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Enalapril

drug
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Also known as C09AA02LexxelOlinaprilVasereticSID11112847SID29214998SID170464969SID144204423ENALAPRIL MALEATEENALAPRILAT MALEATE

Summary

Enalapril (CHEMBL578) is an approved small-molecule prodrug (ATC C09AA02) targeting ACE; indicated across 32 conditions including cardiovascular disorder and acute myeloid leukemia.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: C09AA02
  • Targets: 1 (ACE)
  • Indications: 32 conditions
  • Clinical trials: 94
  • Chemistry: 376.4 Da · C20H28N2O5

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL578
NameEnalapril
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID5388962
ChEBICHEBI:4784
ATCC09AA02
Molecular formulaC20H28N2O5
Molecular weight376.4
InChIKeyGBXSMTUPTTWBMN-XIRDDKMYSA-N

SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CCC[C@H]2C(=O)O

IUPAC name: (2S)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid

ChEBI definition: A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen α to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration).

Pharmacological roles (ChEBI): prodrug, EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, antihypertensive agent, geroprotector.

Also known as: C09AA02, Enalapril, Lexxel, Olinapril, Vaseretic, enalapril, SID11112847, SID29214998, ENALAPRIL, SID170464969, SID144204423, ENALAPRIL MALEATE

Parent form; salt/anhydrous children: CHEMBL1200659

Patent coverage: 14,363 distinct patent families (52,784 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
ACEAngiotensin-converting enzymeInhibition4.30.7%P12821

Broader ChEMBL bioactivity targets: 4 (assay-derived). Sample: Prelamin-A/C, Angiotensin-converting enzyme, Angiotensin-converting enzyme, Angiotensin-converting enzyme.

Bioactivity

ChEMBL activities: 17 potent at pChembl ≥ 5 of 17 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
P128228.7IC502nMCHEMBL_ACT_639213
ACE8.35IC504.5nMCHEMBL_ACT_588708
ACE8.35IC504.5nMCHEMBL_ACT_651378
LMNA7.65Potency22.4nMCHEMBL_ACT_3640897
P128226.91IC50123nMCHEMBL_ACT_15631695
P478206.85IC50140nMCHEMBL_ACT_291875
ACE6.85IC50140nMCHEMBL_ACT_313336
ACE6.85IC50140nMCHEMBL_ACT_347039
ACE6.85IC50140nMCHEMBL_ACT_715452
P128226.1IC50800nMCHEMBL_ACT_481877
ACE5.92IC501200nMCHEMBL_ACT_481878
ACE5.92IC501200nMCHEMBL_ACT_931301
ACE5.89IC501273nMCHEMBL_ACT_307966
LMNA5.5Potency3162nMCHEMBL_ACT_3651851
P128225.48IC503330nMCHEMBL_ACT_7664813
P128225.1IC508000nMCHEMBL_ACT_662844
P128225.1IC508000nMCHEMBL_ACT_677119

Target pathways

Aggregated over 1 target gene(s): ACE.

Top Reactome pathways

3 total, by targets touching each:

PathwayTargetsGenes
Metabolism of Angiotensinogen to Angiotensins1ACE
Peptide hormone metabolism1ACE
Metabolism of proteins1ACE

Dominant GO biological processes

GO termTargets
kidney development1
blood vessel remodeling1
angiotensin maturation1
regulation of renal output by angiotensin1
neutrophil mediated immunity1
antigen processing and presentation of peptide antigen via MHC class I1
regulation of systemic arterial blood pressure by renin-angiotensin1
positive regulation of systemic arterial blood pressure1
proteolysis1
spermatogenesis1
regulation of blood pressure1
male gonad development1
post-transcriptional regulation of gene expression1
negative regulation of gene expression1
substance P catabolic process1

Indications & clinical

Indications

32 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
cardiovascular disorder4MONDO:0004995EFO:0000319
acute myeloid leukemia3MONDO:0018874EFO:0000222
cardiomyopathy3MONDO:0004994EFO:0000318
congestive heart failure3MONDO:0005009EFO:0000373
hypertensive disorder3MONDO:0005044EFO:0000537
plasma cell myeloma3MONDO:0009693EFO:0001378
heart failure3MONDO:0005252EFO:0003144
lymphoid leukemia3MONDO:0005402EFO:0004289
myocardial ischemia3MONDO:0024644EFO:1001375
severe acute respiratory syndrome3MONDO:0005091MONDO:0100096
Chagas cardiomyopathy3MONDO:0005491EFO:0005529
ST-elevation myocardial infarction3MONDO:0041656EFO:0008585
pneumonia3MONDO:0005249EFO:0003106
influenza3MONDO:0005812EFO:0007328
neoplasm3MONDO:0005070MONDO:0004992
lymphoma3MONDO:0005062EFO:0000574
lymphoid neoplasm3MONDO:0005157EFO:0001642
coronary artery disorder3MONDO:0005010EFO:0001645
melanoma2MONDO:0005105EFO:0000756
heart disorder2MONDO:0005267EFO:0003777
IgA glomerulonephritis2MONDO:0005342EFO:0004194
intracerebral hemorrhage2MONDO:0013792EFO:0005669
pseudohypoaldosteronism2MONDO:0018638MONDO:0018638
stroke disorder2MONDO:0005098EFO:0000712
essential hypertension2MONDO:0001134MONDO:0001134
type 1 diabetes mellitus2MONDO:0005147MONDO:0005147
vascular disorder2MONDO:0005385EFO:0004264
ischemic disease1MONDO:0005053EFO:0000556
chronic kidney disease1MONDO:0005300EFO:0003884
erectile dysfunction1MONDO:0005362EFO:0004234
Barrett esophagus0MONDO:0013662EFO:0000280

