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

Similar Structures

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

Ingredient	UNII	CAS	InChI Key
Lisinopril dihydrate	E7199S1YWR	83915-83-7	CZRQXSDBMCMPNJ-ZUIPZQNBSA-N

Product Images

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Act Lisinopril	Tablet		Oral	Actavis Pharma Company	2007-10-17	2018-06-12
Act Lisinopril	Tablet		Oral	Actavis Pharma Company	2007-10-17	2018-06-12
Act Lisinopril	Tablet		Oral	Actavis Pharma Company	2007-10-17	2018-06-12
Lisinopril	Tablet	30 mg/1	Oral	Lek Pharmaceuticals	2007-03-02	Not applicable
Lisinopril	Tablet	20 mg	Oral	Meliapharm Inc	2008-03-12	2014-06-25
Lisinopril	Tablet	10 mg	Oral	Sivem Pharmaceuticals Ulc	2012-06-11	Not applicable
Lisinopril	Tablet	10 mg	Oral	Cobalt Laboratories	Not applicable	Not applicable
Lisinopril	Tablet	20 mg/1	Oral	Lek Pharmaceuticals	2007-03-02	Not applicable
Lisinopril	Tablet	10 mg	Oral	Meliapharm Inc	2008-03-12	2014-06-25
Lisinopril	Tablet	5 mg	Oral	Sivem Pharmaceuticals Ulc	2012-06-11	Not applicable

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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

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

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Generic Prescription Products

Name	Dosage	Route	Labeller	Marketing Start	Marketing End
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Apo-lisinopril Tablet (type P) - 10mg	Tablet	Oral	Apotex Corporation	1996-10-30	2001-08-02
Apo-lisinopril Tablet (type P) - 20mg	Tablet	Oral	Apotex Corporation	1996-10-30	2001-08-02
Apo-lisinopril Tablet (type P) - 40mg	Tablet	Oral	Apotex Corporation	1996-12-30	2001-08-02
Apo-lisinopril Tablet (type P) - 5mg	Tablet	Oral	Apotex Corporation	1996-10-30	2001-08-02
Apo-lisinopril Tablet 10 mg	Tablet	Oral	Apotex Corporation	1996-10-30	Not applicable
Apo-lisinopril Tablet 20 mg	Tablet	Oral	Apotex Corporation	1996-10-30	Not applicable
Apo-lisinopril Tablet 40 mg	Tablet	Oral	Apotex Corporation	1996-10-30	2019-01-21
Apo-lisinopril Tablet 5 mg	Tablet	Oral	Apotex Corporation	1996-10-30	Not applicable
Auro-lisinopril	Tablet	Oral	Auro Pharma Inc	2013-02-12	Not applicable
Auro-lisinopril	Tablet	Oral	Auro Pharma Inc	2013-02-12	Not applicable

