Identification

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Name
Lisinopril
Accession Number
DB00722  (APRD00560)
Type
Small Molecule
Groups
Approved, Investigational
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

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Lisinopril dihydrateE7199S1YWR83915-83-7CZRQXSDBMCMPNJ-ZUIPZQNBSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act LisinoprilTabletOralActavis Pharma Company2007-10-172018-06-12Canada
Act LisinoprilTabletOralActavis Pharma Company2007-10-172018-06-12Canada
Act LisinoprilTabletOralActavis Pharma Company2007-10-172018-06-12Canada
LisinoprilTablet10 mg/1OralLek Pharmaceuticals2007-03-02Not applicableUs
LisinoprilTablet30 mg/1OralWest-ward Pharmaceutical Corp.2008-08-282008-08-28Us
LisinoprilTablet20 mgOralSorres Pharma Inc2009-06-222014-06-20Canada
LisinoprilTablet5 mgOralMeliapharm Inc2008-03-122014-06-25Canada
LisinoprilTablet5 mg/1OralLek Pharmaceuticals2007-03-02Not applicableUs
LisinoprilTablet40 mgOralSivem Pharmaceuticals UlcNot applicableNot applicableCanada
LisinoprilTablet2.5 mg/1OralWest-ward Pharmaceutical Corp.2008-08-282008-08-28Us
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-lisinopril Tablet (type P) - 10mgTabletOralApotex Corporation1996-10-302001-08-02Canada
Apo-lisinopril Tablet (type P) - 20mgTabletOralApotex Corporation1996-10-302001-08-02Canada
Apo-lisinopril Tablet (type P) - 40mgTabletOralApotex Corporation1996-12-302001-08-02Canada
Apo-lisinopril Tablet (type P) - 5mgTabletOralApotex Corporation1996-10-302001-08-02Canada
Apo-lisinopril Tablet 10 mgTabletOralApotex Corporation1996-10-30Not applicableCanada
Apo-lisinopril Tablet 20 mgTabletOralApotex Corporation1996-10-30Not applicableCanada
Apo-lisinopril Tablet 40 mgTabletOralApotex Corporation1996-10-302019-01-21Canada
Apo-lisinopril Tablet 5 mgTabletOralApotex Corporation1996-10-30Not applicableCanada
Auro-lisinoprilTabletOralAuro Pharma Inc2013-02-12Not applicableCanada
Auro-lisinoprilTabletOralAuro Pharma Inc2013-02-12Not 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.

    Learn more
  • 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
Apo-lisinopril/hctzLisinopril (10 mg) + Hydrochlorothiazide (12.5 mg)TabletOralApotex Corporation2007-09-05Not applicableCanada
Apo-lisinopril/hctzLisinopril (20 mg) + Hydrochlorothiazide (25 mg)TabletOralApotex Corporation2007-11-21Not applicableCanada
Apo-lisinopril/hctzLisinopril (20 mg) + Hydrochlorothiazide (12.5 mg)TabletOralApotex Corporation2007-11-21Not applicableCanada
Ava-lisinopril HCTLisinopril (20 mg) + Hydrochlorothiazide (25 mg)TabletOralAvanstra Inc2011-08-182014-08-21Canada
Ava-lisinopril HCTLisinopril (20 mg) + Hydrochlorothiazide (12.5 mg)TabletOralAvanstra Inc2011-08-182014-08-21Canada
Ava-lisinopril HCTLisinopril (10 mg) + Hydrochlorothiazide (12.5 mg)TabletOralAvanstra Inc2011-08-182014-08-21Canada
Lisinopril and HCTZLisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralNorthwind Pharmaceuticals2014-07-10Not applicableUs68180 0520 02 nlmimage10 16088b04
Lisinopril and HydrochlorothiazideLisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralLake Erie Medical Dba Quality Care Produts Llc2010-08-11Not applicableUs
Lisinopril and HydrochlorothiazideLisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (12.5 mg/1)TabletOralNcs Health Care Of Ky, Inc Dba Vangard Labs2011-09-13Not applicableUs00172 5034 60 nlmimage10 052d0288
Lisinopril and HydrochlorothiazideLisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralUDL Laboratories, Inc.2010-06-072014-07-31Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
LytensoprilLisinopril dihydrate (20 mg/1) + Arginine (60 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUs
Lytensopril-90Lisinopril dihydrate (20 mg/1) + Arginine (90 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUs
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)
Categories
UNII
7Q3P4BS2FD
CAS number
76547-98-3
Weight
Average: 405.4879
Monoisotopic: 405.226371117
Chemical Formula
C21H31N3O5
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[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@H]1C(O)=O

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
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
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

