sacubitril   Click here for help

GtoPdb Ligand ID: 7857

Synonyms: AHU377 | Entresto® | Neparvis®
Approved drug
sacubitril is an approved drug (EMA & FDA (2015))
Compound class: Synthetic organic
Comment: Sacubitril is a prodrug activated by de-ethylation via esterases to the neprilysin inhibitor sacubitrilat. Neprilysin is also known as neutral endopeptidase (NEP), and its official gene symbol is MME (membrane metallo-endopeptidase ). The chemical database relationships are detailed in this blogpost. Sabucatril is a component of the approved fixed mixture Entresto®, previously known as LCZ696, and which is now approved for heart failure (see Clinical data tab).
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 13
Topological polar surface area 92.7
Molecular weight 411.2
XLogP 3.86
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CCOC(=O)C(CC(Cc1ccc(cc1)c1ccccc1)NC(=O)CCC(=O)O)C
Isomeric SMILES CCOC(=O)[C@@H](C[C@@H](Cc1ccc(cc1)c1ccccc1)NC(=O)CCC(=O)O)C
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
InChI Key PYNXFZCZUAOOQC-UTKZUKDTSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA & FDA (2015))
Is prodrug? Yes
Active form sacubitrilat
IUPAC Name Click here for help
4-[[(2S,4R)-5-ethoxy-4-methyl-5-oxo-1-(4-phenylphenyl)pentan-2-yl]amino]-4-oxobutanoic acid
International Nonproprietary Names Click here for help
INN number INN
9819 sacubitril
Synonyms Click here for help
AHU377 | Entresto® | Neparvis®
Database Links Click here for help
CAS Registry No. 149709-62-6 (source: Scifinder)
ChEMBL Ligand CHEMBL3137301
DrugCentral Ligand 5012
GtoPdb PubChem SID 223366187
PubChem CID 9811834
Search Google for chemical match using the InChIKey PYNXFZCZUAOOQC-UTKZUKDTSA-N
Search Google for chemicals with the same backbone PYNXFZCZUAOOQC
Search PubMed clinical trials sacubitril
Search PubMed titles sacubitril
Search PubMed titles/abstracts sacubitril
Search UniChem for chemical match using the InChIKey PYNXFZCZUAOOQC-UTKZUKDTSA-N
Search UniChem for chemicals with the same backbone PYNXFZCZUAOOQC
Wikipedia Sacubitril