ChemicalBook > CAS DataBase List > Racecadotril

Racecadotril

Product Name
Racecadotril
CAS No.
81110-73-8
Chemical Name
Racecadotril
Synonyms
ACETORPHAN;Zedott;Redotil;tiorfan;Cadotril;Racecado;RACECADOTRIL;RACECADORTRIL;Racemic Cardo;Racecadotril>
CBNumber
CB3378722
Molecular Formula
C21H23NO4S
Formula Weight
385.48
MOL File
81110-73-8.mol
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Racecadotril Property

Melting point:
89°C
Boiling point:
574.5±50.0 °C(Predicted)
Density 
1.206
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
DMSO: ≥44mg/mL
pka
13.63±0.46(Predicted)
form 
powder
color 
white to tan
Merck 
14,8090
InChI
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)
InChIKey
ODUOJXZPIYUATO-UHFFFAOYSA-N
SMILES
C(OCC1=CC=CC=C1)(=O)CNC(=O)C(CSC(C)=O)CC1=CC=CC=C1
CAS DataBase Reference
81110-73-8(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn,N
Risk Statements 
22-50/53
Safety Statements 
60-61
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3
RTECS 
MB7606872
HS Code 
29309090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H400Very toxic to aquatic life

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0043
Product name
Racecadotril
Purity
≥98% (HPLC)
Packaging
10mg
Price
$97.2
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0043
Product name
Racecadotril
Purity
≥98% (HPLC)
Packaging
50mg
Price
$376
Updated
2024/03/01
TCI Chemical
Product number
R0103
Product name
Racecadotril
Purity
>99.0%(HPLC)(N)
Packaging
1g
Price
$43
Updated
2024/03/01
Cayman Chemical
Product number
20390
Product name
Racecadotril
Purity
≥98%
Packaging
100mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
20390
Product name
Racecadotril
Purity
≥98%
Packaging
250mg
Price
$70
Updated
2024/03/01
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Racecadotril Chemical Properties,Usage,Production

Description

Racecadotril, also known as acetorphan, is a kind of antidiarrheal drug acting as a peripherally acting enkephalinase inhibitor. It belongs to the group of gastrointestinal drugs and is also a lipophilic derivative of Thiorphan. Racecadotril is a dipeptide in which there is a single amide bond. It has an antisecretory effect, reducing the secretion of water and electrolytes into the intestine. Racecadotril is a pro-drug that is metabolized in vivo into the active compound, thiorphan. Thiorphan exerts its inhibitory effect on enkephalinase, reducing the amount of secreted water produced by the intestines. In this case, the body loses less fluid, and the symptoms of diarrhea can be alleviated.

Chemical Properties

White Solid

Originator

Bioprojet (France)

Uses

Racecadotril is an enkephalinase inhibitor that prevents the degradation of endogenous opioids. It demonstrates antidiarrheal activity by reducing hypersecretion of water and electrolytes into the intestinal lumen. It is an effective and safe treatment for acute diarrhea in adults and children.

Definition

ChEBI: Racecadotril is a N-acyl-amino acid. It is a pro-drug that is metabolized in vivo into the active compound, thiorphan. It has been investigated for the basic science and treatment of Diarrhea, Acute Diarrhea, and Acute Gastroenteritis.

brand name

Tiorfan

Mechanism of action

When Racecadotril enters the body, Racecadotril will be rapidly converted into Thiorphan which interacts specifically with the active site of the enzyme enkephalinase (a cell membrane peptidase enzyme found most commonly on the epithelium of the small intestine), blocking the effect of the enzyme and preventing the loss of the effect of endogenous peptides.

Clinical Use

Racecadotril(Acetorphan, 81110-73-8) is an anti-secretory drug that has been used for acute diarrhoea in children as an adjunct to oral rehydration therapy. It displays antidiarrheal activity via a purely antisecretory mechanism without inhibiting intestinal transit.

Side effects

Racecadotril may cause headache, drowsiness, fever, nausea and vomiting. Besides, in special cases, there may be rare side effects such as rash, erythema, acne skin, urticaria, erythema multiforme, tongue edema, face edema, eyelid edema, angioedema.

