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Substrate Report for: Sacubitril

Sacubitril is a prodrug that is activated to sacubitrilat (LBQ657) by de-ethylation via CES1. Sacubitrilat inhibits the enzyme neprilysin, which is responsible for the degradation of atrial and brain natriuretic peptide and is used to reduce the risk of cardiovascular events in patients with chronic heart failure


General
Type Pro-Drug, Not A/B H target, Drug
Chemical_Nomenclature 4-[[(2S,4R)-5-ethoxy-4-methyl-5-oxo-1-(4-phenylphenyl)pentan-2-yl]amino]-4-oxobutanoic acid
Canonical SMILES CCOC(=O)C(C)CC(CC1=CC=C(C=C1)C2=CC=CC=C2)NC(=O)CCC(=O)O
InChI InChI=1S/C24H29NO5/c1-3-30-24(29)17(2)15-21(25-22(26)13-14-23(27)28)16-18-9-11-20(12-10-18)19-7-5-4-6-8-19/h4-12,17,21H,3,13-16H2,1-2H3,(H,25,26)(H,27,28)/t17-,21+/m1/s1
InChIKey PYNXFZCZUAOOQC-UTKZUKDTSA-N
Other name(s) AHU-377 ; AHU377 ; UNII-17ERJ0MKGI ; AHU 377 ; LCZ 696 ; LCZ-696 ; Entresto
________________________________________________________________________________________________
MW|411.49
Formula|C24H29NO5
CAS_number|149709-62-6
PubChem|9811834
UniChem|PYNXFZCZUAOOQC-UTKZUKDTSA-N
IUPHAR|
Wikipedia|Sacubitril

Target
Families | Sacubitril ligand of proteins in family: Carb_B_Chordata

References:
Search PubMed for references concerning: Sacubitril
    Title: Transport properties of valsartan, sacubitril and its active metabolite (LBQ657) as determinants of disposition
    Hanna I, Alexander N, Crouthamel MH, Davis J, Natrillo A, Tran P, Vapurcuyan A, Zhu B
    Ref: Xenobiotica, :1, 2017 : PubMed

            

    Title: A Comprehensive Functional Assessment of Carboxylesterase 1 Nonsynonymous Polymorphisms
    Wang X, Rida N, Shi J, Wu AH, Bleske BE, Zhu HJ
    Ref: Drug Metabolism & Disposition: The Biological Fate of Chemicals, 45:1149, 2017 : PubMed

            

    Title: Sacubitril Is Selectively Activated by Carboxylesterase 1 (CES1) in the Liver and the Activation Is Affected by CES1 Genetic Variation
    Shi J, Wang X, Nguyen J, Wu AH, Bleske BE, Zhu HJ
    Ref: Drug Metabolism & Disposition: The Biological Fate of Chemicals, 44:554, 2016 : PubMed