化合物详情

CAS85441-61-8
分子式C25H30N2O5
分子量438.52 g/mol
非危品

Quinapril is a member of the class of isoquinolines that is (3S)-2-L-alanyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in which the alpha-amino group of the alanyl residue has been substituted by a 1-ethoxycarbonyl-4-phenylbutan-2-yl group (the all-S isomer). A prodrug for quinaprilat (by hydrolysis of the ethyl ester to the corresponding carboxylic acid), it is used as an angiotensin-converting enzyme inhibitor (ACE inhibitor) used (generally as the hydrochloride salt) for the treatment of hypertension and congestive heart failure. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, an antihypertensive agent and a prodrug. It is a tertiary carboxamide, an ethyl ester, a member of isoquinolines and a dicarboxylic acid monoester.

科学粮草官-词典编辑部,修订于:2026-07-06

化合物详情

Toxicity

Toxicity
9
Symptoms
Overdose may lead to severe hypotension. The most common adverse effects observed in controlled clinical trials were dizziness, cough, chest pain, dyspnea, fatigue, and nausea/vomiting.
Toxicity Data
LD<sub>50</sub>=1739mg/kg (orally in mice)
Hepatotoxicity
Likelihood score: E* (unproven but suspected rare cause of clinically apparent liver injury).
Adverse Effects
FDA Safety Alert: In December 2022, quinapril (4 batches) was withdrawn from the market in a voluntary nationwide recall due to nitrosamine impurity. Nitrosamine is a potential carcinogen; in consequence, clinicians should remain cautious while prescribing.
Exposure Routes
Peak plasma concentrations of quinapril occur within one hour following oral administration. The extent of absorption is at least 60%. The rate and extent of quinapril absorption are diminished moderately (approximately 25-30%) when ACCUPRIL tablets are administered during a high-fat meal.
Toxicity Summary
There are two isoforms of ACE: the somatic isoform, which exists as a glycoprotein comprised of a single polypeptide chain of 1277; and the testicular isoform, which has a lower molecular mass and is thought to play a role in sperm maturation and binding of sperm to the oviduct epithelium. Somatic ACE has two functionally active domains, N and C, which arise from tandem gene duplication. Although the two domains have high sequence similarity, they play distinct physiological roles. The C-domain is predominantly involved in blood pressure regulation while the N-domain plays a role in hematopoietic stem cell differentiation and proliferation. ACE inhibitors bind to and inhibit the activity of both domains, but have much greater affinity for and inhibitory activity against the C-domain. Qu...
Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
References: DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation
◉ Effects on Lactation and Breastmilk
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