Additional Data Available

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

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

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Apo-lisinopril/hctz	Lisinopril (20 mg) + Hydrochlorothiazide (25 mg)	Tablet	Oral	Apotex Corporation	2007-11-21	Not applicable
Apo-lisinopril/hctz	Lisinopril (20 mg) + Hydrochlorothiazide (12.5 mg)	Tablet	Oral	Apotex Corporation	2007-11-21	Not applicable
Apo-lisinopril/hctz	Lisinopril (10 mg) + Hydrochlorothiazide (12.5 mg)	Tablet	Oral	Apotex Corporation	2007-09-05	Not applicable
Ava-lisinopril HCT	Lisinopril (20 mg) + Hydrochlorothiazide (12.5 mg)	Tablet	Oral	Avanstra Inc	2011-08-18	2014-08-21
Ava-lisinopril HCT	Lisinopril (10 mg) + Hydrochlorothiazide (12.5 mg)	Tablet	Oral	Avanstra Inc	2011-08-18	2014-08-21
Ava-lisinopril HCT	Lisinopril (20 mg) + Hydrochlorothiazide (25 mg)	Tablet	Oral	Avanstra Inc	2011-08-18	2014-08-21
Lisinopril and HCTZ	Lisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (25 mg/1)	Tablet	Oral	Northwind Pharmaceuticals	2014-07-10	Not applicable
Lisinopril and Hydrochlorothiazide	Lisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (12.5 mg/1)	Tablet	Oral	Solco Healthcare Llc	2015-03-12	Not applicable
Lisinopril and Hydrochlorothiazide	Lisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (25 mg/1)	Tablet	Oral	Actavis Pharma, Inc.	2003-03-04	Not applicable
Lisinopril and Hydrochlorothiazide	Lisinopril dihydrate (10 mg/1) + Hydrochlorothiazide (12.5 mg/1)	Tablet	Oral	Denton Pharma, Inc. Dba Northwind Pharmaceuticals	2019-01-21	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Lytensopril	Lisinopril dihydrate (20 mg/1) + Arginine (60 mg/1)	Kit	Oral	Physician Therapeutics Llc	2011-07-07	Not applicable
Lytensopril-90	Lisinopril dihydrate (20 mg/1) + Arginine (90 mg/1)	Kit	Oral	Physician Therapeutics Llc	2011-07-07	Not applicable

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

Target	Actions	Organism
AAngiotensin-converting enzyme	inhibitor	Humans
URenin	inhibitor	Humans

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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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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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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 C_max of 58ng/mL with a T_max 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 12.6h^2,8,9,10 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

Pathway	Category
Lisinopril Action Pathway	Drug 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.

Drug	Interaction
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1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid	1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Lisinopril.
1-benzylimidazole	1-benzylimidazole may decrease the antihypertensive activities of Lisinopril.
2,5-Dimethoxy-4-ethylamphetamine	2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Lisinopril.
2,5-Dimethoxy-4-ethylthioamphetamine	2,5-Dimethoxy-4-ethylthioamphetamine may decrease the antihypertensive activities of Lisinopril.
4-Bromo-2,5-dimethoxyamphetamine	4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Lisinopril.
4-Methoxyamphetamine	4-Methoxyamphetamine may decrease the antihypertensive activities of Lisinopril.
5-methoxy-N,N-dimethyltryptamine	5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Lisinopril.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Lisinopril.
Abacavir	Lisinopril may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abediterol	Abediterol may decrease the antihypertensive activities of Lisinopril.

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Extended Description

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

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Severity

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

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Evidence Level

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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

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]
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]
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]
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]
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]
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]
Herman LL, Bashir K: Angiotensin Converting Enzyme Inhibitors (ACEI) . [PubMed:28613705]
FDA Approved Drug Products: Lisinopril Oral Tablet [Link]
FDA Approved Drug Products: Lisinopril Oral Solution [Link]
FDA Approved Drug Products: Lisinopril and Hydrochlorothiazide Oral Tablet [Link]
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 diuretics

