Racecadotril | CAS#81110-73-8 | enkephalinase inhibitor

Racecadotril
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 326804

CAS#: 81110-73-8

Description: Racecadotril, also known as acetorphan, is an antidiarrheal drug which acts as a peripherally acting enkephalinase inhibitor. Unlike other opioid medications used to treat diarrhea, which reduce intestinal motility, racecadotril has an antisecretory effect—it reduces the secretion of water and electrolytes into the intestine.

Chemical Structure

Racecadotril

CAS# 81110-73-8

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326804
Name: Racecadotril
CAS#: 81110-73-8
Chemical Formula: C21H23NO4S
Exact Mass: 385.13
Molecular Weight: 385.480
Elemental Analysis: C, 65.43; H, 6.01; N, 3.63; O, 16.60; S, 8.32

Price and Availability

Size	Price	Availability	Quantity
5g	USD -1
100mg	USD 150
200mg	USD 250
500mg	USD 450
1g	USD 750
2g	USD 1250
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Racecadotril; Acetorphan.

IUPAC/Chemical Name: benzyl (3-(acetylthio)-2-benzylpropanoyl)glycinate

InChi Key: ODUOJXZPIYUATO-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(OCC1=CC=CC=C1)CNC(C(CSC(C)=O)CC2=CC=CC=C2)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: It is available in France (where it was first introduced in ~1990) and other European countries (including Germany, Italy, the UK and Spain) as well as most of South America and some South East Asian countries (including China, India and Thailand), but not in the United States. It is sold under the tradenames Hidrasec or, in France, Tiorfan. In Italy it is sold under the tradename Tiorfix.

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Racecadotril is a prodrug form of the neprilysin inhibitor thiorphan. In vivo, racecadotril reduces or prevents castor oil-induced diarrhea without delaying intestinal transit in rats. Racecadotril decreases the duration of diarrhea and increases body weight gain in a neonatal gnotobiotic pig model of human rotavirus-induced diarrhea. Racecadotril formulations have been used in acute diarrhea treatment.
In vitro activity:	This study demonstrated that a chemically long-term stable racecadotril dispersible tablet product, whose taste is efficiently masked using wet granulation method, had an acceptable release profile. It was obtained with Eudragit® NE 30D ratio higher than 1% and equal or lower than 10% by weight of racecadotril. Reference: Turk J Pharm Sci. 2022 Aug 31;19(4):383-390. https://pubmed.ncbi.nlm.nih.gov/36047514/
In vivo activity:	Lacticaseibacillus casei Zhang metabolized racecadotril to its active products in monoculture,a simulated human digestion system, and an ex vivo fecal co-culture system. A personalized effect was observed in the racecadotril-metabolizing activity of L. casei Zhang, depending individual host gut microbiome composition. Reference: Front Pharmacol. 2023 Jan 26;14:1047863. https://pubmed.ncbi.nlm.nih.gov/36778014/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	To be determined	0.0	0.00

