Quinapril

Summary

Quinapril (CHEMBL1592) is an approved small-molecule EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (ATC C09AA06) targeting ACE; indicated across 2 conditions including cardiovascular disorder and type 1 diabetes mellitus.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: C09AA06
• Targets: 1 (ACE)
• Indications: 2 conditions
• Clinical trials: 13
• Chemistry: 438.5 Da · C25H30N2O5

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1592
Name	Quinapril
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	54892
ChEBI	CHEBI:8713
ATC	C09AA06
Molecular formula	C25H30N2O5
Molecular weight	438.5
InChIKey	JSDRRTOADPPCHY-HSQYWUDLSA-N

SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3=CC=CC=C3C[C@H]2C(=O)O

IUPAC name: (3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid

ChEBI definition: A member of the class of isoquinolines that is (3S)-2-L-alanyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in which the α-amino group of the alanyl residue has been substituted by a 1-ethoxycarbonyl-4-phenylbutan-2-yl group (the all-S isomer). A prodrug for quinaprilat (by hydrolysis of the ethyl ester to the corresponding carboxylic acid), it is used as an angiotensin-converting enzyme inhibitor (ACE inhibitor) used (generally as the hydrochloride salt) for the treatment of hypertension and congestive heart failure.

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

Also known as: C09AA06, Quinapril, quinapril, QUINAPRIL

Parent form; salt/anhydrous children: CHEMBL1201011

Patent coverage: 7,581 distinct patent families (31,043 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 31,016 (100%) of the total. 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	8.1	0.7%	P12821

Broader ChEMBL bioactivity targets: 3 (assay-derived). Sample: Angiotensin-converting enzyme, Angiotensin-converting enzyme, Bile salt export pump.

Bioactivity

ChEMBL activities: 6 potent at pChembl ≥ 5 of 9 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
ACE	8.08	IC50	8.3	nM	CHEMBL_ACT_320805
ACE	8.08	IC50	8.3	nM	CHEMBL_ACT_376655
ACE	8.08	IC50	8.3	nM	CHEMBL_ACT_652524
ACE	8.08	IC50	8.3	nM	CHEMBL_ACT_727237
P12822	6.96	IC50	110	nM	CHEMBL_ACT_15631694
P12822	5.4	IC50	4008	nM	CHEMBL_ACT_7720331

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

2 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).

Indication	Trial phase	MONDO	EFO
cardiovascular disorder	4	MONDO:0004995	EFO:0000319
type 1 diabetes mellitus	3	MONDO:0005147	MONDO:0005147

Clinical trials

Total trials: 13.

Phase distribution

Phase	Trials
PHASE4	8
PHASE1	4
Not specified	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00147524	PHASE4	COMPLETED	Non-Comparative Study To Evaluate Changes In FMD After Quinapril Therapy In Hypertensive Women
NCT00150826	PHASE4	COMPLETED	QWISE - Study of Quinapril in Women With Chest Pain, Coronary Flow Reserve Limitations and Evidence of Myocardial Ischemia
NCT00269243	PHASE4	COMPLETED	Management With Accupril Post Bypass Graft
NCT00295542	PHASE4	COMPLETED	Ambulatory Blood Pressure Monitoring in the Prediction of Cardiovascular Events and Effects of Chronotherapy
NCT00313547	PHASE4	TERMINATED	High-Dose Quinapril Versus Low-Dose Quinapril Plus Amlodipine in the Treatment of High-Risk Hypertensive Patients
NCT00651287	PHASE4	COMPLETED	A Study to Evaluate the Efficacy and Safety of Quinapril or Quinapril Plus Hydrochlorothiazide in Patients With Mild to Moderate Hypertension
NCT03031834	PHASE4	COMPLETED	Efficacy of Administration of ACE-Inhibition on Autonomic and Peripheral Neuropathy in Patients With Diabetes Mellitus
NCT05713396	PHASE4	COMPLETED	Diabetic Autonomic Neuropathy and Left Ventricular Function
NCT00648011	PHASE1	COMPLETED	Food Study of Quinapril HCl and Hydrochlorothiazide Tablets 20 mg/25 mg to Accuretic™ Tablets 20 mg/25 mg
NCT00649103	PHASE1	COMPLETED	Fasting Study of Quinapril Hydrochloride Tablets 40 mg and Accupril® Tablets 40 mg
NCT00649441	PHASE1	COMPLETED	Fasting Study of Quinapril HCl and Hydrochlorothiazide Tablets 20 mg/25 mg to Accuretic™ Tablets 20 mg/25 mg
NCT00649649	PHASE1	COMPLETED	Food Study of Quinapril Hydrochloride Tablets 40 mg and Accupril® Tablets 40 mg
NCT00930722	Not specified	COMPLETED	A Non Interventional Study To Asses The Safety, Effectiveness And Tolerability Of Quinapril (Acupil®) In An Indian Population

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 10 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
RAMIPRIL	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