C10BX07 — Rosuvastatin, amlodipine and lisinopril

C09AA03 — Lisinopril

C09BB03 — 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

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Healthy Volunteers	1
1	Completed	Not Available	To Determine Bioequivalence Under Fed Conditions	1
1	Completed	Not Available	Type 2 Diabetes Mellitus	1
1	Completed	Basic Science	Gastroparesis	1
1	Completed	Other	Healthy Volunteers	1
1	Completed	Prevention	High Blood Pressure (Hypertension)	1
1	Completed	Treatment	Diabetes / Healthy Volunteers	2
1	Completed	Treatment	Fasting	2
1	Completed	Treatment	Fed	2
1	Completed	Treatment	High Blood Pressure (Hypertension)	6
1	Completed	Treatment	Stroke	1
1	Completed	Treatment	Type 2 Diabetes Mellitus	1
1	Not Yet Recruiting	Other	Healthy Volunteers	1
1	Recruiting	Treatment	Hypertension, Resistant to Conventional Therapy	1
1, 2	Completed	Treatment	Pre-Hypertension	1
2	Completed	Prevention	High Blood Pressure (Hypertension) / Mild Cognitive Impairment (MCI)	1
2	Completed	Supportive Care	Breast Cancer / Cardiac Toxicity	1
2	Completed	Supportive Care	Dyspnea / Lung Cancer Non-Small Cell Cancer (NSCLC) / Lung Cancer Small Cell Lung Cancer (SCLC)	1
2	Completed	Treatment	Aging / Cognitive Impairments / High Blood Pressure (Hypertension)	1
2	Completed	Treatment	Glomerulosclerosis, Focal Segmental	1
2	Completed	Treatment	Hypertension,Essential	1
2	Completed	Treatment	Oligozoospermia	1
2	Not Yet Recruiting	Prevention	Pacemakers, Heart Failure	1
2	Not Yet Recruiting	Treatment	Albuminuria / Genetic Predisposition / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Kidney Diseases	1
2	Not Yet Recruiting	Treatment	Malignant Lymphomas	1
2	Recruiting	Treatment	Acute Coronary Syndromes (ACS) / Arterial Hypertension	1
2	Recruiting	Treatment	Extracapillary Glomerulonephritis	1
2	Terminated	Treatment	High Blood Pressure (Hypertension) / Unspecified Adult Solid Tumor, Protocol Specific	1
2, 3	Completed	Treatment	Becker's Muscular Dystrophy (BMD) / Duchenne's Muscular Dystrophy (DMD) / Limb Girdle Muscular Dystrophy	1
3	Completed	Prevention	Atherosclerosis / Cardiovascular Heart Disease / Coronary Heart Disease (CHD) / Diabetes Mellitus / High Blood Pressure (Hypertension) / High Cholesterol / Type 2 Diabetes Mellitus	1
3	Completed	Prevention	Cardiovascular Heart Disease / Coronary Heart Disease (CHD) / Diabetes Mellitus / Heart Diseases / Heart Failure / High Blood Pressure (Hypertension) / High Cholesterol / Myocardial Infarction / Myocardial Ischemia	1
3	Completed	Prevention	Diabetic Nephropathies	1
3	Completed	Treatment	Heart Failure	1
3	Completed	Treatment	High Blood Pressure (Hypertension)	3
3	Completed	Treatment	High Blood Pressure (Hypertension) / Obesity, Abdominal	1
3	Completed	Treatment	Kidney, Polycystic	2
3	Completed	Treatment	Left Ventricular Hypertrophy	1
3	Terminated	Treatment	Heart Failure, Congestive and Microalbuminuria / High Blood Pressure (Hypertension) / Microalbuminuria	1
3	Terminated	Treatment	Hemodialysis Treatment / High Blood Pressure (Hypertension) / Left Ventricular Hypertrophy	1
3	Terminated	Treatment	Kidney Diseases / Renal Dysfunction / Type 2 Diabetes Mellitus	1
3	Unknown Status	Treatment	Cardiovascular Heart Disease	1
3	Withdrawn	Prevention	Hyperoxaluria	1
4	Completed	Prevention	Perioperative Hypertension	1
4	Completed	Treatment	Cardiovascular Heart Disease / Chronic Kidney Disease (CKD) / Hypertension,Essential / Stroke	1
4	Completed	Treatment	Diabetic Nephropathies	1
