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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H30N2O5.ClH
Molecular Weight 474.9779
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINAPRIL HYDROCHLORIDE

SMILES

CCOC(=O)[C@]([H])(CCc1ccccc1)N[C@@]([H])(C)C(=O)N2Cc3ccccc3C[C@@]2([H])C(=O)O.Cl

InChI

InChIKey=IBBLRJGOOANPTQ-JKVLGAQCSA-N
InChI=1S/C25H30N2O5.ClH/c1-3-32-25(31)21(14-13-18-9-5-4-6-10-18)26-17(2)23(28)27-16-20-12-8-7-11-19(20)15-22(27)24(29)30;/h4-12,17,21-22,26H,3,13-16H2,1-2H3,(H,29,30);1H/t17-,21-,22-;/m0./s1

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT00651287 | https://www.ncbi.nlm.nih.gov/pubmed/25922179 | https://www.ncbi.nlm.nih.gov/pubmed/1691409

Quinapril is the hydrochloride salt of quinapril, the ethyl ester of a non-sulfhydryl, angiotensin-converting enzyme (ACE) inhibitor, quinaprilat. Quinapril hydrochloride is a white to off-white amorphous powder that is freely soluble in aqueous solvents. Quinapril is indicated for the treatment of high blood pressure (hypertension) and as adjunctive therapy in the management of heart failure. It may be used for the treatment of hypertension by itself or in combination with thiazide diuretics, and with diuretics and digoxin for heart failure.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.8 nM [IC50]
110.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ACCURETIC

Approved Use

INDICATIONS AND USA. Hypertension: ACCURETIC is indicated for the treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. These benefits have been seen in controlled trials of antihypertensive drugs from a wide variety of pharmacologic classes including the class to which this drug principally belongs. There are no controlled trials demonstrating risk reduction with ACCURETIC. Control of high blood pressure should be part of comprehensive cardiovascular risk management, including, as appropriate, lipid control, diabetes management, antithrombotic therapy, smoking cessation, exercise, and limited sodium intake. Many patients will require more than one drug to achieve blood pressure goals. For specific advice on goals and management, see published guidelines, such as those of the National High Blood Pressure Education Program’s Joint National Committee on Prevention, Detection, Evaluation, and Treatment of High Blood Pressure (JNC). Numerous antihypertensive drugs, from a variety of pharmacologic classes and with different mechanisms of action, have been shown in randomized controlled trials to reduce cardiovascular morbidity and mortality, and it can be concluded that it is blood pressure reduction, and not some other pharmacologic property of the drugs, that is largely responsible for those benefits. The largest and most consistent cardiovascular outcome benefit has been a reduction in the risk of stroke, but reductions in myocardial infarction and cardiovascular mortality also have been seen regularly. 6 Reference ID: 3818285 Elevated systolic or diastolic pressure causes increased cardiovascular risk, and the absolute risk increase per mmHg is greater at higher blood pressures, so that even modest reductions of severe hypertension can provide substantial benefit. Relative risk reduction from blood pressure reduction is similar across populations with varying absolute risk, so the absolute benefit is greater in patients who are at higher risk independent of their hypertension (for example, patients with diabetes or hyperlipidemia), and such patients would be expected to benefit from more aggressive treatment to a lower blood pressure goal. Some antihypertensive drugs have smaller blood pressure effects (as monotherapy) in black patients, and many antihypertensive drugs have additional approved indications and effects (e.g., on angina, heart failure, or diabetic kidney disease). These considerations may guide selection of therapy. This fixed combination is not indicated for the initial therapy of hypertension (see DOSAGE AND ADMINISTRATION). In using ACCURETIC, consideration should be given to the fact that another angiotensinconverting enzyme inhibitor, captopril, has caused agranulocytosis, particularly in patients with renal impairment or collagen-vascular disease. Available data are insufficient to show that quinapril does not have a similar risk (see WARNINGS: Neutropenia/Agranulocytosis). Angioedema in Black Patients: Black patients receiving ACE inhibitor monotherapy have been reported to have a higher incidence of angioedema compared to non-blacks. It should also be noted that in controlled clinical trials, ACE inhibitors have an effect on blood pressure that is less in black patients than in non-blacks.

