Name | Racecadotril |
CAS number | 81110-73-8 |
Description | Racecadotril, identified by the Chemical Abstracts Service Registry Number 81110-73-8, is an orally active antidiarrheal agent that functions through a distinctive mechanism distinct from conventional opioid-based treatments such as loperamide. |
Structural formula |  |
Molecular Formula | C21H23NO4S |
Molecular Weight | 385.48 g/mol |
Appearance | White powder |
Quality Standard | 99% |
Storage Condition | Cool dry place( away from the light) |
Shelf Life | >2 years if stored properly |
Sample package | Aluminium foil bag |
Commercial package | Aluminium Tin, Fiber drum |
Origin | China |
Racecadotril, identified by the Chemical Abstracts Service Registry Number 81110-73-8, is an orally active antidiarrheal agent that functions through a distinctive mechanism distinct from conventional opioid-based treatments such as loperamide. Its molecular formula is C₂₁H₂₃NO₄S, with a molecular weight of approximately 385.48 grams per mole, and its IUPAC name is benzyl 2-[(2-benzyl-3-sulfanylpropanoyl)amino]acetate, reflecting a structure that contains a thiol ester group critical for its biological activity. In its physical form, racecadotril appears as a white to off-white crystalline powder that is practically insoluble in water but freely soluble in organic solvents such as ethanol and acetone. The compound is a prodrug that undergoes rapid biotransformation following oral administration to its active metabolite, thiorphan, which is a potent and selective inhibitor of enkephalinase, also known as neutral endopeptidase.
The pharmacological mechanism of racecadotril sets it apart from traditional antidiarrheal agents by preserving intestinal motility while reducing excessive fluid and electrolyte secretion. Upon absorption, racecadotril is hydrolyzed to thiorphan, which inhibits enkephalinase, the enzyme responsible for degrading endogenous enkephalins within the gastrointestinal tract. Enkephalins are endogenous opioid peptides that act locally on delta opioid receptors located on intestinal epithelial cells and submucosal neurons. By preventing the breakdown of these peptides, racecadotril enhances their antisecretory activity without significantly affecting intestinal transit time or causing central nervous system effects. This mechanism leads to a reduction in cyclic adenosine monophosphate levels within enterocytes, thereby decreasing the secretion of water and electrolytes into the intestinal lumen while allowing normal peristalsis to continue, effectively addressing the underlying pathophysiology of acute diarrhea without inducing the constipation or abdominal distension commonly associated with opioid-based antidiarrheals.
The clinical applications of racecadotril are primarily focused on the symptomatic treatment of acute diarrhea in both adults and children. It has been extensively studied in clinical trials across diverse populations, demonstrating efficacy in reducing stool output, shortening the duration of diarrheal episodes, and decreasing the need for rehydration interventions compared to placebo and, in some studies, showing comparable or superior outcomes relative to loperamide with a more favorable safety profile. In pediatric populations, racecadotril has been particularly well studied and is widely used as an adjunct to oral rehydration therapy, the cornerstone of diarrhea management, with meta-analyses confirming its ability to reduce stool volume and duration of illness without increasing the risk of serious adverse events. The World Health Organization has recognized racecadotril as a valuable addition to oral rehydration therapy for the management of acute diarrhea in children, particularly in settings where access to intravenous rehydration may be limited.
The pharmacokinetic and safety profile of racecadotril is characterized by favorable properties that support its use across age groups. Following oral administration, the drug is rapidly absorbed and quickly converted to its active thiorphan metabolite, with peak plasma concentrations achieved within one to two hours. Thiorphan is subsequently further metabolized to inactive compounds that are eliminated primarily in the urine, with an elimination half-life of approximately three hours. Racecadotril does not cross the blood-brain barrier to any clinically significant extent, which accounts for the absence of central opioid effects such as sedation, dependence, or respiratory depression. The adverse effect profile is generally mild and comparable to placebo, with the most commonly reported events being headache, nausea, and rarely, skin reactions. Racecadotril is contraindicated in individuals with known hypersensitivity to the drug or its components, and caution is advised in patients with severe renal or hepatic impairment due to reduced capacity for drug metabolism and elimination. In the context of its distinctive mechanism, racecadotril represents a rational approach to the management of acute diarrhea that targets the underlying secretory processes while preserving the body's natural ability to clear pathogens through normal intestinal motility.
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