Lisinopril

Lisinopril
Structural formula of lisinopril
Ball-and-stick model of the lisinopril zwitterion
Chemical structure of lisinopril
Clinical data
Pronunciation/laɪˈsɪnəprɪl/, ly-SIN-ə-pril
Trade namesPrinivil,[1] Zestril,[2] Qbrelis,[3] Dapril,[4] others[5]
Other names(2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
AHFS/Drugs.comMonograph
MedlinePlusa692051
License data
Pregnancy
category
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityapprox. 25%, but wide range between individuals (6 to 60%)
Protein binding0
MetabolismNone
Elimination half-life12 hours
ExcretionEliminated unchanged in urine
Identifiers
  • (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.071.332 Edit this at Wikidata
Chemical and physical data
FormulaC21H31N3O5
Molar mass405.495 g·mol−1
3D model (JSmol)
  • C1CC(N(C1)C(=O)C(CCCCN)NC(CCC2=CC=CC=C2)C(=O)O)C(=O)O
  • 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 checkY
  • Key:RLAWWYSOJDYHDC-BZSNNMDCSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Lisinopril is a medication belonging to the drug class of angiotensin-converting enzyme (ACE) inhibitors and is used to treat hypertension (high blood pressure), heart failure, and heart attacks.[7] For high blood pressure it is usually a first-line treatment. It is also used to prevent kidney problems in people with diabetes mellitus.[7] Lisinopril is taken orally (swallowed by mouth).[7] Full effect may take up to four weeks to occur.[7]

Common side effects include headache, dizziness, feeling tired, cough, nausea, and rash.[7] Serious side effects may include low blood pressure, liver problems, hyperkalemia (high blood potassium), and angioedema.[7] Use is not recommended during the entire duration of pregnancy as it may harm the baby.[7] Lisinopril works by inhibiting the renin–angiotensin–aldosterone system.[7]

Lisinopril was patented in 1978 and approved for medical use in the United States in 1987.[7][11] It is available as a generic medication.[7] In 2022, it was the third most commonly prescribed medication in the United States, with more than 82 million prescriptions.[12][13] It is available in combination with amlodipine (as lisinopril/amlodipine) and in combination with hydrochlorothiazide (as lisinopril/hydrochlorothiazide).

  1. ^ a b Cite error: The named reference Prinivil FDA Label was invoked but never defined (see the help page).
  2. ^ a b "Zestril- lisinopril tablet". DailyMed. 31 October 2019. Retrieved 5 August 2020.
  3. ^ a b "Qbrelis- lisinopril solution". DailyMed. 31 March 2020. Retrieved 5 August 2020.
  4. ^ "Dapril". Drugs.com. Drugsite Trust. Retrieved 13 August 2021.
  5. ^ Cite error: The named reference Brands was invoked but never defined (see the help page).
  6. ^ a b "Lisinopril Use During Pregnancy". Drugs.com. 22 October 2019. Retrieved 27 February 2020.
  7. ^ a b c d e f g h i j k "Lisinopril Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 23 December 2018.
  8. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  9. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  10. ^ "Summary of Product Characteristics (SmPC) – (emc)". Lisinopril 10mg Tablet. 13 November 2019. Archived from the original on 28 February 2020. Retrieved 27 February 2020.
  11. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 467. ISBN 978-3-527-60749-5.
  12. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  13. ^ "Lisinopril Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.