n-[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]-glycine phenylmethyl ester
Racecadotril
CAS: 81110-73-8
Molecular Formula: C21H23NO4S
n-[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]-glycine phenylmethyl ester - Names and Identifiers
| Name | Racecadotril |
| Synonyms | Redotil Cadotril ACETORPHAN Racecodotril RACECADOTRIL Racecadotril Benzyl 2-(3-(acetylthio)-2-benzylpropanaMido)acetate benzyl N-[3-(acetylsulfanyl)-2-benzylpropanoyl]glycinate (RS)-Benzyl N-[3-(acetylthio)-2-benzylpropanoyl]glycinate benzyl N-[2-benzyl-3-(carboxysulfanyl)propanoyl]glycinate N-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-glycin phenylmethyl ester n-[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]-glycine phenylmethyl ester |
| CAS | 81110-73-8 |
| EINECS | 688-010-7 |
| InChI | InChI=1/C20H21NO5S/c22-18(26-13-16-9-5-2-6-10-16)12-21-19(23)17(14-27-20(24)25)11-15-7-3-1-4-8-15/h1-10,17H,11-14H2,(H,21,23)(H,24,25) |
| InChIKey | ODUOJXZPIYUATO-UHFFFAOYSA-N |
n-[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]-glycine phenylmethyl ester - Physico-chemical Properties
| Molecular Formula | C21H23NO4S |
| Molar Mass | 385.48 |
| Density | 1.206 |
| Melting Point | 89°C |
| Boling Point | 574.5±50.0 °C(Predicted) |
| Solubility | DMSO: ≥44mg/mL |
| Appearance | powder |
| Color | white to tan |
| Merck | 14,8090 |
| pKa | 13.63±0.46(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | 1.601 |
| Use | Anti-diarrheal drugs |
n-[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]-glycine phenylmethyl ester - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| RTECS | MB7606872 |
| HS Code | 29309090 |
n-[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]-glycine phenylmethyl ester - Reference Information
| Anti-Diarrhea drug | racecadotril, also known as acetorphine, Fenghuang, Lodu, dulaber, is a new mechanism of action of anti-Diarrhea drugs, direct inhibition of intestinal excessive secretion, rapid improvement of Diarrhea symptoms, treatment of children with rotavirus Diarrhea significant effect, can significantly shorten the course of disease, to reduce the suffering of children, suitable for adults and 1 months to infants and children with acute Diarrhea, the earliest by the France's Bioprojet company developed successfully in 1993, first in France by trade name Tiorfan listed soon, the Canadian Pediatric Association and the United States Centers for Disease Control and Prevention (CDC) on the racecadotril included in children Diarrhea treatment of essential drugs, Diarrhea years also included in the Chinese national consensus on the treatment of pediatric disease recommended drugs. At present, the domestic clinical front-line pediatricians have been racecadotril as a clinical treatment of children Diarrhea efficient and safe drugs. |
| advantages | racecadotril has almost no common adverse reactions of previous anti-Diarrhea drugs, however, the therapeutic effect was equivalent to that of the conventional clinical medication of lopamil. It is the first Enkephalinase inhibitor to be applied to Diarrhea and has a high specific antisecretory effect. It exerts its anti-Diarrhea effect by inhibiting the activity of enkephalanginase, which in turn inhibits the excessive secretion of water and electrolytes. |
| features | high efficiency, rapid action, high therapeutic index, the central nervous system, respiratory system, cardiovascular system, the endocrine system has no obvious effect and does not cause constipation. It is a safe and effective anti-diarrhea drug. It can reduce the excessive secretion of intestinal water and electrolytes caused by cholera or inflammation, and the intestinal basal secretion was not statistically different from placebo. Racecadotril rapid onset of action within 30 minutes to achieve clinically significant inhibition of Enkephalinase activity, reduce the concentration of intestinal epithelial cells reduce the excessive intestinal secretion of camp, and the intestinal emptying time compared with placebo was not significantly different. 24-hour fecal output was reduced by 56%, far exceeding the WHO clinical evaluation of antidiarrheal (30%), while racecadotril-induced secondary constipation and bloating was significantly lower than traditional antidiarrheal drugs (antikinetic drugs). |
| pharmacokinetics | racecadotril is a prodrug that is easily absorbed from the gastrointestinal tract due to its lipophilic properties, rapid onset of action. racecadotril is metabolized to its active ingredient by tissue lipase in the gastrointestinal tract, an active metabolite that is a potent inhibitor of Enkephalinase and protects endogenous enkephalins from destruction, thus, the effect of physiological antisecretory action is prolonged, which results in rapid control of excessive secretion of water and electrolytes at Diarrhea. 1. Absorption: This product can be rapidly absorbed after oral administration, and the inhibition of plasma endorphin enzyme appears at 30 minutes. The intensity of enzyme inhibition was related to the dose. When the dosage was 1.5mg/Kg, the inhibition of the enzyme reached the peak (the inhibition of the enzyme reached 2.5) after 90% hours, and the inhibition of the enzyme lasted for about 8 hours, t1/2 is approximately 3 hours. 