lisinopril   Click here for help

GtoPdb Ligand ID: 6360

Synonyms: Prinivil® | Zestril®
Approved drug PDB Ligand
lisinopril is an approved drug (FDA (1987))
Compound class: Synthetic organic
Comment: Lisinopril was the third ACE inhibitor (after captopril and enalapril) to be approved for clinical use. Chemically it is the lysine analogue of enalapril. Unlike other ACE inhibitors, it is not a prodrug and is excreted unchanged in the urine.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 13
Topological polar surface area 132.96
Molecular weight 405.23
XLogP -0.93
No. Lipinski's rules broken 1
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Canonical SMILES NCCCCC(C(=O)N1CCCC1C(=O)O)NC(C(=O)O)CCc1ccccc1
Isomeric SMILES NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N[C@H](C(=O)O)CCc1ccccc1
InChI InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1
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Summary of Clinical Use Click here for help
Competitive inhibitor of ACE used to treat hypertension and congestive heart failure. An orally administered lisinopril solution (Qbrelis) is FDA approved (August 2016), and can be used for managing hypertension in adults and children 6 years of age and older.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Binds to angeotensin-converting enzyme and thereby competes with the binding of angiotensin I, inhibiting its conversion to angiotensin II. The resulting decreased levels of angiotensin II leads to decreased blood pressure and an increase in plama renin activity.