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 94.

Phase distribution

PhaseTrials
PHASE428
PHASE324
Not specified16
PHASE214
PHASE16
PHASE2/PHASE33
PHASE1/PHASE22
EARLY_PHASE11

Top trials by phase / activity

NCTPhaseStatusTitle
NCT07547878PHASE4NOT_YET_RECRUITINGRapid and Simultaneous Initiation of Four Guideline-Directed CKD Therapies (RAPID-CKD)
NCT00235287PHASE4UNKNOWNPulse Wave Velocity, Pulse Wave Morphology and Blocking of the Reninangiotensin System in Patients With Chronic Kidney Disease
NCT00292526PHASE4COMPLETEDPrevention of Chemotherapy-induced Cardiotoxicity in High-risk Patients
NCT00295542PHASE4COMPLETEDAmbulatory Blood Pressure Monitoring in the Prediction of Cardiovascular Events and Effects of Chronotherapy
NCT00302705PHASE4COMPLETEDComparison of the Antihypertensive Efficacy of Valsartan and Enalapril After Missing One Dose
NCT00391846PHASE4COMPLETEDEvaluation of Heart Failure Treatment Guided by N-terminal Pro B-type Natriuretic Peptide (NTproBNP) vs Clinical Symptoms and Signs Alone
NCT00419835PHASE4COMPLETEDEffect of Enalapril and Losartan Association Therapy on Proteinuria and Inflammatory Biomarkers in Diabetic Nephropathy: a Clinical Trial on Type 2 Diabetes Mellitus
NCT00456963PHASE4TERMINATEDPrevention of Diabetes and Hypertension
NCT00666848PHASE4COMPLETEDEffect of Sitagliptin and an ACE Inhibitor on Blood Pressure in Metabolic Syndrome
NCT00734123PHASE4UNKNOWNEarly Detection of Atherosclerosis: a Randomized Trial in the Primary Prevention of Cardiovascular Diseases.
NCT00794885PHASE4COMPLETEDChina Stroke Primary Prevention Trial
NCT01041963PHASE4UNKNOWNThe Effect of Enalapril and Losartan on Peritoneal Membrane in Continuous Ambulatory Peritoneal Dialysis Patients
NCT01069042PHASE4UNKNOWNAnti-Hypertensive Agent (ACEi) and Heart Function Improvement in Association With Rho Kinase Activity Changes in Human
NCT01871740PHASE4WITHDRAWNCSPPT- Chronic Kidney Diseases Study
NCT02135263PHASE4COMPLETEDMetabolism of Methylphenidate and Enalapril Based on CES1 Genotype
NCT02177461PHASE4COMPLETEDTelmisartan Compared With Enalapril in Elderly Patients With Blood Hypertension
NCT02214498PHASE4UNKNOWNTreatment of HYpertension: Morning Versus Evening
NCT02554890PHASE4COMPLETEDComparison of Sacubitril/Valsartan Versus Enalapril on Effect on NT-proBNP in Patients Stabilized From an Acute Heart Failure Episode.
NCT02768298PHASE4COMPLETEDExercise Capacity Study of LCZ696 vs. Enalapril in Patients With Chronic Heart Failure and Reduced Ejection Fraction.
NCT02874794PHASE4COMPLETEDStudy of Effects of Sacubitril/Valsartan vs. Enalapril on Aortic Stiffness in Patients With Mild to Moderate HF With Reduced Ejection Fraction
NCT02970669PHASE4COMPLETEDStudy on the Effects of Sacubitril/Valsartan on Physical Activity and Sleep in Heart Failure With Reduced Ejection Fraction Patients.
NCT03051282PHASE4COMPLETEDGenetic Determinants of ACEI Prodrug Activation
NCT03119623PHASE4WITHDRAWNComparing ARNI With ACE Inhibitor on Endothelial Function
NCT03190304PHASE4COMPLETEDThe Effect of Neprilysin (LCZ696) on Exercise Tolerance in Patients With Heart Failure
NCT03472508PHASE4UNKNOWNH-Type Hypertension Precision Medicine Trial
NCT04023227PHASE4COMPLETEDEfficacy and Safety of Sacubitril/Valsartan Compared With Enalapril on Morbidity, Mortality, and NT-proBNP Change in Patients With CCC
NCT04236258PHASE4COMPLETEDComparing Nifedipine and Enalapril in Medical Resources Used in the Postpartum Period
NCT05487261PHASE4UNKNOWNPulmonary REsistance Modification Under Treatment With Sacubitril/valsartaN in paTients With Heart Failure With Reduced Ejection Fraction
NCT04912167PHASE3NOT_YET_RECRUITINGThe Effects of Sacubitril-Valsartan vs Enalapril on Left Ventricular Remodeling in ST-elevation Myocardial Infarction
NCT07222852PHASE3NOT_YET_RECRUITINGCardiovascular Protection After Preeclampsia With Enalapril
NCT00000516PHASE3COMPLETEDStudies of Left Ventricular Dysfunction (SOLVD)
NCT00000547PHASE3COMPLETEDEnalapril After Anthracycline Cardiotoxicity
NCT00003070PHASE3COMPLETEDEnalapril in Treating Heart Damage Patients Who Received Anthracycline Chemotherapy for Childhood Cancer
NCT00113087PHASE3COMPLETEDTrial of Angiotensin Converting Enzyme Inhibition in Infants With Single Ventricle–Pediatric Heart Network
NCT00113698PHASE3TERMINATEDAngiotensin Converting Enzyme Inhibition in Children With Mitral Regurgitation
NCT00274118PHASE3COMPLETEDDETAIL Study: Diabetes Exposed to Telmisartan and Enalapril
NCT00433836PHASE3COMPLETEDEffect of Valsartan Compared to Enalapril on Sitting Systolic Blood Pressure in Children With High Blood Pressure
NCT00446511PHASE3COMPLETEDExtension Study to Assess Long Term Safety, Tolerability, and Efficacy of Valsartan and Enalapril Combined and Alone in Children With Hypertension
NCT00568178PHASE3COMPLETEDAn Extension Study Designed to Assess Effects of Losartan on Proteinuria in Pediatric Populations (MK-0954-326 AM1,EXT1(AM2))
NCT00853658PHASE3COMPLETEDEfficacy and Safety of Aliskiren and Aliskiren/Enalapril Combination on Morbidity-mortality in Patients With Chronic Heart Failure

