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Racecadotril information


Racecadotril
Clinical data
Trade namesHidrasec, Tiorfan, Zedott, others
Other namesBenzyl 2-[3-(acetylthio)-2-benzylpropanamido]acetate
AHFS/Drugs.comInternational Drug Names
Routes of
administration
By mouth
ATC code
  • A07XA04 (WHO)
Legal status
Legal status
  • UK: POM (Prescription only)
  • EU: Rx-only[1]
Pharmacokinetic data
Protein binding90% (active metabolite thiorphan)[2]
MetabolismLiver-mediated[2]
Onset of action30 min
Elimination half-life3 hours[2]
ExcretionUrine (81.4%), feces (8%)[2]
Identifiers
IUPAC name
  • (RS)-Benzyl N-[3-(acetylthio)-2-benzylpropanoyl]glycinate
CAS Number
  • 81110-73-8 checkY
PubChem CID
  • 107751
DrugBank
  • DB11696
ChemSpider
  • 96913 ☒N
UNII
  • 76K53XP4TO
KEGG
  • D08464
ChEMBL
  • ChEMBL2103772 ☒N
CompTox Dashboard (EPA)
  • DTXSID8045513 Edit this at Wikidata
ECHA InfoCard100.214.352 Edit this at Wikidata
Chemical and physical data
FormulaC21H23NO4S
Molar mass385.48 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic mixture
Melting point89 °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) ☒N
  • Key:ODUOJXZPIYUATO-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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]

  1. ^ "Active substance: racecadotril" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 26 November 2020.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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): 147–150. doi:10.1016/0014-2999(86)90094-4. PMID 3015640.

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Racecadotril

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Enkephalin

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Endopeptidase inhibitor

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Narcotic

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Mitragyna speciosa

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Opium

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C21H23NO4S

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