4	Completed	Treatment	Diabetic Nephropathies / High Blood Pressure (Hypertension)	1
4	Completed	Treatment	Heart Failure / Left Ventricular Dysfunction	1
4	Completed	Treatment	High Blood Pressure (Hypertension)	4
4	Completed	Treatment	High Blood Pressure (Hypertension) / Induction of intra-operative hypotension	1
4	Completed	Treatment	Human Immunodeficiency Virus (HIV)	1
4	Completed	Treatment	Hypertension,Essential / Secondary Hypertension	1
4	Completed	Treatment	Stage 2 Diastolic Hypertension	1
4	Not Yet Recruiting	Prevention	Cardiomyopathy Due to Drug / Heart Failure, Systolic	1
4	Not Yet Recruiting	Treatment	High Blood Pressure (Hypertension)	1
4	Recruiting	Treatment	Coronary Artery Disease	1
4	Recruiting	Treatment	Heart Diseases / Type 2 Diabetes Mellitus	1
4	Recruiting	Treatment	High Blood Pressure (Hypertension)	1
4	Recruiting	Treatment	Pediatric Hypertension	1
4	Recruiting	Treatment	Proteinuria / Renal Insufficiency,Chronic	1
4	Terminated	Prevention	Cardiovascular Heart Disease / Osteoarthritis (OA)	1
4	Terminated	Prevention	Neurological Dysphagia / Pneumonia	1
4	Terminated	Treatment	Early Diabetic Nephropathy / High Blood Pressure (Hypertension)	1
4	Unknown Status	Treatment	High Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus	1
Not Available	Completed	Not Available	Anesthesia; Adverse Effect / Delirium	1
Not Available	Completed	Not Available	Cardiovascular Heart Disease / Coronary Heart Disease (CHD) / Heart Diseases / High Blood Pressure (Hypertension) / Myocardial Infarction	1
Not Available	Completed	Not Available	Diabetes Complications / Eye Diseases / Retinopathy, Diabetic / Type 1 Diabetes Mellitus	1
Not Available	Completed	Not Available	High Blood Pressure (Hypertension)	1
Not Available	Completed	Diagnostic	Arterial Hypertension	1
Not Available	Completed	Other	Hyperparathyroidism	1
Not Available	Completed	Prevention	Atherosclerosis / Cardiovascular Heart Disease / Cerebral Arteriosclerosis / Coronary Heart Disease (CHD) / Diabetes Mellitus / Heart Diseases / High Blood Pressure (Hypertension)	1
Not Available	Completed	Prevention	BMI >30 kg/m2 / Type 2 Diabetes Mellitus	1
Not Available	Completed	Prevention	Cardiovascular Risk / Human Immunodeficiency Virus (HIV) Infections	1
Not Available	Completed	Prevention	Diabetic Nephropathies / Type 1 Diabetes Mellitus	1
Not Available	Completed	Treatment	Atrial Fibrillation (AF) / Chronic Heart Failure (CHF)	1
Not Available	Completed	Treatment	Cardiomyopathy / Duchenne's Muscular Dystrophy (DMD)	1
Not Available	Completed	Treatment	Cardiovascular Heart Disease / Cerebrovascular Diseases / Peripheral Arterial Disease (PAD)	1
Not Available	Completed	Treatment	Cardiovascular Heart Disease / Chronic Kidney Disease (CKD)	1
Not Available	Completed	Treatment	Healthy Volunteers	1
Not Available	Completed	Treatment	High Blood Pressure (Hypertension)	1
Not Available	Completed	Treatment	High Blood Pressure (Hypertension) / Hypertension Treatment / Hypertension, Grade 1 / N of 1 Study Design	1
Not Available	Completed	Treatment	High Blood Pressure (Hypertension) / Plasma Renin Activity	1
Not Available	Completed	Treatment	Hypertension,Essential	1
Not Available	Terminated	Prevention	Chest Pain	1
Not Available	Terminated	Treatment	High Blood Pressure (Hypertension)	1
Not Available	Terminated	Treatment	Type 2 Diabetes Mellitus	1
Not Available	Withdrawn	Treatment	Diastolic Heart Failure	1
Not Available	Withdrawn	Treatment	High 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

