4-[(1S,2S,5S,7R,10R,11S,15S,16R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase编号: 273
• 分子式: C41H64O14
• 平均质量: 780.93846
• 单一同位素质量: 780.42960673
• SMILES: O[C@@]12[C@H]3[C@@H]([C@@]4([C@H](CC3)C[C@@H](O[C@@H]3O[C@@H]([C@@H](O[C@@H]5O[C@@H]([C@@H](O[C@@H]6O[C@@H]([C@@H](O)[C@@H](O)C6)C)[C@@H](O)C5)C)[C@@H](O)C3)C)CC4)C)C[C@@H](O)[C@@]1(C(CC2)C1=CC(=O)OC1)C
• Canonical SMILES: O=C1OCC(=C1)C1CC[C@]2([C@]1(C)[C@H](O)C[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@@H](C2)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O)O
• InChI: InChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25?,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1
• InChIKey: LTMHDMANZUZIPE-YUICGFAKSA-N

名称和登记号

名称

• IUPAC标准名: 4-[(1S,2S,5S,7R,10R,11S,15S,16R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one
• IUPAC传统名: digoxin
• 商标名: Cardoxin; Cogoxin; Cordioxil; Davoxin; Digacin; Digitekt; Digoxin Pediatric; Dilanacin; Dixina; Dokim; Dynamos; Eudigox; Homolle's Digitalin; Lanacordin; Lanacrist; Lanicor; Lanoxicaps; Lanoxin; Lenoxicaps; Lenoxin; Longdigox; Neo-Lanicor; Neodioxanin; Rougoxin; SK-Digoxin; Stillacor; Vanoxin
• 别名: Digitalis Glycoside; Digoxin

登记号

• CAS号: 20830-75-5
• PubChem SID: 160963736
• PubChem CID: 30322

理论计算性质

JChem

• Acid pKa: 7.151116
• 质子受体: 13
• 质子供体: 6
• LogD (pH = 5.5): 2.3571007
• LogD (pH = 7.4): 1.9245013
• Log P: 2.3666806
• 摩尔折射率: 193.2328 cm^3
• 极化性: 79.00782 Å^3
• 极化表面积: 203.06 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 1.04
• LOG S: -3.79
• 溶解度: 1.27e-01 g/l

分子性质

理化性质

• 溶解度: Insoluble
• 疏水性(logP): 2.2

详细说明

DrugBank - DB00390

• Drug Groups: approved
• Description: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone digoxigenin. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666)
• Indication: For the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure.
• Pharmacology: Digoxin, a cardiac glycoside similar to digitoxin, is used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation.
• Toxicity: Toxicity includes ventricular tachycardia or ventricular fibrillation, or progressive bradyarrhythmias, or heart block. LD₅₀ = 7.8 mg/kg (orally in mice).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic (but not dependent upon the cytochrome P-450 system). The end metabolites, which include 3 b-digoxigenin, 3-keto-digoxigenin, and their glucuronide and sulfate conjugates, are polar in nature and are postulated to be formed via hydrolysis, oxidation, and conjugation.
• Absorption: Absorption of digoxin from the elixir pediatric formulation has been demonstrated to be 70% to 85% complete (90% to 100% from the capsules, and 60% to 80% for tablets).
• Half Life: 3.5 to 5 days
• Protein Binding: 25%
• Elimination: Following intravenous administration to healthy volunteers, 50% to 70% of a digoxin dose is excreted unchanged in the urine.
• References: Thompson DF, Carter JR: Drug-induced gynecomastia. Pharmacotherapy. 1993 Jan-Feb;13(1):37-45. [Pubmed] ; Doering W, Konig E, Sturm W: [Digitalis intoxication: specifity and significance of cardiac and extracardiac symptoms. part I: Patients with digitalis-induced arrhythmias (author's transl)] Z Kardiol. 1977 Mar;66(3):121-8. [Pubmed] ; Kaplanski J, Weinhouse E, Topaz M, Genchik G: Verapamil and digoxin: interactions in the rat. Res Commun Chem Pathol Pharmacol. 1983 Dec;42(3):377-88. [Pubmed] ; Flanagan RJ, Jones AL: Fab antibody fragments: some applications in clinical toxicology. Drug Saf. 2004;27(14):1115-33. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Thompson DF, Carter JR: Drug-induced gynecomastia. Pharmacotherapy. 1993 Jan-Feb;13(1):37-45. Pubmed
• Doering W, Konig E, Sturm W: [Digitalis intoxication: specifity and significance of cardiac and extracardiac symptoms. part I: Patients with digitalis-induced arrhythmias (author's transl)] Z Kardiol. 1977 Mar;66(3):121-8. Pubmed
• Kaplanski J, Weinhouse E, Topaz M, Genchik G: Verapamil and digoxin: interactions in the rat. Res Commun Chem Pathol Pharmacol. 1983 Dec;42(3):377-88. Pubmed
• Flanagan RJ, Jones AL: Fab antibody fragments: some applications in clinical toxicology. Drug Saf. 2004;27(14):1115-33. Pubmed