Lisinopril (CED0002578)

Record Information
Version1.0
Creation Date2016-05-26 05:37:54 UTC
Update Date2026-05-14 16:47:06 UTC
Accession NumberCHEM035280
Identification
Common NameLisinopril
ClassSmall Molecule
Description
Lisinopril is an organic compound with the formula C21H31N3O5 and an average molecular weight of 405.49 g/mol. Lisinopril belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound acts as an inhibitor of Renin (REN) and Angiotensin-converting enzyme (ACE). In terms of health effects, it is used as a treatment for hypertension (PMC12313093, PMC9505973). The compound is found in or released from 15 recorded sources. These include healthcare, pharmaceuticals & veterinary products such as ACE inhibitors and lipid modifying agents, as well as household cleaning & consumer products including other smoking requisites and non electric simulated smoking devices. It is also associated with food, food processing & cookware, specifically the preparation of vinegar and the preparation of malt. Additional sources include building & construction materials such as floors and ceilings, and electrical & electronic equipment, including power cables, communication cables or conductors, antennas, sparking plugs, emergency protective devices, and two other sources. The recorded exposure route for lisinopril is oral.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(S)-1-(N(2)-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-prolineChEBI
[N2-[(S)-1-CARBOXY-3-phenylpropyl]-L-lysyl-L-prolineChEBI
Lisinopril anhydrousChEBI
ZestrilKegg
AcerbonHMDB
AcercompHMDB
AlaprilHMDB
CaraceHMDB
CipralHMDB
CiprilHMDB
CoricHMDB
InhibrilHMDB
InoprilHMDB
LinoprilHMDB
LinvasHMDB
LiprilHMDB
LisinalHMDB
LisinoprilumHMDB
LisiprilHMDB
LisorilHMDB
LisprilHMDB
LorilHMDB
LPRHMDB
LysinoprilHMDB
NopertenHMDB
NovatecHMDB
PresitenHMDB
PrinilHMDB
PrinivilHMDB
SinoprilHMDB
SinoprylHMDB
TensoprilHMDB
TensynHMDB
TersifHMDB
VivatecHMDB
Lisinopril maleate (1:1)HMDB
Lisinopril sulfate (1:2)HMDB
Chemical FormulaC21H31N3O5
Average Molecular Mass405.488 g/mol
Monoisotopic Mass405.226 g/mol
CAS Registry Number76547-98-3
IUPAC Name(2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
Traditional Namelisinopril
SMILESNCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@H]1C(O)=O
InChI IdentifierInChI=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
InChI KeyRLAWWYSOJDYHDC-BZSNNMDCSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
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
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Organoheterocyclic compound
  • Secondary amine
  • Azacycle
  • Carboxylic acid
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Primary amine
  • Amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity107.37 m³·mol⁻¹ChemAxon
Polarizability43.64 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9344000000-3673a7191e97a0ee02e0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0f6x-9201340000-bc9644b3a3a4109f3722Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4r-0194100000-d9a47a283478b88bb101Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9040000000-8d6d4ae6ba18da11e336Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9000000000-77e20f7eb799eea58ab0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01q0-0940000000-116994867a4e2c649c00Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01q0-0940000000-116994867a4e2c649c00Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9120000000-fd2acaa1eae37a6f7ba6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2010900000-67e85126826eedd63b6cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-9052300000-d651e557fe1ae7eac452Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ik9-0900500000-85d2bfa23ac02fce017dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-b4cd463dbaeec149b805Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-c2a4ab9f5fb48e5480bfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06ri-0229300000-236b576cdfc8112530c7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03xu-4497000000-ad2ca7e02728a51b0051Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-9760000000-517501fe175444669d72Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w29-0119600000-219bea00e0a247bc0888Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-2429100000-404746794cb47e7eb6fcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-3920000000-b1093c7b1913ec8ec8d0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0002900000-a76c25515295bb79175bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0901-2395300000-cc32f663c74e5f0f3306Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9110000000-ccd25ccd5c2ff94948b4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0002900000-ce436e39fbead59af3f2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ik9-3933500000-a236ac37e133779ee0acNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-8910000000-db165b4504f7321c51e0Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
5291.0Log mg/kg[3000:9400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
hypertensionis_treatment_forNot AvailablePMC12313093 , PMC9505973
migraineis_treatment_forNot AvailablePMC12255647
Exposure Sources
Source IDSourceSectorReference
295ACE inhibitorsHealthcare, pharmaceuticals & veterinary productsNot Available
298Lipid modifying agentsHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
594Ship HullsMarine, shipping & aquacultureNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
634BucklesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Angiotensin-converting enzyme structureClick to view 3D structureAngiotensin-converting enzymeP12821HumansPredicted (SEA)0.622794
Click to view 3D structureAngiotensin-converting enzymeP12822Oryctolagus cuniculusPredicted (SEA)0.389246
Click to view 3D structureAngiotensin-converting enzymeP47820Rattus norvegicusPredicted (SEA)0.856341
Click to view 3D structureAngiotensin-converting enzyme 2Q5EGZ1Rattus norvegicusPredicted (SEA)0.233548
Click to view 3D structureC5a anaphylatoxin chemotactic receptor 1P30993Mus musculusPredicted (SEA)38.4575
Click to view 3D structureMu-type opioid receptorP97266Cavia porcellusPredicted (SEA)144.021
Click to view 3D structureProlyl endopeptidaseP23687Sus scrofaPredicted (SEA)1.94623
Click to view 3D structureMu-type opioid receptorP33535Rattus norvegicusPredicted (SEA)157.645
Click to view 3D structureAngiotensin-converting enzymeP09470Mus musculusPredicted (SEA)0.311397
Click to view 3D structureSerine protease 1P00760Bos taurusPredicted (SEA)30.5169
Click to view 3D structure3-hydroxy-3-methylglutaryl-coenzyme A reductaseP09610Mesocricetus auratusPredicted (SEA)13.5458
Click to view 3D structureKappa-type opioid receptorP41144Cavia porcellusPredicted (SEA)137.092
Click to view 3D structureDelta-type opioid receptorP33533Rattus norvegicusPredicted (SEA)132.422
Click to view 3D structureDelta-type opioid receptorP32300Mus musculusPredicted (SEA)150.171
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)81.3524
Coagulation factor X structureClick to view 3D structureCoagulation factor XP00742HumansPredicted (SEA)68.5852
Renin structureClick to view 3D structureReninP00797HumansPredicted (SEA)27.2472
Plasminogen structureClick to view 3D structurePlasminogenP00747HumansPredicted (SEA)57.6863
Click to view 3D structureNeprilysinP08049Oryctolagus cuniculusPredicted (SEA)17.5161
Prostasin structureClick to view 3D structureProstasinQ16651HumansPredicted (SEA)1.32344
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)213.229
Click to view 3D structureNeprilysinP07861Rattus norvegicusPredicted (SEA)14.1686
Click to view 3D structureUncharacterized proteinF1N083Bos taurusPredicted (SEA)32.3074
Click to view 3D structureSubstance-P receptorP14600Rattus norvegicusPredicted (SEA)83.4544
Dipeptidyl peptidase 4 structureClick to view 3D structureDipeptidyl peptidase 4P27487HumansPredicted (SEA)26.0795
Concentrations
Not Available
External Links
DrugBank IDDB00722
HMDB IDHMDB0001938
FooDB IDFDB022753
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID1009
PDB IDNot Available
Wikipedia LinkLisinopril
Chemspider ID4514933
ChEBI ID43755
PubChem Compound ID5362119
Kegg Compound IDD00362
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Corradi HR, Schwager SL, Nchinda AT, Sturrock ED, Acharya KR: Crystal structure of the N domain of human somatic angiotensin I-converting enzyme provides a structural basis for domain-specific inhibitor design. J Mol Biol. 2006 Mar 31;357(3):964-74. Epub 2006 Jan 31.
2. Tashtoush BM, Alali FQ, Najib NM: Liquid chromatographic-mass spectrometric method for quantitative determination of lisinopril in human plasma. Pharmazie. 2004 Jan;59(1):21-4.
3. Swaisland AJ: The pharmacokinetics of co-administered lisinopril and hydrochlorothiazide. J Hum Hypertens. 1991 Dec;5 Suppl 2:69-71.
4. Alves MF, Araujo MC, Juliano MA, Oliveira EM, Krieger JE, Casarini DE, Juliano L, Carmona AK: A continuous fluorescent assay for the determination of plasma and tissue angiotensin I-converting enzyme activity. Braz J Med Biol Res. 2005 Jun;38(6):861-8. Epub 2005 Jun 1.
5. Lanzillo JJ, Stevens J, Dasarathy Y, Yotsumoto H, Fanburg BL: Angiotensin-converting enzyme from human tissues. Physicochemical, catalytic, and immunological properties. J Biol Chem. 1985 Dec 5;260(28):14938-44.
6. Huang J, Xu Y, Liu F, Gao S, Guo Q: Development of a liquid chromatography/tandem mass spectrometry assay for the quantification of lisinopril in human plasma. Rapid Commun Mass Spectrom. 2006;20(2):248-52.
7. Sudoh T, Fujimura A, Shiga T, Tateishi T, Sunaga K, Ohashi K, Ebihara A: Influence of lisinopril on urinary electrolytes excretion after furosemide in healthy subjects. J Clin Pharmacol. 1993 Jul;33(7):640-3.
8. Ranieri G, Andriani A, Lamontanara G, De Cesaris R: Effects of lisinopril and amlodipine on microalbuminuria and renal function in patients with hypertension. Clin Pharmacol Ther. 1994 Sep;56(3):323-30.
9. Haenni A, Reneland R, Andersson PE, Lind L, Lithell H: Skeletal muscle magnesium content is correlated with plasma glucose concentration in patients with essential hypertension treated with lisinopril or bendrofluazide. Am J Hypertens. 2002 Aug;15(8):735-8.
10. Arakawa M, Murata Y, Rikimaru Y, Sasaki Y: Drug-induced isolated visceral angioneurotic edema. Intern Med. 2005 Sep;44(9):975-8.
11. Donohoe JF, Kelly J, Laher MS, Doyle GD: Lisinopril in the treatment of hypertensive patients with renal impairment. Am J Med. 1988 Sep 23;85(3B):31-4.
12. Donohoe JF, Laher M, Doyle GD, Long C, Glover DR, Cooper WD: Lisinopril treatment of hypertension in patients with impaired renal function. Gerontology. 1987;33 Suppl 1:36-41.
13. Yuan AS, Gilbert JD: Time-resolved fluoroimmunoassay for the determination of lisinopril and enalaprilat in human serum. J Pharm Biomed Anal. 1996 May;14(7):773-81.
14. Araujo MC, Melo RI, Del Nery E, Alves MF, Juliano MA, Casarini DE, Juliano L, Carmona AK: Internally quenched fluorogenic substrates for angiotensin I-converting enzyme. J Hypertens. 1999 May;17(5):665-72.
15. Shionoiri H, Shigemasa T, Takasaki I: [Angiotensin-converting enzyme inhibitors: recent therapeutic aspect]. Nihon Rinsho. 1997 Aug;55(8):2067-74.