Identification

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

Quinapril is a prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is metabolized to quinaprilat (quinapril diacid) following oral administration. Quinaprilat is a competitive inhibitor of ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Quinapril may be used to treat essential hypertension and congestive heart failure.

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 coated40 mg/1OralParke Davis Div Of Pfizer Inc1991-11-19Not applicableUs
AccuprilTablet, film coated10 mg/1OralCardinal Health1991-11-192011-10-31Us
AccuprilTablet, film coated5 mg/1OralPhysicians Total Care, Inc.1994-05-102011-06-30Us
AccuprilTablet, film coated40 mg/1Oralbryant ranch prepack1991-11-192006-12-01Us
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 coated20 mg/1OralCardinal Health1991-11-192014-08-31Us
AccuprilTablet, film coated5 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 coated40 mg/1OralPhysicians Total Care, Inc.1994-12-052011-06-30Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-quinaprilTablet5 mgOralApotex Corporation2013-07-02Not applicableCanada
Apo-quinaprilTablet20 mgOralApotex Corporation2013-07-02Not applicableCanada
Apo-quinaprilTablet10 mgOralApotex Corporation2013-07-02Not applicableCanada
Apo-quinaprilTablet40 mgOralApotex Corporation2013-07-02Not applicableCanada
Gd-quinaprilTablet20 mgOralGenmed A Division Of Pfizer Canada Inc2014-06-02Not applicableCanada
Gd-quinaprilTablet5 mgOralGenmed A Division Of Pfizer Canada Inc2014-06-02Not applicableCanada
Gd-quinaprilTablet40 mgOralGenmed A Division Of Pfizer Canada Inc2014-06-02Not applicableCanada
Gd-quinaprilTablet10 mgOralGenmed A Division Of Pfizer Canada Inc2014-06-02Not applicableCanada
PMS-quinaprilTablet5 mgOralPharmascience Inc2013-11-18Not applicableCanada
PMS-quinaprilTablet20 mgOralPharmascience Inc2013-11-18Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AccureticQuinapril Hydrochloride (20 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralParke Davis Div Of Pfizer Inc1999-12-28Not applicableUs
AccureticQuinapril Hydrochloride (10 mg/1) + Hydrochlorothiazide (12.5 mg/1)Tablet, film coatedOralParke Davis Div Of Pfizer Inc1999-12-28Not applicableUs
AccureticQuinapril Hydrochloride (20 mg/1) + Hydrochlorothiazide (25 mg/1)Tablet, film coatedOralParke Davis Div Of Pfizer Inc1999-12-28Not applicableUs
Accuretic 10/12.5 mgQuinapril (10 mg) + Hydrochlorothiazide (12.5 mg)TabletOralPfizer1998-10-01Not applicableCanada
Accuretic 20/12.5 mgQuinapril (20 mg) + Hydrochlorothiazide (12.5 mg)TabletOralPfizer1998-10-01Not applicableCanada
Accuretic 20/25 mgQuinapril (20 mg) + Hydrochlorothiazide (25 mg)TabletOralPfizer2003-06-02Not applicableCanada
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
Gd-quinapril HctzQuinapril (10 mg) + Hydrochlorothiazide (12.5 mg)TabletOralGenmed A Division Of Pfizer Canada IncNot applicableNot 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

For the treatment of hypertension and as adjunct therapy in the treatment of congestive heart failure. May also be used to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.

Associated Conditions
Pharmacodynamics

Quinapril is a nonpeptide, non-sulfhydryl prodrug that is deesterified to quinaprilat (quinapril diacid), its major active metabolite following oral administration. Quinaprilat lowers blood pressure by antagonizing the effect of the RAAS. The RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from the granular cells of the juxtaglomerular apparatus in the kidneys. In the blood stream, renin cleaves circulating angiotensinogen to ATI, which is subsequently cleaved to ATII by ACE. ATII increases blood pressure using a number of mechanisms. First, it stimulates the secretion of aldosterone from the adrenal cortex. Aldosterone travels to the distal convoluted tubule (DCT) and collecting tubule of nephrons where it increases sodium and water reabsorption by increasing the number of sodium channels and sodium-potassium ATPases on cell membranes. Second, ATII stimulates the secretion of vasopressin (also known as antidiuretic hormone or ADH) from the posterior pituitary gland. ADH stimulates further water reabsorption from the kidneys via insertion of aquaporin-2 channels on the apical surface of cells of the DCT and collecting tubules. Third, ATII increases blood pressure through direct arterial vasoconstriction. Stimulation of the Type 1 ATII receptor on vascular smooth muscle cells leads to a cascade of events resulting in myocyte contraction and vasoconstriction. In addition to these major effects, ATII induces the thirst response via stimulation of hypothalamic neurons. ACE inhibitors inhibit the rapid conversion of ATI to ATII and antagonize RAAS-induced increases in blood pressure. ACE (also known as kininase II) is also involved in the enzymatic deactivation of bradykinin, a vasodilator. Inhibiting the deactivation of bradykinin increases bradykinin levels and may sustain the effects of quinaprilat by causing increased vasodilation and decreased blood pressure.

Mechanism of action

There are two isoforms of ACE: the somatic isoform, which exists as a glycoprotein comprised of a single polypeptide chain of 1277; and the testicular isoform, which has a lower molecular mass and is thought to play a role in sperm maturation and binding of sperm to the oviduct epithelium. Somatic ACE has two functionally active domains, N and C, which arise from tandem gene duplication. Although the two domains have high sequence similarity, they play distinct physiological roles. The C-domain is predominantly involved in blood pressure regulation while the N-domain plays a role in hematopoietic stem cell differentiation and proliferation. ACE inhibitors bind to and inhibit the activity of both domains, but have much greater affinity for and inhibitory activity against the C-domain. Quinaprilat, the principle active metabolite of quinapril, competes with ATI for binding to ACE and inhibits and enzymatic proteolysis of ATI to ATII. Decreasing ATII levels in the body decreases blood pressure by inhibiting the pressor effects of ATII as described in the Pharmacology section above. Quinaprilat also causes an increase in plasma renin activity likely due to a loss of feedback inhibition mediated by ATII on the release of renin and/or stimulation of reflex mechanisms via baroreceptors.

