Lisinopril (CHEM035280)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:37:54 UTC
Update Date2016-11-09 01:21:17 UTC
Accession NumberCHEM035280
Identification
Common NameLisinopril
ClassSmall Molecule
DescriptionLisinopril is an angiotensin converting enzyme inhibitor (ACEI) used to treat hypertension, heart failure, and myocardial infarction. Lisinopril and are the only ACEIs that are not prodrugs. It functions by inhibition of angiotensin converting enzyme as well as the renin angiotensin aldosterone system. ACEIs are commonly used as a first line therapy in the treatment of hypertension, along with thiazide diuretics or beta blockers. Lisinopril was granted FDA approval on 29 December 1987.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9344000000-3673a7191e97a0ee02e0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f6x-9201340000-bc9644b3a3a4109f3722Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-0900500000-85d2bfa23ac02fce017dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-03di-0900000000-b4cd463dbaeec149b805Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-c2a4ab9f5fb48e5480bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4r-0194100000-d9a47a283478b88bb101Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9040000000-8d6d4ae6ba18da11e336Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-77e20f7eb799eea58ab0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-01q0-0940000000-116994867a4e2c649c00Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-01q0-0940000000-116994867a4e2c649c00Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9120000000-fd2acaa1eae37a6f7ba6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2010900000-67e85126826eedd63b6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-053r-9052300000-d651e557fe1ae7eac452Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w29-0119600000-219bea00e0a247bc0888Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2429100000-404746794cb47e7eb6fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3920000000-b1093c7b1913ec8ec8d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0002900000-ce436e39fbead59af3f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ik9-3933500000-a236ac37e133779ee0acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-8910000000-db165b4504f7321c51e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06ri-0229300000-236b576cdfc8112530c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xu-4497000000-ad2ca7e02728a51b0051Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9760000000-517501fe175444669d72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0002900000-a76c25515295bb79175bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0901-2395300000-cc32f663c74e5f0f3306Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9110000000-ccd25ccd5c2ff94948b4Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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.