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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

Signal Word

Warning

Hazard Statements

H302,H400

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
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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