1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-{[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyethyl]amino}ethan-1-ol

• ChemBase编号: 4390
• 分子式: C22H25F2NO4
• 平均质量: 405.4350064
• 单一同位素质量: 405.17516473
• SMILES: Fc1cc2CCC(Oc2cc1)C(O)CNCC(O)C1Oc2c(CC1)cc(F)cc2
• Canonical SMILES: OC(C1CCc2c(O1)ccc(c2)F)CNCC(C1CCc2c(O1)ccc(c2)F)O
• InChI: InChI=1S/C22H25F2NO4/c23-15-3-7-19-13(9-15)1-5-21(28-19)17(26)11-25-12-18(27)22-6-2-14-10-16(24)4-8-20(14)29-22/h3-4,7-10,17-18,21-22,25-27H,1-2,5-6,11-12H2
• InChIKey: KOHIRBRYDXPAMZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-{[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-hydroxyethyl]amino}ethan-1-ol
• IUPAC传统名: nebivolol hydrochloride
• 商标名: Nebilet; Nebicard-5; Nubeta; Nebipill; Bystolic; Nebilong; Nodon; Lobivon; PI-21858
• 别名: Nebivololum [latin]; nebivolol; Nebivolol

登记号

• CAS号: 99200-09-6
• PubChem SID: 99443225; 160967822
• PubChem CID: 71301

理论计算性质

JChem

• Acid pKa: 13.520145
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 0.19658114
• LogD (pH = 7.4): 1.7054241
• Log P: 3.208403
• 摩尔折射率: 103.3172 cm^3
• 极化性: 40.23752 Å^3
• 极化表面积: 70.95 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: 2.44
• LOG S: -4.0
• 溶解度: 4.03e-02 g/l

详细说明

DrugBank - DB04861

• Drug Groups: approved; investigational
• Description: Nebivolol is a highly cardioselective vasodilatory beta1 receptor blocker used in treatment of hypertension. In most countries, this medication is available only by prescription. [Wikipedia]
• Indication: For the treatment of essential hypertension.
• Pharmacology: Nebivolol is a competitive and highly selective beta-1 receptor antagonist with mild vasodilating properties, possibly due to an interaction with the L-arginine/nitric oxide pathway. In preclinical studies, nebivolol has been shown to induce endothelium-dependent arterial relaxation in a dose dependent manner, by stimulation of the release of endothelial nitric oxide. Nitric oxide acts to relax vascular smooth muscle cells and inhibits platelet aggregation and adhesion.
• Toxicity: The most common signs and symptoms associated with nebivolol overdosage are bradycardia and hypotension. Other important adverse events reported with nebivolol overdose include cardiac failure, dizziness, hypoglycemia, fatigue and vomiting. Other adverse events associated with β-blocker overdose include bronchospasm and heart block. The largest known ingestion of nebivolol worldwide involved a patient who ingested up to 500 mg of nebivolol along with several 100 mg tablets of acetylsalicylic acid in a suicide attempt. The patient experienced hyperhydrosis, pallor, depressed level of consciousness, hypokinesia, hypotension, sinus bradycardia, hypoglycemia, hypokalemia, respiratory failure and vomiting. The patient recovered.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic (CYP2D6-mediated)
• Absorption: The absorption of nebivolol is rapid and not affected by food.
• Half Life: 10 hours
• Protein Binding: 98%
• References: Gielen W, Cleophas TJ, Agrawal R: Nebivolol: a review of its clinical and pharmacological characteristics. Int J Clin Pharmacol Ther. 2006 Aug;44(8):344-57. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

参考文献

• Gielen W, Cleophas TJ, Agrawal R: Nebivolol: a review of its clinical and pharmacological characteristics. Int J Clin Pharmacol Ther. 2006 Aug;44(8):344-57. Pubmed