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Compound Detail

CHEMBL578

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

Basic Information

ChEMBL ID CHEMBL578
Name ENALAPRIL
Phase Approved
Structure Type MOL
InChI Key GBXSMTUPTTWBMN-XIRDDKMYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL577

Known Names

C09AA02 Enalapril Lexxel Olinapril Vaseretic
3
Targets
19
Activities
2
Assay Types
14
PK Parameters
20
Publications
5
Known Names
20
Indications

Molecular Properties

376.4
MW (Da)
1.60
ALogP
5
HBA
2
HBD
95.9
PSA (Ų)
0.64
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1985
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -pril
USAN Year 1981

Extended Properties

Molecular Formula C20H28N2O5
MW 376.45
Aromatic Rings 1
Heavy Atoms 27
NP-Likeness -0.29

Indications

Cardiovascular Diseases Cardiomyopathies Cardiotoxicity Chagas Cardiomyopathy Coronary Disease Heart Failure Heart Failure Hematologic Neoplasms Hypertension Influenza, Human Leukemia, Lymphoid Leukemia, Myeloid, Acute Lymphoma Multiple Myeloma Myocardial Ischemia Neoplasms Pneumonia Severe Acute Respiratory Syndrome ST Elevation Myocardial Infarction Cerebral Hemorrhage

ATC Classification

C09AA02
enalapril
Level 1: CARDIOVASCULAR SYSTEM
Level 2: AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM

Activity Summary

IC50 18 meas. best 8.7
Ki 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Angiotensin-converting enzyme
CHEMBL4074
 IC50 8.7 6.2317 2.0 6
Angiotensin-converting enzyme
CHEMBL1808
 IC50 8.35 6.8725 4.5 8
Angiotensin-converting enzyme
CHEMBL2625
 IC50 6.85 6.85 140.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 41.0 % Homo sapiens
F 51.0 % Homo sapiens
T1/2 2.5 hr -
T1/2 0.05 hr Rattus norvegicus
T1/2 24.0 hr Rattus norvegicus
T1/2 1.567 hr Rattus norvegicus
T1/2 4.0 hr -
t1/2 - - -
t1/2 - - Homo sapiens
T1/2 0.4167 hr Rattus norvegicus
T1/2 0.3667 hr Rattus norvegicus
t1/2 - - Homo sapiens
T1/2 1.05 hr Mus musculus
T1/2 2.833 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Angiotensin-converting enzyme IC50 = 2.0 nM 8.7 Tested for 50% inhibition of Angiotensin converting enzyme(ACE) obtained from ra... 8021921
Angiotensin-converting enzyme IC50 = 4.5 nM 8.35 In vitro inhibitory activity against Angiotensin I converting enzyme 2999394
Angiotensin-converting enzyme IC50 = 4.5 nM 8.35 Inhibitory activity against angiotensin I converting enzyme (ACE) 10669559
Angiotensin-converting enzyme IC50 = 123.0 nM 6.91 Inhibition of rabbit lung ACE assessed as hippuryl-histidyl-leucine hydrolysis a... 25922179
Angiotensin-converting enzyme IC50 = 140.0 nM 6.85 Inhibition of rat Angiotensin I converting enzyme (ACE), using Hip-Gly-Gly as sy... 3035180
Angiotensin-converting enzyme IC50 = 140.0 nM 6.85 Compound was tested for its inhibitory potency against Angiotensin I converting ... 1995872
Angiotensin-converting enzyme IC50 = 140.0 nM 6.85 Inhibition of guinea pig angiotensin I converting enzyme 3020249
Angiotensin-converting enzyme IC50 = 140.0 nM 6.85 In vitro inhibitory activity against Angiotensin I converting enzyme from unpuri... 2993618
Angiotensin-converting enzyme IC50 = 800.0 nM 6.1 In vitro inhibition of Angiotensin I converting enzyme in rabbit lung 2160536
Angiotensin-converting enzyme IC50 = 1200.0 nM 5.92 In vitro inhibition of Angiotensin I converting enzyme in Hog plasma 2160536
Angiotensin-converting enzyme IC50 = 1200.0 nM 5.92 Inhibition of Angiotensin I converting enzyme (ACE) in Bothrops jararaca venom 12477342
Angiotensin-converting enzyme IC50 = 1273.0 nM 5.89 Compound tested in vitro for inhibition of Angiotensin I converting enzyme 2544729
Angiotensin-converting enzyme IC50 = 3330.0 nM 5.48 DRUGMATRIX: Peptidase, Angiotensin Converting Enzyme enzyme inhibition (substrat... -
Angiotensin-converting enzyme IC50 = 8000.0 nM 5.1 In vitro inhibition of Angiotensin I converting enzyme activity in rabbit lung 3009814
Angiotensin-converting enzyme IC50 = 8000.0 nM 5.1 In vitro inhibitory activity against rabbit lung Angiotensin I converting enzyme... 2981324

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1443
- 10.6019/CHEMBL3885881 Rattus norvegicus 320
- 10.5281/zenodo.13943903 ADMET 79
2999393 10.1021/jm00149a009 Rattus norvegicus 33
2995669 10.1021/jm00148a023 Rattus norvegicus 27
2913292 10.1021/jm00122a003 Rattus norvegicus 22
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
33006888 10.1021/acs.jnatprod.0c00453 Rattus norvegicus 9
3035180 10.1021/jm00389a006 Rattus norvegicus 8
3020249 10.1021/jm00160a026 Rattus norvegicus 8
2160536 10.1021/jm00168a013 Angiotensin-converting enzyme 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
32031812 10.1021/acs.jnatprod.9b00857 Danio rerio 4
2999394 10.1021/jm00149a010 Rattus norvegicus 4
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
1992145 10.1021/jm00105a066 No relevant target 3

Data from ChEMBL 36 via Core Engine