レミキレン
Remikiren
基本情報
- CAS
126222-34-2- 標準SMILES
CC(C)(C)S(=O)(=O)C[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)C1CC1- InChIKey
UXIGZRQVLGFTOU-VQXQMPIVSA-N- 分子式
- C33H50N4O6S
- 平均分子量
- 630.8 g/mol
- 単同位体質量
- 630.3451065
概要
Remikiren is an L-histidine derivative that is L-histidine in which one of the amino hydrogens is replaced by a (2S)-2-[(2-methylpropane-2-sulfonyl)methyl]-3-phenylpropanoyl group and the carboxy group is replaced by a [(2S,3R,4S)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]amino group. It is a renin inhibitor which was under development for the treatment of hypertension (now discontinued). It has a role as an EC 3.4.23.15 (renin) inhibitor, a vasodilator agent, an antihypertensive agent and a peptidomimetic. It is a secondary carboxamide, a diol, a sulfone, a member of cyclopropanes and a L-histidine derivative.
名称と識別子
- 優先名称
- Remikiren
- IUPAC
- (2S)-2-benzyl-3-tert-butylsulfonyl-N-[(2S)-1-[[(2S,3R,4S)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]propanamide
- 現地名
- レミキレン
- 英語名
- Remikiren
- 分子式
- C33H50N4O6S
- 分子量
- 630.84
名称と別名
Remikiren126222-34-2Ro 42-5892Ro-42-5892remikireneremikirenoremikirenumLC7FBL96A4CHEBI:8803DTXSID60155121(S)-alpha-((S)-alpha-((t-butylsulfonyl)methyl)hydrocinnamamido)-N-((1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl)imidazole-4-propionamide(alphaS)-alpha-((alphaS)-alpha-((tert-Butylsulfonyl)methyl)hydrocinnamamido)-N-((1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl)imidazole-4-propionamide
名称をさらに表示
レミキレン4-[(S)-2-[[(S)-1-オキソ-2-(tert-ブチルスルホニルメチル)-3-フェニルプロピル]アミノ]-3-オキソ-3-[[(1S,2R,3S)-1-(シクロヘキシルメチル)-3-シクロプロピル-2,3-ジヒドロキシプロピル]アミノ]プロピル]-1H-イミダゾール(2S)-2-[(2S)-2-ベンジル-3-(2-メチルプロパン-2-スルホニル)プロパンアミド]-N-[(2S,3R,4S)-1-シクロヘキシル-4-シクロプロピル-3,4-ジヒドロキシブタン-2-イル]-3-(1H-イミダゾール-4-イル)プロパンアミド(αS)-α-[[(S)-2-(tert-ブチルスルホニルメチル)-1-オキソ-3-フェニルプロピル]アミノ]-N-[(1S,2R,3S)-1-(シクロヘキシルメチル)-3-シクロプロピル-2,3-ジヒドロキシプロピル]-1H-イミダゾール-4-プロパンアミドD09038C07465AC1O44IV(αS)-α-[[(S)-2-(tert-Butylsulfonylmethyl)-1-oxo-3-phenylpropyl]amino]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-1H-imidazole-4-propanamide
物性
構造計算による物性
- XLogP
- 4
- 極性表面積
- 170 Ų
- 水素結合供与体数
- 5
- 水素結合受容体数
- 7
- 回転可能結合数
- 16
- 重原子数
- 44
- 形式電荷
- 0
- 複雑度
- 1,030
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.75
物理化学的性質
- 沸点
- 970.204 · 970.204±65.00 °C(Press: 760.00 Torr)(predicted)
- 比重(密度)
- 1.241 · 1.241±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- 酸解離定数(Pka)
- 13.378 · 13.378±0.46(predicted)
化学と産業
薬理情報
ATC CodeC - Cardiovascular system
Protein Binding83%
Pharmacodynamics
Remikiren is an orally available renin inhibitor with an established blood pressure-lowering effect in patients with essential hypertension. No data are available on the renal effects of remikiren in humans. In patients with essential hypertension, a single oral dose of remikiren can induce a renal vasodilation, without affecting the GFR and despite a significant decrease in blood pressure. This systemic and renal hemodynamic response is more pronounced in case of a more activated renin-angiotensin system.
Mechanism of ActionSeveral in vivo experiments have shown that remikiren is specific for renin and does not decrease arterial pressure by an unrelated mechanism.
MeSH Pharmacological Classification
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES).
Absorption, Distribution and ExcretionAbsorbed following oral administration.
応用分野
使用Remikiren, is a renin inhibitor under development for the treatment of hypertension (high blood pressure).
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