This page uses content from Wikipedia and is licensed under CC BY-SA.

Racecadotril

Racecadotril
Racecadotril2DCSD.svg
Clinical data
Trade namesHidrasec, Tiorfan, others
Other namesBenzyl 2-[3-(acetylthio)-2-benzylpropanamido]acetate
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
Pharmacokinetic data
Protein binding90% (active thiorphan metabolite)[1]
MetabolismLiver-mediated[1]
Elimination half-life3 hours[1]
ExcretionUrine (81.4%), feces (8%)[1]
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard100.214.352 Edit this at Wikidata
Chemical and physical data
FormulaC21H23NO4S
Molar mass385.47662 g/mol g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
 ☒N☑Y (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 United Kingdom, Spain, 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 enkephalinase.[5]

Medical uses

Racecadotril can be used for treatment of acute diarrhea patients and has better tolerability than loperamide.[6] Several guidelines have recommended racecadotril use in addition to oral rehydration treatment in children with acute diarrhea.[7]

Pharmacology

Pharmacokinetics

Racecadotril is rapidly absorbed after oral administration and doses of 30 mg, 100 mg and 300 mg reached Cmax within 60 min. Food does not affect bioavailability of racecadotril. Racecadotril is rapidly and effectively metabolized to the active metabolite thiorphan which inhibits enkephalinase enzyme and exhibits anti-secretory effect.[8]

Society and culture

Brand names

In France it is sold as Tiorfan and in Italy as Tiorfix. In India it is available as Redotril and Enuff.[4]

See also

References

  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.
  6. ^ Fischbach, Wolfgang; Andresen, Viola; Eberlin, Marion; Mueck, Tobias; Layer, Peter (2016). "A Comprehensive Comparison of the Efficacy and Tolerability of Racecadotril with Other Treatments of Acute Diarrhea in Adults". Frontiers in Medicine. 3: 44. doi:10.3389/fmed.2016.00044. ISSN 2296-858X. PMC 5064048. PMID 27790616.
  7. ^ Eberlin, Marion; Mück, Thomas; Michel, Martin C. (2012). "A Comprehensive Review of the Pharmacodynamics, Pharmacokinetics, and Clinical Effects of the Neutral Endopeptidase Inhibitor Racecadotril". Frontiers in Pharmacology. 3. doi:10.3389/fphar.2012.00093. ISSN 1663-9812. PMC 3362754. PMID 22661949.
  8. ^ Eberlin, Marion; Mück, Thomas; Michel, Martin C. (2012). "A Comprehensive Review of the Pharmacodynamics, Pharmacokinetics, and Clinical Effects of the Neutral Endopeptidase Inhibitor Racecadotril". Frontiers in Pharmacology. 3: 93. doi:10.3389/fphar.2012.00093. ISSN 1663-9812. PMC 3362754. PMID 22661949.