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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Lisinopril
- Accession Number
- DB00722 (APRD00560)
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Description
Lisinopril is an angiotensin converting enzyme inhibitor (ACEI) used to treat hypertension, heart failure, and myocardial infarction.8,9,10 Lisinopril and captopril are the only ACEIs that are not prodrugs.7 It functions by inhibition of angiotensin converting enzyme as well as the renin angiotensin aldosterone system.3,4,5 ACEIs are commonly used as a first line therapy in the treatment of hypertension, along with thiazide diuretics or beta blockers.6
Lisinopril was granted FDA approval on 29 December 1987.8
- Structure
Structure for Lisinopril (DB00722)
- 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 Unlock Additional DataAct Lisinopril Tablet Oral Actavis Pharma Company 2007-10-17 2018-06-12 Canada 
Act Lisinopril Tablet Oral Actavis Pharma Company 2007-10-17 2018-06-12 Canada Act Lisinopril Tablet 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 Sivem Pharmaceuticals Ulc 2012-06-11 Not applicable Canada Lisinopril Tablet 10 mg Oral Cobalt Laboratories Not applicable Not applicable Canada Lisinopril Tablet 5 mg Oral Cobalt Laboratories Not applicable Not applicable Canada Lisinopril Tablet 30 mg/1 Oral West-ward Pharmaceutical Corp. 2008-08-28 2008-08-28 US 
Lisinopril Tablet 2.5 mg/1 Oral West-ward Pharmaceutical Corp. 2008-08-28 2008-08-28 US Lisinopril Tablet 20 mg Oral Sorres Pharma Inc 2009-06-22 2014-06-20 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataApo-lisinopril Tablet (type P) - 10mg Tablet Oral Apotex Corporation 1996-10-30 2001-08-02 Canada Apo-lisinopril Tablet (type P) - 20mg Tablet Oral Apotex Corporation 1996-10-30 2001-08-02 Canada Apo-lisinopril Tablet (type P) - 40mg Tablet Oral Apotex Corporation 1996-12-30 2001-08-02 Canada Apo-lisinopril Tablet (type P) - 5mg Tablet Oral Apotex Corporation 1996-10-30 2001-08-02 Canada Apo-lisinopril Tablet 10 mg Tablet Oral Apotex Corporation 1996-10-30 Not applicable Canada Apo-lisinopril Tablet 20 mg Tablet Oral Apotex Corporation 1996-10-30 Not applicable Canada Apo-lisinopril Tablet 40 mg Tablet Oral Apotex Corporation 1996-10-30 2019-01-21 Canada Apo-lisinopril Tablet 5 mg Tablet Oral Apotex Corporation 1996-10-30 Not applicable Canada Auro-lisinopril Tablet Oral Auro Pharma Inc 2013-02-12 Not applicable Canada Auro-lisinopril Tablet Oral Auro Pharma Inc 2013-02-12 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct 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 Canada Apo-lisinopril/hctz Lisinopril (20 mg) + Hydrochlorothiazide (12.5 mg) Tablet Oral Apotex Corporation 2007-11-21 Not applicable Canada Apo-lisinopril/hctz Lisinopril (10 mg) + Hydrochlorothiazide (12.5 mg) Tablet Oral Apotex Corporation 2007-09-05 Not applicable Canada Ava-lisinopril HCT Lisinopril (20 mg) + Hydrochlorothiazide (25 mg) Tablet Oral Avanstra Inc 2011-08-18 2014-08-21 Canada Ava-lisinopril HCT Lisinopril (20 mg) + Hydrochlorothiazide (12.5 mg) Tablet Oral Avanstra Inc 2011-08-18 2014-08-21 Canada Ava-lisinopril HCT Lisinopril (10 mg) + Hydrochlorothiazide (12.5 mg) Tablet Oral Avanstra Inc 2011-08-18 2014-08-21 Canada Lisinopril and HCTZ Lisinopril dihydrate (20 mg/1) + Hydrochlorothiazide (25 mg/1) Tablet Oral Northwind Pharmaceuticals 2014-07-10 Not applicable US 
Lisinopril and Hydrochlorothiazide Lisinopril dihydrate (10 mg/1) + Hydrochlorothiazide (12.5 mg/1) Tablet Oral International Laboratories, Llc 2014-03-04 Not applicable US Lisinopril and Hydrochlorothiazide Lisinopril dihydrate (10 mg/1) + Hydrochlorothiazide (12.5 mg/1) Tablet Oral Amerincan Health Packaging 2014-05-10 2018-07-31 US Lisinopril and Hydrochlorothiazide Lisinopril dihydrate (10 mg/1) + Hydrochlorothiazide (12.5 mg/1) Tablet Oral Quality Care Products, LLC 2019-03-03 Not applicable US - 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 US Lytensopril-90 Lisinopril dihydrate (20 mg/1) + Arginine (90 mg/1) Kit Oral Physician Therapeutics Llc 2011-07-07 Not applicable US - 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
- 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 that are Mainly Renally Excreted
- Enzyme Inhibitors
- Hypotensive Agents
- Lipid Modifying Agents
- Oligopeptides
- Peptides
- Protease Inhibitors
- Protective Agents
- 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 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
- 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
Unlock Additional Data
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.
Learn more Additional Data Available
Contraindications
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn more Additional Data Available
Blackbox Warnings
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- 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 Unlock Additional Data1-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. Acarbose Acarbose may decrease the excretion rate of Lisinopril which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Avoid hypertensive herbs (e.g. bayberry, blue cohosh, cayenne, ephedra, and licorice).
- Avoid potassium-containing products. Potassium products increase the risk of hyperkalemia.
- Limit salt intake. Salt may attenuate the antihypertensive effect.
- Take with or without food. The absorption is unaffected by food.
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
- 66979
- RxNav
- 1546022
- ChEBI
- 43755
- ChEMBL
- CHEMBL1237
- ZINC
- ZINC000003812863
- Therapeutic Targets Database
- DAP000587
- PharmGKB
- PA450242
- PDBe Ligand
- LPR
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Lisinopril
- 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 — HMG CoA reductase inhibitors, other combinations
- 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
- AHFS Codes
- 24:32.04 — Angiotensin-converting Enzyme Inhibitors
- PDB Entries
- 1j36 / 1o86 / 2c6n / 2x91
- FDA label
- Download (267 KB)
Clinical Trials
- Clinical Trials
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
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- Dispensing Solutions
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- Golden State Medical Supply Inc.
- Greenstone LLC
- Group Health Cooperative
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- 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 DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Unlock Additional DataUS9463183 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 Additional Data Available- Filed On
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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Dipeptides
- Alternative Parents
- Proline and derivatives / N-acyl-L-alpha-amino acids / Alpha amino acid amides / L-alpha-amino acids / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Aralkylamines / Benzene and substituted derivatives / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides show 9 more
- Substituents
- Alpha-dipeptide / N-acyl-alpha-amino acid / Proline or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-l-alpha-amino acid / Alpha-amino acid amide / Alpha-amino acid / Alpha-amino acid or derivatives / L-alpha-amino acid / N-acylpyrrolidine show 28 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- dipeptide (CHEBI:43755)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent...
- Gene Name
- ACE
- Uniprot ID
- P12821
- Uniprot Name
- Angiotensin-converting enzyme
- Molecular Weight
- 149713.675 Da
References
- 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]
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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]
- 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 May 25, 2020 04:16
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