Ecadotril

Ecadotril
Names

Preferred IUPAC name Benzyl [(2S)-3-(acetylsulfanyl)-2-benzylpropanamido]acetate
Identifiers
CAS Number	112573-73-6
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1516410
ChemSpider	54591
PubChem CID	60561
UNII	6XSR933SRK^Y
CompTox Dashboard (EPA)	DTXSID8045513
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)/t19-/m1/s1 Key: ODUOJXZPIYUATO-LJQANCHMSA-N InChI=1/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 Key: ODUOJXZPIYUATO-LJQANCHMBY
SMILES O=C(SC[C@H](C(=O)NCC(=O)OCc1ccccc1)Cc2ccccc2)C
Properties
Chemical formula	C₂₁H₂₃NO₄S
Molar mass	385.48 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Ecadotril is a neutral endopeptidase inhibitor ((NEP^[1]) EC 3.4.24.11^[2]) and determined by the presence of peptidase family M13 as a neutral endopeptidase inhibited by phosphoramidon. Ecadotril is the (S)-enantiomer of racecadotril. NEP-like enzymes include the endothelin-converting enzymes.^[3] The peptidase M13 family believed to activate or inactivate oligopeptide (pro)-hormones such as opioid peptides,^[3] neprilysin^[3] is another member of this group, in the case of the metallopeptidases and aspartic, the nucleophiles clan or family for example MA, is an activated water molecule.^[1] The peptidase domain for members of this family also contains a bacterial member and resembles that of thermolysin the predicted active site residues for members of this family and thermolysin occur in the motif HEXXH.^[4] Thermolysin complexed with the inhibitor (S)-thiorphan are isomeric thiol-containing inhibitors of endopeptidase EC 24-11^[5] (also called "enkephalinase").

References

^ ^a ^b Le Moual H, Roques BP, Crine P, Boileau G (June 1993). "Substitution of potential metal-coordinating amino acid residues in the zinc-binding site of endopeptidase-24.11". FEBS Lett. 324 (2): 196–200. doi:10.1016/0014-5793(93)81392-D. PMID 8099556.
^ Malfroy B, Schofield PR, Kuang WJ, Seeburg PH, Mason AJ, Henzel WJ (April 1987). "Molecular cloning and amino acid sequence of rat enkephalinase". Biochemical and Biophysical Research Communications. 144 (1): 59–66. doi:10.1016/S0006-291X(87)80475-8. PMID 3555489.
^ ^a ^b ^c Turner AJ, Isaac RE, Coates D (March 2001). "The neprilysin (NEP) family of zinc metalloendopeptidases: Genomics and function". BioEssays. 23 (3): 261–9. doi:10.1002/1521-1878(200103)23:3<261::AID-BIES1036>3.0.CO;2-K. PMID 11223883.
^ Rudner DZ, Fawcett P, Losick R (December 1999). "A family of membrane-embedded metalloproteases involved in regulated proteolysis of membrane-associated transcription factors". Proc Natl Acad Sci USA. 96 (26): 14765–14770. doi:10.1073/pnas.96.26.14765. PMC 24722. PMID 10611287.
^ S. L. Roderick; M. C. Fournie-Zaluski; B. P. Roques; B. W. Matthews (February 1989). "Thiorphan and retro-thiorphan display equivalent interactions when bound to crystalline thermolysin". Biochemistry. 28 (4): 1493–7. doi:10.1021/bi00430a011. PMID 2719912.