Lisinopril

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Lisinopril
Structural formula of lisinopril
Ball-and-stick model of the lisinopril zwitterion
Chemical structure of lisinopril
Systematic (IUPAC) name
(2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
Clinical data
Pronunciation /laɪˈsɪnəprɪl/, ly-SIN-ə-pril
Trade names Prinivil, Tensopril, Zestril, Hipril
AHFS/Drugs.com monograph
MedlinePlus a692051
Pregnancy
category
Legal status
  • ℞ (Prescription only)
Routes of
administration		 Oral
Pharmacokinetic data
Bioavailability approx. 25%, but wide range between individuals (6 to 60%)
Protein binding 0
Metabolism None
Biological half-life 12 hours
Excretion Eliminated unchanged in urine
Identifiers
CAS Number 83915-83-7
ATC code C09AA03 (WHO)
PubChem CID: 5362119
IUPHAR/BPS 6360
DrugBank APRD00560 YesY
ChemSpider 4514933 YesY
UNII 7Q3P4BS2FD N
KEGG D00362 YesY
ChEBI CHEBI:43755 N
ChEMBL CHEMBL1237 YesY
Synonyms (2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
PDB ligand ID LPR (PDBe, RCSB PDB)
Chemical data
Formula C21H31N3O5
Molecular mass 405.488 g/mol
  • O=C(O)[C@H]2N(C(=O)[C@@H](N[C@H](C(=O)O)CCc1ccccc1)CCCCN)CCC2
  • 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 YesY
  • Key:RLAWWYSOJDYHDC-BZSNNMDCSA-N YesY
 NYesY (what is this?)  (verify)

Lisinopril is a drug of the angiotensin-converting enzyme (ACE) inhibitor class used primarily in treatment of high blood pressure, heart failure, and after heart attacks. It is also used for preventing kidney and eye complications in people with diabetes. Its indications, contraindications, and side effects are as those for all ACE inhibitors.

Lisinopril was the third ACE inhibitor (after captopril and enalapril) and was introduced into therapy in the early 1990s.[2] A number of properties distinguish it from other ACE inhibitors: It is hydrophilic, has a long half-life and tissue penetration, and is not metabolized by the liver.

Medical uses

Lisinopril is typically used for the treatment of hypertension, congestive heart failure, acute myocardial infarction, and diabetic nephropathy.[3]

Contraindications

Treatment with lisinopril should be avoided in the following situations:

Combination of aliskiren and lisinopril is contraindicated in patients with diabetes, and should be avoided in those with creatinine clearance less than 60ml/min. This combination may heighten the hyperkalemic, hypotensive, and nephrotoxic effects of lisinopril (and other ACE inhibitors). Therefore, serum potassium, blood pressure, and serum creatinine should be carefully monitored for all patients on this combination.

File:PDB 1o86 EBI.jpg
Crystal Structure of Human Angiotensin Converting Enzyme in complex with lisinopril.

Adverse effects

Side effects, incidence differs depending on which disease state the patient is being treated for.[1]

People taking lisinopril for the treatment of hypertension may experience the following side effects:

People taking lisinopril for the treatment of acute myocardial infarction may experience the following side effects:

People taking lisinopril for the treatment of heart failure may experience the following side effects:

Special populations

Caution should be used in the following populations, as dose adjustments may be required.

Kidney problems

The dose must be adjusted in those with poor kidney function. Dose adjustments may be required when creatinine clearance is less than or equal to 30mL/min. Since lisinopril is removed by dialysis, dosing changes must also be considered for people on dialysis.[1]

Pregnancy and breastfeeding

Lisinopril has been assigned to pregnancy category D by the FDA. Animal and human data have revealed evidence of lethal harm to the embryo and teratogenicity associated with ACE inhibitors. No controlled data in human pregnancy are available. Birth defects have been associated with use of lisinopril in any trimester. However, there have been reports of death and increased toxicities to the fetus and newly born child with the use of lisinopril in the second and third trimesters. The Zestril brand manufacturer states, "When pregnancy is detected, discontinue Zestril as soon as possible."[1] The manufacturer recommends mothers should not breastfeed while taking this medication because of the lack of safety data that currently exists.[1]

File:003782076lg Lisinopril Lisinopril 40 MG Oral Tablet.jpg
Lisinopril 40-mg oral tablet

Pharmacology

Lisinopril is the lysine-analog of enalapril. Unlike other ACE inhibitors, it is not a prodrug and is excreted unchanged in the urine. In cases of overdosage, it can be removed from circulation by dialysis.[5]

Mechanism of action

Lisinopril is an ACE Inhibitor, meaning it blocks the actions of angiotensin converting enzyme (ACE) in the renin-angiotensin-aldosterone system (RAAS), keeping Angiotensin I from being converted to Angiotensin II. The inhibition of this system causes an overall decrease in blood pressure.[6]

Pharmacokinetics

The following is a summary of lisinopril's pharmacokinetics: [6][7]

Absorption

  • Lisinopril has a poor bioavailability of 25% (Reduced to 16% in people with NYHA Class II-IV heart failure)
  • Time to peak concentration is 7 hours
  • Food has not been shown to affect absorption

Distribution

  • Does not bind to proteins in the blood
  • Lisinopril does not distribute as well in people with NYHA Class II-IV heart failure

Metabolism

  • Lisinopril does not undergo any form of metabolism in the body

Elimination

  • Lisinopril leaves the body completely unchanged in the urine
  • The half-life of the drug is 12 hours. This is increased in people with kidney problems

Brand names

Lisinopril was developed by Merck & Co., and is marketed worldwide as Prinivil or Tensopril, and by AstraZeneca as Zestril. In India, it is marketed by Micro Labs as Hipril. In Ghana, it is marketed as Lisinova by Pharmanova. In the United States, a generic version is available. Like other ACE inhibitors, it is a synthetic functional and structural analog of a peptide derived from the venom of the jararaca, a Brazilian pit viper (Bothrops jararaca).[8] Lisinopril can also be used in conjunction with the diuretic hydrochlorothiazide, and drugs that combine these two medications are available under the brand names Prinzide, Storetic and Lisinova HTZ.

See also

References

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Further reading

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External links

  1. ↑ 1.0 1.1 1.2 1.3 1.4 Lua error in package.lua at line 80: module 'strict' not found.
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  4. ↑ 4.0 4.1 4.2 Product Information: ZESTRIL(R) oral tablet, lisinopril oral tablet. AstraZeneca Pharmaceuticals LP, Wilmington, DE, 2005.
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  6. ↑ 6.0 6.1 Lua error in package.lua at line 80: module 'strict' not found.
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