Identification

Name
Lisinopril
Accession Number
DB00722
Description

Lisinopril is an angiotensin converting enzyme inhibitor (ACEI) used to treat hypertension, heart failure, and myocardial infarction.8,9,10 Lisinopril and captopril are the only ACEIs that are not prodrugs.7 It functions by inhibition of angiotensin converting enzyme as well as the renin angiotensin aldosterone system.3,4,5 ACEIs are commonly used as a first line therapy in the treatment of hypertension, along with thiazide diuretics or beta blockers.6

Lisinopril was granted FDA approval on 29 December 1987.8

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 405.4879
Monoisotopic: 405.226371117
Chemical Formula
C21H31N3O5
Synonyms
  • (S)-1-(N(2)-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-proline
  • [N2-[(S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline
  • Lisinopril
  • Lisinopril anhydrous
  • Lisinoprilum

Pharmacology

Indication

Lisinopril is indicated for the treatment of acute myocardial infarction, hypertension in patients ≥6 years, and as an adjunct therapy for heart failure.8,9 A combination product with hydrochlorothiazide is indicated for the treatment of hypertension.10

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Lisinopril is an angiotensin converting enzyme inhibitor used to treat hypertension, heart failure, and myocardial infarction.8,9,10 Lisinopril is not a prodrug, and functions by inhibition of angiotensin converting enzyme as well as the renin angiotensin aldosterone system.3,4,5 It has a wide therapeutic index and a long duration of action as patients are generally given 10-80mg daily.8,9,10

Mechanism of action

Angiotensin II constricts coronary blood vessels and is positively inotropic, which under normal circumstances, would increase vascular resistance and oxygen consumption.3 This action can eventually lead to myocyte hypertrophy and vascular smooth muscle cell proliferation.3

Lisinopril is an angiotensin converting enzyme inhibitor (ACEI), preventing the conversion of angiotensin I to angiotensin II.3,4 This action prevents myocyte hypertrophy and vascular smooth muscle cell proliferation seen in untreated patients.4 Increased levels of bradykinin also exhibit vasodilating effects for patients taking ACEIs.4 Lisinopril also inhibits renin's conversion of angiotensin to angiotensin I.5

TargetActionsOrganism
AAngiotensin-converting enzyme
inhibitor
Humans
URenin
inhibitor
Humans
Absorption

Lisinopril is 6-60% orally bioavailable with an average of 25% bioavailability.2,8,9,10 Lisinopril reaches a Cmax of 58ng/mL with a Tmax of 6-8h.2 Lisinopril's absorption is not affected by food.2

Volume of distribution

The apparent volume of distribution of lisinopril is 124L.3

Protein binding

Lisinopril has not been demonstrated to bind to serum proteins.8,9,10

Metabolism

Lisinopril is not metabolized and is excreted as the unchanged drug.8,9,10

Route of elimination

Lisinopril is entirely eliminated exclusively in the urine.8,9,10

Half-life

Lisinopril has an effective half life of accumulation of 12.6h2,8,9,10 and a terminal half life of 46.7h.2

Clearance

A 30kg child has a typical clearance of 10L/h, which increases with renal function.8,9 The mean renal clearance of lisinopril in healthy adult males is 121mL/min.2

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

The oral and subcutaneous LD50 in rats is >8500mg/kg and in mice is >9100mg/kg.11 The oral LDLO in women is 1200µg/kg/16D and in men is 43mg/kg/43W.11

Patients experiencing an overdose of lisinopril may present with hypotension.8,9,10 Patients should be treated with intravenous saline to restore blood pressure.8,9,10 Lisinopril can be removed from the blood by hemodialysis due to it not being protein bound.8,9,10

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Lisinopril 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
AbacavirLisinopril may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Lisinopril which could result in a higher serum level.
AcebutololThe risk or severity of hyperkalemia can be increased when Lisinopril is combined with Acebutolol.
AceclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Lisinopril.
AcemetacinThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acemetacin is combined with Lisinopril.
AcetaminophenAcetaminophen may decrease the excretion rate of Lisinopril which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Lisinopril which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidThe therapeutic efficacy of Lisinopril can be decreased when used in combination with Acetylsalicylic acid.
AclidiniumLisinopril may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineLisinopril may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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

