基本情報
- CAS
62658-63-3- 標準SMILES
Cc1cc2c(OCC(CNC(C)(C)C)OC(=O)c3ccccc3)cccc2[nH]1- InChIKey
UUOJIACWOAYWEZ-UHFFFAOYSA-N- 分子式
- C23H28N2O3
- 平均分子量
- 380.5 g/mol
- 単同位体質量
- 380.20999276
概要
1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate is a methylindole that is 2-methyl-1H-indol-4-ol in which the hydrogen of the hydroxy group is replaced by a 2-(benzoyloxy)-3-(tert-butylamino)propyl group. It is an aromatic ether, a benzoate ester, a methylindole and a secondary amino compound.
名称と識別子
- 優先名称
- Bopindolol
- IUPAC
- [1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl] benzoate
- 現地名
- ボピンドロール
- 英語名
- Bopindolol
- 分子式
- C23H28N2O3
- 分子量
- 380.48
名称と別名
BOPINDOLOL62658-63-3(+-)-BopindololBopindololumDTXSID6022684KT304VZO57DTXCID4026842-Propanol, 1-((1,1-dimethylethyl)amino)-3-((2-methyl-1H-indol-4-yl)oxy)-, benzoate (ester), (+-)-RefChem:569816CHEBI:76749C07AA171-(tert-butylamino)-3-((2-methylindo)-4-yl)-2-propanol benzoate
名称をさらに表示
(±)-ボピンドロールrac-(R*)-1-(tert-ブチルアミノ)-3-[(2-メチル-1H-インドール-4-イル)オキシ]-2-ベンゾイルオキシプロパンRAC ボピンドロールボピンドロール1-(tert-ブチルアミノ)-3-[(2-メチル-1H-インドール-4-イル)オキシ]プロパン-2-イル ベンゾアート1-(tert-ブチルアミノ)-3-[(2-メチル-1H-インドール-4-イル)オキシ]-2-ベンゾイルオキシプロパンBopindolol USP/EP/BP2-[(1,1-Dimethylethyl)amino]-1-{[(2-methyl-1H-indol-4-yl)oxy]methyl}ethyl benzoate1-[(1,1-DiMethylethyl)aMino]-3-[(2-Methyl-1H-indol-4-yl)oxy]-2-propanol 2-Benzoate2-Propanol, 1-[(1,1-dimethylethyl)amino]-3-[(2-methyl-1H-indol-4-yl)oxy]-, 2-benzoate2-PROPANOL, 1-[(1,1-DIMETHYLETHYL)AMINO]-3-[(2-METHYL-1H-INDOL-4-YL)OXY]-, BENZOATE (ESTER)
物性
構造計算による物性
- XLogP
- 4.7
- 極性表面積
- 63.4 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 4
- 回転可能結合数
- 9
- 重原子数
- 28
- 形式電荷
- 0
- 複雑度
- 499
実験および物理化学的性質
Melting Point
152–153 [malonate salt]
152 - 153 °C
Physical DescriptionSolid
物理化学的性質
- 融点
- 117 · 117-120°C
- 沸点
- 557 · 557.0±50.0 °C(Predicted)
- 比重(密度)
- 1.143 · 1.143±0.06 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · Hygroscopic, -20°C Freezer, Under Inert Atmosphere
- 溶解性
- クロロホルム（微量）、DMSO（微量）、メタノール（微量、加温）
- 酸解離定数(Pka)
- 17.59 · 17.59±0.30(Predicted)
- 外見
- 個体
- 色
- ホワイト～ペールベージュ
化学的性質
化学的特性Off-White to pale Yellow Solid
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
- 毒性
- LD50 i.v. in mice: 17 mg/kg (Troxler, Seemann, 1977)
化学と産業
薬理情報
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Pharmacodynamics
Bopindolol is a prodrug of pindolol. Pindolol is a non-selective beta-adrenergic antagonist (beta-blocker) which possesses intrinsic sympathomimetic activity (ISA) in therapeutic dosage ranges but does not possess quinidine-like membrane stabilizing activity. Pindolol impairs AV node conduction and decreases sinus rate and may also increase plasma triglycerides and decrease HDL-cholesterol levels. Pindolol is nonpolar and hydrophobic, with low to moderate lipid solubility. Pindolol has little to no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, pindolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action.
Mechanism of Action
Bopindolol (as pindolol) non-selectively blocks beta-1 adrenergic receptors mainly in the heart, inhibiting the effects of epinephrine and norepinephrine resulting in a decrease in heart rate and blood pressure. By binding beta-2 receptors in the juxtaglomerular apparatus, Pindolol inhibits the production of renin, thereby inhibiting angiotensin II and aldosterone production and therefore inhibits the vasoconstriction and water retention due to angiotensin II and aldosterone, respectively.
MeSH Pharmacological Classification
Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety.
Cellular LocationsMembrane
Metabolite PathwaysBopindolol Action Pathway
応用分野
説明Bopindolol is a potent, long-acting, non-selective β-adrenergic blocker related to pindolol and useful in the treatment of hypertension. Unlike many other agents of this type, it appears to have negligible effects on serum lipoproteins.
関連反応
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化合物ノート
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