5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,3-diol

• ChemBase编号: 695
• 分子式: C11H17NO3
• 平均质量: 211.25758
• 单一同位素质量: 211.12084341
• SMILES: OC(CNC(C)C)c1cc(O)cc(O)c1
• Canonical SMILES: OC(c1cc(O)cc(c1)O)CNC(C)C
• InChI: InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8/h3-5,7,11-15H,6H2,1-2H3
• InChIKey: LMOINURANNBYCM-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,3-diol
• IUPAC传统名: orciprenaline
• 商标名: Alotec; Alupent; Metaprel; Metaproterenol Polistirex; Novasmasol; Prometa
• 别名: 5-[1-Hydroxy-2-[(1-methylethyl)amino]ethyl]-1,3-benzenediol Sulfate; 3,5-Dihydroxy-α-[(isopropylamino)methyl]benzyl Alcohol Sulfate; (±)-Orciprenaline Sulfate; 1-(3,5-Dihydroxyphenyl)-1-hydroxy-2-isopropylaminoethane Sulfate; Alotec; Alupent; Astmopent; Metaprel; Novasmasol; Th 152; dl-Metaproterenol Sulfate; dl-Orciprenaline Sulfate; Metaproterenol Hemisulfate Salt; Metaproterenol Sulfate; Orciprenalina [INN-Spanish]; Orciprenalinum [INN-Latin]; Metaproterenol; Orciprenaline Sulfate; Orciprenaline

登记号

• CAS号: 5874-97-5; 586-06-1
• PubChem SID: 46504464; 160964158
• PubChem CID: 4086

理论计算性质

JChem

• Acid pKa: 8.841109
• 质子受体: 4
• 质子供体: 4
• LogD (pH = 5.5): -2.091526
• LogD (pH = 7.4): -0.94034237
• Log P: 0.21496195
• 摩尔折射率: 58.3977 cm^3
• 极化性: 22.886492 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: -0.32
• LOG S: -1.48
• 溶解度: 6.92e+00 g/l

分子性质

理化性质

• 溶解度: 9.7mg/L
• 疏水性(logP): 1

安全信息

• 保存条件: -20°C Freezer

详细说明

DrugBank - DB00816

• Drug Groups: approved
• Description: A beta-adrenergic agonist used in the treatment of asthma and bronchospasms. [PubChem]
• Indication: For the treatment of bronchospasm, chronic bronchitis, asthma, and emphysema.
• Pharmacology: Orciprenaline (also known as metaproterenol), a synthetic amine, is structurally and pharmacologically similar to isoproterenol. Orciprenaline is used exclusively as a bronchodilator. The pharmacologic effects of beta adrenergic agonist drugs, such as orciprenaline, are at least in part attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (ATP) 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.
• Toxicity: Symptoms of overdose include angina, hypertension or hypotension, arrhythmias, nervousness, headache, tremor, dry mouth, palpitation, nausea, dizziness, fatigue, malaise and insomnia. LD₅₀=42 mg/kg (orally in rat).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic and gastric. The major metabolite, orciprenaline-3-0-sulfate, is produced in the gastrointestinal tract. Orciprenaline is not metabolized by catechol-0-methyltransferase nor have glucuronide conjugates been isolated to date.
• Absorption: 3% (oral bioavailability of 40%)
• Half Life: 6 hours
• External Links: Wikipedia; RxList

Toronto Research Chemicals - M225835

Bronchodilator.

参考文献

• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)