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SML0043

Sigma-Aldrich

Racecadotril

≥98% (HPLC)

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Synonym(s):
(RS)-Benzyl N-[3-(acetylthio)-2-benzylpropanoyl]glycinate, (±)-Acetorphan, Acetorphan, Cadotril, Redotil, Tiorfan, Zedott
Empirical Formula (Hill Notation):
C21H23NO4S
CAS Number:
Molecular Weight:
385.48
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥44 mg/mL

storage temp.

room temp

SMILES string

CC(=O)SCC(Cc1ccccc1)C(=O)NCC(=O)OCc2ccccc2

InChI

1S/C21H23NO4S/c1-16(23)27-15-19(12-17-8-4-2-5-9-17)21(25)22-13-20(24)26-14-18-10-6-3-7-11-18/h2-11,19H,12-15H2,1H3,(H,22,25)

InChI key

ODUOJXZPIYUATO-UHFFFAOYSA-N

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Application

Racecadotril may be used to study enkephalinase-mediated cellular changes.

Biochem/physiol Actions

Inhibition of enkephalinase by Racecadotril prevents the breakdown of enkephalins in the gastrointestinal tract. This reduces secretion of water and electrolytes into the gut without affecting the mobility.
Racecadotril is a neutral endopeptidase inhibitor, an antidiarrheal drug which acts as a peripherally acting enkephalinase inhibitor.

Features and Benefits

This compound is featured on the Neuropeptidases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Hypersensitivity to racecadotril: a case report.
Eleonora Nucera et al.
European journal of pediatrics, 165(6), 418-419 (2006-05-02)
Fan Xu et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 861(1), 130-135 (2007-12-18)
A HPLC method with UV detection was developed and validated for the determination of thiorphan in human plasma. Nevirapine was used as the internal standard. Separation was performed by a Waters sunfire C18 reversed-phase column maintained at 35 degrees C.
Seema Alam et al.
Indian journal of pediatrics, 73(8), 693-696 (2006-08-29)
Each year 1.8 million children die due to diarrheal diseases. Indiscriminate use of antibiotics has resulted in increasing resistance to commonly used antibiotics. Moreover the recent outbreaks of shigella and cholera have revealed multi-drug resistance strains. There is a need
Reshma S Baliga et al.
American journal of respiratory and critical care medicine, 178(8), 861-869 (2008-08-12)
Phosphodiesterase 5 (PDE5) inhibitors (e.g., sildenafil) are selective pulmonary vasodilators in patients with pulmonary arterial hypertension. The mechanism(s) underlying this specificity remains unclear, but studies in genetically modified animals suggest it might be dependent on natriuretic peptide bioactivity. We explored
Alfredo Guarino et al.
Journal of pediatric gastroenterology and nutrition, 48 Suppl 2, S58-S62 (2009-03-28)
The colon is actively implicated in intestinal infections not only as a target of enteric pathogens and their products but also as a target organ for treatment. In the presence of diarrhea, both of osmotic and secretory nature, the colon

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