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

• ChemBase编号: 219
• 分子式: C14H22N2O3
• 平均质量: 266.33608
• 单一同位素质量: 266.16304257
• SMILES: O(CC(O)CNC(C)C)c1ccc(cc1)CC(=O)N
• Canonical SMILES: OC(COc1ccc(cc1)CC(=O)N)CNC(C)C
• InChI: InChI=1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)
• InChIKey: METKIMKYRPQLGS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide
• IUPAC传统名: atenolol
• 商标名: Aircrit; Alinor; Altol; Anselol; Antipressan; Apo-Atenolol; Atcardil; Atecard; Atehexal; Atenblock; Atendol; Atenet; Ateni; Atenil; Atenol; Atenol 1A Pharma; Atenol Acis; Atenol AL; Atenol Atid; Atenol Cophar; Atenol CT; Atenol Fecofar; Atenol Gador; Atenol Genericon; Atenol GNR; Atenol Heumann; Atenol MSD; Atenol NM Pharma; Atenol Nordic; Atenol PB; Atenol Quesada; Atenol Stada; Atenol Tika; Atenol Trom; Atenol Von CT; Atenol-Mepha; Atenol-Ratiopharm; Atenol-Wolff; Atenolin; Atenomel; Atereal; Aterol; Betablok; Betacard; Betasyn; Betatop GE; Blocotenol; Blokium; Cardaxen; Cardiopress; Corotenol; Cuxanorm; Duraatenolol; Duratenol; Evitocor; Farnormin; Felo-Bits; Hipres; Hypoten; Ibinolo; Internolol; Jenatenol; Juvental; Lo-Ten; Loten; Lotenal; Myocord; Normalol; Normiten; Noten; Oraday; Ormidol; Panapres; Plenacor; Premorine; Prenolol; Prenormine; Prinorm; Scheinpharm Atenol; Seles Beta; Selobloc; Serten; Servitenol; Stermin; Tenidon; Teno-Basan; Tenobloc; Tenoblock; Tenolol; Tenoprin; Tenormin; Tenormine; Tensimin; Tredol; Unibloc; Uniloc; Vascoten; Vericordin; Wesipin; Xaten
• 别名: 2-{4-[2-Hydroxy-3-(isopropylamino)propoxy]-phenyl}acetamide; 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxyl]benzeneacetamide; 2-[p-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl]acetamide; (RS)-Atenolol; (+/-)-Atenolol; ICI-66082; Atehexal; Atenol; Cuxanorm; Myocord; Normalol; Normiten; Uniloc; Vericordin; Wesipin; Xaten; dl-Atenolol; Atenolol; (±)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide; 4-[2′-Hydroxy-3′-(isopropylamino)propoxy]phenylacetamide; Atenolol; 2-(4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide; 2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide

登记号

• CAS号: 29122-68-7
• EC号: 249-451-7
• MDL号: MFCD00057645
• PubChem SID: 24277748; 160963682; 46506915
• PubChem CID: 2249

理论计算性质

JChem

• Acid pKa: 14.078504
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): -2.7682068
• LogD (pH = 7.4): -1.8002133
• Log P: 0.42502484
• 摩尔折射率: 73.5053 cm^3
• 极化性: 29.0903 Å^3
• 极化表面积: 84.58 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.57
• LOG S: -2.79
• 溶解度: 4.29e-01 g/l

分子性质

理化性质

• 溶解度: 13.5 mg/mL; Acetic Acid; Dimethyl Sulfoxide; DMSO: soluble18 mg/mL; ethanol: soluble3.4 mg/mL; H2O: soluble0.3 mg/mL; Methanol
• 外观: Crystalline Solid; white to off-white powder
• 熔点: 146-148°C; 148 - 152°C
• 疏水性(logP): -0.109; 0.5

安全信息

• 保存条件: -20°C Freezer
• 保存注意事项: IRRITANT
• RTECS编号: AC3600000
• 德国WGK号: 2
• TSCA收录: false
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: human ... ADRB1(153)rat ... Adrb1(24925)

产品相关信息

• 纯度: ≥98% (TLC); 95%; 97%

详细说明

DrugBank - DB00335

• Drug Groups: approved
• Description: A cardioselective beta-adrenergic blocker possessing properties and potency similar to propranolol, but without a negative inotropic effect. [PubChem]
• Indication: For the management of hypertention and long-term management of patients with angina pectoris
• Pharmacology: Atenolol, a competitive beta(1)-selective adrenergic antagonist, has the lowest lipid solubility of this drug class. Although it is similar to metoprolol, atenolol differs from pindolol and propranolol in that it does not have intrinsic sympathomimetic properties or membrane-stabilizing activity. Atenolol is used alone or with chlorthalidone in the management of hypertension and edema.
• Toxicity: LD₅₀=2000-3000 mg/kg(orally in mice). Symptoms of an atenolol overdose include a slow heart beat, shortness of breath, fainting, dizziness, weakness, confusion, nausea, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic (minimal)
• Absorption: Approximately 50% of an oral dose is absorbed from the gastrointestinal tract, the remainder being excreted unchanged in the feces.
• Half Life: 6-7 hours
• Protein Binding: Plasma protein binding is 6-16%
• Elimination: Approximately 50% of an oral dose is absorbed from the gastrointestinal tract, the remainder being excreted unchanged in the feces. Unlike propranolol or metoprolol, but like nadolol, atenolol undergoes little or no metabolism by the liver, and the absorbed portion is eliminated primarily by renal excretion.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - A7655

Biochem/physiol Actions
Selective β1-adrenoceptor antagonist; antihypertensive; antianginal; antiarrhythmic.
Other Notes
Shelf-life of the solid is at least three years.
Application
Atenolol is a β-adrenergic blocker and used in the management of hypertension. Atenolol has antianginal and antiarrhythmic properties.

Toronto Research Chemicals - A790075

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

参考文献

• Caplar, V., et al.: Anal. Profiles Drug Subs., 13, 1 (1984)