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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
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT01153854 | http://drug.pharmacy.psu.ac.th/wbfile/229254411121.pdf | https://www.ncbi.nlm.nih.gov/pubmed/21657271

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.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Diarfix

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

100 to 200mg 3 times daily for 2 to 4 weeks
Route of Administration: Oral
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
Created
by admin
on Fri Dec 15 16:27:17 GMT 2023
Edited
by admin
on Fri Dec 15 16:27:17 GMT 2023
Record UNII
76K53XP4TO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RACECADOTRIL
EP   INN   MART.   MI   WHO-DD  
INN  
Official Name English
NSC-759828
Code English
RACECADOTRIL [MART.]
Common Name English
TIORFIX
Brand Name English
TIORFAN
Brand Name English
ACETORPHAN
VANDF  
Common Name English
racecadotril [INN]
Common Name English
RACECADOTRIL [MI]
Common Name English
RACECADOTRIL [EP MONOGRAPH]
Common Name English
HIDRASEC
Brand Name English
N-((R,S)-3-ACETYLTHIO-2-BENZYLPROPANOYL)GLYCINE BENZYL ESTER
Common Name English
Racecadotril [WHO-DD]
Common Name English
ACETORPHAN [VANDF]
Common Name English
(±)-N-(.ALPHA.-(MERCAPTOMETHYL)HYDROCINNAMOYL)GLYCINE, BENZYL ESTER, ACETATE (ESTER)
Common Name English
Classification Tree Code System Code
WHO-ATC A07XA04
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
FDA ORPHAN DRUG 732920
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
WHO-VATC QA07XA04
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
Code System Code Type Description
WIKIPEDIA
RACECADOTRIL
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID8045513
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
DRUG CENTRAL
60
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
FDA UNII
76K53XP4TO
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
MERCK INDEX
m9477
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY Merck Index
EVMPD
SUB12435MIG
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
SMS_ID
100000089968
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103772
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
INN
7378
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
CAS
81110-73-8
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
RXCUI
16738
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY RxNorm
MESH
C049331
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
PUBCHEM
107751
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
NCI_THESAURUS
C66503
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
DRUG BANK
DB11696
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
NSC
759828
Created by admin on Fri Dec 15 16:27:17 GMT 2023 , Edited by admin on Fri Dec 15 16:27:17 GMT 2023
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
bulk of its inhibitory actions on enkephalinase.
MAJOR
PLASMA
Related Record Type Details
IMPURITY -> PARENT
REFERENCE SOLUTION USED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity F = 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity E = 0.6
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity C = 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP