基本情報
- CAS
13655-52-2- 標準SMILES
C=CCc1ccccc1OCC(O)CNC(C)C- InChIKey
PAZJSJFMUHDSTF-UHFFFAOYSA-N- 分子式
- C15H23NO2
- 平均分子量
- 249.35 g/mol
- 単同位体質量
- 249.17287898
概要
Alprenolol is a secondary alcohol that is propan-2-ol substituted by a 2-allylphenoxy group at position 1 and an isopropylamino group at position 3. It is a beta-adrenergic antagonist used as a antihypertensive, anti-arrhythmia and a sympatholytic agent. It has a role as a beta-adrenergic antagonist, an antihypertensive agent, an anti-arrhythmia drug and a sympatholytic agent. It is a secondary alcohol and a secondary amino compound.
名称と識別子
- 優先名称
- Alprenolol
- IUPAC
- 1-(propan-2-ylamino)-3-(2-prop-2-enylphenoxy)propan-2-ol
- 現地名
- アルプレノロール
- 英語名
- Alprenolol
- 分子式
- C15H23NO2
- 分子量
- 249.35
名称と別名
alprenolol13655-52-2AlfeprolAlprenololum1-(o-Allylphenoxy)-3-(isopropylamino)-2-propanol1-(2-Allylphenoxy)-3-isopropylamino-2-propanol1-(propan-2-ylamino)-3-(2-prop-2-enylphenoxy)propan-2-olDTXSID00451272-Propanol, 1-[(1-methylethyl)amino]-3-[2-(2-propenyl)phenoxy]-877K5MQ27WNSC-759561DTXCID8025127
名称をさらに表示
1-(o-アリルフェノキシ)-3-(イソプロピルアミノ)-2-プロパノール(R)-アルプレノロール1-(イソプロピルアミノ)-3-[2-(2-プロペニル)フェノキシ]-2-プロパノール(±)-アルプレノロール1-[(3-イソプロピルアミノ-2-ヒドロキシプロピル)オキシ]-2-(2-プロペニル)ベンゼン[R,(+)]-3-[2-(2-プロペニル)フェノキシ]-1-イソプロピルアミノ-2-プロパノール3-(o-アリルフェノキシ)-1-イソプロピルアミノ-2-プロパノール1-[(1-メチルエチル)アミノ]-3-[2-(2-プロペニル)フェノキシ]-2-プロパノール(S)-アルプレノロール[S,(-)]-3-[2-(2-プロペニル)フェノキシ]-1-イソプロピルアミノ-2-プロパノールアルフェプロール(-)-アルプレノロール1-(2-アリルフェノキシ)-3-(イソプロピルアミノ)-2-プロパノールrac-(R*)-3-[2-(2-プロペニル)フェノキシ]-1-イソプロピルアミノ-2-プロパノール(+)-アルプレノロールアルプレノロール
物性
構造計算による物性
- XLogP
- 3.1
- 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
- 8
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 231
実験および物理化学的性質
Chemical ClassesOther Uses -> Pharmaceuticals
LogP2.8
Solubility1.88e-01 g/L
Human DrugsPharmaceuticals
Melting Point
107-109 °C
107 - 109 °C
Physical DescriptionSolid
Dissociation Constants
9.51
9.6
Collision Cross Section
159.5 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
163.63 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
158.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 57.5 °C · 57.5°C
- 沸点
- 392.45 °C · 392.45°C (rough estimate)
- 比重(密度)
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。
危険有害性情報
Other Safety InformationIMAP assessments - 2-Propanol, 1-[(1-methylethyl)amino]-3-[2-(2-propen-1-yl)phenoxy]-: Environment tier I assessment
Hazards SummaryAllergic contact dermatitis reported in pharmaceutical workers; [Kanerva, p. 1181-2]
毒性情報
Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
安全データ
- ridadr
- 3249
- 毒性
- mammal (species unspecified),LD50,intraperitoneal,102mg/kg (102mg/kg),Pharmaceutical Chemistry Journal Vol. 8, Pg. 137, 1974.
- risk_code
- 23/24/25-43
- hazard_code
- T
- safety_code
- 36/37/39-45
- hazard_class
- 6.1(b)
- packing_group
- III
化学と産業
薬理情報
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding80-90%
Pharmacodynamics
Alprenolol is a non-selective beta-blocker used in the treatment of hypertension, edema, ventricular tachycardias, and atrial fibrillation. Alprenolol impairs AV node conduction and decreases sinus rate and may also increase plasma triglycerides and decrease HDL-cholesterol levels. Alprenolol is nonpolar and hydrophobic, with low to moderate lipid solubility. Alprenolol has little to no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, alprenolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action.
Mechanism of Action
Alprenolol 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. Also, with a more minor effect, by binding beta-2 receptors in the juxtaglomerular apparatus, alprenolol 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.
Biological Half-Life2-3 hours
Metabolism/MetabolitesHepatic. One of the active metabolites, 4-OH-alprenolol, is an active beta-blocker.
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.
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.
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