TargetActionsOrganism
AAngiotensin-converting enzyme
inhibitor
Human
Absorption

Peak plasma concentrations of quinapril occur within one hour following oral administration. The extent of absorption is at least 60%. The rate and extent of quinapril absorption are diminished moderately (approximately 25-30%) when ACCUPRIL tablets are administered during a high-fat meal.

Volume of distribution
Not Available
Protein binding

97%

Metabolism

Hepatic.

Route of elimination

Quinaprilat is eliminated primarily by renal excretion, up to 96% of an IV dose

Half life

Elimination half life is 2 hours with a prolonged terminal phase of 25 hours.

Clearance
Not Available
Toxicity

Overdose may lead to severe hypotension. LD50=1739mg/kg (orally in mice). The most common adverse effects observed in controlled clinical trials were dizziness, cough, chest pain, dyspnea, fatigue, and nausea/vomiting.

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

Interactions

Drug Interactions
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidQuinapril may increase the hypotensive activities of 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when Quinapril is combined with 1-benzylimidazole.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of hypertension can be increased when Quinapril is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of hypertension can be increased when Quinapril is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of hypertension can be increased when Quinapril is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of hypertension can be increased when Quinapril is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of hypertension can be increased when Quinapril is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of hypertension can be increased when Quinapril is combined with 5-methoxy-N,N-dimethyltryptamine.
AbediterolThe risk or severity of hypertension can be increased when Quinapril is combined with Abediterol.
AcebutololThe risk or severity of adverse effects can be increased when Quinapril is combined with Acebutolol.
Food Interactions
  • Do not take with a high-fat meal.
  • Herbs that may attenuate the antihypertensive effect of quinapril include: bayberry, blue cohash, cayenne, ephedra, ginger, ginseng (American), kola and licorice.
  • High salt intake may attenuate the antihypertensive effect of quinapril.
  • Quinapril may decrease the excretion of potassium. Salt substitutes containing potassium may increase the risk of hyperkalemia.

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. Khan BV, Sola S, Lauten WB, Natarajan R, Hooper WC, Menon RG, Lerakis S, Helmy T: Quinapril, an ACE inhibitor, reduces markers of oxidative stress in the metabolic syndrome. Diabetes Care. 2004 Jul;27(7):1712-5. [PubMed:15220251]
  2. 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]
  3. Pitt B, O'Neill B, Feldman R, Ferrari R, Schwartz L, Mudra H, Bass T, Pepine C, Texter M, Haber H, Uprichard A, Cashin-Hemphill L, Lees RS: The QUinapril Ischemic Event Trial (QUIET): evaluation of chronic ACE inhibitor therapy in patients with ischemic heart disease and preserved left ventricular function. Am J Cardiol. 2001 May 1;87(9):1058-63. [PubMed:11348602]
  4. 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]
  5. Valles Prats M, Matas Serra M, Bronsoms Artero J, Mate Benito G, Torguet Escuder P, Mauri Nicolas JM: Quinapril ACE-inhibition effects on adrenergic parameters in moderate essential hypertension. Kidney Int Suppl. 1996 Jun;55:S104-6. [PubMed:8743525]
  6. Voors AA, van Geel PP, Oosterga M, Buikema H, van Veldhuisen DJ, van Gilst WH: Vascular effects of quinapril completely depend on ACE insertion/deletion polymorphism. J Renin Angiotensin Aldosterone Syst. 2004 Sep;5(3):130-4. [PubMed:15526248]
  7. Yamada S, Muraoka I, Kato K, Hiromi Y, Takasu R, Seno H, Kawahara H, Nabeshima T: Elimination kinetics of quinaprilat and perindoprilat in hypertensive patients with renal failure on haemodialysis. Biol Pharm Bull. 2003 Jun;26(6):872-5. [PubMed:12808303]
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
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
3CompletedPreventionDiabetes, Diabetes Mellitus Type 11
4CompletedNot AvailableCoronary Artery Bypass Graft Surgery Patients1
4CompletedNot AvailableDiabetic Autonomic Neuropathy1
4CompletedPreventionHigh Blood Pressure (Hypertension)1
4CompletedPreventionNonvalvular Atrial Fibrillation1
4CompletedTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Hypertension,Essential / Strokes1
4CompletedTreatmentHigh Blood Pressure (Hypertension)2
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Menopause1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Induction of intra-operative hypotension1
4CompletedTreatmentIschaemic Heart Diseases1
4TerminatedTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension)1
Not AvailableCompletedTreatmentDiabetes Mellitus (DM) / 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
TabletOral5 mg
TabletOral10 mg
TabletOral20 mg
TabletOral40 mg
TabletOral
TabletOral10 mg/1
TabletOral20 mg/1
TabletOral40 mg/1
TabletOral5 mg/1
TabletOral5 1/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral20 mg/1
Tablet, film coatedOral40 mg/1
Tablet, film coatedOral5 mg/1
Tablet, film coatedOral
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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)120-130 °CNot Available
water solubility1 mg/LNot Available
logP3.2Not Available
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
Human
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]

Transporters

Kind
Protein
Organism
Human
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
Human
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
Human
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 December 14, 2018 16:26