Identification

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

Lisinopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE), the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Lisinopril may be used to treat hypertension and symptomatic congestive heart failure, to improve survival in certain individuals following myocardial infarction, and to prevent progression of renal disease in hypertensive patients with diabetes mellitus and microalbuminuria or overt nephropathy.

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 LisinoprilTablet20 mgOralActavis Pharma Company2007-10-17Not applicableCanada
Act LisinoprilTablet10 mgOralActavis Pharma Company2007-10-17Not applicableCanada
Act LisinoprilTablet5 mgOralActavis Pharma Company2007-10-17Not applicableCanada
LisinoprilTablet5 mgOralCobalt LaboratoriesNot applicableNot applicableCanada
LisinoprilTablet10 mgOralSorres Pharma Inc2009-06-222014-06-20Canada
LisinoprilTablet20 mgOralMeliapharm Inc2008-03-122014-06-25Canada
LisinoprilTablet40 mg/1OralLek Pharmaceuticals2007-03-02Not applicableUs
LisinoprilTablet10 mg/1OralLek Pharmaceuticals2007-03-02Not applicableUs
LisinoprilTablet30 mg/1OralWest-ward Pharmaceutical Corp.2008-08-282008-08-28Us
LisinoprilTablet5 mgOralSivem Pharmaceuticals Ulc2012-06-11Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-lisinopril Tablet (type P) - 10mgTablet10 mgOralApotex Corporation1996-10-302001-08-02Canada
Apo-lisinopril Tablet (type P) - 20mgTablet20 mgOralApotex Corporation1996-10-302001-08-02Canada
Apo-lisinopril Tablet (type P) - 40mgTablet40 mgOralApotex Corporation1996-12-302001-08-02Canada
Apo-lisinopril Tablet (type P) - 5mgTablet5 mgOralApotex Corporation1996-10-302001-08-02Canada
Apo-lisinopril Tablet 10 mgTablet10 mgOralApotex Corporation1996-10-30Not applicableCanada
Apo-lisinopril Tablet 20 mgTablet20 mgOralApotex Corporation1996-10-30Not applicableCanada
Apo-lisinopril Tablet 40 mgTablet40 mgOralApotex Corporation1996-10-30Not applicableCanada
Apo-lisinopril Tablet 5 mgTablet5 mgOralApotex Corporation1996-10-30Not applicableCanada
Auro-lisinoprilTablet5 mgOralAuro Pharma Inc2013-02-12Not applicableCanada
Auro-lisinoprilTablet20 mgOralAuro Pharma Inc2013-02-12Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Apo-lisinopril/hctzLisinopril (20 mg) + Hydrochlorothiazide (12.5 mg)TabletOralApotex Corporation2007-11-21Not applicableCanada
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
Ava-lisinopril HctLisinopril (20 mg) + Hydrochlorothiazide (12.5 mg)TabletOralAvanstra Inc2011-08-182014-08-21Canada
Ava-lisinopril HctLisinopril (20 mg) + Hydrochlorothiazide (25 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)TabletOralMed Pharma Co., Ltd.2011-07-102012-07-31Us
Lisinopril and HydrochlorothiazideLisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (12.5 mg/1)TabletOralRemedy Repack2011-12-122016-02-05Us
Lisinopril and HydrochlorothiazideLisinopril dihydrate (10 mg/1) + Hydrochlorothiazide (12.5 mg/1)TabletOralUDL Laboratories, Inc.2010-06-072014-02-28Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
LytensoprilLisinopril dihydrate (20 mg/1) + L-Arginine (60 mg/1)KitPhysician Therapeutics Llc2011-07-07Not applicableUs
Lytensopril-90Lisinopril dihydrate (20 mg/1) + L-Arginine (90 mg/1)KitPhysician 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

For the treatment of hypertension and symptomatic congestive heart failure. May be used in conjunction with thrombolytic agents, aspirin and/or β-blockers to improve survival in hemodynamically stable individuals following myocardial infarction. May be used to slow the progression of renal disease in hypertensive patients with diabetes mellitus and microalbuminuria or overt nephropathy.

