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Compound Detail

CHEMBL1237

LISINOPRIL ANHYDROUS
💊 Approved Drug
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💊 Approved Drug
NCCCC[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N1CCC[C@H]1C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1237
Name LISINOPRIL ANHYDROUS
Phase Approved
Structure Type MOL
InChI Key RLAWWYSOJDYHDC-BZSNNMDCSA-N
Therapeutic ✓ Yes

Known Names

Lisinopril anhydrous
3
Targets
22
Activities
2
Assay Types
11
PK Parameters
20
Publications
1
Known Names
20
Indications

Molecular Properties

405.5
MW (Da)
1.24
ALogP
5
HBA
4
HBD
133.0
PSA (Ų)
0.38
QED
0
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1987
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -pril
USAN Year 1984

Extended Properties

Molecular Formula C21H31N3O5
MW 405.50
Aromatic Rings 1
Heavy Atoms 29
NP-Likeness 0.20

Indications

Atherosclerosis Cardiovascular Diseases Coronary Disease Diabetes Mellitus Diabetes Mellitus, Type 2 Diabetic Nephropathies Heart Failure Heart Failure Hypercholesterolemia Hyperoxaluria, Primary Hypertension Hypertrophy, Left Ventricular Myocardial Infarction Myocardial Ischemia Polycystic Kidney Diseases Azoospermia Breast Neoplasms Carcinoma, Hepatocellular Cardiomyopathies Essential Hypertension

Activity Summary

IC50 16 meas. best 10.0
Ki 6 meas. best 8.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Angiotensin-converting enzyme
CHEMBL1808
 IC50 10.0 9.1233 0.1 9
Angiotensin-converting enzyme
CHEMBL1808
 Ki 8.92 7.658 1.2 5
Unchecked
CHEMBL612545
 IC50 8.92 8.92 1.2 1
Angiotensin-converting enzyme
CHEMBL4074
 IC50 8.22 6.9625 6.0 4
Angiotensin-converting enzyme
CHEMBL4074
 Ki 7.29 7.29 51.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 252.5 - Chlorocebus sabaeus
CL 1.2 mL.min-1.kg-1 Homo sapiens
CL 1.2 mL.min-1.kg-1 Homo sapiens
CL - mL.min-1.kg-1 Homo sapiens
CL 1.2 mL.min-1.kg-1 Homo sapiens
F 25.0 % Homo sapiens
F 27.0 % Homo sapiens
Fu 1.0 - Homo sapiens
Fu 1.0 - Homo sapiens
MRT 12.0 hr Homo sapiens
T1/2 42.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Angiotensin-converting enzyme IC50 = 0.1 nM 10.0 Inhibition of human serum ACE 24095015
Angiotensin-converting enzyme IC50 = 0.1 nM 10.0 Inhibition of angiotensin converting enzyme (unknown origin) 34624823
Angiotensin-converting enzyme IC50 = 0.1 nM 10.0 Inhibitory activity against Angiotensin I converting enzyme (ACE) from human blo... 12852763
Angiotensin-converting enzyme IC50 = 1.2 nM 8.92 Inhibition of Angiotensin I converting enzyme 8340909
Unchecked IC50 = 1.2 nM 8.92 Compound tested in vitro for inhibition of Angiotensin I converting enzyme in ra... 2544729
Angiotensin-converting enzyme IC50 = 1.202 nM 8.92 Inhibitory activity against angiotensin converting enzyme (ACE) 8360884
Angiotensin-converting enzyme IC50 = 1.2 nM 8.92 Inhibition of Angiotensin I converting enzyme (ACE) in Bothrops jararaca venom 12477342
Angiotensin-converting enzyme IC50 = 1.2 nM 8.92 Inhibition of angiotensin-converting enzyme (unknown origin) 27690430
Angiotensin-converting enzyme Ki = 1.2 nM 8.92 Inhibition of recombinant human ACE C-domain expressed in CHO cells using Cbz-Ph... 35113565
Angiotensin-converting enzyme IC50 = 4.7 nM 8.33 Inhibitory activity against angiotensin I converting enzyme (ACE) 10669559
Angiotensin-converting enzyme Ki = 4.8 nM 8.32 Inhibition of recombinant human ACE N-domain expressed in CHO cells using Cbz-Ph... 35113565
Angiotensin-converting enzyme IC50 = 6.038 nM 8.22 DRUGMATRIX: Peptidase, Angiotensin Converting Enzyme enzyme inhibition (substrat... -
Angiotensin-converting enzyme IC50 = 7.92 nM 8.1 Inhibition of ACE (unknown origin) using Hippuryl-L-Histidyl-L-Leucine as substr... 29032034
Angiotensin-converting enzyme Ki = 51.0 nM 7.29 Inhibition of rabbit testis recombinant ACE C domain 16784850
Angiotensin-converting enzyme Ki = 51.0 nM 7.29 Inhibition of testis ACE C domain 16784843
Angiotensin-converting enzyme Ki = 131.5 nM 6.88 Inhibition of recombinant ACE N domain 16784850
Angiotensin-converting enzyme Ki = 131.5 nM 6.88 Inhibition of somatic ACE N domain 16784843
Angiotensin-converting enzyme IC50 = 262.0 nM 6.58 Inhibition of rabbit lung ACE assessed as hydrolysis of hippuryl-histidyl-leucin... 23777825
Angiotensin-converting enzyme IC50 = 281.0 nM 6.55 Inhibition of rabbit lung ACE using hippuryl-histidyl-leucine as substrate asses... 25300819
Angiotensin-converting enzyme IC50 = 318.0 nM 6.5 Inhibition of rabbit lung ACE assessed as hippuryl-histidyl-leucine hydrolysis a... 25922179

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 320
16472241 10.2174/1570163043334794 Hepatotoxicity 18
32940035 10.1021/acs.jmedchem.0c01541 No relevant target 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3
16784843 10.1016/j.bmcl.2006.06.004 Angiotensin-converting enzyme 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 3
1992145 10.1021/jm00105a066 No relevant target 3
20373811 10.1021/jm901846t No relevant target 3

Data from ChEMBL 36 via Core Engine