6-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol

• ChemBase编号: 1145
• 分子式: C12H20N2O3
• 平均质量: 240.2988
• 单一同位素质量: 240.14739251
• SMILES: OC(CNC(C)(C)C)c1nc(c(O)cc1)CO
• Canonical SMILES: OCc1nc(ccc1O)C(CNC(C)(C)C)O
• InChI: InChI=1S/C12H20N2O3/c1-12(2,3)13-6-11(17)8-4-5-10(16)9(7-15)14-8/h4-5,11,13,15-17H,6-7H2,1-3H3
• InChIKey: VQDBNKDJNJQRDG-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 6-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol
• IUPAC传统名: pyrbuterol; pirbuterol
• 商标名: Maxair
• 别名: Pirbuterol hydrochloride; Pirbuterolum [inn-latin]; Pirbuterol; α6-[[(1,1-Dimethylethyl)amino]methyl]-3-hydroxy-2,6-pyridinedimethanol Hydrochloride; Broncocor; CP 24314-1; Exirel; NSC 355078; Pyrbuterol Hydrochloride; Pirbuterol Dihydrochloride

登记号

• CAS号: 38677-81-5; 38029-10-6
• PubChem SID: 46506379; 160964608
• PubChem CID: 4845

理论计算性质

JChem

• Acid pKa: 8.786121
• 质子受体: 5
• 质子供体: 4
• LogD (pH = 5.5): -3.1210253
• LogD (pH = 7.4): -1.7822901
• Log P: -0.6583083
• 摩尔折射率: 64.7447 cm^3
• 极化性: 25.692781 Å^3
• 极化表面积: 85.61 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.38
• LOG S: -1.59
• 溶解度: 6.22e+00 g/l

详细说明

DrugBank - DB01291

• Drug Groups: approved
• Description: Pirbuterol is a beta-2 adrenergic bronchodilator. In vitro studies and in vivo pharmacologic studies have demonstrated that pirbuterol has a preferential effect on beta-2 Adrenergic receptors compared with isoproterenol. While it is recognized that beta-2 adrenergic receptors are the predominant receptors in bronchial smooth muscle, data indicate that there is a population of beta-2 receptors in the human heart, existing in a concentration between 10-50%. The precise function of these receptors has not been established.; ; The pharmacologic effects of beta adrenergic agonist drugs, including pirbuterol, are at least in proof attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (AlP) to cyclic-3? ,5?-adenosine monophosphate (c-AMP). Increased c-AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.
• Indication: For the prevention and reversal of bronchospasm in patients 12 years of age and older with reversible bronchospasm including asthma.
• Pharmacology: Pirbuterol is a beta-2 adrenergic bronchodilator. In vitro studies and in vivo pharmacologic studies have demonstrated that pirbuterol has a preferential effect on beta-2 adrenergic receptors compared with isoproterenol. While it is recognized that beta-2 adrenergic receptors are the predominant receptors in bronchial smooth muscle, data indicate that there is a population of beta-2 receptors in the human heart, existing in a concentration between 10-50%. The precise function of these receptors has not been established.
• Toxicity: As with all sympathomimetic aerosol medication, cardiac arrest and even death may be associated with abuse of pirbuterol.
• Affected Organisms: Humans and other mammals
• Half Life: The plasma half-life measured after oral administration is about two hours.
• External Links: RxList; Drugs.com

Toronto Research Chemicals - P502500

An analogue of Albuterol (A514500) with β2-adrenergic stimulating activity. Bronchodilator.

参考文献

• Constantine, J.W., et al.: J. Pharmacol. Exp. Ther., 208, 371 (1979)
• Awan, N.A., et al.: Clin. Res., 28, 17 (1979)
• Richards, D.M., et al.: Drugs, 30, 6 (1979)