Lisinopril

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

Similar Structures

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

Poor quality drug data slowing you down?

Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.

Download eBook

Poor quality drug data slowing you down?

Download eBook

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 rates

Build, train, & validate machine-learning models
with evidence-based and structured datasets.

See how

Build, train, & validate predictive machine-learning models with structured datasets.

See how

Associated Conditions

Indication Type	Indication	Approval Level
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 Today

Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.

Learn more

Avoid life-threatening adverse drug events with our Clinical API

Learn more

Pharmacodynamics

Lisinopril is an angiotensin converting enzyme inhibitor used to treat hypertension, heart failure, and myocardial infarction.^8,9,10 Lisinopril is not a prodrug, and functions by inhibition of angiotensin converting enzyme as well as the renin angiotensin aldosterone system.^3,4,5 It has a wide therapeutic index and a long duration of action as patients are generally given 10-80mg daily.^8,9,10

Mechanism of action

Angiotensin II constricts coronary blood vessels and is positively inotropic, which under normal circumstances, would increase vascular resistance and oxygen consumption.³ This action can eventually lead to myocyte hypertrophy and vascular smooth muscle cell proliferation.³

Lisinopril is an angiotensin converting enzyme inhibitor (ACEI), preventing the conversion of angiotensin I to angiotensin II.^3,4 This action prevents myocyte hypertrophy and vascular smooth muscle cell proliferation seen in untreated patients.⁴ Increased levels of bradykinin also exhibit vasodilating effects for patients taking ACEIs.⁴ Lisinopril also inhibits renin's conversion of angiotensin to angiotensin I.⁵

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

Absorption

Lisinopril is 6-60% orally bioavailable with an average of 25% bioavailability.^2,8,9,10 Lisinopril reaches a C_max of 58ng/mL with a T_max of 6-8h.² Lisinopril's absorption is not affected by food.²

Volume of distribution

The apparent volume of distribution of lisinopril is 124L.³

Protein binding

Lisinopril has not been demonstrated to bind to serum proteins.^8,9,10

Metabolism

Lisinopril is not metabolized and is excreted as the unchanged drug.^8,9,10

Route of elimination

Lisinopril is entirely eliminated exclusively in the urine.^8,9,10

Half-life

Lisinopril has an effective half life of accumulation of 12.6h^2,8,9,10 and a terminal half life of 46.7h.²

Clearance

A 30kg child has a typical clearance of 10L/h, which increases with renal function.^8,9 The mean renal clearance of lisinopril in healthy adult males is 121mL/min.²

Adverse Effects

Improve decision support & research outcomes

With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!

See the data

Improve decision support & research outcomes with our structured adverse effects data.

See a data sample

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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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 software
Abacavir	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 regions

Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.

Access now

Access drug product information from over 10 global regions.

Access now

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
Act Lisinopril	Tablet	10 mg	Oral	Actavis Pharma Company	2007-10-17	2018-06-12
Act Lisinopril	Tablet	5 mg	Oral	Actavis Pharma Company	2007-10-17	2018-06-12
Act Lisinopril	Tablet	20 mg	Oral	Actavis Pharma Company	2007-10-17	2018-06-12
Lisinopril	Tablet	20 mg	Oral	Sorres Pharma Inc	2009-06-22	2014-06-20
Lisinopril	Tablet	20 mg	Oral	Meliapharm Inc	2008-03-12	2014-06-25

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-lisinopril	Tablet	5 mg	Oral	Apotex Corporation	1996-10-30	Not applicable
Apo-lisinopril	Tablet	10 mg	Oral	Apotex Corporation	1996-10-30	Not applicable
Apo-lisinopril	Tablet	20 mg	Oral	Apotex Corporation	1996-10-30	Not applicable
Apo-lisinopril Tablet (type P) - 10mg	Tablet	10 mg	Oral	Apotex Corporation	1996-10-30	2001-08-02
Apo-lisinopril Tablet (type P) - 20mg	Tablet	20 mg	Oral	Apotex Corporation	1996-10-30	2001-08-02

