Lisinopril

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Lisinopril

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Catalog Number	PR76547983
CAS	76547-98-3
Description	Lisinopril is an angiotensin converting enzyme inhibitor (ACEI) used to treat hypertension, heart failure, and myocardial infarction. Lisinopril and [captopril] are the only ACEIs that are not prodrugs. It functions by inhibition of angiotensin converting enzyme as well as the renin angiotensin aldosterone system.
Synonyms	Zestril; Lisinopril anhydrous; Lysinopril; Tensopril
IUPAC Name	(2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
Molecular Weight	405.5
Molecular Formula	C21H31N3O5
InChI	RLAWWYSOJDYHDC-BZSNNMDCSA-N
InChI Key	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
Drug Categories	ACE Inhibitors and Calcium Channel Blockers; ACE Inhibitors and Diuretics; Agents Acting on the Renin-Angiotensin System; Agents causing angioedema; Agents causing hyperkalemia; Amino Acids, Peptides, and Proteins; Angiotensin-Converting Enzyme Inhibitors; Antihypertensive Agents; Antihypertensive Agents Indicated for Hypertension; Cardiotonic Agents; Cardiovascular Agents; Compounds used in a research, industrial, or household setting; Dipeptides; Drugs causing inadvertant photosensitivity; Drugs that are Mainly Renally Excreted; Enzyme Inhibitors; Hypotensive Agents; Lipid Modifying Agents; Oligopeptides; Peptides; Photosensitizing Agents; Protease Inhibitors; Protective Agents
Drug Interactions	Abacavir-Lisinopril may decrease the excretion rate of Abacavir which could result in a higher serum level. Abaloparatide-The risk or severity of adverse effects can be increased when Lisinopril is combined with Abaloparatide. Acebutolol-Lisinopril may increase the hypotensive activities of Acebutolol. Aceclofenac-The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Lisinopril. Acemetacin-The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acemetacin is combined with Lisinopril.
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
Type	Small Molecule
Therapeutic Category	Antihypertensive

Pharmacology

Indications

Lisinopril is a medication indicated for several cardiovascular conditions. It is employed in the management of acute myocardial infarction and hypertension in patients aged six years and older. Additionally, it serves as an adjunct therapy in the treatment of heart failure. Lisinopril is also available in a combination formulation with hydrochlorothiazide specifically for the treatment of hypertension.

Pharmacodynamics

As an angiotensin-converting enzyme (ACE) inhibitor, Lisinopril effectively reduces vascular resistance by inhibiting the conversion of angiotensin I to angiotensin II, thereby modulating the renin-angiotensin-aldosterone system. Unlike some other ACE inhibitors, Lisinopril is not a prodrug, meaning it is active in its administered form. It exhibits a broad therapeutic index and maintains efficacy over a prolonged period, typically administered in dosages ranging from 10 to 80 mg daily.

Absorption

Lisinopril is characterized by an oral bioavailability that ranges from 6% to 60%, with an average bioavailability of 25%. The maximum concentration (Cmax) of Lisinopril reaches approximately 58 ng/mL, with a time to reach maximum concentration (Tmax) of 6 to 8 hours post-administration. Notably, the absorption of Lisinopril is not influenced by the presence of food.

Metabolism

Lisinopril is not metabolized and is excreted as the unchanged drug.

Mechanism of Action

Lisinopril is an angiotensin-converting enzyme inhibitor (ACEI) that plays a crucial role in mitigating cardiovascular strain by inhibiting the conversion of angiotensin I to angiotensin II. This inhibition is significant because angiotensin II typically constricts coronary blood vessels and increases the workload and oxygen demand of the heart, which, over time, can lead to myocyte hypertrophy and the proliferation of vascular smooth muscle cells. By preventing these processes, lisinopril effectively reduces myocyte hypertrophy and smooth muscle cell proliferation in patients. Additionally, lisinopril increases the levels of bradykinin, which contributes to its vasodilatory effects, further benefiting patients by relaxing blood vessels. Moreover, lisinopril also impedes the conversion of angiotensin by renin into angiotensin I, offering a comprehensive approach to managing conditions associated with elevated angiotensin activity.

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