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  • Evidence Level
    Evidence Level
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    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
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Food Interactions
  • 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.
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Lisinopril dihydrateE7199S1YWR83915-83-7CZRQXSDBMCMPNJ-ZUIPZQNBSA-N
Product Images
International/Other Brands
Acebitor (GlaxoSmithKline) / Acemin (AstraZeneca) / Acerbon (AstraZeneca) / Acinopril (sanofi-aventis) / Bellisin (Ranbaxy) / Biopril (Biochem) / Dapril (Medochemie) / Fibsol (Sigma) / Fisopril (Sanofi-Aventis) / Hipril (Micro Labs) / Linopril (Klinger (Brazil)) / Lisipril (Hexal (Czech Republic), Orion (Finland)) / Noperten (Dexa (Indonesia)) / Presiten (Magnachem) / Ranolip (Ranbaxy) / Ranopril (Ranbaxy) / Rantex (Biotech) / Sinopren (Ranbaxy) / Sinopril (Eczacibasi (Russia)) / Tensopril (Merck)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act LisinoprilTabletOralActavis Pharma Company2007-10-172018-06-12Canada flag
Act LisinoprilTabletOralActavis Pharma Company2007-10-172018-06-12Canada flag
Act LisinoprilTabletOralActavis Pharma Company2007-10-172018-06-12Canada flag
LisinoprilTablet30 mg/1OralLek Pharmaceuticals2007-03-02Not applicableUS flag
LisinoprilTablet5 mgOralMeliapharm Inc2008-03-122014-06-25Canada flag
LisinoprilTablet5 mg/1OralLek Pharmaceuticals2007-03-02Not applicableUS flag
LisinoprilTablet10 mgOralSivem Pharmaceuticals Ulc2012-06-11Not applicableCanada flag
LisinoprilTablet20 mgOralCobalt LaboratoriesNot applicableNot applicableCanada flag
LisinoprilTablet20 mgOralSorres Pharma Inc2009-06-222014-06-20Canada flag
LisinoprilTablet2.5 mg/1OralWest-ward Pharmaceutical Corp.2008-08-282008-08-28US flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    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
    Available for Purchase