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Acecomb - Tabletten	Lisinopril (20 mg) + Hydrochlorothiazide (25 mg)	Tablet	Oral	Atnahs Pharma Netherlands B.V.	1991-11-15	Not applicable
Acecomb mite - Tabletten	Lisinopril (20 mg) + Hydrochlorothiazide (12.5 mg)	Tablet	Oral	Atnahs Pharma Netherlands B.V.	1991-11-15	Not applicable
Acecomb semi - Tabletten	Lisinopril (10 mg) + Hydrochlorothiazide (12.5 mg)	Tablet	Oral	Atnahs Pharma Netherlands B.V.	1995-08-25	Not applicable
Acelisino comp. forte - Tabletten	Lisinopril (20 mg) + Hydrochlorothiazide (25 mg)	Tablet	Oral	G.L. Pharma Gmb H	2004-02-19	Not applicable
Acelisino comp. mite - Tabletten	Lisinopril (20 mg) + Hydrochlorothiazide (12.5 mg)	Tablet	Oral	G.L. Pharma Gmb H	2004-02-19	Not applicable

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
Lytensopril-90	Lisinopril dihydrate (20 mg/1) + Arginine (90 mg/1)	Kit	Oral	Physician Therapeutics Llc	2011-07-07	Not applicable

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
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

PDB Entries

1j36 / 1o86 / 2c6n / 2x91

FDA label

Download (267 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Prevention	Atherosclerosis / Cardiovascular Disease (CVD) / Cerebral Arteriosclerosis / Coronary Heart Disease (CHD) / Diabetes Mellitus / Hypertension	1
4	Completed	Prevention	Perioperative Hypertension	1
4	Completed	Treatment	Cardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Hypertension, Essential Hypertension / Stroke	1
4	Completed	Treatment	Diabetic Nephropathy	1
4	Completed	Treatment	Diabetic Nephropathy / Hypertension	1

Pharmacoeconomics

Manufacturers

Actavis elizabeth llc
Apotex inc etobicoke site
Aurobindo pharma ltd
Ivax pharmaceuticals inc sub teva pharmaceuticals usa
Lek pharmaceuticals d d
Lupin ltd
Mylan pharmaceuticals inc
Ranbaxy pharmaceuticals inc
Sandoz inc
Teva pharmaceuticals usa inc
Vintage pharmaceuticals llc
Watson laboratories inc
West ward pharmaceutical corp
Wockhardt ltd
Merck research laboratories div merck co inc
Astrazeneca uk ltd

Packagers

Advanced Pharmaceutical Services Inc.
Aidarex Pharmacuticals LLC
Amerisource Health Services Corp.
Apotex Inc.
Apotheca Inc.
A-S Medication Solutions LLC
AstraZeneca Inc.
Aurobindo Pharma Ltd.
Blu Pharmaceuticals LLC
Bryant Ranch Prepack
Cardinal Health
Comprehensive Consultant Services Inc.
Coupler Enterprises Inc.
Dept Health Central Pharmacy
DHHS Program Support Center Supply Service Center
Direct Dispensing Inc.
Dispensing Solutions
Diversified Healthcare Services Inc.
Eon Labs
Golden State Medical Supply Inc.
Greenstone LLC
Group Health Cooperative
H.J. Harkins Co. Inc.
Heartland Repack Services LLC
Innoviant Pharmacy Inc.
International Laboratories Inc.
IPR Pharmaceuticals Inc.
Ivax Pharmaceuticals
Kaiser Foundation Hospital
Lake Erie Medical and Surgical Supply
Lek Pharmaceuticals Inc.
Liberty Pharmaceuticals
Lupin Pharmaceuticals Inc.
Major Pharmaceuticals
Mckesson Corp.
Medvantx Inc.
Merck & Co.
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Neighborcare Repackaging Inc.
Novartis AG
Nucare Pharmaceuticals Inc.
Ohm Laboratories Inc.
Palmetto Pharmaceuticals Inc.
PCA LLC
PD-Rx Pharmaceuticals Inc.
Pharmaceutical Utilization Management Program VA Inc.
Physicians Total Care Inc.
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prepak Systems Inc.
Prescript Pharmaceuticals
Professional Co.
Promex Medical Inc.
Qualitest
Ranbaxy Laboratories
Rebel Distributors Corp.
Remedy Repack
Resource Optimization and Innovation LLC
Sandhills Packaging Inc.
Sandoz
Southwood Pharmaceuticals
Stat Rx Usa
Stat Scripts LLC
Talbert Medical Management Corp.
Teva Pharmaceutical Industries Ltd.
Torpharm Inc.
Tya Pharmaceuticals
UDL Laboratories
Va Cmop Dallas
Vangard Labs Inc.
Watson Pharmaceuticals
West-Ward Pharmaceuticals
Wockhardt Ltd.

