{{drugbox | IUPAC_name = N2-1-L-lysyl-L-proline |synonyms = (2S)-1-[(2S)-6-amino-2-{2amino}hexanoyl]pyrrolidine-2-carboxylic acid | image = Lisinopril.svg | CAS_number = 83915-83-7 | ChemSpiderID = 4514933 | ATC_prefix = C09 | ATC_suffix = AA03 | ATC_supplemental = | PubChem = 5362119 | DrugBank = APRD00560 | C=21 | H=31 | N=3 | O=5 | molecular_weight = 405.488 g/mol | smiles = NCCCC3(N4(CCc1ccccc1)C(=O)O)C(=O)N1CCC51C(=O)O | bioavailability = approx. 25%, but wide range between individuals (6 to 60%) | protein_bound = 0 | metabolism = None | elimination_half-life = 12 hours | excretion = Eliminated unchanged in Urine | pregnancy_category = D - teratogenic | legal_status = Rx-only | routes_of_administration = PO }} Lisinopril (lye-SIN-o-pril) is a drug of the angiotensin converting enzyme (ACE) inhibitor class that is primarily used in treatment of hypertension, congestive heart failure, heart attacks and also in preventing renal and retinal complications of diabetes. It has been compared with omapatrilat which is of similar function.
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{{drugbox | IUPAC_name = N2-1-L-lysyl-L-proline |synonyms = (2S)-1-[(2S)-6-amino-2-{2amino}hexanoyl]pyrrolidine-2-carboxylic acid | image = Lisinopril.svg | CAS_number = 83915-83-7 | ChemSpiderID = 4514933 | ATC_prefix = C09 | ATC_suffix = AA03 | ATC_supplemental = | PubChem = 5362119 | DrugBank = APRD00560 | C=21 | H=31 | N=3 | O=5 | molecular_weight = 405.488 g/mol | smiles = NCCCC3(N4(CCc1ccccc1)C(=O)O)C(=O)N1CCC51C(=O)O | bioavailability = approx. 25%, but wide range between individuals (6 to 60%) | protein_bound = 0 | metabolism = None | elimination_half-life = 12 hours | excretion = Eliminated unchanged in Urine | pregnancy_category = D - teratogenic | legal_status = Rx-only | routes_of_administration = PO }} Lisinopril (lye-SIN-o-pril) is a drug of the angiotensin converting enzyme (ACE) inhibitor class that is primarily used in treatment of hypertension, congestive heart failure, heart attacks and also in preventing renal and retinal complications of diabetes. It has been compared with omapatrilat which is of similar function.
Historically, lisinopril was the third ACE inhibitor, after captopril and enalapril, and was introduced into therapy in the early 1990s. Lisinopril has a number of properties that distinguish it from other ACE inhibitors: it is hydrophilic, has long half-life and tissue penetration and is not metabolized by the liver.
Pharmacology
Lisinopril is the lysine-analog of enalapril. Unlike other ACE inhibitors, lisinopril is not a prodrug and is excreted unchanged in the urine. In cases of overdosage, it can be removed from circulation by dialysis.
Pharmacokinetics and Metabolism
Adult Patients: Following oral administration of PRINIVIL, peak serum concentrations of lisinopril occur within about 7 hours, although there was a trend to a small delay in time taken to reach peak serum concentrations in acute myocardial infarction patients. Declining serum concentrations exhibit a prolonged terminal phase which does not contribute to drug accumulation. This terminal phase probably represents saturable binding to ACE and is not proportional to dose. Lisinopril does not appear to be bound to other serum proteins.
Lisinopril does not undergo metabolism and is excreted unchanged entirely in the urine. Based on urinary recovery, the mean extent of absorption of lisinopril is approximately 25 percent, with large inter-subject variability (6-60 percent) at all doses tested (5-80 mg). Lisinopril absorption is not influenced by the presence of food in the gastrointestinal tract. The absolute bioavailability of lisinopril is reduced to about 16 percent in patients with stable NYHA Class II-IV congestive heart failure, and the volume of distribution appears to be slightly smaller than that in normal subjects.
