Identification

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Name
Quinapril
Accession Number
DB00881  (APRD00523)
Type
Small Molecule
Groups
Approved, Investigational
Description

Quinapril is the ethyl ester prodrug of the non-sulfhydryl angiotensin converting enzyme inhibitor quinaprilat.6,7 It is used to treat hypertension and heart failure.6,7 ACE inhibitors are commonly used as a first line therapy in the treatment of hypertension, along with thiazide diuretics or beta blockers.5

Quinapril was granted FDA approval on 19 November 1991.6 A combination tablet with hydrochlorothiazide was also approved on 28 December 1999.7

Structure
Thumb
Synonyms
  • Quinapril
  • Quinaprilum
External IDs
C09AA06
Product Ingredients
IngredientUNIICASInChI Key
Quinapril Hydrochloride33067B3N2M82586-55-8IBBLRJGOOANPTQ-JKVLGAQCSA-N
Active Moieties
NameKindUNIICASInChI Key
Quinaprilatprodrug34SSX5LDE582768-85-2FLSLEGPOVLMJMN-YSSFQJQWSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AccuprilTablet, film coated10 mg/1OralCardinal Health1991-11-192011-10-31Us
AccuprilTablet, film coated40 mg/1OralParke Davis Div Of Pfizer Inc1991-11-19Not applicableUs
AccuprilTablet, film coated40 mg/1OralPhysicians Total Care, Inc.1994-12-052011-06-30Us
AccuprilTablet, film coated20 mg/1OralParke Davis Div Of Pfizer Inc1991-11-19Not applicableUs
AccuprilTablet, film coated20 mg/1OralPhysicians Total Care, Inc.1995-07-202011-06-30Us
AccuprilTablet, film coated10 mg/1OralParke Davis Div Of Pfizer Inc1991-11-19Not applicableUs
AccuprilTablet, film coated10 mg/1OralPhysicians Total Care, Inc.2003-09-222011-06-30Us
AccuprilTablet, film coated5 mg/1OralParke Davis Div Of Pfizer Inc1991-11-19Not applicableUs
AccuprilTablet, film coated20 mg/1OralCardinal Health1991-11-192014-08-31Us
AccuprilTablet, film coated5 mg/1OralPhysicians Total Care, Inc.1994-05-102011-06-30Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-quinaprilTabletOralApotex Corporation2013-07-02Not applicableCanada
Apo-quinaprilTabletOralApotex Corporation2013-07-02Not applicableCanada
Apo-quinaprilTabletOralApotex Corporation2013-07-02Not applicableCanada
Apo-quinaprilTabletOralApotex Corporation2013-07-02Not applicableCanada
Gd-quinaprilTabletOralGenmed A Division Of Pfizer Canada Ulc2014-06-022018-09-26Canada
Gd-quinaprilTabletOralGenmed A Division Of Pfizer Canada Ulc2014-06-022018-09-26Canada
Gd-quinaprilTabletOralGenmed A Division Of Pfizer Canada Ulc2014-06-022019-04-16Canada
Gd-quinaprilTabletOralGenmed A Division Of Pfizer Canada Ulc2014-06-022019-02-01Canada
PMS-quinaprilTabletOralPharmascience Inc2013-11-18Not applicableCanada
PMS-quinaprilTabletOralPharmascience Inc2013-11-18Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AccureticQuinapril Hydrochloride (10 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralParke-Davis Div of Pfizer Inc1999-12-28Not applicableUs
AccureticQuinapril (20 mg) + Hydrochlorothiazide (25 mg)TabletOralPfizer Canada Ulc2003-06-02Not applicableCanada
AccureticQuinapril (20 mg) + Hydrochlorothiazide (12.5 mg)TabletOralPfizer Canada Ulc1998-10-01Not applicableCanada
AccureticQuinapril Hydrochloride (20 mg/1) + Hydrochlorothiazide (25 mg/1)Tablet, film coatedOralParke-Davis Div of Pfizer Inc1999-12-28Not applicableUs
AccureticQuinapril (10 mg) + Hydrochlorothiazide (12.5 mg)TabletOralPfizer Canada Ulc1998-10-01Not applicableCanada
AccureticQuinapril Hydrochloride (20 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralParke-Davis Div of Pfizer Inc1999-12-28Not applicableUs
Apo-quinapril/hctzQuinapril (20 mg) + Hydrochlorothiazide (12.5 mg)TabletOralApotex Corporation2013-08-13Not applicableCanada
Apo-quinapril/hctzQuinapril (10 mg) + Hydrochlorothiazide (12.5 mg)TabletOralApotex Corporation2013-08-13Not applicableCanada
Apo-quinapril/hctzQuinapril (20 mg) + Hydrochlorothiazide (25 mg)TabletOralApotex Corporation2013-08-13Not applicableCanada
Auro-quinapril HctzQuinapril (20 mg) + Hydrochlorothiazide (25 mg)TabletOralAuro Pharma Inc2019-02-01Not applicableCanada
International/Other Brands
Accuprin (Pfizer (Italy)) / Accupro (Pfizer (Austria, Denmark, Finland, Germany, Hungary, Ireland, Sweden, Switzerland, United Kingdom, Ukraine), Godecke (Czech Republic, Germany, Poland, Russia), Parke, Davis (Germany)) / Acequin / Acuitel / Korec / Quinazil
Categories
UNII
RJ84Y44811
CAS number
85441-61-8
Weight
Average: 438.5161
Monoisotopic: 438.21547208
Chemical Formula
C25H30N2O5
InChI Key
JSDRRTOADPPCHY-HSQYWUDLSA-N
InChI
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
IUPAC Name
(3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(O)=O