Form	Route	Strength
Tablet	Oral
Tablet	Oral	10 mg/1
Tablet	Oral	10 mg/301
Tablet	Oral	2.5 mg/1
Tablet	Oral	20 mg/1
Tablet	Oral	30 mg/1
Tablet	Oral	40 mg
Tablet	Oral	40 mg/1
Tablet	Oral	5 mg
Tablet	Oral	5 mg/1
Tablet	Oral	5.0 mg/1
Tablet, film coated	Oral	10 mg/1
Tablet, film coated	Oral	2.5 mg/1
Tablet, film coated	Oral	20 mg/1
Tablet, film coated	Oral	30 mg/1
Tablet, film coated	Oral	40 mg/1
Tablet, film coated	Oral	5 mg/1
Tablet	Oral
Kit	Oral
Tablet	Oral	10 mg
Tablet	Oral	2.5 mg
Tablet	Oral	20 mg
Solution	Oral	1 mg/1mL

Prices

Unit description	Cost	Unit
Prinivil 90 20 mg tablet Bottle	111.71USD	bottle
Prinzide 30 20-12.5 mg tablet Bottle	45.99USD	bottle
Prinivil 30 2.5 mg tablet Bottle	22.48USD	bottle
Lisinopril 100% powder	21.6USD	g
Zestril 40 mg tablet	2.53USD	tablet
Zestril 30 mg tablet	2.41USD	tablet
Prinivil 40 mg tablet	2.23USD	tablet
Zestoretic 20-25 mg tablet	2.01USD	tablet
Zestoretic 20-12.5 mg tablet	2.0USD	tablet
Prinzide 20-25 mg tablet	1.98USD	tablet
Zestoretic 10-12.5 mg tablet	1.89USD	tablet
Zestoretic 10-12.5 tablet	1.75USD	tablet
Lisinopril 30 mg tablet	1.53USD	tablet
Lisinopril 40 mg tablet	1.44USD	tablet
Prinzide 20-12.5 mg tablet	1.38USD	tablet
Prinzide 10-12.5 mg tablet	1.37USD	tablet
Zestril 20 mg tablet	1.37USD	tablet
Zestril 10 mg tablet	1.33USD	tablet
Zestoretic 20-25 tablet	1.28USD	tablet
Zestril 5 mg tablet	1.28USD	tablet
Zestoretic 20-12.5 tablet	1.26USD	tablet
Lisinopril 20 mg tablet	1.09USD	tablet
Prinivil 20 mg tablet	1.05USD	tablet
Zestril 2.5 mg tablet	1.04USD	tablet
Lisinopril 10 mg tablet	1.01USD	tablet
Prinivil 10 mg tablet	1.01USD	tablet
Lisinopril 5 mg tablet	0.99USD	tablet
Prinivil 5 mg tablet	0.96USD	tablet
Apo-Lisinopril 20 mg Tablet	0.71USD	tablet
Co Lisinopril 20 mg Tablet	0.71USD	tablet
Mylan-Lisinopril 20 mg Tablet	0.71USD	tablet
Novo-Lisinopril (Type P) 20 mg Tablet	0.71USD	tablet
Novo-Lisinopril (Type Z) 20 mg Tablet	0.71USD	tablet
Pms-Lisinopril 20 mg Tablet	0.71USD	tablet
Ran-Lisinopril 20 mg Tablet	0.71USD	tablet
Ratio-Lisinopril P 20 mg Tablet	0.71USD	tablet
Ratio-Lisinopril Z 20 mg Tablet	0.71USD	tablet
Sandoz Lisinopril 20 mg Tablet	0.71USD	tablet
Lisinopril 2.5 mg tablet	0.65USD	tablet
Apo-Lisinopril 10 mg Tablet	0.59USD	tablet
Co Lisinopril 10 mg Tablet	0.59USD	tablet
Mylan-Lisinopril 10 mg Tablet	0.59USD	tablet
Novo-Lisinopril (Type P) 10 mg Tablet	0.59USD	tablet
Novo-Lisinopril (Type Z) 10 mg Tablet	0.59USD	tablet
Pms-Lisinopril 10 mg Tablet	0.59USD	tablet
Ran-Lisinopril 10 mg Tablet	0.59USD	tablet
Ratio-Lisinopril P 10 mg Tablet	0.59USD	tablet
Ratio-Lisinopril Z 10 mg Tablet	0.59USD	tablet
Sandoz Lisinopril 10 mg Tablet	0.59USD	tablet
Apo-Lisinopril 5 mg Tablet	0.49USD	tablet
Co Lisinopril 5 mg Tablet	0.49USD	tablet
Mylan-Lisinopril 5 mg Tablet	0.49USD	tablet
Novo-Lisinopril (Type P) 5 mg Tablet	0.49USD	tablet
Novo-Lisinopril (Type Z) 5 mg Tablet	0.49USD	tablet
Pms-Lisinopril 5 mg Tablet	0.49USD	tablet
Ran-Lisinopril 5 mg Tablet	0.49USD	tablet
Ratio-Lisinopril P 5 mg Tablet	0.49USD	tablet
Ratio-Lisinopril Z 5 mg Tablet	0.49USD	tablet
Sandoz Lisinopril 5 mg Tablet	0.49USD	tablet

