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Details

Stereochemistry RACEMIC
Molecular Formula C21H23NO4S
Molecular Weight 385.477
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RACECADOTRIL

SMILES

CC(=O)SCC(CC1=CC=CC=C1)C(=O)NCC(=O)OCC2=CC=CC=C2

InChI

InChIKey=ODUOJXZPIYUATO-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C21H23NO4S
Molecular Weight 385.477
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Racecadotril (acetorphan) is an oral enkephalinase inhibitor for use in the treatment of acute diarrhea. Racecadotril reduces hypersecretion of water and electrolytes into the intestinal lumen, by preventing the degradation of endogenous enkephalins. Treatment with racecadotril reduces the incidence and duration of acute diarrhea and reduces diarrhea-associated symptoms compared with placebo in adults. Racecadotril treatment also results in significant reductions in stool output compared with placebo in infants and young children aged 2 months to 4 years with acute diarrhea. Both rotavirus-negative and rotavirus-positive infections appear to respond to treatment in the pediatric populations investigated for this infection. Racecadotril shows similar or slightly reduced efficacy to loperamide in the treatment of diarrhea in adults and children aged up to 10 years. However, in comparative trials, racecadotril was associated with fewer adverse events than loperamide, in particular, post-treatment constipation. Racecadotril is available in France (where it was first introduced in ~1990) and other European countries (including Germany, Italy, the UK, Spain and the Czech Republic) as well as most of South America and some South East Asian countries (including China, India and Thailand), but not in the United States.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.2 nM [Ki]
110.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Diarfix

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
100 to 200mg 3 times daily for 2 to 4 weeks
Route of Administration: Oral
In Vitro Use Guide
Cytotoxicity was measured with a colorimetric viability assay using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). Cells (5000 cells per well of a 96-well plate) were allowed to attach for 24 h. Stock solutions of Racecadotril (3 M) were prepared in H2O and then 2-fold serially diluted in medium to give a range of final tissue culture concentrations of 20 mM to 78 μM. After 72 h, cell viability was examined. Cytotoxicity (IC50) was defined as the drug concentration that reduced cell viability to 50% of the untreated control.
Substance Class Chemical
Record UNII
76K53XP4TO
Record Status Validated (UNII)
Record Version