Associated Conditions
Pharmacodynamics

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

Mechanism of action

There are two isoforms of ACE: the somatic isoform, which exists as a glycoprotein comprised of a single polypeptide chain of 1277; and the testicular isoform, which has a lower molecular mass and is thought to play a role in sperm maturation and binding of sperm to the oviduct epithelium. Somatic ACE has two functionally active domains, N and C, which arise from tandem gene duplication. Although the two domains have high sequence similarity, they play distinct physiological roles. The C-domain is predominantly involved in blood pressure regulation while the N-domain plays a role in hematopoietic stem cell differentiation and proliferation. ACE inhibitors bind to and inhibit the activity of both domains, but have much greater affinity for and inhibitory activity against the C-domain. Lisinopril, one of the few ACE inhibitors that is not a prodrug, competes with ATI for binding to ACE and inhibits and enzymatic proteolysis of ATI to ATII. Decreasing ATII levels in the body decreases blood pressure by inhibiting the pressor effects of ATII as described in the Pharmacology section above. Lisinopril also causes an increase in plasma renin activity likely due to a loss of feedback inhibition mediated by ATII on the release of renin and/or stimulation of reflex mechanisms via baroreceptors.

TargetActionsOrganism
AAngiotensin-converting enzyme
inhibitor
Human
Absorption

Approximately 25%, but widely variable between individuals (6 to 60%) in all doses tested (5-80 mg); absorption is unaffected by food

Volume of distribution
Not Available
Protein binding

Lisinopril does not appear to be bound to serum proteins other than ACE.

Metabolism

Does not undergo metabolism, excreted unchanged in urine.

Route of elimination

Lisinopril does not undergo metabolism and is excreted unchanged entirely in the urine.

Half life

Effective half life of accumulation following multiple dosing is 12 hours.

Clearance
  • 10 L/h [child weighting 30 kg receiving doses of 0.1 to 0.2 mg/kg]
Toxicity

Symptoms of overdose include severe hypotension, electrolyte disturbances, and renal failure. LD50= 2000 mg/kg(orally in rat). Most frequent adverse effects include headache, dizziness, cough, fatigue and diarrhea.