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

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-lisinopril Tablet (type P) - 10mgTabletOralApotex Corporation1996-10-302001-08-02Canada flag
Apo-lisinopril Tablet (type P) - 20mgTabletOralApotex Corporation1996-10-302001-08-02Canada flag
Apo-lisinopril Tablet (type P) - 40mgTabletOralApotex Corporation1996-12-302001-08-02Canada flag
Apo-lisinopril Tablet (type P) - 5mgTabletOralApotex Corporation1996-10-302001-08-02Canada flag
Apo-lisinopril Tablet 10 mgTabletOralApotex Corporation1996-10-30Not applicableCanada flag
Apo-lisinopril Tablet 20 mgTabletOralApotex Corporation1996-10-30Not applicableCanada flag
Apo-lisinopril Tablet 40 mgTabletOralApotex Corporation1996-10-302019-01-21Canada flag
Apo-lisinopril Tablet 5 mgTabletOralApotex Corporation1996-10-30Not applicableCanada flag
Auro-lisinoprilTabletOralAuro Pharma Inc2013-02-12Not applicableCanada flag
Auro-lisinoprilTabletOralAuro Pharma Inc2013-02-12Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    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
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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Apo-lisinopril/hctzLisinopril (10 mg) + Hydrochlorothiazide (12.5 mg)TabletOralApotex Corporation2007-09-05Not applicableCanada flag
Apo-lisinopril/hctzLisinopril (20 mg) + Hydrochlorothiazide (25 mg)TabletOralApotex Corporation2007-11-21Not applicableCanada flag
Apo-lisinopril/hctzLisinopril (20 mg) + Hydrochlorothiazide (12.5 mg)TabletOralApotex Corporation2007-11-21Not applicableCanada flag
Ava-lisinopril HCTLisinopril (20 mg) + Hydrochlorothiazide (25 mg)TabletOralAvanstra Inc2011-08-182014-08-21Canada flag
Ava-lisinopril HCTLisinopril (20 mg) + Hydrochlorothiazide (12.5 mg)TabletOralAvanstra Inc2011-08-182014-08-21Canada flag
Ava-lisinopril HCTLisinopril (10 mg) + Hydrochlorothiazide (12.5 mg)TabletOralAvanstra Inc2011-08-182014-08-21Canada flag
Lisinopril and HCTZLisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralNorthwind Pharmaceuticals2014-07-10Not applicableUS flag68180 0520 02 nlmimage10 16088b04
Lisinopril and HydrochlorothiazideLisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralUnit Dose Services2006-04-102017-12-31US flag50436 890020180907 15195 1gfn0hi
Lisinopril and hydrochlorothiazideLisinopril dihydrate (10 mg/1) + Hydrochlorothiazide (12.5 mg/1)TabletOralPreferred Pharmaceuticals Inc.2017-06-07Not applicableUS flag
Lisinopril and HydrochlorothiazideLisinopril dihydrate (10 mg/1) + Hydrochlorothiazide (12.5 mg/1)TabletOralNcs Health Care Of Ky, Inc Dba Vangard Labs2011-09-13Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
LytensoprilLisinopril dihydrate (20 mg/1) + Arginine (60 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag
Lytensopril-90Lisinopril dihydrate (20 mg/1) + Arginine (90 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag

Categories

ATC Codes
C09BA03 — Lisinopril and diureticsC10BX07 — Rosuvastatin, amlodipine and lisinoprilC09AA03 — LisinoprilC09BB03 — Lisinopril and amlodipine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Proline and derivatives / N-acyl-L-alpha-amino acids / Alpha amino acid amides / L-alpha-amino acids / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Aralkylamines / Benzene and substituted derivatives / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides
show 9 more
Substituents
Alpha-amino acid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
dipeptide (CHEBI:43755)

Chemical Identifiers

UNII
7Q3P4BS2FD
CAS number
76547-98-3
InChI Key
RLAWWYSOJDYHDC-BZSNNMDCSA-N
InChI
InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1
IUPAC Name
(2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
SMILES
NCCCC[[email protected]](N[[email protected]@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[[email protected]]1C(O)=O

References

Synthesis Reference

Vincenzo Cannata, Valeriano Merli, Stefano Saguatti, "Process for the production of alkoxycarbonyldipeptides intermediates in the synthesis of the lisinopril." U.S. Patent US6166217, issued September, 1972.