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Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
Unlock Additional Data
US9463183	No	2016-10-11	2035-11-06
US9616096	No	2017-04-11	2035-11-06
US9814751	No	2017-11-14	2035-11-06
US10039800	No	2018-08-07	2035-11-06
US10265370	No	2019-04-23	2035-11-06
US10406199	No	2015-11-06	2035-11-06

Additional Data Available

Filed On

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

Learn more

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	148	ChemSpider
water solubility	9.7E+004 mg/L	MERCK INDEX (1996)
logP	-1.01	MERCK INDEX (1996); pH 7
pKa	2.5 (at 25 °C)	MERCK INDEX (1996)

Predicted Properties

Property	Value	Source
Water Solubility	0.216 mg/mL	ALOGPS
logP	-1.2	ALOGPS
logP	-3.1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.96 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	107.37 m³·mol^-1	ChemAxon
Polarizability	43.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.6426
Blood Brain Barrier	-	0.8815
Caco-2 permeable	-	0.7605
P-glycoprotein substrate	Substrate	0.6515
P-glycoprotein inhibitor I	Non-inhibitor	0.9512
P-glycoprotein inhibitor II	Non-inhibitor	0.969
Renal organic cation transporter	Non-inhibitor	0.8574
CYP450 2C9 substrate	Non-substrate	0.8793
CYP450 2D6 substrate	Non-substrate	0.7622
CYP450 3A4 substrate	Non-substrate	0.725
CYP450 1A2 substrate	Non-inhibitor	0.8999
CYP450 2C9 inhibitor	Non-inhibitor	0.9708
CYP450 2D6 inhibitor	Non-inhibitor	0.9653
CYP450 2C19 inhibitor	Non-inhibitor	0.8266
CYP450 3A4 inhibitor	Non-inhibitor	0.907
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9821
Ames test	Non AMES toxic	0.9133
Carcinogenicity	Non-carcinogens	0.9389
Biodegradation	Not ready biodegradable	0.6844
Rat acute toxicity	1.8723 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9641
hERG inhibition (predictor II)	Non-inhibitor	0.8708

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
MS/MS Spectrum - Quattro_QQQ 10V, Positive	LC-MS/MS	splash10-0a4r-0194100000-d9a47a283478b88bb101
MS/MS Spectrum - Quattro_QQQ 25V, Positive	LC-MS/MS	splash10-001i-9040000000-8d6d4ae6ba18da11e336
MS/MS Spectrum - Quattro_QQQ 40V, Positive	LC-MS/MS	splash10-001i-9000000000-77e20f7eb799eea58ab0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
1H NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not 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

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	1.2	N/A	N/A	8340909 / 8360884 / 12477342
IC 50 (nM)	3.98	N/A	N/A	9379435
IC 50 (nM)	4.7	N/A	N/A	10669559

Details1. Angiotensin-converting enzyme

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

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]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Piepho RW: Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm. 2000 Oct 1;57 Suppl 1:S3-7. [PubMed:11030016]
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]
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]

Details2. Renin

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

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

Details1. Solute carrier family 15 member 1

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

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]
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]

Details2. Solute carrier family 15 member 2

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

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 January 24, 2020 15:33

Lisinopril

Identification

Structure for Lisinopril (DB00722)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References

Transporters

References

References