Preparing Stock Solutions

The following data is based on the product molecular weight 385.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Pınarbaşlı O, Bulut B, Gurbetoğlu GP, Atılgan N, Sarraçoğlu N, Aybey A. Evaluation of the Effect of Ethyl Acrylate-Methyl Methacrylate Copolymer in Racecadotril Dispersible Tablet. Turk J Pharm Sci. 2022 Aug 31;19(4):383-390. doi: 10.4274/tjps.galenos.2021.50432. PMID: 36047514; PMCID: PMC9438762. 2. Li B, Kwok LY, Wang D, Li L, Guo S, Chen Y. Integrating metabolomics, bionics, and culturomics to study probiotics-driven drug metabolism. Front Pharmacol. 2023 Jan 26;14:1047863. doi: 10.3389/fphar.2023.1047863. PMID: 36778014; PMCID: PMC9908756. 3. Liang Y, Zhang L, Zeng L, Gordon M, Wen J. Racecadotril for acute diarrhoea in children. Cochrane Database Syst Rev. 2019 Dec 19;12(12):CD009359. doi: 10.1002/14651858.CD009359.pub2. PMID: 31858591; PMCID: PMC6923519.
In vitro protocol:	1. Pınarbaşlı O, Bulut B, Gurbetoğlu GP, Atılgan N, Sarraçoğlu N, Aybey A. Evaluation of the Effect of Ethyl Acrylate-Methyl Methacrylate Copolymer in Racecadotril Dispersible Tablet. Turk J Pharm Sci. 2022 Aug 31;19(4):383-390. doi: 10.4274/tjps.galenos.2021.50432. PMID: 36047514; PMCID: PMC9438762.
In vivo protocol:	1. Li B, Kwok LY, Wang D, Li L, Guo S, Chen Y. Integrating metabolomics, bionics, and culturomics to study probiotics-driven drug metabolism. Front Pharmacol. 2023 Jan 26;14:1047863. doi: 10.3389/fphar.2023.1047863. PMID: 36778014; PMCID: PMC9908756. 2. Liang Y, Zhang L, Zeng L, Gordon M, Wen J. Racecadotril for acute diarrhoea in children. Cochrane Database Syst Rev. 2019 Dec 19;12(12):CD009359. doi: 10.1002/14651858.CD009359.pub2. PMID: 31858591; PMCID: PMC6923519.

Molarity Calculator

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

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1: Sáez J, Cifuentes L. Is racecadotril effective for acute diarrhea in children? -First update. Version 2. Medwave. 2016 May 6 [revised 2016 May 24];16(Suppl2):e6438. doi: 10.5867/medwave.2016.6438. Spanish, English. PubMed PMID: 26731112.

2: Racecadotril + ACE inhibitors: angioedema. Prescrire Int. 2016 Mar;25(169):71. PubMed PMID: 27213193.

3: Chiguru V, Lingesh A, R S, N S. Forced degradation study of racecadotril: Effect of co-solvent, characterization of degradation products by UHPLC-Q-TOF-MS/MS, NMR and cytotoxicity assay. J Pharm Biomed Anal. 2016 May 6;128:9-17. doi: 10.1016/j.jpba.2016.05.008. [Epub ahead of print] PubMed PMID: 27209450.

4: Gordon M, Akobeng A. Racecadotril for acute diarrhoea in children: systematic review and meta-analyses. Arch Dis Child. 2016 Mar;101(3):234-40. doi: 10.1136/archdischild-2015-309676. Epub 2015 Dec 29. Review. PubMed PMID: 26715673; PubMed Central PMCID: PMC4789705.

5: Gutiérrez-Castrellón P, Ortíz-Hernández AA, Llamosas-Gallardo B, Acosta-Bastidas MA, Jiménez-Gutiérrez C, Diaz-García L, Anzo-Osorio A, Estevez-Jiménez J, Jiménez-Escobar I, Vidal-Vázquez RP. [Efficacy of racecadotril vs. smectite, probiotics or zinc as an integral part of treatment of acute diarrhea in children under five years: A meta-analysis of multiple treatments]. Gac Med Mex. 2015 May-Jun;151(3):329-37. Review. Spanish. PubMed PMID: 26089269.

6: Semalty M, Panchpuri M, Singh D, Semalty A. Cyclodextrin inclusion complex of racecadotril: effect of drug-β- cyclodextrin ratio and the method of complexation. Curr Drug Discov Technol. 2014 Jun;11(2):154-61. PubMed PMID: 24188445.

7: Kurklinsky S, Abdul-Hay SO, McGuire MP, Howard EA, Knight J, Leissring MA. The blood glucose-lowering effect of racecadotril is not attributable to inhibition of insulin-degrading enzyme. Horm Metab Res. 2014 Jan;46(1):73-4. doi: 10.1055/s-0033-1353211. Epub 2013 Aug 23. PubMed PMID: 23975847.

8: Mehta S, Khandelwal PD, Jain VK, Sihag M. A comparative study of racecadotril and single dose octreotide as an anti-secretory agent in acute infective diarrhoea. J Assoc Physicians India. 2012 Nov;60:12-5. PubMed PMID: 23767196.

