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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H30N2O5
Molecular Weight 438.5161
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINAPRIL

SMILES

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

InChI

InChIKey=JSDRRTOADPPCHY-HSQYWUDLSA-N
InChI=1S/C25H30N2O5/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)/t17-,21-,22-/m0/s1

HIDE SMILES / InChI
Molecular Formula C25H30N2O5
Molecular Weight 438.5161
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

1991
96
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7468
 2.8 nM [IC50]
Inhibitor
7468
Hypertension
 110.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Angiotensin-converting enzyme
Approved
7883
ACCURETIC
PubMed

PubMed

TitleDatePubMed
The influence of angiotensin-converting enzyme inhibitors on the aorta elastin metabolism in diet-induced hypercholesterolaemia in rabbits.
2001 Mar
[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
Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update.
2002
Angiotensin II induced inflammation in the kidney and in the heart of double transgenic rats.
2002
Rapid increase in cardiac adrenomedullin gene expression caused by acute pressure overload: effect of the renin-angiotensin system on gene expression.
2002 Apr
Quinapril prevents restenosis after coronary stenting in patients with angiotensin-converting enzyme D allele.
2002 Apr
Inhibition of left ventricular fibrosis by tranilast in rats with renovascular hypertension.
2002 Apr
[Is mild essential hypertension without obvious organ complications and risk factors associated with increased levels of circulating markers of endothelial dysfunction? Effect of ACE inhibitor therapy].
2002 Aug
Influence of antihypertensive drugs on renal microcirculation and renal hemodynamics in cyclosporine A-treated rats.
2002 Aug
AT1 receptor blockade increases cardiac bradykinin via neutral endopeptidase after induction of myocardial infarction in rats.
2002 Aug
Circulating intercellular cell adhesion molecule-1, endothelin-1 and von Willebrand factor-markers of endothelial dysfunction in uncomplicated essential hypertension: the effect of treatment with ACE inhibitors.
2002 Aug
Using ACE inhibitors appropriately.
2002 Aug 1
Enalapril and quinapril improve endothelial vasodilator function and aortic eNOS gene expression in L-NAME-treated rats.
2002 Aug 16
Time-effect profile of antihypertensive agents assessed with trough/peak ratio, smoothness index and dose omission: an ambulatory blood pressure monitoring study with trandolapril vs. quinapril.
2002 Dec
The ACE inhibitor, quinapril, ameliorates peritoneal fibrosis in an encapsulating peritoneal sclerosis model in mice.
2002 Dec
Effects of antihypertensive drugs in experimental type 2 diabetes-related nephropathy.
2002 Dec
Angiotensin II regulates the synthesis of proinflammatory cytokines and chemokines in the kidney.
2002 Dec
Influence of angiotensinogen M253T gene polymorphism and an angiotensin converting enzyme inhibitor on restenosis after percutaneous coronary intervention.
2002 Feb
Angiotensin II as an inflammatory mediator: evolving concepts in the role of the renin angiotensin system in the failing heart.
2002 Jan
Effects of quinapril on myocardial function, ventricular remodeling and cardiac cytokine expression in congestive heart failure in the rat.
2002 Jan
Effects of a citrate buffer system on the solid-state chemical stability of lyophilized quinapril preparations.
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
The mechanism of the angiotensin-converting enzyme inhibitor quinapril is not related to bradykinin level in heart tissue.
2002 Jun
Subacute and chronic effects of quinapril on cardiac cytokine expression, remodeling, and function after myocardial infarction in the rat.
2002 Jun
Blockade of endothelial enzymes: new therapeutic targets.
2002 Mar
Effects of a long-term pharmacological interruption of the renin-angiotensin system on the fibrinolytic system in essential hypertension.
2002 Mar-Apr
Ventricular remodeling after myocardial infarction and effects of ACE inhibition on hemodynamics and scar formation in SHR.
2002 Mar-Apr
Lowering of blood pressure improves endothelial dysfunction by increase of nitric oxide production in hypertensive rats.
2002 May
Pretreatment with angiotensin-converting enzyme inhibitors attenuates ischemia-reperfusion injury.
2002 May
Bradykinin as a major endogenous regulator of endothelial function.
2002 May-Jun
Quinapril treatment restores the vasodilator action of insulin in fructose-hypertensive rats.
2002 May-Jun
Ischemia Management with Accupril post bypass Graft via Inhibition of angiotensin coNverting enzyme (IMAGINE): a multicentre randomized trial - design and rationale.
2002 Nov
Effect of losartan on nocturnal blood pressure in patients with stroke: comparison with angiotensin converting enzyme inhibitor.
2002 Nov
Optimisation by experimental design of a capillary electrophoretic method for the separation of several inhibitors of angiotensin-converting enzyme using alkylsulphonates.
2002 Nov 29
Captopril and quinapril reduce reactive oxygen species.
2002 Oct
Prevention of vascular damage in scleroderma with angiotensin-converting enzyme (ACE) inhibition.
2002 Sep
[Angiotensin-converting enzyme, quinapril, in treating chronic cardiac failure].
2003
Role of PKC in autocrine regulation of rat ventricular K+ currents by angiotensin and endothelin.
2003 Apr
Pharmacokinetics of quinapril in children: assessment during substitution for chronic angiotensin-converting enzyme inhibitor treatment.
2003 Feb
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
Moexipril and quinapril inhibition of tissue angiotensin-converting enzyme activity in the rat: evidence for direct effects in heart, lung and kidney and stimulation of prostacyclin generation.
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
Square wave voltammetric determination of the angiotensin-converting enzyme inhibitors cilazapril, quinapril and ramipril in pharmaceutical formulations.
2003 May
Usefulness of quinapril and irbesartan to improve the anti-inflammatory response of atorvastatin and aspirin in patients with coronary heart disease.
2003 May 1
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

