Racecadotril
 | |
| Clinical data | |
|---|---|
| Trade names | Hidrasec, Tiorfan, others |
| Other names | Benzyl 2-[3-(acetylthio)-2-benzylpropanamido]acetate |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral |
| ATC code | |
| Legal status | |
| Legal status |
|
| Pharmacokinetic data | |
| Protein binding | 90% (active thiorphan metabolite)[1] |
| Metabolism | Liver-mediated[1] |
| Elimination half-life | 3 hours[1] |
| Excretion | Urine (81.4%), feces (8%)[1] |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.214.352 |
| Chemical and physical data | |
| Formula | C21H23NO4S |
| Molar mass | 385.47662 g/mol g·mol−1 |
| 3D model (JSmol) | |
| Chirality | Racemic mixture |
| |
| |
  (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
- Ecadotril, the (S)-enantiomer of racecadotril
- D/DL-Phenylalanine
- RB-101
References
- ^ 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.
- ^ Matheson AJ, Noble S (April 2000). "Racecadotril". Drugs. 59 (4): 829–35, discussion 836–7. doi:10.2165/00003495-200059040-00010. PMID 10804038.
- ^ Matheson, AJ; Noble, S (April 2000). "Racecadotril". Drugs. 59 (4): 829–35, discussion 836–7. doi:10.2165/00003495-200059040-00010. PMID 10804038.
- ^ a b 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): 147–50. doi:10.1016/0014-2999(86)90094-4. PMID 3015640.
- ^ 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.
{{cite journal}}: CS1 maint: unflagged free DOI (link) - ^ 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.
{{cite journal}}: CS1 maint: unflagged free DOI (link) - ^ 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.
{{cite journal}}: CS1 maint: unflagged free DOI (link)