Launch Date

9.4625281E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1526 ng/mL
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
QUINAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
345 ng/mL
2.5 mg single, intravenous
dose: 2.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
QUINAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1706 μg × h/L
10 mg 2 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
QUINAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2670 ng × h/mL
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
QUINAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
580 ng × h/mL
2.5 mg single, intravenous
dose: 2.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
QUINAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.7 h
10 mg 2 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
QUINAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2.29 h
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
QUINAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.26 h
2.5 mg single, intravenous
dose: 2.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
QUINAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 11
unhealthy, adult
n = 1563
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 1563
Sources: Page: 11
Disc. AE: Headache, Dizziness...
AEs leading to
discontinuation/dose reduction:
Headache (0.7%)
Dizziness (0.8%)
Fatigue (0.3%)
Coughing (0.5%)
Nausea and vomiting (0.3%)
Abdominal pain (0.2%)
Sources: Page: 11
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 12
unhealthy, adult
n = 585
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 585
Sources: Page: 12
Disc. AE: Dizziness, Coughing...
AEs leading to
discontinuation/dose reduction:
Dizziness (0.7%)
Coughing (0.3%)
Fatigue (0.2%)
Nausea and vomiting (0.2%)
Hypotension (0.5%)
Dyspnea (0.2%)
Rash (0.2%)
Sources: Page: 12
AEs

AEs

AESignificanceDosePopulation
Abdominal pain 0.2%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 11
unhealthy, adult
n = 1563
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 1563
Sources: Page: 11
Fatigue 0.3%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 11
unhealthy, adult
n = 1563
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 1563
Sources: Page: 11
Nausea and vomiting 0.3%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 11
unhealthy, adult
n = 1563
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 1563
Sources: Page: 11
Coughing 0.5%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 11
unhealthy, adult
n = 1563
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 1563
Sources: Page: 11
Headache 0.7%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 11
unhealthy, adult
n = 1563
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 1563
Sources: Page: 11
Dizziness 0.8%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 11
unhealthy, adult
n = 1563
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 1563
Sources: Page: 11
Dyspnea 0.2%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 12
unhealthy, adult
n = 585
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 585
Sources: Page: 12
Fatigue 0.2%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 12
unhealthy, adult
n = 585
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 585
Sources: Page: 12
Nausea and vomiting 0.2%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 12
unhealthy, adult
n = 585
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 585
Sources: Page: 12
Rash 0.2%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 12
unhealthy, adult
n = 585
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 585
Sources: Page: 12
Coughing 0.3%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 12
unhealthy, adult
n = 585
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 585
Sources: Page: 12
Hypotension 0.5%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 12
unhealthy, adult
n = 585
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 585
Sources: Page: 12
Dizziness 0.7%
Disc. AE
40 mg 1 times / day multiple, oral (max)
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: 12
unhealthy, adult
n = 585
Health Status: unhealthy
Condition: Hypertension
Age Group: adult
Sex: M+F
Population Size: 585
Sources: Page: 12
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 6.2 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Preservation of cardiac function and energy reserve by the angiotensin-converting enzyme inhibitor quinapril during postmyocardial infarction remodeling in the rat.
2001
Comparative effects of ACE inhibitors and an angiotensin receptor blocker on atherosclerosis and vascular function.
2001 Apr
ACE inhibitors for hypertension--again.
2001 Apr 27
Beneficial effect of quinapril in patients with angiotensin-converting enzyme D allele after coronary stenting.
2001 Dec
Quinapril ischemic event trial.
2001 Dec 1
Effect of quinapril on intimal hyperplasia after coronary stenting as assessed by intravascular ultrasound.
2001 Feb 15
ACE inhibitors for hypertension.
2001 Feb 23
Effects of dehydroepiandrosterone and quinapril on nephropathy in obese Zucker rats.
2001 Jan
The quantitative determination of several inhibitors of the angiotensin-converting enzyme by CE.
2001 Jul
Simultaneous determination of hydrochlorothiazide and several inhibitors of angiotensin-converting enzyme by capillary electrophoresis.
2001 Jul 27
[Quality of life and psychosocial factors during treatment with antihypertensive drugs. A comparison of captopril and quinapril in geriatric patients].
2001 Nov
Potentiation of bradykinin-induced tissue plasminogen activator release by angiotensin-converting enzyme inhibition.
2001 Nov 1
Inhibition of the formation or action of angiotensin II reverses attenuated K+ currents in type 1 and type 2 diabetes.
2001 Nov 15
[Some new data concerning effectiveness of amlodipine, atorvastatine and quinaprile for heart diseases].
2002
[Clinical sequelae of tissue angiotensin converting enzyme inhibition: practicability of use in ischemic heart disease].
2002
Quinapril: a further update of its pharmacology and therapeutic use in cardiovascular disorders.
2002
Angiotensin II as an inflammatory mediator: evolving concepts in the role of the renin angiotensin system in the failing heart.
2002 Jan
Simultaneous determination of quinapril and its active metabolite quinaprilat in human plasma using high-performance liquid chromatography with ultraviolet detection.
2002 Jan 25
Subacute and chronic effects of quinapril on cardiac cytokine expression, remodeling, and function after myocardial infarction in the rat.
2002 Jun
Effects of a long-term pharmacological interruption of the renin-angiotensin system on the fibrinolytic system in essential hypertension.
2002 Mar-Apr
Pretreatment with angiotensin-converting enzyme inhibitors attenuates ischemia-reperfusion injury.
2002 May
Quinapril treatment restores the vasodilator action of insulin in fructose-hypertensive rats.
2002 May-Jun
Effect of combination therapy with dipyridamole and quinapril in diabetic nephropathy.
2003 Feb
Comparative effects of angiotensin II receptor blockade (candesartan) with angiotensin-converting enzyme inhibitor (quinapril) in rats with dilated cardiomyopathy.
2003 Jan
Effects of angiotensin-converting enzyme inhibition and calcium channel blockade on cardiac apoptosis in rats with 2K1C (two-kidney/one-clip) renovascular hypertension.
2003 Jan
Attenuation of heart failure due to coronary stenosis by ACE inhibitor and angiotensin receptor blocker.
2003 Jul
Improvement of endothelial dysfunction by angiotensin II blockade accompanied by induction of vascular hepatocyte growth factor system in diabetic spontaneously hypertensive rats.
2003 Mar
In vitro study on binding interaction of quinapril with bovine serum albumin (BSA) using multi-spectroscopic and molecular docking methods.
2017 Aug
Genetic variants associated with angiotensin-converting enzyme inhibitor-induced cough: a genome-wide association study in a Swedish population.
2017 Feb
Patents

