Ramipril

Summary

Ramipril (CHEMBL1168) is an approved small-molecule EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (ATC C09AA05) targeting ACE; indicated across 29 conditions including hypertensive disorder and heart failure.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: C09AA05
• Targets: 1 (ACE)
• Indications: 29 conditions
• Clinical trials: 125
• Chemistry: 416.5 Da · C23H32N2O5

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1168
Name	Ramipril
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	5362129
ChEBI	CHEBI:8774
ATC	C09AA05
Molecular formula	C23H32N2O5
Molecular weight	416.5
InChIKey	HDACQVRGBOVJII-JBDAPHQKSA-N

SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2[C@H]3CCC[C@H]3C[C@H]2C(=O)O

IUPAC name: (2S,3aS,6aS)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid

ChEBI definition: A dipeptide that is the prodrug for ramiprilat, the active metabolite obtained by hydrolysis of the ethyl ester group. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.

Pharmacological roles (ChEBI): EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, prodrug, cardioprotective agent, matrix metalloproteinase inhibitor, bradykinin receptor B2 agonist.

Also known as: Altace, C09AA05, Cardace, Corpril, Delix, Ecator, HOE 498, HOE-498, Hopace, Lopace, NSC-758933, Pramace

Patent coverage: 12,976 distinct patent families (46,990 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).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
ACE	Angiotensin-converting enzyme	Inhibition	7.6	0.7%	P12821

Broader ChEMBL bioactivity targets: 4 (assay-derived). Sample: Angiotensin-converting enzyme, Polyunsaturated fatty acid lipoxygenase ALOX15, Cytochrome P450 3A4, Angiotensin-converting enzyme.

Bioactivity

ChEMBL activities: 5 potent at pChembl ≥ 5 of 7 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
ACE	8.4	IC50	4	nM	CHEMBL_ACT_640523
ACE	8.38	IC50	4.2	nM	CHEMBL_ACT_25090621
P12822	6.6	IC50	253	nM	CHEMBL_ACT_13397916
P12822	6.6	IC50	253	nM	CHEMBL_ACT_15631692
ALOX15	5.5	Potency	3162	nM	CHEMBL_ACT_4444174

Target pathways

Aggregated over 1 target gene(s): ACE.

Top Reactome pathways

3 total, by targets touching each:

Pathway	Targets	Genes
Metabolism of Angiotensinogen to Angiotensins	1	ACE
Peptide hormone metabolism	1	ACE
Metabolism of proteins	1	ACE

Dominant GO biological processes

GO term	Targets
kidney development	1
blood vessel remodeling	1
angiotensin maturation	1
regulation of renal output by angiotensin	1
neutrophil mediated immunity	1
antigen processing and presentation of peptide antigen via MHC class I	1
regulation of systemic arterial blood pressure by renin-angiotensin	1
positive regulation of systemic arterial blood pressure	1
proteolysis	1
spermatogenesis	1
regulation of blood pressure	1
male gonad development	1
post-transcriptional regulation of gene expression	1
negative regulation of gene expression	1
substance P catabolic process	1

Indications & clinical

Indications

29 indications (9 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).

Indication	Trial phase	MONDO	EFO
hypertensive disorder	4	MONDO:0005044	EFO:0000537
heart failure	4	MONDO:0005252	EFO:0003144
diabetes mellitus	4	MONDO:0005015	EFO:0000400
cardiovascular disorder	4	MONDO:0004995	EFO:0000319
myocardial infarction	4	MONDO:0005068	EFO:0000612
coronary artery disorder	4	MONDO:0005010	EFO:0001645
congestive heart failure	4	MONDO:0005009	EFO:0000373
stroke disorder	4	MONDO:0005098	EFO:0000712
acute myocardial infarction	4	MONDO:0004781	EFO:0008583
atrial fibrillation	3	MONDO:0004981	EFO:0000275
chronic kidney disease	3	MONDO:0005300	EFO:0003884
heart disorder	3	MONDO:0005267	EFO:0003777
diabetic kidney disease	3	MONDO:0005016	EFO:0000401
atrial flutter	3	MONDO:0005310	EFO:0003911
myocardial ischemia	3	MONDO:0024644	EFO:1001375
metabolic disease	3	MONDO:0005066	EFO:0000589
glucose intolerance	3	MONDO:0001076	EFO:0002546
atherosclerosis	3	MONDO:0005311	EFO:0003914
glomerulonephritis	3	MONDO:0002462	MONDO:0002462
type 1 diabetes mellitus	3	MONDO:0005147	MONDO:0005147
type 2 diabetes mellitus	3	MONDO:0005148	MONDO:0005148
rheumatoid arthritis	2	MONDO:0008383	EFO:0000685
kidney disorder	2	MONDO:0005240	EFO:0003086
severe acute respiratory syndrome	2	MONDO:0005091	MONDO:0100096
systemic lupus erythematosus	2	MONDO:0007915	MONDO:0007915
metabolic syndrome X	0	MONDO:0011565	EFO:0000195

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

Clinical trials

Total trials: 125.

