基本情報
- CAS
37517-30-9- 標準SMILES
CCCC(=O)Nc1ccc(OCC(O)CNC(C)C)c(C(C)=O)c1- InChIKey
GOEMGAFJFRBGGG-UHFFFAOYSA-N- 分子式
- C18H28N2O4
- 平均分子量
- 336.4 g/mol
- 単同位体質量
- 336.20490738
概要
Acebutolol is an ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol. It has a role as a sympathomimetic agent, a beta-adrenergic antagonist, an antihypertensive agent and an anti-arrhythmia drug. It is a member of ethanolamines, an ether, a monocarboxylic acid amide, a propanolamine, a secondary amino compound and an aromatic amide. It is a conjugate base of an acebutolol(1+).
名称と識別子
- 優先名称
- Acebutolol
- IUPAC
- N-[3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]butanamide
- 現地名
- アセブトロール
- 英語名
- Acebutolol
- 分子式
- C18H28N2O4
- 分子量
- 336.43
名称と別名
acebutolol37517-30-9AcetobutololAcebutololoAcebutololum(+-)-Acebutolol5'-Butyramido-2'-(2-hydroxy-3-isopropylaminopropoxy)acetophenoneCHEBI:2379C07AB0467P356D8GHN-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide3'-Acetyl-4'-(2-hydroxy-3-(isopropylamino)propoxy)butyranilide
名称をさらに表示
アセトブトロールアセブトロールDL-アセブトロールrac-N-[3-アセチル-4-[(R*)-2-ヒドロキシ-3-[(1-メチルエチル)アミノ]プロポキシ]フェニル]ブタンアミドrac-N-[3-アセチル-4-[(R*)-2-ヒドロキシ-3-(イソプロピルアミノ)プロポキシ]フェニル]ブタンアミド(±)-アセブトロール(±)-N-[3-アセチル-4-[2-ヒドロキシ-3-[(1-メチルエチル)アミノ]プロポキシ]フェニル]ブタンアミドN-[4-[2-ヒドロキシ-3-(イソプロピルアミノ)プロポキシ]-3-アセチルフェニル]ブタンアミドN-[3-アセチル-4-[2-ヒドロキシ-3-(イソプロピルアミノ)プロポキシ]フェニル]ブチルアミドN-[3-アセチル-4-[2-ヒドロキシ-3-(イソプロピルアミノ)プロポキシ]フェニル]ブタンアミド1-[2-アセチル-4-(ブチリルアミノ)フェノキシ]-3-(イソプロピルアミノ)-2-プロパノールN-(3-アセチル-4-{2-ヒドロキシ-3-[(プロパン-2-イル)アミノ]プロポキシ}フェニル)ブタンアミドN-(3-acetyl-4-(2-hydroxy-3-(isopropylaMino)propoxy)phenyl)butyraMide
物性
構造計算による物性
- XLogP
- 1.7
- 極性表面積
- 87.7 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 5
- 回転可能結合数
- 10
- 重原子数
- 24
- 形式電荷
- 0
- 複雑度
- 400
実験および物理化学的性質
DrugsPharmaceuticals
LogP
1.7
1.71
Solubility1.72e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiarrhythmics
Pharmaceuticals
Melting Point
136-138
119 - 123 °C
Physical DescriptionSolid
Dissociation Constants
9.52
9.67
Collision Cross Section
187.43 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
190.2 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
物理化学的性質
- 融点
- 119 · 119-123°C
- 沸点
- 472.9 °C · 472.9°C (rough estimate)
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。
GHS分類
GHS Classification
H362 (100%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]
P203, P260, P263, P264, P270, and P318 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
危険有害性情報
Other Safety InformationIMAP assessments - Butanamide, N-[3-acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]-, (.+-.)-: Environment tier I assessment
Hazard Classes and CategoriesLact. (100%)
毒性情報
Hepatotoxicity
Acebutolol is associated with a low rate of mild-to-moderate elevations of serum aminotransferase levels during treatment. These enzyme elevations are usually asymptomatic and transient and resolve even with continuation of therapy. There have been few documented cases of clinically apparent, acute liver injury attributed to acebutolol. The time to onset of injury was typically between 1 and 6 weeks of starting. The pattern of liver enzyme elevations was usually hepatocellular with an acute hepatitis-like presentation, although some cases present with a mixed pattern of enzymes. Fever commonly accompanied the liver injury, but usually without rash and eosinophia. Acebutolol is known to induce autoantibodies such as antinuclear antibody in 10% to 30% of patients, some of whom develop a lupus-like syndrome with fatigue, skin rash and arthralgias. Serum enzyme elevations may accompany this syndrome, but jaundice and symptoms of liver injury are uncommon. The published cases of hepatotoxicity due to acebutolol were relatively mild, self-limited and recovery was rapid upon stopping. Rechallenge resulted in rapid recurrence of injury.
Drug Induced Liver Injury
化学と産業
薬理情報
ATC Code
C07AB04
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding26%
Pharmacodynamics
Acebutolol is a cardioselective, beta-adrenoreceptor blocking agent, which possesses mild intrinsic sympathomimetic activity (ISA) in its therapeutically effective dose range. In general, beta-blockers reduce the work the heart has to do and allow it to beat more regularly. Acebutolol has less antagonistic effects on peripheral vascular ß2-receptors at rest and after epinephrine stimulation than nonselective beta-antagonists. Low doses of acebutolol produce less evidence of bronchoconstriction than nonselective agents like propranolol but more than atenolol.
Mechanism of Action
Acebutolol is a selective β1-receptor antagonist. Activation of β1-receptors by epinephrine increases the heart rate and the blood pressure, and the heart consumes more oxygen. Acebutolol blocks these receptors, lowering the heart rate and blood pressure. This drug then has the reverse effect of epinephrine. In addition, beta blockers prevent the release of renin, which is a hormone produced by the kidneys which leads to constriction of blood vessels.
Biological Half-LifeThe plasma elimination half-life is approximately 3 to 4 hours. The half-life of its metabolite, diacetolol, is 8 to 13 hours.
Metabolism/MetabolitesSubject to extensive first-pass hepatic biotransformation (primarily to diacetolol).
FDA Pharmacological Classification
67P356D8GH
ACEBUTOLOL
Mechanisms of Action [MoA] - Adrenergic beta-Antagonists
Established Pharmacologic Class [EPC] - beta-Adrenergic Blocker
Acebutolol is a beta-Adrenergic Blocker. The mechanism of action of acebutolol is as an Adrenergic beta-Antagonist.
MeSH Pharmacological Classification
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