Patents

4656188
4
4743450
4
JP2001521898A
4
JP2003503381A
35
JP2003507418A
29
JP2006513266A
23
JP2011510003A
43
JP2011528275A
416
JP4729259B2
35
JPH04253923A
4

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Mon Oct 21 22:32:10 UTC 2019
Edited
by admin
on Mon Oct 21 22:32:10 UTC 2019
Record UNII
RJ84Y44811
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUINAPRIL
INN   MI   USP   VANDF   WHO-DD  
INN  
Official Name English
QUINAPRIL [INN]
Common Name English
QUINAPRIL [WHO-DD]
Common Name English
QUINAPRIL [VANDF]
Common Name English
QUINAPRIL [MI]
Common Name English
QUINAPRIL [USP]
Common Name English
C09AA06
Code English
Classification Tree Code System Code
NDF-RT N0000175562
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
NDF-RT N0000000181
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
WHO-VATC QC09BA06
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
WHO-ATC C09BA06
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
NCI_THESAURUS C247
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
WHO-VATC QC09AA06
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
WHO-ATC C09AA06
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
LIVERTOX 824
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
Code System Code Type Description
RXCUI
35208
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY RxNorm
IUPHAR
6350
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY
EVMPD
SUB10201MIG
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY
LactMed
85441-61-8
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY
DRUG BANK
DB00881
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY
ChEMBL
CHEMBL1592
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY
WIKIPEDIA
QUINAPRIL
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY
PUBCHEM
54892
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY
MERCK INDEX
M9437
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY Merck Index
INN
5780
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY
NCI_THESAURUS
C62074
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY
CAS
85441-61-8
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY
EPA CompTox
85441-61-8
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY
MESH
C041125
Created by admin on Mon Oct 21 22:32:10 UTC 2019 , Edited by admin on Mon Oct 21 22:32:10 UTC 2019
PRIMARY
Related Record Type Details
OAT-3
TRANSPORTER -> INHIBITOR
ANGIOTENSIN-CONVERTING ENZYME
TARGET -> INHIBITOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
LIVER CARBOXYLESTERASE 1
METABOLIC ENZYME -> SUBSTRATE
Structure of QUINAPRIL HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of QUINAPRILAT
METABOLITE ACTIVE -> PARENT
Related Record Type Details
Structure of QUINAPRILAT
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
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