N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide

• ChemBase编号: 1063
• 分子式: C18H28N2O4
• 平均质量: 336.42592
• 单一同位素质量: 336.20490739
• SMILES: O(CC(O)CNC(C)C)c1c(cc(NC(=O)CCC)cc1)C(=O)C
• Canonical SMILES: CCCC(=O)Nc1ccc(c(c1)C(=O)C)OCC(CNC(C)C)O
• InChI: InChI=1S/C18H28N2O4/c1-5-6-18(23)20-14-7-8-17(16(9-14)13(4)21)24-11-15(22)10-19-12(2)3/h7-9,12,15,19,22H,5-6,10-11H2,1-4H3,(H,20,23)
• InChIKey: GOEMGAFJFRBGGG-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide
• IUPAC传统名: acebutolol
• 商标名: Monitan; Neptal; Prent; Sectral
• 别名: dl-Acebutolol; Acetobutolol; Acebutololo; Acebutolol HCL; Acebutolol Hydrochloride; Acebutolol; N-[3-Acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamide Hydrochloride; DL-1-(2-Acetyl-4-butyramido)-3-(isopropylamino)propan-2-ol Hydrochloride; IL-17803A; Acecor; Acetanol; Neptal; Prent; Sectral; Acebutolol Hydrochloride

登记号

• CAS号: 34381-68-5; 37517-30-9
• PubChem SID: 160964526; 46509113
• PubChem CID: 1978
• CHEBI ID: 2379
• ATC码: C07AB04
• CHEMBL: 642
• Chemspider ID: 1901
• DrugBank ID: DB01193
• KEGG ID: D02338
• 美国药典/FDA物质标识码: 67P356D8GH
• 维基百科标题: Acebutolol
• Medline Plus: a687003

理论计算性质

JChem

• Acid pKa: 13.912071
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -1.6467636
• LogD (pH = 7.4): -0.5997952
• Log P: 1.5346816
• 摩尔折射率: 94.8692 cm^3
• 极化性: 36.50459 Å^3
• 极化表面积: 87.66 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.43
• LOG S: -3.29
• 溶解度: 1.72e-01 g/l

分子性质

理化性质

• 溶解度: 259 mg/L; DMSO; Methanol; Water
• 外观: Off-White Powder
• 熔点: 121°C (249.8°F); 141-143°C
• 疏水性(logP): 1.7

安全信息

• 保存条件: -20°C Freezer

药理学性质

• 给药途径: oral, iv
• 生物利用度: 40% (range 35 to 50%)
• 排泄: Renal: 30%; Biliary: 60%
• 半衰期: 3-4 hours (parent drug); 8-13 hours (active metabolite)
• 代谢: Hepatic
• 法定药品分级: Rx-only
• 妊娠期药物分类: B (US); C (Australia)
• 美国（FDA）药品许可证: Acebutolol

详细说明

DrugBank - DB01193

• Drug Groups: approved
• Description: A cardioselective beta-adrenergic antagonist with little effect on the bronchial receptors. The drug has stabilizing and quinidine-like effects on cardiac rhythm as well as weak inherent sympathomimetic action. [PubChem]
• Indication: For the management of hypertension and ventricular premature beats in adults.
• Pharmacology: 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.
• Toxicity: Symptoms of overdose include extreme bradycardia, advanced atrioventricular block, intraventricular conduction defects, hypotension, severe congestive heart failure, seizures, and in susceptible patients, bronchospasm, and hypoglycemia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Subject to extensive first-pass hepatic biotransformation (primarily to diacetolol).
• Absorption: Well absorbed from the Gl tract with an absolute bioavailability of approximately 40% for the parent compound. In
• Half Life: The plasma elimination half-life is approximately 3 to 4 hours. The half-life of its metabolite, diacetolol, is 8 to 13 hours.
• Protein Binding: 26%
• Elimination: Elimination via renal excretion is approximately 30% to 40% and by non-renal mechanisms 50% to 60%, which includes excretion into the bile and direct passage through the intestinal wall.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - A123800

Cardioselective β-adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II).

参考文献

• Cuthbert, O.A., et al.: Br. J. Pharmacol., 43, 639 (1971)
• Singh, B.N., et al.: Drugs, 29, 531 (1971)
• Foster, R.T., et al.: Anal. Profiles Drug Subs., 19, 1 (1971)