基本情報
- 標準SMILES
CC(C)COCC(CN(Cc1ccccc1)c1ccccc1)N1CCCC1- InChIKey
UIEATEWHFDRYRU-UHFFFAOYSA-N- 分子式
- C24H34N2O
- 平均分子量
- 366.5 g/mol
- 単同位体質量
- 366.26711371
概要
Bepridil is a tertiary amine in which the substituents on nitrogen are benzyl, phenyl and 3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl. It has a role as a vasodilator agent, an antihypertensive agent, an anti-arrhythmia drug and a calcium channel blocker. It is a tertiary amine and a member of pyrrolidines.
名称と識別子
- 優先名称
- Bepridil
- IUPAC
- N-benzyl-N-[3-(2-methylpropoxy)-2-pyrrolidin-1-ylpropyl]aniline
- 現地名
- ベプリジル
- 英語名
- BEPRIDIL
- 分子式
- C24H34N2O
- 分子量
- 366.54
名称と別名
名称をさらに表示
データベース識別子
- CAS
49571-04-2、64706-54-3- PubChem CID
- 2351
- DTXSID
DTXSID3022663- ChEMBL
CHEMBL1008- ChEBI
CHEBI:3061- UNII
- 755BO701MA
- EC Number
- 256-384-7
- Nikkaji
- J19.767J
物性
構造計算による物性
- XLogP
- 5.3
- 極性表面積
- 15.7 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 10
- 重原子数
- 27
- 形式電荷
- 0
- 複雑度
- 382
実験および物理化学的性質
Solubility
Slightly soluble
6.55e-03 g/L
物理化学的性質
- 沸点
- 0.1 · bp0.1 184°; bp0.5 192°
- 比重(密度)
- 1.0392 · 1.0392 (rough estimate)
- 屈折率
- 20 · nD20 1.5538
- 貯蔵温度
- 2 · 2-8°C
- 酸解離定数(Pka)
- 9.21 · 9.21±0.20(Predicted)
- 水溶解度
- 7.43 g/L · 7.43g/L(37℃)
安全と法規制
毒性情報
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
bepridil
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
安全データ
- 注意喚起語
- 警告
- 危険有害性情報
- コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H302
化学と産業
薬理情報
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Pharmacodynamics
Bepridil is a calcium channel blocker that has well characterized anti-anginal properties and known but poorly characterized type 1 anti-arrhythmic and anti-hypertensive properties. It is not related chemically to other calcium channel blockers such as diltiazem hydrochloride, nifedipine and verapamil hydrochloride.
Mechanism of Action
Bepridil has inhibitory effects on both the slow calcium (L-type) and fast sodium inward currents in myocardial and vascular smooth muscle, interferes with calcium binding to calmodulin, and blocks both voltage and receptor operated calcium channels. Bepridil inhibits the transmembrane influx of calcium ions into cardiac and vascular smooth muscle. This has been demonstrated in isolated myocardial and vascular smooth muscle preparations in which both the slope of the calcium dose response curve and the maximum calcium-induced inotropic response were significantly reduced by bepridil. In cardiac myocytes <i>in vitro</i>, bepridil was shown to be tightly bound to actin. Bepridil regularly reduces heart rate and arterial pressure at rest and at a given level of exercise by dilating peripheral arterioles and reducing total peripheral resistance (afterload) against which the heart works.
MeSH Pharmacological Classification
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
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.
A class of drugs that act by selective inhibition of calcium influx through cellular membranes.
Drugs used to cause dilation of the blood vessels.
応用分野
用途カルシウム拮抗薬（Ⅳ群薬）抗不整脈薬
上流・下流製品情報
上流原料
サプライヤー13 社
補足説明
定義ChEBI: A tertiary amine in which the substituents on nitrogen are benzyl, phenyl and 3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl.
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