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

MedKoo Cat#: 326804 | Name: Racecadotril

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Description:

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

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

Theoretical Analysis

MedKoo Cat#: 326804

Name: Racecadotril

CAS#: 81110-73-8

Chemical Formula: C21H23NO4S

Exact Mass: 385.1348

Molecular Weight: 385.48

Elemental Analysis: C, 65.43; H, 6.01; N, 3.63; O, 16.60; S, 8.32

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 150.00
200mg	USD 250.00
500mg	USD 450.00
1g	USD 750.00
2g	USD 1,250.00

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Related CAS #

No Data

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/

	Solvent	mg/mL	mM
Solubility
	To be determined	0.0	0.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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:

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.

1: Said R, Arafat B, Arafat T. Quantitation of thiorphan in human plasma using LC-MS/MS and its application to a bioequivalence study. J Chromatogr B Analyt Technol Biomed Life Sci. 2024 Aug 1;1243:124190. doi: 10.1016/j.jchromb.2024.124190. Epub 2024 Jun 15. PMID: 38941717. 2: Tras B, Ok M, Ider M, Parlak TM, Yildiz R, Eser Faki H, Ozdemir Kutahya Z, Uney K. Evaluation of the clinical efficacy of racecadotril in the treatment of neonatal calves with infectious diarrhea. Pol J Vet Sci. 2023 Dec 12;26(4):559-569. doi: 10.24425/pjvs.2023.148276. PMID: 38088300. 3: P B A, Sudha SP, Mohan P, Patil N, Rahman A, Gundapuneedi BS, M H. Racecadotril Versus Loperamide in Acute Radiation Enteritis: A Randomized, Double-Masked, Phase 3, Noninferiority Trial. Int J Radiat Oncol Biol Phys. 2024 Mar 1;118(3):616-625. doi: 10.1016/j.ijrobp.2023.09.021. Epub 2023 Sep 22. PMID: 37742773. 4: 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. 5: Le Dault E, Sicard S, Desplans J, Mayet A, Simon F, Aigle L, Savini H, Coton T, Marimoutou C; TAMIDOPEX team. A single dose of ciprofloxacin reduces the duration of diarrhea among service members deployed in Africa. Infect Dis Now. 2023 Mar;53(2):104643. doi: 10.1016/j.idnow.2023.01.003. Epub 2023 Jan 13. PMID: 36642099. 6: Rawashdeh M, Al-Zoubi B, Aliwat MB, Burayzat S, Alhindawi E, Al-Matti AA, Altamimi E. National Consensus for the Management of Acute Gastroenteritis in Jordanian Children: Consensus Recommendations Endorsed by the Jordanian Paediatric Society. Int J Pediatr. 2022 Aug 30;2022:4456232. doi: 10.1155/2022/4456232. PMID: 36082204; PMCID: PMC9448628. 7: 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. 8: Kechichian E, Weill A, Ingen-Housz-Oro S, Assier H. Cimetidine and racecadotril: Unusual culprit drugs of a severe cutaneous adverse reaction. Contact Dermatitis. 2022 Nov;87(5):451-452. doi: 10.1111/cod.14176. Epub 2022 Jul 1. PMID: 35715974. 9: Tras B, Ok M, Parlak TM, Ider M, Yildiz R, Eser Faki H, Ozdemir Kutahya Z, Uney K. Can diarrhea affect the pharmacokinetics of racecadotril in neonatal calves? J Vet Pharmacol Ther. 2022 Sep;45(5):426-431. doi: 10.1111/jvp.13078. Epub 2022 Jun 15. PMID: 35706330. 10: Calzada F, Bautista E, Hidalgo-Figueroa S, García-Hernández N, Velázquez C, Barbosa E, Valdes M, Solares-Pascasio JI. Understanding the Anti-Diarrhoeal Properties of Incomptines A and B: Antibacterial Activity against Vibrio cholerae and Its Enterotoxin Inhibition. Pharmaceuticals (Basel). 2022 Feb 3;15(2):196. doi: 10.3390/ph15020196. PMID: 35215308; PMCID: PMC8875560. 11: Rautenberg TA, Downes M, Kiet PHT, Ashoush N, Dennis AR, Kim K. Evaluating the cost utility of racecadotril in addition to oral rehydration solution versus oral rehydration solution alone for children with acute watery diarrhea in four low middle-income countries: Egypt, Morocco, Philippines and Vietnam. J Med Econ. 2022 Jan-Dec;25(1):274-281. doi: 10.1080/13696998.2022.2037918. PMID: 35125049. 12: Asadi M, Mohammadi-Khanaposhtani M, Hosseini FS, Gholami M, Dehpour AR, Amanlou M. Design, synthesis, and evaluation of novel racecadotril-tetrazole- amino acid derivatives as new potent analgesic agents. Res Pharm Sci. 2021 Jun 30;16(4):341-357. doi: 10.4103/1735-5362.319573. PMID: 34447443; PMCID: PMC8356715. 13: Wang B, Yang L, Wang B, Luo C, Wang Y, Wang H, Chen F, Xiang X. Development, In Vitro and In Vivo Evaluation of Racecadotril Orodispersible Films for Pediatric Use. AAPS PharmSciTech. 2021 Jan 3;22(1):15. doi: 10.1208/s12249-020-01896-6. PMID: 33389269. 14: Twardowska A, Fichna J, Binienda A. Enkefalinazy jako nowy cel farmakologiczny w leczeniu chorób czynnościowych i zapalnych przewodu pokarmowego [Enkephalinases as a new pharmacological target in the treatment of gastrointestinal tract disorders]. Postepy Biochem. 2020 Sep 2;66(3):263-269. Polish. doi: 10.18388/pb.2020_344. PMID: 33315316. 15: Yohannes A, Feng X, Yao S. Dispersive solid-phase extraction of racemic drugs using chiral ionic liquid-metal-organic framework composite sorbent. J Chromatogr A. 2020 Sep 13;1627:461395. doi: 10.1016/j.chroma.2020.461395. Epub 2020 Jul 6. PMID: 32823100. 16: Li L, Shen C, Tang L, Yu Y, Zhou Q, Huang X, Xue S. Determination of thiorphan, a racecadotril metabolite, in human plasma by LC-MS/MS and its application to a bioequivalence study in Chinese subjects . Int J Clin Pharmacol Ther. 2020 Jul;58(7):408-414. doi: 10.5414/CP203588. PMID: 32352368. 17: Pienar C, Benninga MA, Broekaert IJ, Dolinsek J, Mas E, Miele E, Orel R, Ribes-Koninckx C, Thomassen RA, Thomson M, Tzivinikos C, Thapar N. Drugs in Focus: The Use of Racecadotril in Paediatric Gastrointestinal Disease. J Pediatr Gastroenterol Nutr. 2020 Feb;70(2):162-164. doi: 10.1097/MPG.0000000000002574. PMID: 31978009. 18: 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. 19: Wielgos K, Setkowicz W, Pasternak G, Lewandowicz-Uszyńska A. Postępowanie w ostrej biegunce infekcyjnej u dzieci [Management of acute gastroenteritis in children]. Pol Merkur Lekarski. 2019 Aug 30;47(278):76-79. Polish. PMID: 31473758. 20: Fica A, Cataldo P, Aceituno D, Villarroel MI, Escalona A. Fatal nosocomial hemorrhagic enterocolitis probably caused by adenovirus. Report of one case. Rev Med Chil. 2019 Feb;147(2):256-260. doi: 10.4067/s0034-98872019000200256. PMID: 31095177.