Lisinopril

Lisinopril
(IUPAC) ime
N2-[(1S)-1-karboksi-3-fenilpropil]-L-lizil-L-prolin
Klinički podaci
Robne marke Prinivil, Tensopril, Zestril, Hipril
AHFS/Drugs.com Monografija
MedlinePlus a692051
Identifikatori
CAS broj 83915-83-7
ATC kod C09AA03
PubChem[1][2] 5362119
DrugBank APRD00560
ChemSpider[3] 4514933
UNII 7Q3P4BS2FD DaY
KEGG[4] D00362 DaY
ChEBI CHEBI:43755 DaY
ChEMBL[5] CHEMBL1237 DaY
Hemijski podaci
Formula C21H31N3O5 
Mol. masa 405,488 g/mol
SMILES eMolekuli & PubHem
Sinonimi (2S)-1-[(2S)-6-amino-2[(1S)-1-karboksi-3-fenilpropil]amino}heksanoil]pirolidin-2-karboksilna kiselina
Farmakokinetički podaci
Bioraspoloživost oko 25%
Vezivanje za proteine plazme 0
Metabolizam None
Poluvreme eliminacije 12 sata
Izlučivanje Eliminiše se nepromenje u urinu
Farmakoinformacioni podaci
Trudnoća ?
Pravni status ℞ Prescription only
Način primene Oralno

Lisinopril je lek klase inhibitora angiotenzin konvertujućeg enzima (ACE). On se prvenstveno koristi u tretmanu hipertenzije, zatajenja srca, i srčanog udara, kao i za sprečavanje renalnih i retinalnih komplikacija uzrokovanih dijabetesom. Njegove indikacije, kontraindikacije i nuspojave su tipične za sve ACE inhibitore.

Istorijski, lisinopril je bio treći ACE inhibitor (nakon kaptoprila i enalaprila) i uveden je u upotrebu tokm ranih 1990-tih.[6]

Osobine

Osobina Vrednost
Broj akceptora vodonika 7
Broj donora vodonika 4
Broj rotacionih veza 12
Particioni koeficijent[7] (ALogP) -3,7
Rastvorljivost[8] (logS, log(mol/L)) -4,2
Polarna površina[9] (PSA, Å2) 132,9

Reference

  1. ↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519.  edit
  2. ↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1. 
  3. ↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846.  edit
  4. ↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H. 
  5. ↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594.  edit
  6. ↑ Patchett A, Harris E, Tristram E, Wyvratt M, Wu M, Taub D, Peterson E, Ikeler T, ten Broeke J, Payne L, Ondeyka D, Thorsett E, Greenlee W, Lohr N, Hoffsommer R, Joshua H, Ruyle W, Rothrock J, Aster S, Maycock A, Robinson F, Hirschmann R, Sweet C, Ulm E, Gross D, Vassil T, Stone C (1980). „A new class of angiotensin-converting enzyme inhibitors”. Nature 288 (5788): 280–3. DOI:10.1038/288280a0. PMID 6253826. 
  7. ↑ Ghose, A.K., Viswanadhan V.N., and Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A 102: 3762-3772. DOI:10.1021/jp980230o. 
  8. ↑ Tetko IV, Tanchuk VY, Kasheva TN, Villa AE. (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488-1493. DOI:10.1021/ci000392t. PMID 11749573.  edit
  9. ↑ Ertl P., Rohde B., Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714-3717. DOI:10.1021/jm000942e. PMID 11020286.  edit

Literatura

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