キナプリル
(3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]azaniumyl]propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylate
基本情報
- CAS
85441-61-8- 標準SMILES
CCOC(=O)[C@H](CCc1ccccc1)[NH2+][C@@H](C)C(=O)N1Cc2ccccc2C[C@H]1C(=O)[O-]- InChIKey
JSDRRTOADPPCHY-HSQYWUDLSA-N- 分子式
- C25H30N2O5
- 平均分子量
- 438.5 g/mol
- 単同位体質量
- 438.21547206
概要
Quinapril is the ethyl ester prodrug of the non-sulfhydryl angiotensin converting enzyme inhibitor quinaprilat. It is used to treat hypertension and heart failure. ACE inhibitors are commonly used as a first line therapy in the treatment of hypertension, along with thiazide diuretics or beta blockers. Quinapril was granted FDA approval on 19 November 1991. A combination tablet with [hydrochlorothiazide] was also approved on 28 December 1999.
名称と識別子
- 優先名称
- (3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]azaniumyl]propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylate
- IUPAC
- (3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]azaniumyl]propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylate
- 現地名
- キナプリル
- 英語名
- Quinapril
- 分子式
- C25H30N2O5
- 分子量
- 438.52
名称と別名
(3S)-2-[(2S)-2-[[(1S)-1-(エトキシカルボニル)-3-フェニルプロピル]アミノ]プロピオニル]-1,2,3,4-テトラヒドロ-3-イソキノリンカルボン酸(3S)-2-[(S)-2-[[(S)-1-(エトキシカルボニル)-3-フェニルプロピル]アミノ]-1-オキソプロピル]-1,2,3,4-テトラヒドロ-3-イソキノリンカルボン酸キナプリルACCUPRILAsigCI-906EctrenACCUPROKoreticACCUPRINQuniaprilQuinapril
名称をさらに表示
PD-109452-2
データベース識別子
- CAS
85441-61-8- PubChem CID
- 40466957
物性
構造計算による物性
- XLogP
- 1.9
- 極性表面積
- 103 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 5
- 回転可能結合数
- 9
- 重原子数
- 32
- 形式電荷
- 0
- 複雑度
- 643
実験および物理化学的性質
LogP3.2
Solubility8.50e-03 g/L
Melting Point
120-130 °C
120 - 130 °C
Physical DescriptionSolid
Dissociation Constants2.8
物理化学的性質
- 融点
- 120 · 120-130°C
- 沸点
- 662 · 662.0±55.0 °C(Predicted)
- 比重(密度)
- 1.217 · 1.217±0.06 g/cm3(Predicted)
- 酸解離定数(Pka)
- 3.39 · 3.39±0.20(Predicted)
- BCS Class
- 1 · 1
- CAS データベース
- 85441 · 85441-61-8(CAS DataBase Reference)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- safety_code
- 22-24/25
化学と産業
薬理情報
Protein BindingQuinapril and the active metabolite quinaprilat are 97% protein bound in plasma.
Pharmacodynamics
Quinapril is a prodrug of an angiotensin converting enzyme (ACE) inhibitor used in the treatment of hypertension or adjunct in the treatment of heart failure. Quinapril has a wide therapeutic window and a long duration of action as it is given in doses of 10-80mg once daily.
Mechanism of Action
Angiotensin II constricts coronary blood vessels and is positively inotropic, which under normal circumstances, would increase vascular resistance and oxygen consumption. This action can eventually lead to myocyte hypertrophy and vascular smooth muscle cell proliferation. Angiotensin II also stimulates production of plasminogen activator inhibitor-1 (PAI-1), increasing the risk of thrombosis. Quinaprilat prevents the conversion of angiotensin I to angiotensin II by inhibition of angiotensin converting enzyme, and also reduces the breakdown of bradykinin. Reduced levels of angiotensin II lead to lower levels of PAI-1, reducing the risk of thrombosis, especially after a myocardial infarction.
Biological Half-LifeThe active metabolite quinaprilat has an elimination half life of 2.3 hours.
Metabolism/MetabolitesQuinapril is de-esterified to the active quinaprilat or dehydrated to form the inactive PD109488. PD109488 can undergo O-deethylation to form another inactive metabolite, PD113413.
Absorption, Distribution and Excretion
Quinapril if 50-80% bioavailable. Quinapril has a Tmax of <1 hour, while quinaprilat has a Tmax of 2.5h. The Cmax of quinaprilat is highly variable but reaches 1526ng/mL with an AUC of 2443ng\*h/mL in healthy males given a 10mg dose. A high fat meal reduces the absorption of quinapril by 25-30%.
Quinaprilat is up to 96% eliminated in the urine. The eliminated metabolites PD109488 and PD113413 account for approximately 6% of a dose of quinapril each. A small fraction of the dose recovered in the urine is accounted for by unmetabolized quinapril.
The mean volume of distribution of quinaprilat is 13.9L.
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