US6166217
General References
  1. Thomson AH, Kelly JG, Whiting B: Lisinopril population pharmacokinetics in elderly and renal disease patients with hypertension. Br J Clin Pharmacol. 1989 Jan;27(1):57-65. doi: 10.1111/j.1365-2125.1989.tb05335.x. [PubMed:2539850]
  2. Beermann B: Pharmacokinetics of lisinopril. Am J Med. 1988 Sep 23;85(3B):25-30. doi: 10.1016/0002-9343(88)90346-4. [PubMed:2844083]
  3. 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]
  4. Laurent S: Antihypertensive drugs. Pharmacol Res. 2017 Oct;124:116-125. doi: 10.1016/j.phrs.2017.07.026. Epub 2017 Aug 2. [PubMed:28780421]
  5. Te Riet L, van Esch JH, Roks AJ, van den Meiracker AH, Danser AH: Hypertension: renin-angiotensin-aldosterone system alterations. Circ Res. 2015 Mar 13;116(6):960-75. doi: 10.1161/CIRCRESAHA.116.303587. [PubMed:25767283]
  6. 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]
  7. Herman LL, Bashir K: Angiotensin Converting Enzyme Inhibitors (ACEI) . [PubMed:28613705]
  8. FDA Approved Drug Products: Lisinopril Oral Tablet [Link]
  9. FDA Approved Drug Products: Lisinopril Oral Solution [Link]
  10. FDA Approved Drug Products: Lisinopril and Hydrochlorothiazide Oral Tablet [Link]
  11. Cayman Chemicals: Lisinopril MSDS [Link]
Human Metabolome Database
HMDB0001938
KEGG Drug
D00362
PubChem Compound
5362119
PubChem Substance
46504893
ChemSpider
4514933
BindingDB
66979
RxNav
1546022
ChEBI
43755
ChEMBL
CHEMBL1237
ZINC
ZINC000003812863
Therapeutic Targets Database
DAP000587
PharmGKB
PA450242
PDBe Ligand
LPR
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Lisinopril
AHFS Codes
  • 24:32.04 — Angiotensin-converting Enzyme Inhibitors
PDB Entries
1j36 / 1o86 / 2c6n / 2x91
FDA label
Download (267 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentHigh Blood Pressure (Hypertension)1
4CompletedPreventionAtherosclerosis / Cardiovascular Heart Disease / Cerebral Arteriosclerosis / Coronary Heart Disease (CHD) / Diabetes Mellitus / Heart Diseases / High Blood Pressure (Hypertension)1
4CompletedPreventionPerioperative Hypertension1
4CompletedTreatmentCardiovascular Heart Disease / Chronic Kidney Disease (CKD) / Hypertension,Essential / Stroke1
4CompletedTreatmentHeart Failure / Left Ventricular Dysfunction1
4CompletedTreatmentHigh Blood Pressure (Hypertension)5
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Nephropathy, Diabetic1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHypertension,Essential / Secondary Hypertension1
4CompletedTreatmentInduction of intra-operative hypotension1