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

32 molecules share ≥1 primary target. Top 32 by shared-target count:

MoleculeSourceStatusShared targets
CAPTOPRILChEMBL + PubChemPhase 4 (approved)ACE
LOSARTANChEMBL + PubChemPhase 4 (approved)ACE
PERINDOPRILChEMBL + PubChemPhase 4 (approved)ACE
SITAGLIPTINChEMBL + PubChemPhase 4 (approved)ACE
BENAZEPRILChEMBLPhase 4 (approved)ACE
ENALAPRILATChEMBLPhase 4 (approved)ACE
FOSINOPRILChEMBLPhase 4 (approved)ACE
IMIDAPRILChEMBLPhase 4 (approved)ACE
LISINOPRILChEMBLPhase 4 (approved)ACE
MOEXIPRILChEMBLPhase 4 (approved)ACE
QUINAPRILChEMBLPhase 4 (approved)ACE
RAMIPRILChEMBLPhase 4 (approved)ACE
TELMISARTANChEMBLPhase 4 (approved)ACE
TRANDOLAPRILChEMBLPhase 4 (approved)ACE
EDETIC ACIDChEMBLPhase 3ACE
QUINAPRILATChEMBL + PubChemPhase 2 (approved)ACE
BENAZEPRILATChEMBLPhase 2ACE
CERONAPRILChEMBLPhase 2ACE
FOSINOPRILATChEMBLPhase 2ACE
IMIDAPRILATChEMBLPhase 2ACE
LIBENZAPRILChEMBLPhase 2ACE
MOEXIPRILATChEMBLPhase 2ACE
OMAPATRILATChEMBLPhase 2ACE
PROLINEChEMBLPhase 2ACE
RENTIAPRILChEMBLPhase 2ACE
SAMPATRILATChEMBLPhase 2ACE
SPIRAPRILATChEMBLPhase 2ACE
TEPROTIDEChEMBLPhase 2ACE
ZOFENOPRILChEMBLPhase 2ACE
Gallic AcidPubChemApprovedACE
HydrochlorothiazidePubChemApprovedACE
PaclitaxelPubChemApprovedACE

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot