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Record Information
Version3.6
Creation Date2006-05-18 09:03:34 UTC
Update Date2013-05-13 23:04:19 UTC
HMDB IDHMDB01938
Secondary Accession NumbersNone
Metabolite Identification
Common NameLisinopril
DescriptionOne of the Angiotensin-converting enzyme inhibitors (ACE inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure. -- Pubchem; Lisinopril is a drug of the angiotensin converting enzyme (ACE) inhibitor class that is primarily used in treatment of hypertension, congestive heart failure and heart attacks. Historically, lisinopril was the third ACE inhibitor, after captopril and enalapril that was introduced into therapy in early 1990s. Lisinopril has a number of properties that distinguish it from other ACE inhibitors: it is hydrophilic, has long half life and tissue penetration and is not metabolized by the liver. -- Wikipedia; Lisinopril is solely excreted in urine in the unchanged form. Elimination of the drug depends on glomerular filtration and tubular excretion. Rate of lisinopril elimination decreases with old age and kidney or heart failure. There is a relation between creatinine and lisinopril clearance. With prolonged therapy dose reduction can be necessary to avoid accumulation. -- Wikipedia.
Structure
Thumb
Synonyms
  1. Acerbon
  2. Acercomp
  3. Alapril
  4. Carace
  5. Cipral
  6. Cipril
  7. Coric
  8. Inhibril
  9. Inopril
  10. Linopril
  11. Linvas
  12. Lipril
  13. Lisinal
  14. Lisinopril
  15. Lisinopril anhydrous
  16. Lisinoprilum
  17. Lisipril
  18. Lisoril
  19. Lispril
  20. Loril
  21. LPR
  22. Lysinopril
  23. Noperten
  24. Novatec
  25. Presiten
  26. Prinil
  27. Prinivil
  28. Sinopril
  29. Sinopryl
  30. Tensopril
  31. Tensyn
  32. Tersif
  33. Vivatec
  34. Zestril
Chemical FormulaC21H31N3O5
Average Molecular Weight405.4879
Monoisotopic Molecular Weight405.226371117
IUPAC Name(2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
Traditional Namelisinopril
CAS Registry Number83915-83-7
SMILES
NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@H]1C(O)=O
InChI Identifier
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
InChI KeyRLAWWYSOJDYHDC-BZSNNMDCSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassPeptides
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • dipeptide(ChEBI)
Substituents
  • Alpha Amino Acid Or Derivative
  • Carboxamide Group
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • N Substituted Alpha Amino Acid
  • Phenylpropylamine
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
  • Pyrrolidine
  • Pyrrolidine Carboxylic Acid
  • Secondary Aliphatic Amine (Dialkylamine)
  • Tertiary Carboxylic Acid Amide
Direct ParentPeptides
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility97 mg/mLNot Available
LogPNot AvailableNot 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 Area132.96ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity107.37ChemAxon
Polarizability43.35ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Kidney
  • Pancreas
  • Skeletal Muscle
  • Testes
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022753
KNApSAcK IDNot Available
Chemspider ID4514933
KEGG Compound IDD00362
BioCyc IDCPD-7021
BiGG IDNot Available
Wikipedia LinkLisinopril
NuGOwiki LinkHMDB01938
Metagene LinkHMDB01938
METLIN ID1009
PubChem Compound5362119
PDB IDLPR
ChEBI ID43755
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. Pubmed: 16476442
  2. 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. Pubmed: 15933779
  3. 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. Pubmed: 14964416
  4. Swaisland AJ: The pharmacokinetics of co-administered lisinopril and hydrochlorothiazide. J Hum Hypertens. 1991 Dec;5 Suppl 2:69-71. Pubmed: 1665181
  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. Pubmed: 2999099
  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. Pubmed: 16345121
  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. Pubmed: 8396158
  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. Pubmed: 7924128
  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. Pubmed: 12160198
  10. Arakawa M, Murata Y, Rikimaru Y, Sasaki Y: Drug-induced isolated visceral angioneurotic edema. Intern Med. 2005 Sep;44(9):975-8. Pubmed: 16258215
  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. Pubmed: 2844084
  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. Pubmed: 2831115
  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. Pubmed: 8809701
  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. Pubmed: 10403610
  15. Shionoiri H, Shigemasa T, Takasaki I: [Angiotensin-converting enzyme inhibitors: recent therapeutic aspect] Nippon Rinsho. 1997 Aug;55(8):2067-74. Pubmed: 9284425

Enzymes

General function:
Involved in metallopeptidase activity
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 vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety
Gene Name:
ACE
Uniprot ID:
P12821
Molecular weight:
149713.7
General function:
Involved in serine-type endopeptidase inhibitor activity
Specific function:
Angiotensin 1-7 is a ligand for the G-protein coupled receptor MAS1. Has vasodilator and antidiuretic effects. Has an antithrombotic effect that involves MAS1-mediated release of nitric oxide from platelets
Gene Name:
AGT
Uniprot ID:
P01019
Molecular weight:
53153.7