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racecadotril

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racecadotril

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Racecadotril, also known as acetorphan, is an antidiarrheal medication which acts as a peripheral enkephalinase inhibitor. 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. 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, Slovakia, Russia and Czechia ) as well as most of South America and some South East Asian countr

Chemical data

Formula
C21H23NO4S
Molecular weight
385.5 g/mol
IUPAC name
benzyl 2-[[2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetate
SMILES
CC(=O)SCC(CC1=CC=CC=C1)C(=O)NCC(=O)OCC2=CC=CC=C2
InChIKey
ODUOJXZPIYUATO-UHFFFAOYSA-N
XLogP
3.3
Polar surface area
97.8 Ų
H-bond donors
1
H-bond acceptors
5
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Approved
Molecule type
Small molecule
Indications
Diarrhea, Diarrhea, Infantile

via ChEMBL · EBI

Wikidata facts

Mass
385.135
Has use
medication
Show 4 more facts
chemical formula
C₂₁H₂₃NO₄S
canonical SMILES
CC(=O)SCC(CC1=CC=CC=C1)C(=O)NCC(=O)OCC2=CC=CC=C2
subject has role
protease inhibitor
Commons category
Racecadotril
Sources (2)

via Wikidata · CC0

~5 min read

Encyclopedic overview

13 sections
Contents
  • Medical uses
  • Contraindications
  • Side effects
  • Overdose
  • Interactions
  • Pharmacology
  • Mechanism of action
  • Pharmacokinetics
  • Society and culture
  • Brand names
  • See also
  • References
  • External links

Racecadotril, also known as acetorphan, is an antidiarrheal medication which acts as a peripheral enkephalinase inhibitor. 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. 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, Slovakia, Russia and Czechia ) 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. Thiorphan is the active metabolite of racecadotril, which exerts the bulk of its inhibitory actions on enkephalinases.

== Medical uses == Racecadotril is used for the treatment of acute diarrhea in children and adults and has better tolerability than loperamide, as it causes less constipation and flatulence. Several guidelines have recommended racecadotril use in addition to oral rehydration treatment in children with acute diarrhea.

Excerpted from Wikipedia’s “racecadotril” article, available under the CC BY-SA 4.0 licence.

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