(2R,3S)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol

• ChemBase编号: 1073
• 分子式: C17H27NO4
• 平均质量: 309.40058
• 单一同位素质量: 309.19400835
• SMILES: O[C@@H]1[C@H](O)Cc2c(C1)c(OCC(O)CNC(C)(C)C)ccc2
• Canonical SMILES: OC(COc1cccc2c1C[C@H](O)[C@@H](C2)O)CNC(C)(C)C
• InChI: InChI=1S/C17H27NO4/c1-17(2,3)18-9-12(19)10-22-16-6-4-5-11-7-14(20)15(21)8-13(11)16/h4-6,12,14-15,18-21H,7-10H2,1-3H3/t12?,14-,15+/m1/s1
• InChIKey: VWPOSFSPZNDTMJ-UCWKZMIHSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3S)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol
• IUPAC传统名: nadolol
• 商标名: Anabet; Corgard; Solgol
• 别名: 纳多洛尔; Nadolol; Nadolol; (2R,3S)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol

登记号

• CAS号: 42200-33-9
• EC号: 255-706-3
• MDL号: MFCD00079476
• PubChem SID: 46505509; 24897535; 160964536
• PubChem CID: 39147
• ATC码: C07AA12
• CHEMBL: 649
• Chemspider ID: 35815
• DrugBank ID: DB01203
• IUPHAR配体索引: 554
• KEGG ID: D00432
• 美国药典/FDA物质标识码: FEN504330V
• 维基百科标题: Nadolol
• Medline Plus: a682666

理论计算性质

JChem

• Acid pKa: 13.586201
• 质子受体: 5
• 质子供体: 4
• LogD (pH = 5.5): -2.3368313
• LogD (pH = 7.4): -1.4429477
• Log P: 0.8654279
• 摩尔折射率: 85.5269 cm^3
• 极化性: 33.76481 Å^3
• 极化表面积: 81.95 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.23
• LOG S: -2.14
• 溶解度: 2.25e+00 g/l

分子性质

理化性质

• 溶解度: 8330 mg/L
• 疏水性(logP): 0.379; 1.2

安全信息

• RTECS编号: QJ4870000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 给药途径: Oral
• 排泄: Renal and fecal (unchanged)
• 半衰期: 14-24 hours
• 代谢: Nil
• 蛋白结合率: 30%
• 法定药品分级: POM (UK); Rx-only (US)
• 妊娠期药物分类: C (US)
• 相关基因信息: human ... CYP1A2(1544)

产品相关信息

• 纯度: 95%
• 级别: analytical standard
• Empirical Formula (Hill Notation): C17H27NO4

详细说明

DrugBank - DB01203

• Drug Groups: approved
• Description: A non-selective beta-adrenergic antagonist with a long half-life, used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension. Nadolol is also used for migraine disorders and for tremor. [PubChem]
• Indication: Used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension.
• Pharmacology: Nadolol is a nonselective beta-adrenergic receptor antagonist with a long half-life, and is structurally similar to propranolol. Clinical pharmacology studies have demonstrated beta-blocking activity by showing (1) reduction in heart rate and cardiac output at rest and on exercise, (2) reduction of systolic and diastolic blood pressure at rest and on exercise, (3) inhibition of isoproterenol-induced tachycardia, and (4) reduction of reflex orthostatic tachycardia. Nadolol has no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, nadolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action.
• Toxicity: Oral, mouse: LD₅₀ = 4500mg/kg. Symptoms of overdose include abdominal irritation, central nervous system depression, coma, extremely slow heartbeat, heart failure, lethargy, low blood pressure, and wheezing.
• Affected Organisms: Humans and other mammals
• Biotransformation: Not metabolized by the liver and excreted unchanged primarily by the kidneys.
• Absorption: Absorption of nadolol after oral dosing is variable, averaging about 30 percent.
• Half Life: 14-24 hours
• Protein Binding: 30%
• Elimination: Unlike many other beta-adrenergic blocking agents, nadolol is not metabolized by the liver and is excreted unchanged, principally by the kidneys. Nadolol is excreted predominantly in the urine.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - N1892

Biochem/physiol Actions
β-肾上腺素阻断剂