Sample Use Guides

The recommended initial dosage of ACCUPRIL in patients not on diuretics is 10 or 20 mg once daily. Dosage should be adjusted according to blood pressure response measured at peak (2–6 hours after dosing) and trough (predosing). Generally, dosage adjustments should be made at intervals of at least 2 weeks. Most patients have required dosages of 20, 40, or 80 mg/day, given as a single dose or in two equally divided doses.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
QUINAPRIL HYDROCHLORIDE
HSDB   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
QUINAPRIL HYDROCHLORIDE [ORANGE BOOK]
Common Name English
QUINAPRIL HYDROCHLORIDE [MI]
Common Name English
ACCURETIC COMPONENT QUINAPRIL HYDROCHLORIDE
Common Name English
QUINAPRIL HCL
Common Name English
QUINARETIC COMPONENT QUINAPRIL HYDROCHLORIDE
Common Name English
QUINAPRIL HYDROCHLORIDE COMPONENT OF ACCURETIC
Common Name English
QUINAPRIL HYDROCHLORIDE COMPONENT OF QUINARETIC
Common Name English
ACCUPRIL
Common Name English
2-(2-((1-ETHOXYCARBONYL-3-PHENYLPROPYL)AMINO)-1-OXOPROPYL)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID MONOHYDROCHLORIDE(3S-(2(R*(R*)),3R*)
Common Name English
QUINAPRIL HYDROCHLORIDE [HSDB]
Common Name English
CI 906
Code English
QUINAPRIL HYDROCHLORIDE [USP-RS]
Common Name English
QUINAPRIL HYDROCHLORIDE [VANDF]
Common Name English
NSC-758222
Code English
QUINAPRIL HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
(S)-2-((S)-N-((S)-1-CARBOXY-3-PHENYLPROPYL)ALANYL)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID, 1-ETHYL ESTER, MONOHYDROCHLORIDE
Common Name English
QUINAPRIL HYDROCHLORIDE [USAN]
Common Name English
QUINAPRIL HYDROCHLORIDE [WHO-DD]
Common Name English
QUINAPRIL HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
QUINAPRIL HYDROCHLORIDE [MART.]
Common Name English
QUINAPRIL HYDROCHLORIDE [USP]
Common Name English
QUINAPRIL HYDROCHLORIDE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C247
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
Code System Code Type Description
EVMPD
SUB04164MIG
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
PRIMARY
RXCUI
235759
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL1592
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
PRIMARY
PUBCHEM
54891
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
PRIMARY
HSDB
7046
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
PRIMARY
MERCK INDEX
M9437
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
PRIMARY Merck Index
CAS
82586-55-8
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
PRIMARY
NCI_THESAURUS
C29398
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
PRIMARY
EPA CompTox
82586-55-8
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
PRIMARY
DRUG BANK
DBSALT000465
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
PRIMARY
FDA UNII
33067B3N2M
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
PRIMARY
USP_CATALOG
1593401
Created by admin on Fri Jun 25 21:04:26 UTC 2021 , Edited by admin on Fri Jun 25 21:04:26 UTC 2021
PRIMARY USP-RS