5-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate

• ChemBase编号: 777
• 分子式: C28H31NO5
• 平均质量: 461.54944
• 单一同位素质量: 461.2202231
• SMILES: OC(CNC(C)(C)C)c1cc(OC(=O)c2ccc(cc2)C)c(OC(=O)c2ccc(cc2)C)cc1
• Canonical SMILES: Cc1ccc(cc1)C(=O)Oc1cc(ccc1OC(=O)c1ccc(cc1)C)C(CNC(C)(C)C)O
• InChI: InChI=1S/C28H31NO5/c1-18-6-10-20(11-7-18)26(31)33-24-15-14-22(23(30)17-29-28(3,4)5)16-25(24)34-27(32)21-12-8-19(2)9-13-21/h6-16,23,29-30H,17H2,1-5H3
• InChIKey: FZGVEKPRDOIXJY-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate
• IUPAC传统名: 5-[2-(tert-butylamino)-1-hydroxyethyl]-2-(4-methylbenzoyloxy)phenyl 4-methylbenzoate
• 商标名: Tornalate
• 别名: Bitolterolum [INN-Latin]; Bitolterol Mesylate; Bitolterol

登记号

• CAS号: 30392-40-6
• PubChem SID: 46506895; 160964240
• PubChem CID: 35330

理论计算性质

JChem

• Acid pKa: 13.996354
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 3.1208308
• LogD (pH = 7.4): 4.151406
• Log P: 6.304933
• 摩尔折射率: 132.7623 cm^3
• 极化性: 51.34794 Å^3
• 极化表面积: 84.86 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 4.69
• LOG S: -5.98
• 溶解度: 4.80e-04 g/l

分子性质

理化性质

• 疏水性(logP): 5.8

详细说明

DrugBank - DB00901

• Drug Groups: withdrawn
• Description: Bitolterol mesylate is a beta-2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and COPD. Bitolterol was withdrawn from the market by Elan Pharmaceuticals in 2001. [Wikipedia]
• Indication: Used to dilate air passages in the lungs that have become narrowed as a result of disease or inflammation. It is used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).
• Pharmacology: Bitolterol, an adrenergic bronchodilator, is a prodrug that widens constricted airways in the lungs by relaxing the smooth muscles that surround the bronchial passages. Bitolterol probably does not affect the inflammation in the lung, such as in bronchitis. Bitolterol is unique in that it is a prodrug because it must first be metabolized by the body before it becomes active.
• Affected Organisms: Humans and other mammals
• References: Bierman CW, Kemp JP, Nathan RA: Efficacy and safety of inhaled bitolterol mesylate via metered-dose inhaler in children with asthma. Ann Allergy Asthma Immunol. 1996 Jan;76(1):27-35. [Pubmed] ; Friedel HA, Brogden RN: Bitolterol. A preliminary review of its pharmacological properties and therapeutic efficacy in reversible obstructive airways disease. Drugs. 1988 Jan;35(1):22-41. [Pubmed] ; Nathan RA, Bronsky EA, Dockhorn RJ, Kemp JP: Multicenter dose-ranging study of bitolterol mesylate solution for nebulization in children with asthma. Ann Allergy. 1994 Mar;72(3):209-16. [Pubmed] ; Messina MS: Retrospective study of bitolterol mesylate in the treatment of conditions associated with reversible bronchospasm. Adv Ther. 1995 May-Jun;12(3):157-63. [Pubmed]
• External Links: Wikipedia; Drugs.com

参考文献

• Bierman CW, Kemp JP, Nathan RA: Efficacy and safety of inhaled bitolterol mesylate via metered-dose inhaler in children with asthma. Ann Allergy Asthma Immunol. 1996 Jan;76(1):27-35. Pubmed
• Friedel HA, Brogden RN: Bitolterol. A preliminary review of its pharmacological properties and therapeutic efficacy in reversible obstructive airways disease. Drugs. 1988 Jan;35(1):22-41. Pubmed
• Nathan RA, Bronsky EA, Dockhorn RJ, Kemp JP: Multicenter dose-ranging study of bitolterol mesylate solution for nebulization in children with asthma. Ann Allergy. 1994 Mar;72(3):209-16. Pubmed
• Messina MS: Retrospective study of bitolterol mesylate in the treatment of conditions associated with reversible bronchospasm. Adv Ther. 1995 May-Jun;12(3):157-63. Pubmed