2. Distribution: the tissue distribution of this product is less, and only 1% of the drug is distributed to the tissue. The plasma protein binding rate was 90% (mainly albumin binding). 3. Metabolism: after entering the body, the product is rapidly transformed into its active metabolite Thiorphan, that is, (±)N-(1-oxo-2-mercaptomethyl-3-phenylpropyl) glycine is then converted to the inactive metabolites disulfide and mercaptomethyl ether and finally excreted in the urine, feces and lungs. 92% of the drug is eliminated from the urine and feces at 24 hours, with no accumulation in the body or Rapid Immunization. This product has no inducing effect on cytochrome P450 enzyme system in adults. 4, elimination: radiolabeling study found that this product mainly through the feces and urine excretion. Repeated administration will not change the pharmacokinetic properties of this product. Diet prolonged the onset of Enkephalinase inhibition but had no effect on peak height and area under the curve (AUC). |
| dosage | orally, three times a day, 1.5m per kg of body weight; the total daily dose should not exceed 6mg per kg. Continuous use should not exceed 7 days. When necessary, oral rehydration or intravenous rehydration is given. recommended dosage: 1. Dosage for infants: 1-9 months old (body weight <9kg), 10mg each time, three times a day; 9~30 months old (body weight 9 ~ 13kg), each 20mg, three times a day. 2. Children's dosage: 30 months to 9 years old (13kg ~ 27kg), 30mg each time, three times a day; Over 9 years old (weight> 27kg), 60mg each time, three times daily. |
| toxicity | It has been reported in the literature that no toxic reaction was found in primates taking 100 times the therapeutic dose of racecadotril for 12 months. The mice were intraperitoneally injected with racecadotril at a dose of 50mg/Kg (twice/day) for 10 days, and no toxic reaction was observed during the administration and after the drug withdrawal. |
| drug interaction | 1. Cytochrome P450-3A4 inhibitors such as erythromycin and ketoconazole may reduce the metabolism of racecadotril and increase toxicity. 2. Rifampicin-like cytochrome P450-3A4 inducer may reduce the anti-Diarrhea effect of racecadotril. |
| adverse reaction | 1. Patients with acute Diarrhea of central nervous system experienced dizziness, discomfort and Head Pain. 2. Persistent hypokalemia was reported in Diarrhea of children with inflammatory water in the endocrine and metabolic system. 3, gastrointestinal tract is rare, there are reports of rebound constipation, rare intestinal obstruction. Symptoms were noted in Vomit of the children. 4. Occasional somnolence, rash, Nausea and Abdominal Pain, etc. |
| synthesis method | 1. Benzaldehyde and diethyl malonate are condensed, reduced and hydrolyzed to give benzylmalonic acid. Benzylacrylic acid obtained by reaction with paraformaldehyde and diethylamine is added with Thio: acetic acid, and finally condensed with glycine benzyl ester p-toluenesulfonate to give racecadotril, the overall yield was 66%. 2. Using 2-[(acetyl sulfur) methyl]-3-phenyl propionic acid as the starting material, 2-[(acetyl sulfur) methyl]-3-phenyl propionyl chloride is produced by acylation reaction, after condensation with glycine benzyl ester p-toluenesulfonate, racecadotril is formed. 3. Benzyl chloride was selected as the starting material, and diethyl benzyl malonate was obtained by reaction with diethyl malonate in ethanol solution of sodium ethoxide; Diethyl benzyl malonate was hydrolyzed into benzyl propylene glycol acid in aqueous sodium hydroxide solution, the reaction with paraformaldehyde yields 2-[(acetylthio) methyl]-3-phenylpropionic acid. Benzyl alcohol, glycine and p-toluenesulfonic acid were reacted at 110-115 ℃ for 6h, and the intermediate benzyl glycine Ester P-toluenesulfonate was obtained by post-treatment. Finally, the intermediate 2-[(acetylthio) methyl]-3-phenylpropionic acid is condensed with glycine benzyl ester p-toluenesulfonate under the action of condensing agent DCC, HOBT to obtain racecadotril. |
| patent information | racecadotril was developed by the French company Bioproject. The earliest patent number of compound and use is EP38758, the patent was granted on April 17, 1980. This product has not applied for a patent in China. According to the Patent Law and the Regulations on Administrative protection of pharmaceuticals, this drug is not protected by Chinese patents and there is no administrative protection problem. |
| Use | anti-diarrheal drug |
Last Update：2024-04-09 21:48:26
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Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Multiple SpecificationsSpot supply
Product Name: Racecadotril Visit Supplier Webpage Request for quotationCAS: 81110-73-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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