QUINAPRIL

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

SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3=C(C[C@H]2C(O)=O)C=CC=C3

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
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

Targets

Primary Target	Pharmacology	Condition	Potency
Angiotensin-converting enzyme 97	Inhibitor 8,297		2.8 nM [IC50]
Angiotensin-converting enzyme 97	Inhibitor 8,297		110.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567	Primary		Approved 8,429	ACCURETIC

C_max

Value	Dose	Co-administered	Analyte	Population
1526 ng/mL	10 mg single, intravenous		QUINAPRILAT plasma	Homo sapiens
345 ng/mL	2.5 mg single, intravenous		QUINAPRILAT plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
1706 μg × h/L	10 mg 2 times / day steady-state, oral	QUINAPRILAT plasma	Homo sapiens
2670 ng × h/mL	10 mg single, intravenous	QUINAPRILAT plasma	Homo sapiens
580 ng × h/mL	2.5 mg single, intravenous	QUINAPRILAT plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
3.7 h	10 mg 2 times / day steady-state, oral	QUINAPRILAT plasma	Homo sapiens
2.29 h	10 mg single, intravenous	QUINAPRILAT plasma	Homo sapiens
2.26 h	2.5 mg single, intravenous	QUINAPRILAT plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
40 mg 1 times / day multiple, oral (max) Recommended	unhealthy, adult n = 1563	Disc. AE: Headache, Dizziness...
40 mg 1 times / day multiple, oral (max) Recommended	unhealthy, adult n = 585	Disc. AE: Dizziness, Coughing...

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AEs

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AE	Significance	Dose	Population
Abdominal pain	0.2% Disc. AE	40 mg 1 times / day multiple, oral (max) Recommended	unhealthy, adult n = 1563
Fatigue	0.3% Disc. AE	40 mg 1 times / day multiple, oral (max) Recommended	unhealthy, adult n = 1563
Nausea and vomiting	0.3% Disc. AE	40 mg 1 times / day multiple, oral (max) Recommended	unhealthy, adult n = 1563
Coughing	0.5% Disc. AE	40 mg 1 times / day multiple, oral (max) Recommended	unhealthy, adult n = 1563
Headache	0.7% Disc. AE	40 mg 1 times / day multiple, oral (max) Recommended	unhealthy, adult n = 1563

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT3 642	esterase 72 OAT1 326 OAT3 339

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
OAT3 644	inhibitor 3,277	yes [IC50 6.2 uM]

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Drug as victim

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Target	Modality	Activity
OAT1 326	substrate 3,367	yes
OAT3 339	substrate 3,367	yes
esterase 72	substrate 3,367	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:140296	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:140296
ChemicalBook	CB0247832	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0247832
ZINC	ZINC000004217387	http://zinc15.docking.org/substances/ZINC000004217387
eMolecules	33507669	https://www.emolecules.com/cgi-bin/more?vid=33507669

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PubMed

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Title	Date	PubMed
Comparison of a vasopeptidase inhibitor with neutral endopeptidase and angiotensin-converting enzyme inhibitors on bradykinin metabolism in the rat coronary bed.	2001 Apr	11300648
A single (investigator)-blind randomised control trial comparing the effects of quinapril and nifedipine on platelet function in patients with mild to moderate hypertension.	2001 Aug	11487379
[Hypertensive patients with signs of coronary heart disease. An ACE inhibitor improves endothelial function].	2001 Aug 23	11561465
Beneficial effect of quinapril in patients with angiotensin-converting enzyme D allele after coronary stenting.	2001 Dec	11730835
ACE inhibitors for hypertension.	2001 Feb 23	11280436

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Patents

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

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	RJ84Y44811
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

QUINAPRIL

Official Name

English

quinapril [INN]

Common Name

English

QUINAPRIL [VANDF]

Common Name

English

Quinapril [WHO-DD]

Common Name

English

QUINAPRIL [USP IMPURITY]

Common Name

English

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Classification Tree

Code System

Code

Established Pharmacologic Class

NDF-RT

N0000175562

Protease Inhibitors

NDF-RT

N0000000181

ACE inhibitors and diuretics

WHO-VATC

QC09BA06

ACE inhibitors and diuretics

WHO-ATC

C09BA06

Antihypertensive Agent

NCI_THESAURUS

C247

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Code System

Code

Type

Description

LACTMED

Quinapril

PRIMARY

RXCUI

35208

PRIMARY

RxNorm

IUPHAR

6350

PRIMARY

DRUG CENTRAL

2340

PRIMARY

EVMPD

SUB10201MIG

PRIMARY

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Related Record

Type

Details


					51FM2R4Y24

ANGIOTENSIN-CONVERTING ENZYME

TARGET -> INHIBITOR


					ZWJ2Y6JZWY

OAT-3

TRANSPORTER -> INHIBITOR


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

97 % (average)


					HPN66MJEK8

LIVER CARBOXYLESTERASE 1

METABOLIC ENZYME -> SUBSTRATE

Amount:


					33067B3N2M

QUINAPRIL HYDROCHLORIDE

SALT/SOLVATE -> PARENT

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Type

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					34SSX5LDE5

QUINAPRILAT

METABOLITE ACTIVE -> PARENT


					482564RI35

PD-109488

METABOLITE -> PARENT

Amount:

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Type

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					52C66L723S

QUINAPRIL METHYL ESTER

IMPURITY -> PARENT

Amount:

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					34SSX5LDE5

QUINAPRILAT

ACTIVE MOIETY

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Name	Property Type	Amount	Parameters
Volume of Distribution	PHARMACOKINETIC	1.5 Liters/Kilogram (average)

Biological Half-life	PHARMACOKINETIC	2 hours (average)	Elimination PHARMACOKINETIC 0.8 hours (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator