Lisinopril
Explore a selection of our essential drug information below, or:
Identification
- Summary
Lisinopril is an ACE inhibitor used to treat hypertension, heart failure, and acute myocardial infarction.
- Brand Names
- Prinivil, Qbrelis, Zestoretic, Zestril
- Generic Name
- Lisinopril
- DrugBank Accession Number
- DB00722
- Background
Lisinopril is an angiotensin converting enzyme inhibitor (ACEI) used to treat hypertension, heart failure, and myocardial infarction.8,9,10 Lisinopril and captopril are the only ACEIs that are not prodrugs.7 It functions by inhibition of angiotensin converting enzyme as well as the renin angiotensin aldosterone system.3,4,5 ACEIs are commonly used as a first line therapy in the treatment of hypertension, along with thiazide diuretics or beta blockers.6
Lisinopril was granted FDA approval on 29 December 1987.8
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 405.4879
Monoisotopic: 405.226371117 - Chemical Formula
- C21H31N3O5
- Synonyms
- (S)-1-(N(2)-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-proline
- [N2-[(S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline
- Lisinopril
- Lisinopril anhydrous
- Lisinoprilum
Pharmacology
- Indication
Lisinopril is indicated for the treatment of acute myocardial infarction, hypertension in patients ≥6 years, and as an adjunct therapy for heart failure.8,9 A combination product with hydrochlorothiazide is indicated for the treatment of hypertension.10
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Acute myocardial infarction •••••••••••• Prevention of Cardiovascular events ••• ••••• Adjunct therapy in management of Congestive heart failure •••••••••••• Management of Diabetic nephropathy ••• ••••• Management of Diabetic nephropathy ••• ••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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 inhibitorHumans URenin inhibitorHumans - Absorption
Lisinopril is 6-60% orally bioavailable with an average of 25% bioavailability.2,8,9,10 Lisinopril reaches a Cmax of 58ng/mL with a Tmax of 6-8h.2 Lisinopril's absorption is not affected by food.2
- Volume of distribution
The apparent volume of distribution of lisinopril is 124L.3
- Protein binding
Lisinopril has not been demonstrated to bind to serum proteins.8,9,10
- Metabolism
Lisinopril is not metabolized and is excreted as the unchanged drug.8,9,10
- Route of elimination
Lisinopril is entirely eliminated exclusively in the urine.8,9,10
- Half-life
Lisinopril has an effective half life of accumulation of 12.6h2,8,9,10 and a terminal half life of 46.7h.2
- Clearance
A 30kg child has a typical clearance of 10L/h, which increases with renal function.8,9 The mean renal clearance of lisinopril in healthy adult males is 121mL/min.2
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- 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 Integrate drug-drug
interactions in your softwareAbacavir Lisinopril may decrease the excretion rate of Abacavir which could result in a higher serum level. Abaloparatide The risk or severity of adverse effects can be increased when Lisinopril is combined with Abaloparatide. Acebutolol Lisinopril may increase the hypotensive activities of Acebutolol. Aceclofenac The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Lisinopril. Acemetacin The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acemetacin is combined with Lisinopril. - Food Interactions
- Avoid hypertensive herbs (e.g. bayberry, blue cohosh, cayenne, ephedra, and licorice).
- Avoid potassium-containing products. Potassium products increase the risk of hyperkalemia.
- Limit salt intake. Salt may attenuate the antihypertensive effect.
- Take with or without food. The absorption is unaffected by food.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Lisinopril dihydrate E7199S1YWR 83915-83-7 CZRQXSDBMCMPNJ-ZUIPZQNBSA-N - Product Images
- International/Other Brands
- Acebitor (GlaxoSmithKline) / Acemin (AstraZeneca) / Acerbon (AstraZeneca) / Acinopril (sanofi-aventis) / Bellisin (Ranbaxy) / Biopril (Biochem) / Dapril (Medochemie) / Fibsol (Sigma) / Fisopril (Sanofi-Aventis) / Hipril (Micro Labs) / Linopril (Klinger (Brazil)) / Lisipril (Hexal (Czech Republic), Orion (Finland)) / Noperten (Dexa (Indonesia)) / Presiten (Magnachem) / Ranolip (Ranbaxy) / Ranopril (Ranbaxy) / Rantex (Biotech) / Sinopren (Ranbaxy) / Sinopril (Eczacibasi (Russia)) / Tensopril (Merck)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Lisinopril Tablet 5 mg Oral Actavis Pharma Company 2007-10-17 2018-06-12 Canada Act Lisinopril Tablet 20 mg Oral Actavis Pharma Company 2007-10-17 2018-06-12 Canada Act Lisinopril Tablet 10 mg Oral Actavis Pharma Company 2007-10-17 2018-06-12 Canada Lisinopril Tablet 40 mg Oral Sivem Pharmaceuticals Ulc Not applicable Not applicable Canada Lisinopril Tablet 5 mg Oral Sanis Health Inc 2022-04-12 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-lisinopril Tablet 5 mg Oral Apotex Corporation 1996-10-30 Not applicable Canada Apo-lisinopril Tablet 10 mg Oral Apotex Corporation 1996-10-30 Not applicable Canada Apo-lisinopril Tablet 20 mg Oral Apotex Corporation 1996-10-30 Not applicable Canada Apo-lisinopril Tablet (type P) - 10mg Tablet 10 mg Oral Apotex Corporation 1996-10-30 2001-08-02 Canada Apo-lisinopril Tablet (type P) - 20mg Tablet 20 mg Oral Apotex Corporation 1996-10-30 2001-08-02 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Acecomb - Tabletten Lisinopril (20 mg) + Hydrochlorothiazide (25 mg) Tablet Oral Atnahs Pharma Netherlands B.V. 1991-11-15 Not applicable Austria Acecomb mite - Tabletten Lisinopril (20 mg) + Hydrochlorothiazide (12.5 mg) Tablet Oral Atnahs Pharma Netherlands B.V. 1991-11-15 Not applicable Austria Acecomb semi - Tabletten Lisinopril (10 mg) + Hydrochlorothiazide (12.5 mg) Tablet Oral Atnahs Pharma Netherlands B.V. 1995-08-25 Not applicable Austria Acelisino comp. forte - Tabletten Lisinopril (20 mg) + Hydrochlorothiazide (25 mg) Tablet Oral G.L. Pharma Gmb H 2004-02-19 Not applicable Austria Acelisino comp. mite - Tabletten Lisinopril (20 mg) + Hydrochlorothiazide (12.5 mg) Tablet Oral G.L. Pharma Gmb H 2004-02-19 Not applicable Austria - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Lytensopril Lisinopril dihydrate (20 mg/1) + Arginine (60 mg/1) Kit Oral Physician Therapeutics Llc 2011-07-07 Not applicable US Lytensopril-90 Lisinopril dihydrate (20 mg/1) + Arginine (90 mg/1) Kit Oral Physician Therapeutics Llc 2011-07-07 Not applicable US
Categories
- ATC Codes
- C09BA03 — Lisinopril and diuretics
- C09BA — ACE inhibitors and diuretics
- C09B — ACE INHIBITORS, COMBINATIONS
- C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
- C — CARDIOVASCULAR SYSTEM
- C10BX — Lipid modifying agents in combination with other drugs
- C10B — LIPID MODIFYING AGENTS, COMBINATIONS
- C10 — LIPID MODIFYING AGENTS
- C — CARDIOVASCULAR SYSTEM
- C09AA — ACE inhibitors, plain
- C09A — ACE INHIBITORS, PLAIN
- C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- ACE Inhibitors and Calcium Channel Blockers
- ACE Inhibitors and Diuretics
- Agents Acting on the Renin-Angiotensin System
- Agents causing angioedema
- Agents causing hyperkalemia
- Amino Acids, Peptides, and Proteins
- Angiotensin-Converting Enzyme Inhibitors
- Antihypertensive Agents
- Antihypertensive Agents Indicated for Hypertension
- Cardiotonic Agents
- Cardiovascular Agents
- Compounds used in a research, industrial, or household setting
- Dipeptides
- Drugs causing inadvertant photosensitivity
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Hypotensive Agents
- Lipid Modifying Agents
- Oligopeptides
- Peptides
- Photosensitizing Agents
- Protease Inhibitors
- Protective Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Dipeptides
- Alternative Parents
- Proline and derivatives / N-acyl-L-alpha-amino acids / Alpha amino acid amides / L-alpha-amino acids / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Aralkylamines / Benzene and substituted derivatives / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides show 9 more
- Substituents
- Alpha-amino acid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle show 28 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- dipeptide (CHEBI:43755)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 7Q3P4BS2FD
- CAS number
- 76547-98-3
- InChI Key
- RLAWWYSOJDYHDC-BZSNNMDCSA-N
- InChI
- InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1
- IUPAC Name
- (2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
- SMILES
- NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@H]1C(O)=O
References
- Synthesis Reference
Vincenzo Cannata, Valeriano Merli, Stefano Saguatti, "Process for the production of alkoxycarbonyldipeptides intermediates in the synthesis of the lisinopril." U.S. Patent US6166217, issued September, 1972.
US6166217- General References
- 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. [Article]
- Beermann B: Pharmacokinetics of lisinopril. Am J Med. 1988 Sep 23;85(3B):25-30. doi: 10.1016/0002-9343(88)90346-4. [Article]
- 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. [Article]
- Laurent S: Antihypertensive drugs. Pharmacol Res. 2017 Oct;124:116-125. doi: 10.1016/j.phrs.2017.07.026. Epub 2017 Aug 2. [Article]
- 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. [Article]
- 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. [Article]
- Herman LL, Bashir K: Angiotensin Converting Enzyme Inhibitors (ACEI) . [Article]
- 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
- 1546022
- ChEBI
- 43755
- ChEMBL
- CHEMBL1237
- ZINC
- ZINC000003812863
- Therapeutic Targets Database
- DAP000587
- PharmGKB
- PA450242
- PDBe Ligand
- LPR
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Lisinopril
- PDB Entries
- 1j36 / 1o86 / 2c6n / 2x91
- FDA label
- Download (267 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Active Not Recruiting Treatment Coronary Artery Disease (CAD) 1 somestatus stop reason just information to hide 4 Completed Prevention Atherosclerosis / Cardiovascular Disease (CVD) / Cerebral Arteriosclerosis / Coronary Heart Disease (CHD) / Diabetes Mellitus / Hypertension 1 somestatus stop reason just information to hide 4 Completed Prevention Perioperative Hypertension 1 somestatus stop reason just information to hide 4 Completed Treatment Cardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Hypertension, Essential Hypertension / Stroke 1 somestatus stop reason just information to hide 4 Completed Treatment Diabetic Nephropathy 1 somestatus stop reason just information to hide
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, film coated Oral Tablet Oral 40 mg Tablet Oral 10.000 mg 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/1 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 10.89 mg Tablet Oral 2.72 mg Tablet Oral 21.78 mg Tablet Oral 32.67 mg Tablet Oral 5.44 mg Tablet Oral Tablet Oral 30 MG Tablet Oral 10.8 MG Tablet Oral 5.4 MG Tablet Oral 5445 MG Tablet Oral 2.5 mg Solution Oral 1 mg/ml Kit Oral Tablet Oral 10 MG Solution Oral 1 mg/1mL Tablet, film coated Oral 10 mg Tablet, film coated Oral 20 mg Tablet, film coated Oral 5 mg Tablet Oral 20 mg Tablet Oral 5 mg - 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 DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US9463183 No 2016-10-11 2035-11-06 US US9616096 No 2017-04-11 2035-11-06 US US9814751 No 2017-11-14 2035-11-06 US US10039800 No 2018-08-07 2035-11-06 US US10265370 No 2019-04-23 2035-11-06 US US10406199 No 2019-09-10 2035-11-06 US US10940177 No 2021-03-09 2035-11-06 US US11179434 No 2021-11-23 2035-11-06 US US11771733 No 2015-11-06 2035-11-06 US
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 43.64 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 218.749176 predictedDarkChem Lite v0.1.0 [M-H]- 194.37709 predictedDeepCCS 1.0 (2019) [M+H]+ 218.591576 predictedDarkChem Lite v0.1.0 [M+H]+ 196.77266 predictedDeepCCS 1.0 (2019) [M+Na]+ 218.241776 predictedDarkChem Lite v0.1.0 [M+Na]+ 202.70561 predictedDeepCCS 1.0 (2019)
Targets
![](/assets/locked/DrugTargets2-1d1d534575da54e734c316d80c9fb35f8210c070dca913c026f8e58660e3e71a.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dipeptidyl carboxypeptidase that removes dipeptides from the C-terminus of a variety of circulating hormones, such as angiotensin I, bradykinin or enkephalins, thereby playing a key role in the regulation of blood pressure, electrolyte homeostasis or synaptic plasticity (PubMed:15615692, PubMed:20826823, PubMed:2558109, PubMed:4322742, PubMed:7523412, PubMed:7683654). Composed of two similar catalytic domains, each possessing a functional active site, with different selectivity for substrates (PubMed:10913258, PubMed:1320019, PubMed:1851160, PubMed:19773553, PubMed:7683654, PubMed:7876104). Plays a major role in the angiotensin-renin system that regulates blood pressure and sodium retention by the kidney by converting angiotensin I to angiotensin II, resulting in an increase of the vasoconstrictor activity of angiotensin (PubMed:11432860, PubMed:1851160, PubMed:19773553, PubMed:23056909, PubMed:4322742). Also able to inactivate bradykinin, a potent vasodilator, and therefore enhance the blood pressure response (PubMed:15615692, PubMed:2558109, PubMed:4322742, PubMed:6055465, PubMed:6270633, PubMed:7683654). Acts as a regulator of synaptic transmission by mediating cleavage of neuropeptide hormones, such as substance P, neurotensin or enkephalins (PubMed:15615692, PubMed:6208535, PubMed:6270633, PubMed:656131). Catalyzes degradation of different enkephalin neuropeptides (Met-enkephalin, Leu-enkephalin, Met-enkephalin-Arg-Phe and possibly Met-enkephalin-Arg-Gly-Leu) (PubMed:2982830, PubMed:6270633, PubMed:656131). Acts as a regulator of synaptic plasticity in the nucleus accumbens of the brain by mediating cleavage of Met-enkephalin-Arg-Phe, a strong ligand of Mu-type opioid receptor OPRM1, into Met-enkephalin (By similarity). Met-enkephalin-Arg-Phe cleavage by ACE decreases activation of OPRM1, leading to long-term synaptic potentiation of glutamate release (By similarity). Also acts as a regulator of hematopoietic stem cell differentiation by mediating degradation of hemoregulatory peptide N-acetyl-SDKP (AcSDKP) (PubMed:26403559, PubMed:7876104, PubMed:8257427, PubMed:8609242). Acts as a regulator of cannabinoid signaling pathway by mediating degradation of hemopressin, an antagonist peptide of the cannabinoid receptor CNR1 (PubMed:18077343). Involved in amyloid-beta metabolism by catalyzing degradation of Amyloid-beta protein 40 and Amyloid-beta protein 42 peptides, thereby preventing plaque formation (PubMed:11604391, PubMed:16154999, PubMed:19773553). Catalyzes cleavage of cholecystokinin (maturation of Cholecystokinin-8 and Cholecystokinin-5) and Gonadoliberin-1 (both maturation and degradation) hormones (PubMed:10336644, PubMed:2983326, PubMed:7683654, PubMed:9371719). Degradation of hemoregulatory peptide N-acetyl-SDKP (AcSDKP) and amyloid-beta proteins is mediated by the N-terminal catalytic domain, while angiotensin I and cholecystokinin cleavage is mediated by the C-terminal catalytic region (PubMed:10336644, PubMed:19773553, PubMed:7876104)
- Specific Function
- Actin binding
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Piepho RW: Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm. 2000 Oct 1;57 Suppl 1:S3-7. [Article]
- Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [Article]
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General 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 blood pressure and increased sodium retention by the kidney
- Specific Function
- Aspartic-type endopeptidase activity
- 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. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Electrogenic proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides. Transports neutral and monovalently charged peptides with a proton to peptide stoichiometry of 1:1 or 2:1 (By similarity) (PubMed:15521010, PubMed:18367661, PubMed:19685173, PubMed:26320580, PubMed:7896779, PubMed:8914574, PubMed:9835627). Primarily responsible for the absorption of dietary di- and tripeptides from the small intestinal lumen (By similarity). Mediates transepithelial transport of muramyl and N-formylated bacterial dipeptides contributing to recognition of pathogenic bacteria by the mucosal immune system (PubMed:15521010, PubMed:9835627)
- Specific Function
- Dipeptide transmembrane transporter activity
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides (PubMed:16434549, PubMed:18367661, PubMed:7756356). Transports neutral and anionic dipeptides with a proton to peptide stoichiometry of 2:1 or 3:1 (By similarity). In kidney, involved in the absorption of circulating di- and tripeptides from the glomerular filtrate (PubMed:7756356). Can also transport beta-lactam antibiotics, such as the aminocephalosporin cefadroxil, and other antiviral and anticancer drugs (PubMed:16434549). Transports the dipeptide-like aminopeptidase inhibitor bestatin (By similarity). Also able to transport carnosine (PubMed:31073693). Involved in innate immunity by promoting the detection of microbial pathogens by NOD-like receptors (NLRs) (By similarity). Mediates transport of bacterial peptidoglycans across the plasma membrane or, in macrophages, the phagosome membrane: catalyzes the transport of certain bacterial peptidoglycans, such as muramyl dipeptide (MDP), the NOD2 ligand (PubMed:20406817)
- Specific Function
- Dipeptide transmembrane transporter activity
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 06, 2024 08:57