9: Garala K, Patel J, Patel A, Raval M, Dharamsi A. Influence of excipients and processing conditions on the development of agglomerates of racecadotril by crystallo-co-agglomeration. Int J Pharm Investig. 2012 Oct;2(4):189-200. doi: 10.4103/2230-973X.106996. PubMed PMID: 23580935; PubMed Central PMCID: PMC3618635.

10: Duh D, Tanret I. [Racecadotril (Tiorfix), oral]. J Pharm Belg. 2012 Dec;(4):51-2. French. PubMed PMID: 23350211.

11: Eberlin M, Mück T, Michel MC. A comprehensive review of the pharmacodynamics, pharmacokinetics, and clinical effects of the neutral endopeptidase inhibitor racecadotril. Front Pharmacol. 2012 May 30;3:93. doi: 10.3389/fphar.2012.00093. eCollection 2012. PubMed PMID: 22661949; PubMed Central PMCID: PMC3362754.

12: Rautenberg TA, Zerwes U, Foerster D, Aultman R. Evaluating the cost utility of racecadotril for the treatment of acute watery diarrhea in children: the RAWD model. Clinicoecon Outcomes Res. 2012;4:109-16. doi: 10.2147/CEOR.S31238. Epub 2012 Apr 20. PubMed PMID: 22570557; PubMed Central PMCID: PMC3345933.

13: López-Campos JL, Gutiérrez C, Calero C. The potential role of racecadotril in the treatment of diarrhea associated with roflumilast. Arch Bronconeumol. 2012 Nov;48(11):426. doi: 10.1016/j.arbres.2012.03.002. Epub 2012 May 4. English, Spanish. PubMed PMID: 22560927.

14: Lee JP, Cheng KC, Chung HH, Wu HT, Chen CT, Cheng JT. Inhibition of insulin degrading enzyme by racecadotril in the brain of Wistar rats. Horm Metab Res. 2011 Jun;43(7):489-93. doi: 10.1055/s-0031-1277183. Epub 2011 May 9. PubMed PMID: 21557151.

15: Lehert P, Chéron G, Calatayud GA, Cézard JP, Castrellón PG, Garcia JM, Santos M, Savitha MR. Racecadotril for childhood gastroenteritis: an individual patient data meta-analysis. Dig Liver Dis. 2011 Sep;43(9):707-13. doi: 10.1016/j.dld.2011.03.001. Epub 2011 Apr 22. PubMed PMID: 21514257.

16: Ali NW, Elghobashy MR, Mahmoud MG, Mohammed MA. Spectrophotometric and spectrofluorimetric methods for determination of Racecadotril. Pak J Pharm Sci. 2011 Jan;24(1):19-23. PubMed PMID: 21190913.

17: Tebruegge M. Racecadotril did not improve diarrhoeal symptoms in children with moderate acute gastroenteritis. Arch Dis Child Educ Pract Ed. 2010 Dec;95(6):197. doi: 10.1136/adc.2010.192427. Epub 2010 Sep 30. PubMed PMID: 20889447.

18: Chacón J. Analysis of factors influencing the overall effect of racecadotril on childhood acute diarrhea. Results from a real-world and post-authorization surveillance study in Venezuela. Ther Clin Risk Manag. 2010 Jul 21;6:293-9. PubMed PMID: 20668711; PubMed Central PMCID: PMC2909495.

19: Hofmann R. Remarks and questions on the article "Prospective randomized double-blind trial of racecadotril compared with loperamide in elderly people with gastroenteritis living in nursing homes". Eur J Clin Pharmacol. 2010 Aug;66(8):839; author reply 841-2. doi: 10.1007/s00228-010-0843-0. Epub 2010 Jun 5. PubMed PMID: 20526590.

20: Wu HT, Chang CK, Cheng KC, Chang CH, Yeh CH, Cheng JT. Increase of plasma insulin by racecadotril, an inhibitor of enkephalinase, in Wistar rats. Horm Metab Res. 2010 Apr;42(4):261-7. doi: 10.1055/s-0029-1246190. Epub 2010 Feb 8. PubMed PMID: 20143290.

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