Racecadotril
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| Systematic (IUPAC) name | |
|---|---|
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(RS)-Benzyl N-[3-(acetylthio)-2-benzylpropanoyl]glycinate
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| Clinical data | |
| Trade names | Hidrasec, Tiorfan |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration |
Oral |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Protein binding | 90% (active thiorphan metabolite)[1] |
| Metabolism | Liver-mediated[1] |
| Biological half-life | 3 hours[1] |
| Excretion | Urine (81.4%), feces (8%)[1] |
| Identifiers | |
| CAS Number | 81110-73-8  |
| ATC code | A07XA04 (WHO) |
| PubChem | CID 107751 |
| ChemSpider | 96913  |
| UNII | 76K53XP4TO |
| ChEMBL | CHEMBL2103772 |
| Synonyms | Benzyl 2-[3-(acetylthio)-2-benzylpropanamido]acetate |
| Chemical data | |
| Formula | C21H23NO4S |
| Molar mass | 385.47662 g/mol |
| Chirality | Racemic mixture |
| 3D model (Jmol) | Interactive image |
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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, Spain 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 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]
- Ecadotril, the (S)-enantiomer of racecadotril
- D/DL-Phenylalanine
- RB-101
References[edit]
- ^ 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.
