4-[(1S,2S,5S,7R,10R,11S,14R,15R)-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-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase编号: 1207
• 分子式: C41H64O13
• 平均质量: 764.93906
• 单一同位素质量: 764.43469211
• 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)CC[C@@]1([C@H](CC2)C1=CC(=O)OC1)C
• Canonical SMILES: O=C1OCC(=C1)[C@H]1CC[C@]2([C@]1(C)CC[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/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
• InChIKey: WDJUZGPOPHTGOT-XUDUSOBPSA-N

名称和登记号

名称

• IUPAC标准名: 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-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-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydrofuran-2-one; 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-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-hydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]-2,5-dihydrofuran-2-one; 4-[(1S,2S,5S,7R,10R,11S,14R,15R)-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-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one
• IUPAC传统名: digitoxin
• 商标名: Digitaline; Crystodigin; Unidigin; Tardigal
• 别名: 洋地黄毒苷; Digitoxin; 5β,20(22)-Cardenolide-3β,14-diol-3-(O-2,6-dideoxy-β-D-ribo-hexopyranosyl-[1→4]-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-[1→4]-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy; Digitoxinum; Digitoxoside; Digitoksin; Digitalin; Digitoxin

登记号

• CAS号: 71-63-6
• EC号: 200-760-5
• MDL号: MFCD00003686
• Beilstein号: 76678
• PubChem SID: 24893976; 160964669; 46506035
• PubChem CID: 441207
• CHEBI ID: 28544
• ATC码: C01AA04
• CHEMBL: 254219
• Chemspider ID: 389987
• DrugBank ID: DB01396
• KEGG ID: D00297
• 美国药典/FDA物质标识码: E90NZP2L9U
• 维基百科标题: Digitoxin

理论计算性质

JChem

• Acid pKa: 7.182636
• 质子受体: 12
• 质子供体: 5
• LogD (pH = 5.5): 3.5885735
• LogD (pH = 7.4): 3.175141
• Log P: 3.5974917
• 摩尔折射率: 191.7173 cm^3
• 极化性: 78.34437 Å^3
• 极化表面积: 182.83 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: 2.33
• LOG S: -4.42
• 溶解度: 2.89e-02 g/l

分子性质

理化性质

• 溶解度: 0.0039 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; chloroform: soluble
• 外观: powder
• 熔点: 240 °C (dec.)(lit.); 256-257°C
• 比旋光度: [α]20/D +17±1°, 7 hr, c = 2% in chloroform; [α]23/D +5.4°, c = 1.2 in dioxane
• 疏水性(logP): 1.85 [SANGSTER (1993)]

安全信息

• 保存条件: Room Temperature (15-30°C), Desiccate, Store Under Nitrogen
• RTECS编号: IH2275000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 1544; 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 1; I
• 澳大利亚Hazchem: 2X
• 危险公开号: 23/25-33; R:23/25-33
• 安全公开号: 45; S:45
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 151
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H331-H373
• GHS警示性声明: P261-P301 + P310-P311
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1

药理学性质

• 生物利用度: 95% (Oral)
• 半衰期: 5~7 days
• 代谢: Liver

产品相关信息

• 纯度: ≥92% (HPLC); ≥98.0% (HPLC); 97%
• 燃烧残渣: ≤0.05%
• Empirical Formula (Hill Notation): C41H64O13

详细说明

MP Biomedicals - 02190514

Crystalline

DrugBank - DB01396

• Drug Groups: approved
• Description: A cardiac glycoside sometimes used in place of digoxin. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665)
• Indication: For the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure.
• Pharmacology: Digitoxin is a cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting (From Martindale, The Extra Pharmacopoeia, 30th ed, p665). Unlike digoxin (which is eliminated from the body via the kidneys), it is eliminated via the liver, so could be used in patients with poor or erratic kidney function. However, it is now rarely used in current UK medical practice. While there have been several controlled trials which have shown digoxin to be effective in a proportion of patients treated for heart failure, there is not the same strong evidence base for digitoxin, although it is presumed to be similarly effective.
• Toxicity: Digitoxin exhibits similar toxic effects to the more-commonly used digoxin, namely: anorexia, nausea, vomiting, diarrhoea, confusion, visual disturbances, and cardiac arrhythmias.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• References: Belz GG, Breithaupt-Grogler K, Osowski U: Treatment of congestive heart failure--current status of use of digitoxin. Eur J Clin Invest. 2001;31 Suppl 2:10-7. [Pubmed] ; Kurowski V, Iven H, Djonlagic H: Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies. Intensive Care Med. 1992;18(7):439-42. [Pubmed] ; Johansson S, Lindholm P, Gullbo J, Larsson R, Bohlin L, Claeson P: Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. Anticancer Drugs. 2001 Jun;12(5):475-83. [Pubmed] ; Hippius M, Humaid B, Sicker T, Hoffmann A, Gottler M, Hasford J: Adverse drug reaction monitoring--digitoxin overdosage in the elderly. Int J Clin Pharmacol Ther. 2001 Aug;39(8):336-43. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - D5878

包装
1, 5, 10 g in glass bottle
250, 500 mg in glass bottle

参考文献

• Belz GG, Breithaupt-Grogler K, Osowski U: Treatment of congestive heart failure--current status of use of digitoxin. Eur J Clin Invest. 2001;31 Suppl 2:10-7. Pubmed
• Kurowski V, Iven H, Djonlagic H: Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies. Intensive Care Med. 1992;18(7):439-42. Pubmed
• Johansson S, Lindholm P, Gullbo J, Larsson R, Bohlin L, Claeson P: Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. Anticancer Drugs. 2001 Jun;12(5):475-83. Pubmed
• Hippius M, Humaid B, Sicker T, Hoffmann A, Gottler M, Hasford J: Adverse drug reaction monitoring--digitoxin overdosage in the elderly. Int J Clin Pharmacol Ther. 2001 Aug;39(8):336-43. Pubmed