基本情報
- CAS
36507-48-9- 標準SMILES
CC(C)(C)NC[C@H](O)COc1ccccc1C1CCCC1- InChIKey
KQXKVJAGOJTNJS-HNNXBMFYSA-N- 分子式
- C18H29NO2
- 平均分子量
- 291.4 g/mol
- 単同位体質量
- 291.21982917
概要
Penbutolol is a member of ethanolamines.
名称と識別子
- 優先名称
- Penbutolol
- IUPAC
- (2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-ol
- 現地名
- ペンブトロール
- 英語名
- Penbutolol
- 分子式
- C18H29NO2
- 分子量
- 291.43
名称と別名
penbutolol(-)-Penbutolol38363-40-5Penbutololum(2S)-1-(tert-butylamino)-3-(2-cyclopentylphenoxy)propan-2-olCHEBI:795478W62V43DYDTXSID80234282-Propanol, 1-(2-cyclopentylphenoxy)-3-((1,1-dimethylethyl)amino)-tert-butyl[(2S)-3-(2-cyclopentylphenoxy)-2-hydroxypropyl]aminepenbutololotert-butyl((2S)-3-(2-cyclopentylphenoxy)-2-hydroxypropyl)amine
名称をさらに表示
ペンブトロールC07416HOE 893HOE 893DLevopenbutolLevopenbutolol(-)-(S)-Penbutolol
RefChem:859296DTXCID903428C07AA23(s)-penbutololBetapressinPenbutolol (INN)(-)-Isopenbutololl-Penbutolol
データベース識別子
- CAS
36507-48-9、38363-40-5- PubChem CID
- 37464
- DTXSID
DTXSID8023428- ChEMBL
CHEMBL1290、CHEMBL87418- ChEBI
物性
構造計算による物性
- XLogP
- 4.2
- 極性表面積
- 41.5 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 3
- 回転可能結合数
- 7
- 重原子数
- 21
- 形式電荷
- 0
- 複雑度
- 294
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
LogP
4.15
3.61
Solubility2.12e-02 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiarrhythmics
Pharmaceuticals
Physical DescriptionSolid
Dissociation Constants9.92
物理化学的性質
- 融点
- 68 · 68-72°
- 比旋光度
- 20 D · 20D -11.5° (c = 1 in methanol)
- 沸点
- 433.43 °C · 433.43°C (rough estimate)
- 比重(密度)
- 1.0344 · 1.0344 (rough estimate)
- 屈折率
- 1.5 · 1.5000 (estimate)
- 酸解離定数(Pka)
- 9.3 · 9.3 (1.5 mmol/l in 25% ethanol)
- 色
- クリスタル
- 水溶解度
- 7 g/L · 7g/L(室温)
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。
毒性情報
Hepatotoxicity
Mild-to-moderate elevations in serum aminotransferase levels occur in less than 2% of patients on penbutolol and are usually transient and asymptomatic, resolving even with continuation of therapy. Despite its wide spread use, penbutolol has not been convincingly linked to instances of clinically apparent liver injury. Other beta-blockers have been linked to rare instances of acute liver injury with a latency to onset of 4 to 24 weeks, a hepatocellular pattern of serum enzyme elevations and a rather mild, self-limiting course without evidence of hypersensitivity or autoimmune reactions.
Drug Induced Liver Injury
Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)
penbutolol
Levatol®
Beta blockers
Not Applicable
no-DILI-concern
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- 毒性
- LD50 oral in rabbit: 300mg/kg
化学と産業
薬理情報
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding80-98% bound to plasma proteins. Extensively bound to Alpha-1-acid glycoprotein 1.
Pharmacodynamics
Penbutolol is a ß-1, ß-2 (nonselective) adrenergic receptor antagonist. Experimental studies showed a dose-dependent increase in heart rate in reserpinized (norepinephrine-depleted) rats given penbutolol intravenously at doses of 0.25 to 1.0 mg/kg, suggesting that penbutolol has some intrinsic sympathomimetic activity. In human studies, however, heart rate decreases have been similar to those seen with propranolol.
Mechanism of Action
Penbutolol acts on the β1 adrenergic receptors in both the heart and the kidney. When β1 receptors are activated by catecholamines, they stimulate a coupled G protein that leads to the conversion of adenosine triphosphate (ATP) to cyclic adenosine monophosphate (cAMP). The increase in cAMP leads to activation of protein kinase A (PKA), which alters the movement of calcium ions in heart muscle and increases the heart rate. Penbutolol blocks the catecholamine activation of β1 adrenergic receptors and decreases heart rate, which lowers blood pressure.
Biological Half-LifePlasma= approximately 5h Conjugated= approximately 20h in healthy persons, 25h in healthy elderly persons, and 100h in patients on renal dialysis.
Metabolism/MetabolitesMetabolized in the liver by hydroxylation and glucuroconjugation forming a glucuronide metabolite and a semi-active 4-hydroxy metabolite.
FDA Pharmacological Classification
78W62V43DY
PENBUTOLOL
Mechanisms of Action [MoA] - Adrenergic beta-Antagonists
Established Pharmacologic Class [EPC] - beta-Adrenergic Blocker
Penbutolol is a beta-Adrenergic Blocker. The mechanism of action of penbutolol is as an Adrenergic beta-Antagonist.
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