Dosage Forms

Form	Route	Strength
Tablet	Oral
Tablet, 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	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	10.89 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)
US9463183	No	2016-10-11	2035-11-06
US9616096	No	2017-04-11	2035-11-06
US9814751	No	2017-11-14	2035-11-06
US10039800	No	2018-08-07	2035-11-06
US10265370	No	2019-04-23	2035-11-06
US10406199	No	2019-09-10	2035-11-06
US10940177	No	2021-03-09	2035-11-06
US11179434	No	2021-11-23	2035-11-06
US11771733	No	2015-11-06	2035-11-06

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

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

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0006-9344000000-3673a7191e97a0ee02e0
MS/MS Spectrum - Quattro_QQQ 10V, Positive	LC-MS/MS	splash10-0a4r-0194100000-d9a47a283478b88bb101
MS/MS Spectrum - Quattro_QQQ 25V, Positive	LC-MS/MS	splash10-001i-9040000000-8d6d4ae6ba18da11e336
MS/MS Spectrum - Quattro_QQQ 40V, Positive	LC-MS/MS	splash10-001i-9000000000-77e20f7eb799eea58ab0
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-01q0-0940000000-116994867a4e2c649c00
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-01q0-0940000000-116994867a4e2c649c00
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0017900000-a0407758df517a69cb1a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-1310900000-5a41a72381c98109b301
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0aos-4596300000-6d5968c75fc45065a9f6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-5945400000-d99369667c4b2948680c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-3922000000-31cbda43c479dbaae81a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001j-9130000000-a8ac57e28695083574a4
1H NMR Spectrum	1D NMR	Not Applicable
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	218.749176	predicted	DarkChem Lite v0.1.0
[M-H]-	194.37709	predicted	DeepCCS 1.0 (2019)
[M+H]+	218.591576	predicted	DarkChem Lite v0.1.0
[M+H]+	196.77266	predicted	DeepCCS 1.0 (2019)
[M+Na]+	218.241776	predicted	DarkChem Lite v0.1.0
[M+Na]+	202.70561	predicted	DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models

Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.

Learn more

Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.

Learn more

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	1.2	N/A	N/A	A28844 / A28845 / A28635
IC 50 (nM)	3.98	N/A	N/A	A28846
IC 50 (nM)	4.7	N/A	N/A	A27344

Details1. Angiotensin-converting enzyme

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Zinc ion binding
Specific Function: Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent...
Gene Name: ACE
Uniprot ID: P12821
Uniprot Name: Angiotensin-converting enzyme
Molecular Weight: 149713.675 Da

References

Andujar-Sanchez M, Jara-Perez V, Camara-Artigas A: Thermodynamic determination of the binding constants of angiotensin-converting enzyme inhibitors by a displacement method. FEBS Lett. 2007 Jul 24;581(18):3449-54. Epub 2007 Jun 27. [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]

Details2. Renin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Receptor binding
Specific Function: Renin is a highly specific endopeptidase, whose only known function is to generate angiotensin I from angiotensinogen in the plasma, initiating a cascade of reactions that produce an elevation of b...
Gene Name: REN
Uniprot ID: P00797
Uniprot Name: Renin
Molecular Weight: 45057.125 Da

References

Te Riet L, van Esch JH, Roks AJ, van den Meiracker AH, Danser AH: Hypertension: renin-angiotensin-aldosterone system alterations. Circ Res. 2015 Mar 13;116(6):960-75. doi: 10.1161/CIRCRESAHA.116.303587. [Article]

Transporters

Details1. Solute carrier family 15 member 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name: SLC15A1
Uniprot ID: P46059
Uniprot Name: Solute carrier family 15 member 1
Molecular Weight: 78805.265 Da

References

Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [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]

Details2. Solute carrier family 15 member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Peptide:proton symporter activity
Specific Function: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name: SLC15A2
Uniprot ID: Q16348
Uniprot Name: Solute carrier family 15 member 2
Molecular Weight: 81782.77 Da

References

Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Lisinopril

Identification

Structure for Lisinopril (DB00722)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

Transporters

References

References