Human Metabolome Database Version 3.5

Showing metabocard for Lisinopril (HMDB01938)

Record Information
Version 3.5
Creation Date 2006-05-18 03:03:34 -0600
Update Date 2013-05-13 17:04:19 -0600
HMDB ID HMDB01938
Secondary Accession Numbers None
Metabolite Identification
Common Name Lisinopril
Description One 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C21H31N3O5
Average Molecular Weight 405.4879
Monoisotopic Molecular Weight 405.226371117
IUPAC Name (2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
Traditional IUPAC Name lisinopril
CAS Registry Number 83915-83-7
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 Key RLAWWYSOJDYHDC-BZSNNMDCSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptides
Sub Class N/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 Parent Peptides
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility 97 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.22 g/L ALOGPS
LogP -1.23 ALOGPS
LogP -3.1 ChemAxon
LogS -3.27 ALOGPS
pKa (strongest acidic) 3.17 ChemAxon
pKa (strongest basic) 10.21 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 132.96 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 107.37 ChemAxon
Polarizability 43.35 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location
  • Skeletal Muscle
  • Pancreas
  • Testes
  • Kidney
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022753
KNApSAcK ID Not Available
Chemspider ID 4514933 Link_out
KEGG Compound ID D00362 Link_out
BioCyc ID CPD-7021 Link_out
BiGG ID Not Available
Wikipedia Link Lisinopril Link_out
NuGOwiki Link HMDB01938 Link_out
Metagene Link HMDB01938 Link_out
METLIN ID 1009 Link_out
PubChem Compound 5362119 Link_out
PDB ID LPR Link_out
ChEBI ID 43755 Link_out
References
Synthesis Reference Not 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 Link_out
  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. Pubmed: 14964416 Link_out
  3. Swaisland AJ: The pharmacokinetics of co-administered lisinopril and hydrochlorothiazide. J Hum Hypertens. 1991 Dec;5 Suppl 2:69-71. Pubmed: 1665181 Link_out
  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. Pubmed: 15933779 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  15. Shionoiri H, Shigemasa T, Takasaki I: [Angiotensin-converting enzyme inhibitors: recent therapeutic aspect] Nippon Rinsho. 1997 Aug;55(8):2067-74. Pubmed: 9284425 Link_out

Enzymes
Name: Angiotensin-converting enzyme
Reactions: Not Available
Gene Name: ACE
Uniprot ID: P12821 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Angiotensinogen
Reactions: Not Available
Gene Name: AGT
Uniprot ID: P01019 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA