Racecadotril

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Racecadotril
Racecadotril2DCSD.svg
Systematic (IUPAC) name
(RS)-benzyl N-[3-(acetylthio)-2-benzylpropanoyl]glycinate
Clinical data
Trade names Hidrasec, Tiorfan
AHFS/Drugs.com International Drug Names
Legal status
Routes of
administration
Oral
Pharmacokinetic data
Protein binding 90% (active thiorphan metabolite)[1]
Metabolism Liver-mediated[1]
Biological half-life 3 hours[1]
Excretion Urine (81.4%), faeces (8%)[1]
Identifiers
CAS Registry Number 81110-73-8 YesY
ATC code A07XA04
PubChem CID: 107751
ChemSpider 96913 N
UNII 76K53XP4TO N
ChEMBL CHEMBL2103772 N
Synonyms benzyl 2-[3-(acetylthio)-2-benzylpropanamido]acetate
Chemical data
Formula C21H23NO4S
Molecular mass 385.47662 g/mol
 N (what is this?)  (verify)

Racecadotril, also known as acetorphan, is an antidiarrheal drug which acts as a peripherally acting enkephalinase inhibitor.[2] 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 UK and Spain) 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.[4] In Italy it is sold under the tradename Tiorfix.[4]

Thiorphan is the active metabolite of racecadotril, which exerts the bulk of its inhibitory actions on enkephalinase.[5]

See also[edit]

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References[edit]

  1. ^ 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. 
  2. ^ Matheson AJ, Noble S (April 2000). "Racecadotril". Drugs 59 (4): 829–35; discussion 836–7. doi:10.2165/00003495-200059040-00010. PMID 10804038. 
  3. ^ Matheson, AJ; Noble, S (April 2000). "Racecadotril.". Drugs 59 (4): 829–35; discussion 836–7. doi:10.2165/00003495-200059040-00010. PMID 10804038. 
  4. ^ a b Brayfield, A, ed. (13 December 2013). "Racecadotril". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 6 May 2014. 
  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): 147–50. doi:10.1016/0014-2999(86)90094-4. PMID 3015640.