–7. doi:10.2165/00003495-200059040-00010. PMID 10804038.
^ Brayfield A, ed. (13 December 2013). "Racecadotril". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 6 May 2014.
^ Spillantini MG, Geppetti P, Fanciullacci M, Michelacci S, Lecomte JM, Sicuteri F (June 1986). "In vivo 'enkephalinase' inhibition by acetorphan in human plasma and CSF". European Journal of Pharmacology. 125 (1): 147–150. doi:10.1016/0014-2999(86)90094-4. PMID 3015640.

[1] "Active substance: racecadotril" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 26 November 2020.

[SPC-2] "SPC-DOC_PL 39418-0003.PDF" (PDF). Medicines and Healthcare Products Regulatory Agency. Bioprojet Europe Ltd. 26 December 2012. Retrieved 7 May 2014.^{[permanent dead link]}

[Matheson-3] Matheson AJ, Noble S (April 2000). "Racecadotril". Drugs. 59 (4): 829–35, discussion 836–7. doi:10.2165/00003495-200059040-00010. PMID 10804038.

[MD-4] Brayfield A, ed. (13 December 2013). "Racecadotril". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 6 May 2014.

[pmid3015640-5] Spillantini MG, Geppetti P, Fanciullacci M, Michelacci S, Lecomte JM, Sicuteri F (June 1986). "In vivo 'enkephalinase' inhibition by acetorphan in human plasma and CSF". European Journal of Pharmacology. 125 (1): 147–150. doi:10.1016/0014-2999(86)90094-4. PMID 3015640.

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