Pharmacoeconomics

Manufacturers
  • Actavis elizabeth llc
  • Apotex inc etobicoke site
  • Aurobindo pharma ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lek pharmaceuticals d d
  • Lupin ltd
  • Mylan pharmaceuticals inc
  • Ranbaxy pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Vintage pharmaceuticals llc
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Wockhardt ltd
  • Merck research laboratories div merck co inc
  • Astrazeneca uk ltd
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • AstraZeneca Inc.
  • Aurobindo Pharma Ltd.
  • Blu Pharmaceuticals LLC
  • Bryant Ranch Prepack
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Coupler Enterprises Inc.
  • Dept Health Central Pharmacy
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Eon Labs
  • Golden State Medical Supply Inc.
  • Greenstone LLC
  • Group Health Cooperative
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • International Laboratories Inc.
  • IPR Pharmaceuticals Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Lek Pharmaceuticals Inc.
  • Liberty Pharmaceuticals
  • Lupin Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medvantx Inc.
  • Merck & Co.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neighborcare Repackaging Inc.
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • Palmetto Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Professional Co.
  • Promex Medical Inc.
  • Qualitest
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Sandoz
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Stat Scripts LLC
  • Talbert Medical Management Corp.
  • Teva Pharmaceutical Industries Ltd.
  • Torpharm Inc.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • Va Cmop Dallas
  • Vangard Labs Inc.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
  • Wockhardt Ltd.
Dosage Forms
FormRouteStrength
TabletOral12.5 mg
TabletOral25 mg
Tablet, film coatedOral10 mg
Tablet, film coatedOral5 mg
TabletOral
TabletOral10 MG
TabletOral20 MG
TabletOral5 MG
TabletOral10.89 mg
TabletOral2.5 MG
TabletOral21.78 mg
TabletOral10 mg/301
TabletOral10 mg/1
TabletOral2.5 mg/1
TabletOral20 mg/1
TabletOral30 mg/1
TabletOral40 mg/1
TabletOral5 mg/1
TabletOral5.0 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral2.5 mg/1
Tablet, film coatedOral20 mg/1
Tablet, film coatedOral30 mg/1
Tablet, film coatedOral40 mg/1
Tablet, film coatedOral5 mg/1
TabletOral2.72 mg
TabletOral32.67 mg
TabletOral5.44 mg
TabletOral
SolutionOral1 mg/ml
KitOral
SolutionOral1 mg/1mL
TabletOral40 mg
TabletOral30 MG
Prices
Unit descriptionCostUnit
Prinivil 90 20 mg tablet Bottle111.71USD bottle
Prinzide 30 20-12.5 mg tablet Bottle45.99USD bottle
Prinivil 30 2.5 mg tablet Bottle22.48USD bottle
Lisinopril 100% powder21.6USD g
Zestril 40 mg tablet2.53USD tablet
Zestril 30 mg tablet2.41USD tablet
Prinivil 40 mg tablet2.23USD tablet
Zestoretic 20-25 mg tablet2.01USD tablet
Zestoretic 20-12.5 mg tablet2.0USD tablet
Prinzide 20-25 mg tablet1.98USD tablet
Zestoretic 10-12.5 mg tablet1.89USD tablet
Zestoretic 10-12.5 tablet1.75USD tablet
Lisinopril 30 mg tablet1.53USD tablet
Lisinopril 40 mg tablet1.44USD tablet
Prinzide 20-12.5 mg tablet1.38USD tablet
Prinzide 10-12.5 mg tablet1.37USD tablet
Zestril 20 mg tablet1.37USD tablet
Zestril 10 mg tablet1.33USD tablet
Zestoretic 20-25 tablet1.28USD tablet
Zestril 5 mg tablet1.28USD tablet
Zestoretic 20-12.5 tablet1.26USD tablet
Lisinopril 20 mg tablet1.09USD tablet
Prinivil 20 mg tablet1.05USD tablet
Zestril 2.5 mg tablet1.04USD tablet
Lisinopril 10 mg tablet1.01USD tablet
Prinivil 10 mg tablet1.01USD tablet
Lisinopril 5 mg tablet0.99USD tablet
Prinivil 5 mg tablet0.96USD tablet
Apo-Lisinopril 20 mg Tablet0.71USD tablet
Co Lisinopril 20 mg Tablet0.71USD tablet
Mylan-Lisinopril 20 mg Tablet0.71USD tablet
Novo-Lisinopril (Type P) 20 mg Tablet0.71USD tablet
Novo-Lisinopril (Type Z) 20 mg Tablet0.71USD tablet
Pms-Lisinopril 20 mg Tablet0.71USD tablet
Ran-Lisinopril 20 mg Tablet0.71USD tablet
Ratio-Lisinopril P 20 mg Tablet0.71USD tablet
Ratio-Lisinopril Z 20 mg Tablet0.71USD tablet
Sandoz Lisinopril 20 mg Tablet0.71USD tablet
Lisinopril 2.5 mg tablet0.65USD tablet
Apo-Lisinopril 10 mg Tablet0.59USD tablet
Co Lisinopril 10 mg Tablet0.59USD tablet
Mylan-Lisinopril 10 mg Tablet0.59USD tablet
Novo-Lisinopril (Type P) 10 mg Tablet0.59USD tablet
Novo-Lisinopril (Type Z) 10 mg Tablet0.59USD tablet
Pms-Lisinopril 10 mg Tablet0.59USD tablet
Ran-Lisinopril 10 mg Tablet0.59USD tablet
Ratio-Lisinopril P 10 mg Tablet0.59USD tablet