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

Interactions

Drug Interactions
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 adverse effects 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.
Acetylsalicylic acidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acetylsalicylic acid is combined with Lisinopril.
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.
AcyclovirAcyclovir may decrease the excretion rate of Lisinopril which could result in a higher serum level.
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. Abdelmalek MF, Douglas DD: Lisinopril-induced isolated visceral angioedema: review of ACE-inhibitor-induced small bowel angioedema. Dig Dis Sci. 1997 Apr;42(4):847-50. [PubMed:9125659]
  2. Hasslacher C: Influence of the ACE inhibitor lisinopril on blood pressure, metabolism, and renal function parameter in hypertensive type II diabetic patients: a postmarketing surveillance study. J Diabetes Complications. 1996 May-Jun;10(3):136-8. [PubMed:8807458]
  3. Nielsen SE, Sugaya T, Tarnow L, Lajer M, Schjoedt KJ, Astrup AS, Baba T, Parving HH, Rossing P: Tubular and glomerular injury in diabetes and the impact of ACE inhibition. Diabetes Care. 2009 Sep;32(9):1684-8. doi: 10.2337/dc09-0429. Epub 2009 Jun 5. [PubMed:19502542]
  4. Patchett AA, Harris E, Tristram EW, Wyvratt MJ, Wu MT, Taub D, Peterson ER, Ikeler TJ, ten Broeke J, Payne LG, Ondeyka DL, Thorsett ED, Greenlee WJ, Lohr NS, Hoffsommer RD, Joshua H, Ruyle WV, Rothrock JW, Aster SD, Maycock AL, Robinson FM, Hirschmann R, Sweet CS, Ulm EH, Gross DM, Vassil TC, Stone CA: A new class of angiotensin-converting enzyme inhibitors. Nature. 1980 Nov 20;288(5788):280-3. [PubMed:6253826]
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
C09AA03 — LisinoprilC09BB03 — Lisinopril and amlodipineC09BA03 — Lisinopril and diureticsC10BX07 — Rosuvastatin, amlodipine and 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
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)5
1CompletedTreatmentStrokes1
1CompletedTreatmentType 2 Diabetes Mellitus1
1Not Yet RecruitingTreatmentBladder Small Cell Neuroendocrine Carcinoma / Castration-Resistant Prostate Carcinoma / Metastatic Bladder Urothelial Carcinoma / Metastatic Urethral Urothelial Carcinoma / Prostate Carcinoma Metastatic in the Bone / Prostate Neuroendocrine Neoplasm / Prostate Small Cell Carcinoma / Stage III Bladder Cancer AJCC v8 / Stage III Prostate Cancer AJCC v8 / Stage III Urethral Cancer AJCC v8 / Stage IV Bladder Cancer AJCC v8 / Stage IV Prostate Cancer AJCC v8 / Stage IV Urethral Cancer AJCC v8 / Stage IVA Bladder Cancer AJCC v8 / Stage IVB Bladder Cancer AJCC v8 / Transitional Cell Carcinoma / Ureter Small Cell Carcinoma1
1RecruitingTreatmentHypertension, Resistant to Conventional Therapy1
1, 2CompletedTreatmentPre-Hypertension1
1, 2Not Yet RecruitingTreatmentBladder Cancers / Cancer of the Bladder / Genitourinary tract neoplasm / Malignant Tumor of the Urinary Bladder / Transitional Cell Carcinoma / Urinary Bladder Cancer / Urinary Bladder Neoplasms / Urologic Cancer / Urologic Neoplasms1
2Active Not RecruitingSupportive CareCancer, Breast / Cardiac Toxicity1
2CompletedTreatmentAging / Cognitive Impairments / High Blood Pressure (Hypertension)1
2CompletedTreatmentGlomerulosclerosis, Focal Segmental1
2CompletedTreatmentHypertension,Essential1
2CompletedTreatmentOligozoospermia1
2Not Yet RecruitingPreventionPacemakers, Heart Failure1
2RecruitingTreatmentAcute Coronary Syndromes (ACS) / Arterial Hypertension1
2RecruitingTreatmentAlbuminuria / Genetic Predisposition / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Kidney Diseases1
2RecruitingTreatmentExtracapillary Glomerulonephritis1
2RecruitingTreatmentNon-driver Mutation Advanced Non-Squamous Non Small Cell Lung Cancer / Non-Squamous Non Small Cell Lung Cancer1
2RecruitingTreatmentTriple-Negative Breast Cancer (TNBC)1
2TerminatedTreatmentHigh Blood Pressure (Hypertension) / Unspecified Adult Solid Tumor, Protocol Specific1
2TerminatedTreatmentMediastinal Neoplasms1
2, 3CompletedTreatmentBecker's Muscular Dystrophy (BMD) / Duchenne's Muscular Dystrophy (DMD) / Limb Girdle Muscular Dystrophy1
2, 3RecruitingTreatmentProstate Cancer1
3Active Not RecruitingPreventionHigh Blood Pressure (Hypertension) / Mild Cognitive Impairment (MCI)1
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, Unspecified / High Blood Pressure (Hypertension) / High Cholesterol / Myocardial Infarction / Myocardial Ischemia1
3CompletedPreventionDiabetic Nephropathies1
3CompletedTreatmentHigh Blood Pressure (Hypertension)3
3CompletedTreatmentHigh Blood Pressure (Hypertension) / Obesity, Abdominal1
3CompletedTreatmentKidney, Polycystic2
3CompletedTreatmentLeft Ventricular Hypertrophy1
3Not Yet RecruitingTreatmentNon-Small-Cell Lung1
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 / Strokes1
4CompletedTreatmentDiabetic Nephropathies1
4CompletedTreatmentDiabetic Nephropathies / High Blood Pressure (Hypertension)1
4CompletedTreatmentHeart Failure, Unspecified / Ventricular Dysfunction, Left1
4CompletedTreatmentHigh Blood Pressure (Hypertension)3
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
4RecruitingTreatmentHigh Blood Pressure (Hypertension)1
4RecruitingTreatmentPediatric Hypertension1
4RecruitingTreatmentProteinuria / Renal Insufficiency,Chronic1
4SuspendedPreventionCardiovascular Disease (CVD) / Osteoarthritis (OA)1
4TerminatedPreventionNeurological Dysphagia / Pneumonia1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
Not AvailableActive Not RecruitingSupportive CareDyspnea / Lung Cancer Non-Small Cell Cancer (NSCLC) / Lung Cancer Small Cell Lung Cancer (SCLC)1
Not AvailableActive Not RecruitingTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableCompletedNot AvailableCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / High Blood Pressure (Hypertension) / Myocardial Infarction1
Not AvailableCompletedNot AvailableDiabetes Complications / Diabetes, Diabetes Mellitus Type 1 / Eye Diseases / Retinopathy, Diabetic1
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 AvailableCompletedPreventionDiabetes, Diabetes Mellitus Type 1 / Diabetic Nephropathies1
Not AvailableCompletedTreatmentBMI >30 kg/m2 / Pre-Diabetic1
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 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 AvailableTerminatedPreventionThoracic Pain1
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
TabletOral40 mg
TabletOral5 mg
TabletOral10 1/1
TabletOral10 mg/1
TabletOral10 mg/301
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
Kit
TabletOral10 mg
TabletOral2.5 mg
TabletOral20 mg
SolutionOral1 mg/1mL
TabletOral
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
US10039800No2015-11-062035-11-06Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
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
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent...
Gene Name
ACE
Uniprot ID
P12821
Uniprot Name
Angiotensin-converting enzyme
Molecular Weight
149713.675 Da
References
  1. 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]

Drug created on June 13, 2005 07:24 / Updated on November 21, 2018 07:14