Phase distribution

Phase	Trials
PHASE4	49
PHASE3	29
PHASE2	16
Not specified	13
PHASE1	11
PHASE2/PHASE3	6
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT02842424	PHASE4	RECRUITING	Ramipril Treatment of Claudication: Oxidative Damage and Muscle Fibrosis
NCT06562582	PHASE4	RECRUITING	STunning in Acute Myocardial Infarction - BAS
NCT07259512	PHASE4	RECRUITING	Single and Twice-daily Dosing of Ramipril on Renal Function in Chronic Kidney Disease Patients With Reduced Ejection Fraction Heart Failure
NCT07547878	PHASE4	NOT_YET_RECRUITING	Rapid and Simultaneous Initiation of Four Guideline-Directed CKD Therapies (RAPID-CKD)
NCT00044265	PHASE4	COMPLETED	Treatment of Pediatric Hypertension With Altace Trial
NCT00095290	PHASE4	COMPLETED	Irbesartan Versus Placebo in Combination With Ramipril for Treatment of Albuminuria
NCT00153101	PHASE4	COMPLETED	Effectiveness and Safety of Ramipril Alone Compared With Telmisartan Alone and in Combination With Ramipril in Patients at High Risk for Cardiovascular Events. Patients Intolerant to Ramipril Were Entered in TRANSCEND, Telmisartan Compared to Placebo.
NCT00168467	PHASE4	COMPLETED	The Effects of Ramipril on Clinical Symptoms in Patients With Peripheral Arterial Disease
NCT00240422	PHASE4	COMPLETED	Trial to Compare the Effects of Either Telmisartan (40-80 mg PO Once Daily) or Ramipril (5-10 mg PO Once Daily) on Renal Endothelial Dysfunction in Hypertensive Patients With Type 2 Diabetes
NCT00274599	PHASE4	COMPLETED	PROBE Investigation of the Safety & Efficacy of Telmisartan (Micardis®) vs Ramipril (Altace®) Using ABPM in HTN
NCT00274612	PHASE4	COMPLETED	Prospective Randomised Investigation of the Safety and Efficacy of Micardis® vs Ramipril Using ABPM
NCT00325806	PHASE4	COMPLETED	Ramipril - Hypertension
NCT00356395	PHASE4	COMPLETED	Safety and Effects of Ramipril Combined With Candesartan
NCT00366119	PHASE4	UNKNOWN	Safety and Efficacy of Ramipril in the Treatment of Essential Hypertension
NCT00391846	PHASE4	COMPLETED	Evaluation of Heart Failure Treatment Guided by N-terminal Pro B-type Natriuretic Peptide (NTproBNP) vs Clinical Symptoms and Signs Alone
NCT00421863	PHASE4	COMPLETED	Italian Study on the Cardiovascular Effects of Systolic Blood Pressure Control - CARDIOSIS Study
NCT00473174	PHASE4	COMPLETED	Comparison of Awakening Versus Bedtime Dosing of Ramipril in Subjects With Essential Hypertension
NCT00502242	PHASE4	COMPLETED	Study Evaluating The Effect Of Ramipril On Urinary Protein Excretion In Renal Transplant Patients Converted To Sirolimus
NCT00517322	PHASE4	UNKNOWN	Left Atrial Remodelling in Hypertension: Effects of Ramipril or Irbesartan
NCT00535925	PHASE4	COMPLETED	Nephropathy In Type 2 Diabetes and Cardio-renal Events
NCT00542269	PHASE4	TERMINATED	Efficacy and Safety of Aliskiren/Ramipril/Amlodipine Compared With Ramipril/Amlodipine and Aliskiren/Amlodipine in Patients With Metabolic Syndrome
NCT00607672	PHASE4	COMPLETED	The RAS, Fibrinolysis and Cardiopulmonary Bypass
NCT00608465	PHASE4	TERMINATED	Defining Strategies for Improving Endothelial and Fibrinolytic Dysfunction in Obesity
NCT00631917	PHASE4	COMPLETED	A Study Evaluating the Gastrointestinal (GI) Safety and Tolerability of Aliskiren Compared to Ramipril in Essential Hypertension
NCT00657865	PHASE4	COMPLETED	Gene Expression Profiling in Skeletal Muscle of Healthy Subjects Treated With Ramipril
NCT00674596	PHASE4	COMPLETED	The Effect of Renin Angiotensin System Blockage (RAS) Blockade On PTX3 Levels In Diabetic Patients With Proteinuria
NCT00702936	PHASE4	UNKNOWN	Telmisartan Versus Ramipril After Acute Coronary Syndrome
NCT00772577	PHASE4	COMPLETED	Study of the Efficacy and Safety of Aliskiren HCTZ vs Ramipril in Obese Patients (BMI ≥ 30) With Stage 2 Hypertension
NCT00819845	PHASE4	UNKNOWN	Ramipril Versus Carvedilol in Duchenne and Becker Patients
NCT00841880	PHASE4	COMPLETED	China Medical University Hospital (CMUH) Triapin Listing
NCT00893425	PHASE4	COMPLETED	Effect of Renin Angiotensin System Blockade on the Fas Antigen (CD95) and Asymmetric Dimethylarginine (ADMA) Levels in Type-2 Diabetic Patients With Proteinuria
NCT00980785	PHASE4	COMPLETED	Studying the Effects of Antihypertensives on Individuals at Risk for Alzheimer’s
NCT01037530	PHASE4	COMPLETED	Clinical and Cost Effectiveness of ACE Inhibitor, Ramipril, in Intermittent Claudicants
NCT01038895	PHASE4	UNKNOWN	Aliskiren Versus Ramipril on Antiproteinuric Effect in Hypertensive, Type 2 Diabetic Patients With Microalbuminuria
NCT01042392	PHASE4	COMPLETED	Efficacy of Aliskiren Compared to Ramipril in the Treatment of Moderate Systolic Hypertensive Patients
NCT01053910	PHASE4	COMPLETED	Ramipril 10 mg/Day Prevention
NCT01180413	PHASE4	COMPLETED	Intensive Vasodilator Therapy in Patients With Essential Hypertension
NCT01703234	PHASE4	COMPLETED	FGF-23 and Endothelial Dysfunction in Diabetic Proteinuric Patients
NCT01743014	PHASE4	UNKNOWN	Ramipril and Clopidogrel in Oxidative Stress, Vascular Inflammation and Endothelial Dysfunction in Type 2 Diabetes and Diabetic Nephropathy
NCT01922141	PHASE4	WITHDRAWN	Aliskiren Study of Safety and Efficacy in Senior Hypertensives

