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SML0043

Sigma-Aldrich

Racecadotril

≥98% (HPLC)

Synonym(s):

(RS)-Benzyl N-[3-(acetylthio)-2-benzylpropanoyl]glycinate, (±)-Acetorphan, Acetorphan, Cadotril, Redotil, Tiorfan, Zedott

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About This Item

Empirical Formula (Hill Notation):
C21H23NO4S
CAS Number:
81110-73-8
Molecular Weight:
385.48
MDL number:
MFCD00865520
UNSPSC Code:
12352200
PubChem Substance ID:
329825113
NACRES:
NA.77

Quality Level

100

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
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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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.
Yu Xu et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 852(1-2), 101-107 (2007-01-24)
Orally administered racecadotril is rapidly hydrolyzed to the more potent enkephalinase inhibitor thiorphan in vivo. A sensitive and specific liquid chromatography/tandem mass spectrometry method was developed and validated to quantify thiorphan in human plasma using lisinopril as the internal standard.
K Mallikarjun Reddy et al.
Die Pharmazie, 61(12), 994-998 (2007-02-08)
Three unknown impurities in racecadotril bulk drug at levels below 0.5% were detected by simple reverse phase isocratic high performance liquid chromatography (HPLC). Structures for these impurities were proposed by molecular ion information and their fragmentation pattern obtained by LC-MS
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
Mar Santos et al.
The Journal of pediatrics, 155(1), 62-67 (2009-04-28)
To compare the efficacy of therapy with racecadotril plus oral rehydration versus oral rehydration alone in children with gastroenteritis in an outpatient setting care. Prospective, randomized, open and parallel study performed in a Pediatric Emergency Service of a tertiary care
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