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

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
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Lisinopril.
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Lisinopril.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Lisinopril.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the antihypertensive activities of Lisinopril.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Lisinopril.
4-Methoxyamphetamine4-Methoxyamphetamine may decrease the antihypertensive activities of Lisinopril.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Lisinopril.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Lisinopril.
AbacavirLisinopril may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbediterolAbediterol may decrease the antihypertensive activities of Lisinopril.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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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

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

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Herbs that may attenuate the antihypertensive effect of lisinopril include: bayberry, blue cohash, cayenne, ephedra, ginger, ginseng (American), kola and licorice.
  • High salt intake may attenuate the antihypertensive effect of lisinopril.
  • Lisinopril decreases the excretion of potassium. Salt substitutes containing potassium increase the risk of hyperkalemia.
  • Take without regard to meals.

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]
External Links
Human Metabolome Database
HMDB0001938
KEGG Drug
D00362
PubChem Compound
5362119
PubChem Substance
46504893
ChemSpider
4514933
BindingDB
50367879
ChEBI
43755
ChEMBL
CHEMBL1237
Therapeutic Targets Database
DAP000587
PharmGKB
PA450242
HET
LPR
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Lisinopril
ATC Codes
C09BA03 — Lisinopril and diureticsC10BX07 — Rosuvastatin, amlodipine and lisinoprilC09AA03 — LisinoprilC09BB03 — Lisinopril and amlodipine
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
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableTo Determine Bioequivalence Under Fed Conditions1
1CompletedNot AvailableType 2 Diabetes Mellitus1
1CompletedBasic ScienceGastroparesis1
1CompletedOtherHealthy Volunteers1
1CompletedPreventionHigh Blood Pressure (Hypertension)1
1CompletedTreatmentDiabetes Mellitus (DM) / Healthy Volunteers2
1CompletedTreatmentFasting2
1CompletedTreatmentFed2
1CompletedTreatmentHigh Blood Pressure (Hypertension)6
1CompletedTreatmentStroke1
1CompletedTreatmentType 2 Diabetes Mellitus1
1Not Yet RecruitingOtherHealthy Volunteers1
1RecruitingTreatmentHypertension, Resistant to Conventional Therapy1
1, 2CompletedTreatmentPre-Hypertension1
2Active Not RecruitingSupportive CareDyspnea / Lung Cancer Non-Small Cell Cancer (NSCLC) / Lung Cancer Small Cell Lung Cancer (SCLC)1
2CompletedSupportive CareBreast Cancer / Cardiac Toxicity1
2CompletedTreatmentAging / Cognitive Impairments / High Blood Pressure (Hypertension)1
2CompletedTreatmentGlomerulosclerosis, Focal Segmental1
2CompletedTreatmentHypertension,Essential1
2CompletedTreatmentOligozoospermia1
2Not Yet RecruitingPreventionPacemakers, Heart Failure1
2Not Yet RecruitingTreatmentAlbuminuria / Genetic Predisposition / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Kidney Diseases1
2RecruitingTreatmentAcute Coronary Syndromes (ACS) / Arterial Hypertension1
2RecruitingTreatmentExtracapillary Glomerulonephritis1
2TerminatedTreatmentHigh Blood Pressure (Hypertension) / Unspecified Adult Solid Tumor, Protocol Specific1
2, 3CompletedTreatmentBecker's Muscular Dystrophy (BMD) / Duchenne's Muscular Dystrophy (DMD) / Limb Girdle Muscular Dystrophy1
3CompletedPreventionAtherosclerosis / Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / High Blood Pressure (Hypertension) / High Cholesterol / Type 2 Diabetes Mellitus1
3CompletedPreventionCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / Heart Diseases / Heart Failure / High Blood Pressure (Hypertension) / High Cholesterol / Myocardial Infarction / Myocardial Ischemia1
3CompletedPreventionDiabetic Nephropathies1
3CompletedPreventionHigh Blood Pressure (Hypertension) / Mild Cognitive Impairment (MCI)1
3CompletedTreatmentHeart Failure1
3CompletedTreatmentHigh Blood Pressure (Hypertension)3
3CompletedTreatmentHigh Blood Pressure (Hypertension) / Obesity, Abdominal1
3CompletedTreatmentKidney, Polycystic2
3CompletedTreatmentLeft Ventricular Hypertrophy1
3TerminatedTreatmentHeart Failure, Congestive and Microalbuminuria / High Blood Pressure (Hypertension) / Microalbuminuria1
3TerminatedTreatmentHemodialysis Treatment / High Blood Pressure (Hypertension) / Left Ventricular Hypertrophy1
3TerminatedTreatmentKidney Diseases / Renal Dysfunction / Type 2 Diabetes Mellitus1