Ratio-Lisinopril Z 10 mg Tablet0.59USD tablet
Sandoz Lisinopril 10 mg Tablet0.59USD tablet
Apo-Lisinopril 5 mg Tablet0.49USD tablet
Co Lisinopril 5 mg Tablet0.49USD tablet
Mylan-Lisinopril 5 mg Tablet0.49USD tablet
Novo-Lisinopril (Type P) 5 mg Tablet0.49USD tablet
Novo-Lisinopril (Type Z) 5 mg Tablet0.49USD tablet
Pms-Lisinopril 5 mg Tablet0.49USD tablet
Ran-Lisinopril 5 mg Tablet0.49USD tablet
Ratio-Lisinopril P 5 mg Tablet0.49USD tablet
Ratio-Lisinopril Z 5 mg Tablet0.49USD tablet
Sandoz Lisinopril 5 mg Tablet0.49USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US9463183No2016-10-112035-11-06US flag
US9616096No2017-04-112035-11-06US flag
US9814751No2017-11-142035-11-06US flag
US10039800No2018-08-072035-11-06US flag
US10265370No2019-04-232035-11-06US flag
US10406199No2019-09-102035-11-06US flag
Additional Data Available
  • Filed On
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    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)148ChemSpider
water solubility9.7E+004 mg/LMERCK INDEX (1996)
logP-1.01MERCK INDEX (1996); pH 7
pKa2.5 (at 25 °C)MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.216 mg/mLALOGPS
logP-1.2ALOGPS
logP-3.1ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.96 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity107.37 m3·mol-1ChemAxon
Polarizability43.5 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6426
Blood Brain Barrier-0.8815
Caco-2 permeable-0.7605
P-glycoprotein substrateSubstrate0.6515
P-glycoprotein inhibitor INon-inhibitor0.9512
P-glycoprotein inhibitor IINon-inhibitor0.969
Renal organic cation transporterNon-inhibitor0.8574
CYP450 2C9 substrateNon-substrate0.8793
CYP450 2D6 substrateNon-substrate0.7622
CYP450 3A4 substrateNon-substrate0.725
CYP450 1A2 substrateNon-inhibitor0.8999
CYP450 2C9 inhibitorNon-inhibitor0.9708
CYP450 2D6 inhibitorNon-inhibitor0.9653
CYP450 2C19 inhibitorNon-inhibitor0.8266
CYP450 3A4 inhibitorNon-inhibitor0.907
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9821
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9389
BiodegradationNot ready biodegradable0.6844
Rat acute toxicity1.8723 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9641
hERG inhibition (predictor II)Non-inhibitor0.8708
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0a4r-0194100000-d9a47a283478b88bb101
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-001i-9040000000-8d6d4ae6ba18da11e336
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-001i-9000000000-77e20f7eb799eea58ab0
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
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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. Andujar-Sanchez M, Jara-Perez V, Camara-Artigas A: Thermodynamic determination of the binding constants of angiotensin-converting enzyme inhibitors by a displacement method. FEBS Lett. 2007 Jul 24;581(18):3449-54. Epub 2007 Jun 27. [PubMed:17618628]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  3. Piepho RW: Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm. 2000 Oct 1;57 Suppl 1:S3-7. [PubMed:11030016]
  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]
  5. Tellez-Sanz R, Garcia-Fuentes L, Baron C: Calorimetric analysis of lisinopril binding to angiotensin I-converting enzyme. FEBS Lett. 1998 Feb 13;423(1):75-80. [PubMed:9506845]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Receptor binding
Specific Function
Renin is a highly specific endopeptidase, whose only known function is to generate angiotensin I from angiotensinogen in the plasma, initiating a cascade of reactions that produce an elevation of b...
Gene Name
REN
Uniprot ID
P00797
Uniprot Name
Renin
Molecular Weight
45057.125 Da
References
  1. Te Riet L, van Esch JH, Roks AJ, van den Meiracker AH, Danser AH: Hypertension: renin-angiotensin-aldosterone system alterations. Circ Res. 2015 Mar 13;116(6):960-75. doi: 10.1161/CIRCRESAHA.116.303587. [PubMed:25767283]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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]
  2. Ma K, Hu Y, Smith DE: Peptide transporter 1 is responsible for intestinal uptake of the dipeptide glycylsarcosine: studies in everted jejunal rings from wild-type and Pept1 null mice. J Pharm Sci. 2011 Feb;100(2):767-74. doi: 10.1002/jps.22277. Epub 2010 Sep 22. [PubMed:20862774]
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]

Drug created on June 13, 2005 07:24 / Updated on November 25, 2020 08:53

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