CAS 71-63-6|Digitoksin|Tardigal|Digitoxinum|Digitalin|Crystodigin|Digitoxoside|digitoxin|Unidigin|Digitoxin|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...

基本信息

化学结构

分子式

C₄₁H₆₄O₁₃

分子量

764.93906

精确质量

764.43469211

电荷

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

Canonic 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

Isomeric 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

计算属性

Enamine提供

CLogP

2.85

质子供体

极化表面积

182.83

可自由旋转的化学键

JChem

极化表面积

182.83

质子供体

质子受体

可自由旋转的化学键

里宾斯基五规则

false

Log P

3.60

LogD (pH = 5.5)

3.60

LogD (pH = 7.4)

3.60

Acid pKa

13.03

摩尔折射率

191.72

极化性

78.34

LOG S

-3.79

数据来源

名称和标识

别名

DigitoksinDigitoxinumDigitalinDigitoxosideDigitoxin5β,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洋地黄毒苷Digitoxin

商标名

TardigalCrystodiginUnidiginDigitaline

IUPAC传统名

digitoxin

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^{11,15}]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[8.7.0.0²,⁷.0¹¹,¹⁵]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-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-7-{[(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}-3a-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2,5-dihydrofuran-2-one

API名称

Digitoxin

名称和标识

数据登录号

PubChem CID

441207

CAS号

71-63-6

PubChem SID

4650603516096466924893976

EC号

Beilstein号

MDL号

CHEMBL

美国药典/FDA物质标识码

CHEBI ID

ATC码

DrugBank ID

维基百科标题

KEGG ID

Chemspider ID

数据登录号

化合物性质

理化性质

溶解度

0.0039 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

chloroform: soluble

疏水性(logP)

1.85 [SANGSTER (1993)]

熔点

256-257°C

240 °C (dec.)(lit.)

外观

powder

[α]23/D +5.4°, c = 1.2 in dioxane

[α]20/D +17±1°, 7 hr, c = 2% in chloroform

安全信息

R:23/25-33

23/25-33

151

药理学性质

5~7 days

95% (Oral)

Liver

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

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]

Crystalline

D5878

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

描述信息

参考文献

PubChem文献

数据源提供

• 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

• 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

• 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

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

商标名

TardigalCrystodiginUnidiginDigitaline

IUPAC传统名

digitoxin

IUPAC标准名

API名称

Digitoxin

数据登录号

PubChem CID

441207

CAS号

71-63-6

PubChem SID

4650603516096466924893976

EC号

Beilstein号

MDL号

CHEMBL

美国药典/FDA物质标识码

CHEBI ID

ATC码

DrugBank ID

维基百科标题

KEGG ID

Chemspider ID

参考文献

PubChem文献

数据源提供

• 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

• 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

• 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

生物活性

PubChem BioAssay

化合物性质

理化性质

溶解度

0.0039 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

chloroform: soluble

疏水性(logP)

1.85 [SANGSTER (1993)]

熔点

256-257°C

240 °C (dec.)(lit.)

外观

powder

[α]23/D +5.4°, c = 1.2 in dioxane

[α]20/D +17±1°, 7 hr, c = 2% in chloroform

安全信息

R:23/25-33

23/25-33

151

药理学性质

5~7 days

95% (Oral)

Liver

描述信息

DrugBank

DB01396

Drug Groups

approved

Description

Indication

For the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure.

Pharmacology

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]

Crystalline

D5878

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

化合物信息

ID:1207