Synthesis

Benzaldehyde and diethyl malonate were combined, reduced, and hydrolyzed to form benzyl malonic acid. This acid was then reacted with paraformaldehyde and diethylamine to produce benzyl acrylic acid. Thioacetic acid was then added to this compound, and it was condensed with benzyl glycinate p-toluenesulphonate to obtain racecadotril. Overall, the process had a yield of 66%.

Metabolism

Quickly metabolised by hydrolysis to active metabolite, thiorphan. Racecadotril is eliminated as active and inactive metabolites. Elimination is mainly via the renal route, and to a much lesser extent via the faecal route (around 8%). The pulmonary route is not significant (less than 1% of the dose).

Mode of action

Acetorphan acts as rapidly as loperamide, a classical muopiate receptor agonist that exhibits its antidiarrheal effect via an antitransit mechanism, without producing constipation or other side effects. The novel mechanism of action may render acetorphan potentially useful in the management of infectious diarrhea.

References

[1] https://en.wikipedia.org/wiki/Racecadotril
[2] https://patient.info/medicine/racecadotril-for-acute-diarrhoea-hidrasec
[3] LIANGYI. Racecadotril for acute diarrhoea in children.[J]. Cochrane Database of Systematic Reviews, 2019. DOI:10.1002/14651858.CD009359.pub2.
[4] WUH T. Increase of plasma insulin by racecadotril, an inhibitor of enkephalinase, in Wistar rats.[J]. Hormone and Metabolic Research, 2010. DOI:10.1055/s-0029-1246190.
[5] ASADIMEHDI. Design, synthesis, and evaluation of novel racecadotril-tetrazole-amino acid derivatives as new potent analgesic agents.[J]. Research in Pharmaceutical Sciences, 2021. DOI:10.4103/1735-5362.319573.

Racecadotril Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Racecadotril manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Racecadotril 81110-73-8
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98%-102%
Supply Ability
1000KG
Release date
2021-06-09
shandong perfect biotechnology co.ltd
Product
Racecadotril 81110-73-8
Price
US $0.00/KG
Min. Order
1KG
Purity
98% HPLC
Supply Ability
500KG
Release date
2023-11-16
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Racecadotril 81110-73-8
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-10-16

81110-73-8, RacecadotrilRelated Search:

Racanisodamine Sodium thioglycolate 6-Mercaptopurine Calcium thioglycolate Methylparaben Methyl acrylate Basic Violet 1 3-Mercaptopropionic acid Mercaptoacetic acid Acetonitrile 2-Ethylhexyl mercaptoacetate POTASSIUM THIOGLYCOLATE Glycine Methanol Methyl Diethyl benzylmalonate Thiorphan Disulfide DL-THIORPHAN

  • ACETORPHAN
  • RACECADOTRIL
  • n-[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]-glycine phenylmethyl ester
  • Redotil
  • Benzyl 2-(3-(acetylthio)-2-benzylpropanaMido)acetate
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  • RACECADORTRIL
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  • Glycine, N-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-, phenylmethyl ester
  • tiorfan
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  • n-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-,phenylmethylester,(+-)-glycin
  • n-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-glycinphenylmethylester
  • 2-[[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]acetic acid (phenylmethyl) ester
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  • Racecadotril for peak identification CRS
  • Racecadotril&gt
  • Benzyl N-[3-(Acetylthio)-2-benzylpropionyl]glycinate
  • N-[3-(Acetylthio)-2-benzylpropionyl]glycine Benzyl Ester
  • Racecadotril USP/EP/BP
  • RacecadotrilQ: What is Racecadotril Q: What is the CAS Number of Racecadotril Q: What is the storage condition of Racecadotril Q: What are the applications of Racecadotril
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  • RACECADOTRIL 1% GRANULES
  • 81110-73-8
  • 8110-73-8
  • 115229-09-3
  • C21H23NO4S
  • API
  • TIORFAN
  • Pharmaceutical raw material
  • Pharmaceuticals
  • Sulfur & Selenium Compounds
  • Antidiarrheal
  • Pharmaceutical Intermediates
  • Aromatics
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