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 2 clinical and 8 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

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:

Molecule	Source	Status	Shared targets
CAPTOPRIL	ChEMBL + PubChem	Phase 4 (approved)	ACE
LOSARTAN	ChEMBL + PubChem	Phase 4 (approved)	ACE
PERINDOPRIL	ChEMBL + PubChem	Phase 4 (approved)	ACE
SITAGLIPTIN	ChEMBL + PubChem	Phase 4 (approved)	ACE
BENAZEPRIL	ChEMBL	Phase 4 (approved)	ACE
ENALAPRIL	ChEMBL	Phase 4 (approved)	ACE
ENALAPRILAT	ChEMBL	Phase 4 (approved)	ACE
FOSINOPRIL	ChEMBL	Phase 4 (approved)	ACE
IMIDAPRIL	ChEMBL	Phase 4 (approved)	ACE
LISINOPRIL	ChEMBL	Phase 4 (approved)	ACE
MOEXIPRIL	ChEMBL	Phase 4 (approved)	ACE
QUINAPRIL	ChEMBL	Phase 4 (approved)	ACE
TELMISARTAN	ChEMBL	Phase 4 (approved)	ACE
TRANDOLAPRIL	ChEMBL	Phase 4 (approved)	ACE
EDETIC ACID	ChEMBL	Phase 3	ACE
QUINAPRILAT	ChEMBL + PubChem	Phase 2 (approved)	ACE
BENAZEPRILAT	ChEMBL	Phase 2	ACE
CERONAPRIL	ChEMBL	Phase 2	ACE
FOSINOPRILAT	ChEMBL	Phase 2	ACE
IMIDAPRILAT	ChEMBL	Phase 2	ACE
LIBENZAPRIL	ChEMBL	Phase 2	ACE
MOEXIPRILAT	ChEMBL	Phase 2	ACE
OMAPATRILAT	ChEMBL	Phase 2	ACE
PROLINE	ChEMBL	Phase 2	ACE
RENTIAPRIL	ChEMBL	Phase 2	ACE
SAMPATRILAT	ChEMBL	Phase 2	ACE
SPIRAPRILAT	ChEMBL	Phase 2	ACE
TEPROTIDE	ChEMBL	Phase 2	ACE
ZOFENOPRIL	ChEMBL	Phase 2	ACE
Gallic Acid	PubChem	Approved	ACE
Hydrochlorothiazide	PubChem	Approved	ACE
Paclitaxel	PubChem	Approved	ACE