Pharmacology

Indication

Quinapril is indicated for the treatment of hypertension and as an adjunct therapy in the treatment of heart failure.6 Quinapril in combination with hydrochlorothiazide is indicated for the treatment of hypertension.7

Associated Conditions
Pharmacodynamics

Quinapril is a prodrug of an angiotensin converting enzyme (ACE) inhibitor used in the treatment of hypertension or adjunct in the treatment of heart failure.1,2,6 Quinapril has a wide therapeutic window and a long duration of action as it is given in doses of 10-80mg once daily.6

Mechanism of action

Angiotensin II constricts coronary blood vessels and is positively inotropic, which under normal circumstances, would increase vascular resistance and oxygen consumption.4 This action can eventually lead to myocyte hypertrophy and vascular smooth muscle cell proliferation.4 Angiotensin II also stimulates production of plasminogen activator inhibitor-1 (PAI-1), increasing the risk of thrombosis.2

Quinaprilat prevents the conversion of angiotensin I to angiotensin II by inhibition of angiotensin converting enzyme, and also reduces the breakdown of bradykinin.1,2 Reduced levels of angiotensin II lead to lower levels of PAI-1, reducing the risk of thrombosis, especially after a myocardial infarction.2

TargetActionsOrganism
AAngiotensin-converting enzyme
inhibitor
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Quinapril if 50-80% bioavailable.1 Quinapril has a Tmax of <1 hour,6 while quinaprilat has a Tmax of 2.5h.1 The Cmax of quinaprilat is highly variable but reaches 1526ng/mL with an AUC of 2443ng*h/mL in healthy males given a 10mg dose.1 A high fat meal reduces the absorption of quinapril by 25-30%.1

Volume of distribution

The mean volume of distribution of quinaprilat is 13.9L.1

Protein binding

Quinapril and the active metabolite quinaprilat are 97% protein bound in plasma.6,7

Metabolism

Quinapril is de-esterified to the active quinaprilat or dehydrated to form the inactive PD109488.1,3 PD109488 can undergo O-deethylation to form another inactive metabolite, PD113413.1,3

Route of elimination

Quinaprilat is up to 96% eliminated in the urine.6 The eliminated metabolites PD109488 and PD113413 account for approximately 6% of a dose of quinapril each.1,3 A small fraction of the dose recovered in the urine is accounted for by unmetabolized quinapril.3

Half life

The active metabolite quinaprilat has an elimination half life of 2.3 hours.1,6

Clearance

The clearance of quinaprilat is 68mL/min.1

Toxicity

The oral LD50 in rats is 3541mg/kg and in mice is 1739mg/kg.8

Patients experiencing an overdose may present with symptoms of severe hypotension.6,7 Due to the extensive protein binding of quinapril and the active metabolite quinaprilat, hemodialysis is not expected to remove the drug from circulation.6,7 Treat patients with symptomatic and supportive measures, including normal saline infusions to restore normal blood pressure.6,7

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Quinapril Metabolism PathwayDrug metabolism
Quinapril Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Quinapril.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Quinapril.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the antihypertensive activities of Quinapril.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Quinapril.
4-Methoxyamphetamine4-Methoxyamphetamine may decrease the antihypertensive activities of Quinapril.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Quinapril.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Quinapril.
AbediterolAbediterol may decrease the antihypertensive activities of Quinapril.
AcebutololThe risk or severity of hyperkalemia can be increased when Quinapril is combined with Acebutolol.
AceclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Quinapril.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Avoid fatty foods.
  • Avoid hypertensive herbs (e.g. bayberry, blue cohosh, cayenne, ephedra, and licorice).
  • Avoid potassium-containing products. Potassium products increase the risk of hyperkalemia.
  • Limit salt intake. Salt may attenuate the antihypertensive effect.

References

Synthesis Reference

Om P. Goel, Uldis Krolls, "Crystalline quinapril and a process for producing the same." U.S. Patent US4761479, issued August, 1982.

