Ecadotril

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

MedKoo CAT#: 524975

CAS#: 112573-73-6

Description: Ecadotril is a neutral endopeptidase (NEP) inhibitor. Ecadotril is the (S)-enantiomer of racecadotril. It acts as an antihypertensive.


Price and Availability

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Ecadotril is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 524975
Name: Ecadotril
CAS#: 112573-73-6
Chemical Formula: C21H23NO4S
Exact Mass: 385.13478
Molecular Weight: 385.48
Elemental Analysis: C, 65.43; H, 6.01; N, 3.63; O, 16.60; S, 8.32


Synonym: Ecadotril; BAY y 7432; BAY-y 7432; BP 1.02; S049; S.049; Sinorphan.

IUPAC/Chemical Name: Glycine, N-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-, phenylmethyl ester, (S)-

InChi Key: ODUOJXZPIYUATO-LJQANCHMSA-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)/t19-/m1/s1

SMILES Code: CC(=O)SC[C@@H](Cc1ccccc1)C(=O)NCC(=O)OCc2ccccc2


Technical Data

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:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

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

Harmonized System Code:
293490


References

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: Griggs DW, Prinsen MJ, Oliva J, Campbell MA, Arnett SD, Tajfirouz D, Ruminski PG, Yu Y, Bond BR, Ji Y, Neckermann G, Choy RK, de Hostos E, Meyers MJ. Pharmacologic Comparison of Clinical Neutral Endopeptidase Inhibitors in a Rat Model of Acute Secretory Diarrhea. J Pharmacol Exp Ther. 2016 May;357(2):423-31. doi: 10.1124/jpet.115.231167. Epub 2016 Feb 23. PubMed PMID: 26907621; PubMed Central PMCID: PMC4851326.

5: Kaloudi A, Nock BA, Lymperis E, Valkema R, Krenning EP, de Jong M, Maina T. Impact of clinically tested NEP/ACE inhibitors on tumor uptake of [(111)In-DOTA]MG11-first estimates for clinical translation. EJNMMI Res. 2016 Dec;6(1):15. doi: 10.1186/s13550-015-0158-3. Epub 2016 Feb 16. PubMed PMID: 26882895; PubMed Central PMCID: PMC4755954.

6: Florez ID, Al-Khalifah R, Sierra JM, Granados CM, Yepes-Nuñez JJ, Cuello-Garcia C, Perez-Gaxiola G, Zea AM, Hernandez GN, Veroniki AA, Guyatt GH, Thabane L. The effectiveness and safety of treatments used for acute diarrhea and acute gastroenteritis in children: protocol for a systematic review and network meta-analysis. Syst Rev. 2016 Jan 20;5:14. doi: 10.1186/s13643-016-0186-8. PubMed PMID: 26818403; PubMed Central PMCID: PMC4728803.

7: 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. PubMed PMID: 26715673; PubMed Central PMCID: PMC4789705.

8: Vamecq J, Mention-Mulliez K, Leclerc F, Dobbelaere D. Opioid Facilitation of β-Adrenergic Blockade: A New Pharmacological Condition? Pharmaceuticals (Basel). 2015 Sep 25;8(4):664-74. doi: 10.3390/ph8040664. PubMed PMID: 26426025; PubMed Central PMCID: PMC4695804.

9: 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.

10: Heather CS. Travellers' diarrhoea. BMJ Clin Evid. 2015 Apr 30;2015. pii: 0901. PubMed PMID: 25928418.

11: Vardeny O, Miller R, Solomon SD. Combined neprilysin and renin-angiotensin system inhibition for the treatment of heart failure. JACC Heart Fail. 2014 Dec;2(6):663-70. doi: 10.1016/j.jchf.2014.09.001. Epub 2014 Oct 8. Review. PubMed PMID: 25306450.

12: Pelc R, Redant S, Julliand S, Llor J, Lorrot M, Oostenbrink R, Gajdos V, Angoulvant F. Pediatric gastroenteritis in the emergency department: practice evaluation in Belgium, France, The Netherlands and Switzerland. BMC Pediatr. 2014 May 16;14:125. doi: 10.1186/1471-2431-14-125. PubMed PMID: 24884619; PubMed Central PMCID: PMC4045874.

13: Leemans L. [The treatment of acute diarrhea]. J Pharm Belg. 2013 Sep;(3):4-11. Review. French. PubMed PMID: 24804407.

14: Guarino A, Ashkenazi S, Gendrel D, Lo Vecchio A, Shamir R, Szajewska H; European Society for Pediatric Gastroenterology, Hepatology, and Nutrition; European Society for Pediatric Infectious Diseases. European Society for Pediatric Gastroenterology, Hepatology, and Nutrition/European Society for Pediatric Infectious Diseases evidence-based guidelines for the management of acute gastroenteritis in children in Europe: update 2014. J Pediatr Gastroenterol Nutr. 2014 Jul;59(1):132-52. doi: 10.1097/MPG.0000000000000375. PubMed PMID: 24739189.

15: Baliga RS, Scotton CJ, Trinder SL, Chambers RC, MacAllister RJ, Hobbs AJ. Intrinsic defence capacity and therapeutic potential of natriuretic peptides in pulmonary hypertension associated with lung fibrosis. Br J Pharmacol. 2014 Jul;171(14):3463-75. doi: 10.1111/bph.12694. PubMed PMID: 24641440; PubMed Central PMCID: PMC4105933.

16: Ciccarelli S, Stolfi I, Caramia G. Management strategies in the treatment of neonatal and pediatric gastroenteritis. Infect Drug Resist. 2013 Oct 29;6:133-61. doi: 10.2147/IDR.S12718. Review. PubMed PMID: 24194646; PubMed Central PMCID: PMC3815002.

17: 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.

18: 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.

19: Assathiany R, Guedj R, Bocquet A, Thiebault G, Salinier C, Girardet JP; l’Association française de pédiatrie ambulatoire. [Treatment of acute gastroenteritis in private practice: a survey of 641 pediatricians]. Arch Pediatr. 2013 Oct;20(10):1113-9. doi: 10.1016/j.arcped.2013.06.029. Epub 2013 Aug 13. French. PubMed PMID: 23953626.

20: 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.