[2-hydroxy-3-(1H-indol-4-yloxy)propyl](propan-2-yl)amine

• ChemBase编号: 836
• 分子式: C14H20N2O2
• 平均质量: 248.3208
• 单一同位素质量: 248.15247789
• SMILES: O(CC(O)CNC(C)C)c1c2c([nH]cc2)ccc1
• Canonical SMILES: OC(COc1cccc2c1cc[nH]2)CNC(C)C
• InChI: InChI=1S/C14H20N2O2/c1-10(2)16-8-11(17)9-18-14-5-3-4-13-12(14)6-7-15-13/h3-7,10-11,15-17H,8-9H2,1-2H3
• InChIKey: JZQKKSLKJUAGIC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: [2-hydroxy-3-(1H-indol-4-yloxy)propyl](propan-2-yl)amine; 1-(1H-indol-4-yloxy)-3-[(propan-2-yl)amino]propan-2-ol
• IUPAC传统名: [2-hydroxy-3-(1H-indol-4-yloxy)propyl](propan-2-yl)amine; pindolol; 1-(1H-indol-4-yloxy)-3-(isopropylamino)propan-2-ol
• 商标名: Blockin L; Blocklin L; Calvisken; Cardilate; Decreten; Durapindol; Glauco-Visken; Pectobloc; Pinbetol; Pynastin; Visken
• 别名: Prindolol; Visken; (+/-)-4-[2-Hydroxy-3-(isopropylamino)propoxy]indole; Apo-pindol; Decreten; Pectobloc; Betapindol; Prinodolol; Pindolol; 1-(1H-Indol-4-yloxy)-3-(isopropylamino)-2-propanol; 1-(1H-Indol-4-yloxy)-3-[(1-methylethyl)amino]-2-propanol; Pindolol

登记号

• CAS号: 13523-86-9
• EC号: 236-867-9
• MDL号: MFCD00010530
• PubChem SID: 160964299; 46508362; 24277795
• PubChem CID: 4828
• CHEBI ID: 8214
• ATC码: C07AA03
• CHEMBL: 500
• Chemspider ID: 4662
• DrugBank ID: DB00960
• IUPHAR配体索引: 91
• KEGG ID: D00513
• 美国药典/FDA物质标识码: BJ4HF6IU1D
• 维基百科标题: Pindolol
• Medline Plus: a684032

理论计算性质

JChem

• Acid pKa: 14.086726
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -1.5002506
• LogD (pH = 7.4): -0.5322574
• Log P: 1.6929811
• 摩尔折射率: 71.462 cm^3
• 极化性: 29.42685 Å^3
• 极化表面积: 57.28 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: 2.17
• LOG S: -2.46
• 溶解度: 8.61e-01 g/l

分子性质

理化性质

• 溶解度: 0.1 M HCl: soluble20 mg/mL; 0.1 M NaOH: soluble0.2 mg/mL; 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.2 mg/mL; 7880 mg/L; DMSO; H2O: insoluble; Methanol
• 外观: White Solid; white to off-white powder
• 熔点: 165-167°C; 167-171 °C(lit.)
• 疏水性(logP): 1.9

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: UB6660000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 作用靶点: Others
• 给药途径: oral, iv
• 生物利用度: 50% to 95%
• 排泄: Renal
• 半衰期: 3–4 hours
• 代谢: Hepatic
• 法定药品分级: Rx-only
• 妊娠期药物分类: B (US); C (Australia)
• 相关基因信息: human ... ADRB1(153), HTR1A(3350)
• 生物活性机理: 5HT1A serotonin receptor antagonist; Non-cardioselective beta-Adrenoceptor antagonist; Partial agonist; Possesses intrinsic sympathomimetic actions (ISA), but little membrane-stabilizing activity; Sympatholytic-Beta; Vasodilator

产品相关信息

• 纯度: ≥98% (TLC)
• 成盐信息: Free Base
• 应用领域: Used in treatment of Angina pectoris and hypertension; Vasodilator

详细说明

DrugBank - DB00960

• Drug Groups: approved
• Description: A moderately lipophilic beta blocker (adrenergic beta-antagonists). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638)
• Indication: For the management of hypertension, edema, ventricular tachycardias, and atrial fibrillation.
• Pharmacology: Pindolol is a non-selective beta-adrenergic antagonist (beta-blocker) which possesses intrinsic sympathomimetic activity (ISA) in therapeutic dosage ranges but does not possess quinidine-like membrane stabilizing activity. Pindolol impairs AV node conduction and decreases sinus rate and may also increase plasma triglycerides and decrease HDL-cholesterol levels. Pindolol is nonpolar and hydrophobic, with low to moderate lipid solubility. Pindolol has little to no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, pindolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action.
• Toxicity: LD₅₀=263 mg/kg (orally in rats). Signs of overdose include excessive bradycardia, cardiac failure, hypotension, and bronchospasm.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. In man, 35% to 40% is excreted unchanged in the urine and 60% to 65% is metabolized primarily to hydroxy-metabolites which are excreted as glucuronides and ethereal sulfates.
• Absorption: Rapidly and reproducibly absorbed (bioavailability greater than 95%).
• Half Life: 3 to 4 hours
• Protein Binding: 40%
• Elimination: Pindolol undergoes extensive metabolism in animals and man. In man, 35% to 40% is excreted unchanged in the urine and 60% to 65% is metabolized primarily to hydroxy-metabolites which are excreted as glucuronides and ethereal sulfates. About 6% to 9% of an administered intravenous dose is excreted by the bile into the feces.
• Distribution: * 2 L/kg
• Clearance: * 50-300 mL/min [cirrhotic patients]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - P0778

Biochem/physiol Actions
β1-adrenoceptor antagonist; putative 5-HT1A serotonin receptor agonist; vasodilator.
Features and Benefits
Shelf-life of the powder is at least five years.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P0778.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - P468000

Mixed β-adrenergic blocker and serotonin 5HT1A-receptor antagonist. Antihypertensive; antianginal; antiarrhythmic; antiglaucoma.

参考文献

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