US4761479
General References
  1. Kieback AG, Felix SB, Reffelmann T: Quinaprilat: a review of its pharmacokinetics, pharmacodynamics, toxicological data and clinical application. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1337-47. doi: 10.1517/17425250903282773. [PubMed:19761414]
  2. Tsikouris JP, Suarez JA, Meyerrose GE, Ziska M, Fike D, Smith J: Questioning a class effect: does ACE inhibitor tissue penetration influence the degree of fibrinolytic balance alteration following an acute myocardial infarction? J Clin Pharmacol. 2004 Feb;44(2):150-7. [PubMed:14747423]
  3. Kaplan HR, Taylor DG, Olson SC, Andrews LK: Quinapril--a preclinical review of the pharmacology, pharmacokinetics, and toxicology. Angiology. 1989 Apr;40(4 Pt 2):335-50. doi: 10.1177/000331978904000403. [PubMed:2539761]
  4. Goa KL, Balfour JA, Zuanetti G: Lisinopril. A review of its pharmacology and clinical efficacy in the early management of acute myocardial infarction. Drugs. 1996 Oct;52(4):564-88. doi: 10.2165/00003495-199652040-00011. [PubMed:8891468]
  5. Wright JM, Musini VM, Gill R: First-line drugs for hypertension. Cochrane Database Syst Rev. 2018 Apr 18;4:CD001841. doi: 10.1002/14651858.CD001841.pub3. [PubMed:29667175]
  6. FDA Approved Drug Products: Quinapril Oral Tablet [Link]
  7. FDA Approved Drug Products: Quinapril and Hydrochlorothiazide Oral Tablets [Link]
  8. Cayman Chemicals: Quinapril MSDS [Link]
  9. Pfizer Canada: Quinapril Oral Tablets [Link]
External Links
Human Metabolome Database
HMDB0015019
KEGG Drug
D03752
KEGG Compound
C07398
PubChem Compound
54892
PubChem Substance
46506309
ChemSpider
49565
BindingDB
50368166
ChEBI
8713
ChEMBL
CHEMBL1592
ZINC
ZINC000003801163
Therapeutic Targets Database
DAP000588
PharmGKB
PA451205
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Quinapril
ATC Codes
C09AA06 — QuinaprilC09BA06 — Quinapril and diuretics
AHFS Codes
  • 24:32.04 — Angiotensin-converting Enzyme Inhibitors

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers4
3CompletedPreventionType 1 Diabetes Mellitus1
4CompletedNot AvailableCoronary Artery Bypass Graft Surgery Patients1
4CompletedNot AvailableDiabetic Autonomic Neuropathy1
4CompletedPreventionAtrial Fibrillation (AF)1
4CompletedTreatmentCardiovascular Heart Disease / Chronic Kidney Disease (CKD) / Hypertension,Essential / Stroke1
4CompletedTreatmentHigh Blood Pressure (Hypertension)2
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Menopause1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Induction of intra-operative hypotension1
4CompletedTreatmentIschemic Heart Disease1
4RecruitingTreatmentHeart Diseases / Type 2 Diabetes Mellitus1
4TerminatedTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension)1
Not AvailableCompletedTreatmentArterial Occlusive Diseases1
Not AvailableCompletedTreatmentDiabetes / High Blood Pressure (Hypertension)1

