5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol

• ChemBase编号: 749
• 分子式: C12H19NO3
• 平均质量: 225.28416
• 单一同位素质量: 225.13649347
• SMILES: OC(CNC(C)(C)C)c1cc(O)cc(O)c1
• Canonical SMILES: OC(c1cc(O)cc(c1)O)CNC(C)(C)C
• InChI: InChI=1S/C12H19NO3/c1-12(2,3)13-7-11(16)8-4-9(14)6-10(15)5-8/h4-6,11,13-16H,7H2,1-3H3
• InChIKey: XWTYSIMOBUGWOL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol
• IUPAC传统名: terbutaline
• 商标名: Brethaire; Brethine; Brican; Bricanyl; Bricar; Bricaril; Bricyn
• 别名: 2-tert-Butylamino-1-(3,5-dihydroxyphenyl)ethanol Hemisulfate; Brethaire; Brethine; Butalire; Monovent; Terbasmin; Terbul; Terbutaline Hemisulfate Salt; 5-(2-(tert-ButylaMino)-1-hydroxyethyl)benzene-1,3-diol; Terbutalina [Dcit]; Terbutaline Sulfate; Terbutalino [INN-Spanish]; Terbutalinum [INN-Latin]; Terbutalin; Terbutaline

登记号

• CAS号: 23031-25-6; 23031-32-5
• PubChem SID: 160964212; 46506887
• PubChem CID: 5403

理论计算性质

JChem

• Acid pKa: 8.85872
• 质子受体: 4
• 质子供体: 4
• LogD (pH = 5.5): -1.8226097
• LogD (pH = 7.4): -0.726437
• Log P: 0.44103742
• 摩尔折射率: 63.0359 cm^3
• 极化性: 24.725668 Å^3
• 极化表面积: 72.72 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.55
• LOG S: -1.59
• 溶解度: 5.84e+00 g/l

分子性质

理化性质

• 溶解度: 213 mg/mL; DMSO; Ethanol; Methanol
• 外观: White to Off-White Solid
• 熔点: 246-248°C
• 疏水性(logP): 1.4

安全信息

• 保存条件: -20°C Freezer

产品相关信息

• 纯度: 98%

详细说明

DrugBank - DB00871

• Drug Groups: approved
• Description: A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic. [PubChem]
• Indication: For the prevention and reversal of bronchospasm in patients 12 years of age and older with reversible, obstructive airway disease, as well as symptomatic management of reversible bronchospasm associated with bronchitis and emphysema. Also used acute IV and sub-Q therapy in selected women to inhibit uterine contractions in preterm labor (tocolysis) and prolong gestation when beneficial.
• Pharmacology: Terbutaline is a relatively selective beta2-adrenergic bronchodilator that has little or no effect on alpha-adrenergic receptors. The drug has exerts a preferential effect on beta2-adrenergic receptors but stimulates beta-adrenergic receptors less selectively than relatively selective beta2-agonists. Terbutaline appears to have a greater stimulating effect on beta-receptors of the bronchial, vascular, and uterine smooth muscles (beta2 receptors) than on the beta-receptors of the heart (beta1 receptors). This drug relaxes smooth muscle and inhibits uterine contractions, but may also cause some cardiostimulatory effects and CNS stimulation.
• Toxicity: Terbutaline Sulfate: Oral LD₅₀(rat) = 8.7 g/kg; Oral LD₅₀(mouse) = 205 mg/kg; Oral LD₅₀(dog) = 1.5 g/kg; IP LD₅₀(rat)= 220 mg/kg ; IP LD₅₀(mouse) = 130 mg/kg; Oral LD₅₀(rabbit) = >8 g/kg; IV LD₅₀(mouse) = 36 mg/kg; IV LD₅₀(dog) = 116 mg/kg; IV LD₅₀(rabbit) = 110 mg/kg
• Affected Organisms: Humans and other mammals
• Absorption: Approximately 30-50% if administered orally and well absorbed subcutaneously.
• Half Life: 5.5-5.9 hours
• Elimination: About 90% of the drug was excreted in the urine at 96 hours after subcutaneous administration, with about 60% of this being unchanged drug. It appears that the sulfate conjugate is a major metabolite of terbutaline and urinary excretion is the primary route of elimination
• Clearance: * 311 +/- 112 mL/min
• References: Rhodes MC, Seidler FJ, Abdel-Rahman A, Tate CA, Nyska A, Rincavage HL, Slotkin TA: Terbutaline is a developmental neurotoxicant: effects on neuroproteins and morphology in cerebellum, hippocampus, and somatosensory cortex. J Pharmacol Exp Ther. 2004 Feb;308(2):529-37. Epub 2003 Nov 10. [Pubmed] ; Hochhaus G, Mollmann H: Pharmacokinetic/pharmacodynamic characteristics of the beta-2-agonists terbutaline, salbutamol and fenoterol. Int J Clin Pharmacol Ther Toxicol. 1992 Sep;30(9):342-62. [Pubmed] ; Haahtela T, Jarvinen M, Kava T, Kiviranta K, Koskinen S, Lehtonen K, Nikander K, Persson T, Reinikainen K, Selroos O, et al.: Comparison of a beta 2-agonist, terbutaline, with an inhaled corticosteroid, budesonide, in newly detected asthma. N Engl J Med. 1991 Aug 8;325(6):388-92. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - T109750

A B-Adrenergic receptor agonist. A Bronchodilator.

参考文献

• Rhodes MC, Seidler FJ, Abdel-Rahman A, Tate CA, Nyska A, Rincavage HL, Slotkin TA: Terbutaline is a developmental neurotoxicant: effects on neuroproteins and morphology in cerebellum, hippocampus, and somatosensory cortex. J Pharmacol Exp Ther. 2004 Feb;308(2):529-37. Epub 2003 Nov 10. Pubmed
• Hochhaus G, Mollmann H: Pharmacokinetic/pharmacodynamic characteristics of the beta-2-agonists terbutaline, salbutamol and fenoterol. Int J Clin Pharmacol Ther Toxicol. 1992 Sep;30(9):342-62. Pubmed
• Haahtela T, Jarvinen M, Kava T, Kiviranta K, Koskinen S, Lehtonen K, Nikander K, Persson T, Reinikainen K, Selroos O, et al.: Comparison of a beta 2-agonist, terbutaline, with an inhaled corticosteroid, budesonide, in newly detected asthma. N Engl J Med. 1991 Aug 8;325(6):388-92. Pubmed
• Akhtar, S., et al.: J. Vet. Pharmacol. Ther., 21, 388 (1998)
• Kasprowicz, D.J., et al.: J. Immunol., 165, 680 (2000)