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Lisinopril information


Lisinopril
Structural formula of lisinopril
Ball-and-stick model of the lisinopril zwitterion
Chemical structure of lisinopril
Clinical data
Pronunciation/lˈsɪnəprɪl/, 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
  • US DailyMed: Lisinopril
Pregnancy
category
  • AU: D[6]
  • not recommended[7][6]
Routes of
administration
Oral
ATC code
  • C09AA03 (WHO) C09BA03 (WHO) C10BX07 (WHO) C09BB03 (WHO)
Legal status
Legal status
  • CA: ℞-only[9]
  • UK: POM (Prescription only)[10]
  • US: WARNING[8]Rx-only[1][2][3]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailabilityapprox. 25%, but wide range between individuals (6 to 60%)
Protein binding0
MetabolismNone
Elimination half-life12 hours
ExcretionEliminated unchanged in urine
Identifiers
IUPAC name
  • (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
CAS Number
  • 83915-83-7
  • anhydrous: 76547-98-3 checkY
PubChem CID
  • 5362119
IUPHAR/BPS
  • 6360
DrugBank
  • DB00722 checkY
ChemSpider
  • 4514933 checkY
UNII
  • E7199S1YWR
  • anhydrous: 7Q3P4BS2FD checkY
KEGG
  • D00362 checkY
ChEBI
  • CHEBI:43755 ☒N
ChEMBL
  • ChEMBL1237 checkY
PDB ligand
  • LPR (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID6040537 Edit this at Wikidata
ECHA InfoCard100.071.332 Edit this at Wikidata
Chemical and physical data
FormulaC21H31N3O5
Molar mass405.495 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • C1CC(N(C1)C(=O)C(CCCCN)NC(CCC2=CC=CC=C2)C(=O)O)C(=O)O
InChI
  • 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 2021, it was the fourth most commonly prescribed medication in the United States, with more than 88 million prescriptions.[12][13] In July 2016, an oral solution formulation of lisinopril was approved for use in the United States.[7][14]

  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 l "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 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  13. ^ "Lisinopril – Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  14. ^ "Drug Approval Package: Qbrelis (lisinopril)". U.S. Food and Drug Administration (FDA). 29 July 2016. Retrieved 5 August 2020.

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