Pharmacoeconomics

Manufacturers
  • Pfizer pharmaceuticals ltd
  • Actavis totowa llc
  • Apotex inc
  • Genpharm inc
  • Invagen pharmaceuticals inc
  • Lupin ltd
  • Mylan pharmaceuticals inc
  • Ranbaxy laboratories ltd
  • Sandoz inc
  • Sun pharmaceutical industries ltd
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc florida
Packagers
  • Actavis Group
  • Apotex Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Aurobindo Pharma Ltd.
  • Cardinal Health
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Doctor Reddys Laboratories Ltd.
  • Eon Labs
  • Goedecke GmbH
  • Greenstone LLC
  • Heartland Repack Services LLC
  • InvaGen Pharmaceuticals Inc.
  • Lupin Pharmaceuticals Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacia Inc.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Southwood Pharmaceuticals
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
Dosage forms
FormRouteStrength
TabletOral10 mg/1
TabletOral20 mg/1
TabletOral40 mg/1
TabletOral5 1/1
TabletOral5 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral20 mg/1
Tablet, film coatedOral40 mg/1
Tablet, film coatedOral5 mg/1
Tablet, film coatedOral
TabletOral
TabletOral
Prices
Unit descriptionCostUnit
Accupril 10 mg tablet2.02USD tablet
Accupril 20 mg tablet2.02USD tablet
Accupril 40 mg tablet2.02USD tablet
Accupril 5 mg tablet2.02USD tablet
Quinapril 10 mg tablet1.57USD tablet
Quinapril 20 mg tablet1.57USD tablet
Quinapril 40 mg tablet1.57USD tablet
Quinapril 5 mg tablet1.57USD tablet
Quinapril HCl 10 mg tablet1.27USD tablet
Quinapril HCl 20 mg tablet1.27USD tablet
Quinapril HCl 40 mg tablet1.27USD tablet
Quinapril HCl 5 mg tablet1.27USD tablet
Quinaretic 10-12.5 mg tablet1.27USD tablet
Quinaretic 20-12.5 mg tablet1.27USD tablet
Quinaretic 20-25 mg tablet1.27USD tablet
Accupril 10 mg Tablet0.96USD tablet
Accupril 20 mg Tablet0.96USD tablet
Accupril 40 mg Tablet0.96USD tablet
Accupril 5 mg Tablet0.96USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5684016No1997-11-042015-05-04Us
CA2023089No2003-01-142010-08-10Canada
CA1331615No1994-08-232011-08-23Canada
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)120-130 °CChemspider
logP0.86Pfizer Canada Monograph
pKa2.8Pfizer Canada Monograph
Predicted Properties
PropertyValueSource
Water Solubility0.0085 mg/mLALOGPS
logP1.39ALOGPS
logP1.96ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.7ChemAxon
pKa (Strongest Basic)5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity119.96 m3·mol-1ChemAxon
Polarizability47.36 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5597
Blood Brain Barrier-0.9409
Caco-2 permeable-0.8208
P-glycoprotein substrateSubstrate0.8895
P-glycoprotein inhibitor IInhibitor0.7344
P-glycoprotein inhibitor IIInhibitor0.5869
Renal organic cation transporterNon-inhibitor0.8258
CYP450 2C9 substrateNon-substrate0.8594
CYP450 2D6 substrateNon-substrate0.8412
CYP450 3A4 substrateSubstrate0.5356
CYP450 1A2 substrateNon-inhibitor0.8597
CYP450 2C9 inhibitorNon-inhibitor0.6832
CYP450 2D6 inhibitorNon-inhibitor0.8636
CYP450 2C19 inhibitorNon-inhibitor0.6016
CYP450 3A4 inhibitorInhibitor0.5347
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5162
Ames testNon AMES toxic0.9091
CarcinogenicityNon-carcinogens0.9294
BiodegradationNot ready biodegradable0.9596
Rat acute toxicity2.2690 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9763
hERG inhibition (predictor II)Inhibitor0.7176
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Alpha amino acid esters / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Tetrahydroisoquinolines / Fatty acid esters / Aralkylamines / Dicarboxylic acids and derivatives / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Amino acids
show 8 more
Substituents
Alpha-dipeptide / Alpha-amino acid ester / N-acyl-l-alpha-amino acid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Tetrahydroisoquinoline / Fatty acid ester / Aralkylamine / Monocyclic benzene moiety / Dicarboxylic acid or derivatives
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dicarboxylic acid monoester, ethyl ester, isoquinolines (CHEBI:8713)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent...
Gene Name
ACE
Uniprot ID
P12821
Uniprot Name
Angiotensin-converting enzyme
Molecular Weight
149713.675 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Culy CR, Jarvis B: Quinapril: a further update of its pharmacology and therapeutic use in cardiovascular disorders. Drugs. 2002;62(2):339-85. [PubMed:11817979]
  3. Klutchko S, Blankley CJ, Fleming RW, Hinkley JM, Werner AE, Nordin I, Holmes A, Hoefle ML, Cohen DM, Essenburg AD, et al.: Synthesis of novel angiotensin converting enzyme inhibitor quinapril and related compounds. A divergence of structure-activity relationships for non-sulfhydryl and sulfhydryl types. J Med Chem. 1986 Oct;29(10):1953-61. [PubMed:3020249]
  4. Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [PubMed:11929321]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Tarkiainen EK, Tornio A, Holmberg MT, Launiainen T, Neuvonen PJ, Backman JT, Niemi M: Effect of carboxylesterase 1 c.428G > A single nucleotide variation on the pharmacokinetics of quinapril and enalapril. Br J Clin Pharmacol. 2015 Nov;80(5):1131-8. doi: 10.1111/bcp.12667. Epub 2015 Jun 11. [PubMed:25919042]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Shi JH, Pan DQ, Jiang M, Liu TT, Wang Q: In vitro study on binding interaction of quinapril with bovine serum albumin (BSA) using multi-spectroscopic and molecular docking methods. J Biomol Struct Dyn. 2017 Aug;35(10):2211-2223. doi: 10.1080/07391102.2016.1213663. Epub 2016 Aug 7. [PubMed:27418394]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Quinaprilat is the active metabolite of quinapril; its substrate profile was demonstrated in vitro using HEK293 cells.
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [PubMed:19953504]

Drug created on June 13, 2005 07:24 / Updated on February 22, 2020 15:33