lisinopril

Also known as Prinivil®, Zestril®, (S)-1-(N(2)-(1-carboxy-3-phenylpropyl)-L-lysyl)-L-proline, lisinopril anhydrous, (S)-1-(N(2)-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-proline, Lisinopril anhydrous, [N2-[(S)-1-CARBOXY-3-phenylpropyl]-L-lysyl-L-proline

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. For high blood pressure it is usually a first-line treatment. It is also used to prevent kidney problems in people with diabetes mellitus. Lisinopril is taken orally (swallowed by mouth). Full effect may take up to four weeks to occur.

Key facts

Drug.KEGG: D00362
Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 432833853
Drug.image: Lisinopril structure.svg
Drug.image_class: skin-invert-image
Drug.alt: Structural formula of lisinopril
Drug.image2: Lisinopril zwitterion 3D ball.png
Drug.image_class2: bg-transparent
Drug.alt2: Ball-and-stick model of the lisinopril zwitterion
Drug.caption: Chemical structure of lisinopril
Drug.pronounce: ,
Drug.tradename: Prinivil, Zestril, Qbrelis, Dapril, others
Drug.MedlinePlus: a692051
Drug.DailyMedID: Lisinopril
Drug.pregnancy_AU: D
Drug.pregnancy_category: not recommended
Drug.routes_of_administration: Oral

via Wikipedia infobox

Chemical data

Formula: C21H31N3O5
Molecular weight: 405.5 g/mol
IUPAC name: (2S)-1-[(2S)-6-azaniumyl-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylate
SMILES: C1C[C@H](N(C1)C(=O)[C@H](CCCC[NH3+])N[C@@H](CCC2=CC=CC=C2)C(=O)O)C(=O)[O-]
InChIKey: RLAWWYSOJDYHDC-BZSNNMDCSA-N
XLogP: -2.2
Polar surface area: 137 Å²
H-bond donors: 3
H-bond acceptors: 6
Formal charge: 0

via PubChem

Research

3,431 papers

Lisinopril-Induced Acute Pancreatitis.American journal of therapeutics · 2019
Lisinopril: a nonsulfhydryl angiotensin-converting enzyme inhibitor.Clinical pharmacy · 1988
[Lisinopril].Medicina (Florence, Italy) · 1990
Lisinopril: a review of its use in congestive heart failure.Drugs · 2000
Lisinopril. A review of its pharmacology and use in the management of the complications of diabetes mellitus.Drugs · 1997

via PubMed

Wikidata facts

Mass: 405.226

Show 5 more facts

chemical formula: C₂₁H₃₁N₃O₅
isomeric SMILES: C1C[C@H](N(C1)C(=O)[C@H](CCCCN)N[C@@H](CCC2=CC=CC=C2)C(=O)O)C(=O)O
canonical SMILES: C1CC(N(C1)C(=O)C(CCCCN)NC(CCC2=CC=CC=C2)C(=O)O)C(=O)O
defined daily dose: 10
Commons category: Lisinopril

Sources (8)

via Wikidata · CC0

~11 min read

Article

18 sections

Contents

Medical uses
Contraindications
Adverse effects
Pregnancy and breastfeeding
Interactions
Dental care
Pharmacology
Mechanism of action
Pharmacokinetics
Absorption
Distribution
Elimination
Chemistry
History
Society and culture
Legal status
References
Further reading

{{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 432833853 | image = Lisinopril structure.svg | image_class = skin-invert-image | width = | alt = Structural formula of lisinopril | image2 = Lisinopril zwitterion 3D ball.png | image_class2 = bg-transparent | width2 = | alt2 = Ball-and-stick model of the lisinopril zwitterion | caption = Chemical structure of lisinopril