3Unknown StatusTreatmentCardiovascular Disease (CVD)1
3WithdrawnPreventionHyperoxaluria1
4CompletedPreventionPerioperative Hypertension1
4CompletedTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Hypertension,Essential / Stroke1
4CompletedTreatmentDiabetic Nephropathies1
4CompletedTreatmentDiabetic Nephropathies / High Blood Pressure (Hypertension)1
4CompletedTreatmentHeart Failure / Ventricular Dysfunction, Left1
4CompletedTreatmentHigh Blood Pressure (Hypertension)4
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Induction of intra-operative hypotension1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
4CompletedTreatmentHypertension,Essential / Secondary Hypertension1
4CompletedTreatmentStage 2 Diastolic Hypertension1
4Not Yet RecruitingPreventionCardiomyopathy Due to Drug / Heart Failure, Systolic1
4Not Yet RecruitingTreatmentHigh Blood Pressure (Hypertension)1
4RecruitingTreatmentCoronary Artery Disease1
4RecruitingTreatmentHeart Diseases / Type 2 Diabetes Mellitus1
4RecruitingTreatmentHigh Blood Pressure (Hypertension)1
4RecruitingTreatmentPediatric Hypertension1
4RecruitingTreatmentProteinuria / Renal Insufficiency,Chronic1
4TerminatedPreventionCardiovascular Disease (CVD) / Osteoarthritis (OA)1
4TerminatedPreventionNeurological Dysphagia / Pneumonia1
4TerminatedTreatmentEarly Diabetic Nephropathy / High Blood Pressure (Hypertension)1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableAnesthesia; Adverse Effect / Delirium1
Not AvailableCompletedNot AvailableCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / High Blood Pressure (Hypertension) / Myocardial Infarction1
Not AvailableCompletedNot AvailableDiabetes Complications / Eye Diseases / Retinopathy, Diabetic / Type 1 Insulin-Dependent Diabetes Mellitus1
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension)1
Not AvailableCompletedDiagnosticArterial Hypertension1
Not AvailableCompletedOtherHyperparathyroidism1
Not AvailableCompletedPreventionAtherosclerosis / Cardiovascular Disease (CVD) / Cerebral Arteriosclerosis / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / Heart Diseases / High Blood Pressure (Hypertension)1
Not AvailableCompletedPreventionBMI >30 kg/m2 / Type 2 Diabetes Mellitus1
Not AvailableCompletedPreventionCardiovascular Disease Risk / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedPreventionDiabetic Nephropathies / Type 1 Insulin-Dependent Diabetes Mellitus1
Not AvailableCompletedTreatmentAtrial Fibrillation (AF) / Chronic Heart Failure (CHF)1
Not AvailableCompletedTreatmentCardiovascular Disease (CVD) / Cerebrovascular Diseases / Peripheral Arterial Disease (PAD)1
Not AvailableCompletedTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD)1
Not AvailableCompletedTreatmentDuchenne's Muscular Dystrophy (DMD) / Prophylaxis of cardiomyopathy1
Not AvailableCompletedTreatmentHealthy Volunteers1
Not AvailableCompletedTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableCompletedTreatmentHigh Blood Pressure (Hypertension) / Hypertension Treatment / Hypertension, Grade 1 / N of 1 Study Design1
Not AvailableCompletedTreatmentHigh Blood Pressure (Hypertension) / Plasma Renin Activity1
Not AvailableCompletedTreatmentHypertension,Essential1
Not AvailableTerminatedPreventionChest Pain1
Not AvailableTerminatedTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableTerminatedTreatmentType 2 Diabetes Mellitus1
Not AvailableWithdrawnTreatmentDiastolic Heart Failure1
Not AvailableWithdrawnTreatmentHigh Blood Pressure (Hypertension)1

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
TabletOral
TabletOral10 mg/1
TabletOral10 mg/301
TabletOral2.5 mg/1
TabletOral20 mg/1
TabletOral30 mg/1
TabletOral40 mg
TabletOral40 mg/1
TabletOral5 mg
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
TabletOral
KitOral
TabletOral10 mg
TabletOral2.5 mg
TabletOral20 mg
SolutionOral1 mg/1mL
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
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Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US9463183No2016-10-112035-11-06Us
US9616096No2017-04-112035-11-06Us
US9814751No2017-11-142035-11-06Us
US10039800No2018-08-072035-11-06Us
US10265370No2015-11-062035-11-06Us
Additional Data Available
  • Filed On
    Filed On

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

    Learn more

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

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
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-dipeptide / N-acyl-alpha-amino acid / Proline or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-l-alpha-amino acid / Alpha-amino acid amide / Alpha-amino acid / Alpha-amino acid or derivatives / L-alpha-amino acid / N-acylpyrrolidine
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
dipeptide (CHEBI:43755)

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 16, 2019 10:27