LISINOPRIL

Search structure
Synonyms:
Status: Approved (1987)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C09AA03
UNII: 7Q3P4BS2FD

Structure
InChI Key RLAWWYSOJDYHDC-BZSNNMDCSA-N
Smile NCCCC[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N1CCC[C@H]1C(=O)O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H35N3O7
Molecular Weight 441.53
AlogP 1.24
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 12.0
Polar Surface Area 132.96
Molecular species ZWITTERION
Aromatic Rings 1.0
Heavy Atoms 29.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Angiotensin-converting enzyme inhibitor FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M2 family
- 0-8 - 51-132 7
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 5-83

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Heart Failure 4 D006333 FDA
Myocardial Infarction 4 D009203 FDA
Hypertrophy, Left Ventricular 3 D017379 ClinicalTrials
Hyperoxaluria, Primary 3 D006960 ClinicalTrials
Cardiovascular Diseases 3 D002318 ClinicalTrials
Diabetes Mellitus 3 D003920 ClinicalTrials
Diabetic Nephropathies 3 D003928 ClinicalTrials
Hypertension 3 D006973 ClinicalTrials
Diabetes Mellitus, Type 2 3 D003924 ClinicalTrials
Heart Failure 3 D006333 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Atherosclerosis 3 D050197 ClinicalTrials
Polycystic Kidney Diseases 3 D007690 ClinicalTrials
Myocardial Ischemia 3 D017202 ClinicalTrials
Hypercholesterolemia 3 D006937 ClinicalTrials
Heart Failure 3 D006333 ClinicalTrials
Coronary Disease 3 D003327 ClinicalTrials
Non-alcoholic Fatty Liver Disease 2 D065626 ClinicalTrials
Glomerulosclerosis, Focal Segmental 2 D005923 ClinicalTrials
Essential Hypertension 2 D000075222 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Carcinoma, Hepatocellular 2 D006528 ClinicalTrials
Lupus Erythematosus, Systemic 2 D008180 ClinicalTrials
Glomerulonephritis 2 D005921 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Azoospermia 2 D053713 ClinicalTrials
Stroke 1 D020521 ClinicalTrials
Gastroparesis 1 D018589 ClinicalTrials
Lecithin Cholesterol Acyltransferase Deficiency 1 D007863 ClinicalTrials
Vascular Diseases 1 D014652 ClinicalTrials

Related Entries

Scaffolds

Cross References

Resources Reference
ChEBI 43755
ChEMBL CHEMBL1237
DrugBank DB00722
DrugCentral 1587
EPA CompTox DTXSID6040537
FDA SRS 7Q3P4BS2FD
Human Metabolome Database HMDB0001938
Guide to Pharmacology 6360
PDB LPR
PharmGKB PA450242
SureChEMBL SCHEMBL15680
ZINC ZINC000003812863
ChEBI 6503
ChEMBL CHEMBL419213
EPA CompTox DTXSID2045600
FDA SRS E7199S1YWR
SureChEMBL SCHEMBL542591
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