Structure via PubChem · Public domain (PubChem)
digitoxin
Sign in to saveAlso known as digitoxoside, unidigin, Crystodigin (TN), Digitoxinum, Digitoxoside, Crystodigin (tn), Digitoksin
Digitoxin is a cardiac glycoside used for the treatment of heart failure and certain kinds of heart arrhythmia. It is a phytosteroid and is similar in structure and effects to digoxin, though the effects are longer-lasting. Unlike digoxin, which is eliminated from the body via the kidneys, it is eliminated via the liver, and so can be used in patients with poor or erratic kidney function. While several controlled trials have shown digoxin to be effective in a proportion of patients treated for heart failure, the evidence base for digitoxin is not as strong, although it is presumed to be simila
Chemical data
- Formula
- C41H64O13
- Molecular weight
- 764.9 g/mol
- IUPAC name
- 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-[(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-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
- SMILES
- C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2O)O[C@@H]3[C@H](O[C@H](C[C@@H]3O)O[C@H]4CC[C@]5([C@@H](C4)CC[C@@H]6[C@@H]5CC[C@]7([C@@]6(CC[C@@H]7C8=CC(=O)OC8)O)C)C)C)C)O)O
- InChIKey
- WDJUZGPOPHTGOT-XUDUSOBPSA-N
- XLogP
- 2.3
- Polar surface area
- 183 Ų
- H-bond donors
- 5
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Research
3,069 papers- Digitoxin accumulation.British journal of clinical pharmacology · 1982
- [Digitoxin].Nihon rinsho. Japanese journal of clinical medicine · 1995
- Digitoxin.Journal of the American Pharmaceutical Association · 1976
- [Digitoxin--rediscovered].Medizinische Klinik · 1980
- Digitoxin as an anticancer agent with selectivity for cancer cells: possible mechanisms involved.Expert opinion on therapeutic targets · 2007
via PubMed
Wikidata facts
- Mass
- 764.434692
Show 6 more facts
- chemical formula
- C₄₁H₆₄O₁₃
- Commons category
- Digitoxin
- World Health Organisation international non-proprietary name
- digitoxin
- defined daily dose
- 0.1
- isomeric SMILES
- C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2O)O[C@@H]3[C@H](O[C@H](C[C@@H]3O)O[C@H]4CC[C@]5([C@@H](C4)CC[C@@H]6[C@@H]5CC[C@]7([C@@]6(CC[C@@H]7C8=CC(=O)OC8)O)C)C)C)C)O)O
- canonical SMILES
- CC1C(C(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CCC7(C6(CCC7C8=CC(=O)OC8)O)C)C)C)C)O)O
Sources (7)
via Wikidata · CC0
~6 min read
Article
14 sectionsContents
- Medical uses
- Contraindications
- Adverse effects and toxicity
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- History
- Use as a weapon
- In fiction
- Research
- References
- Further reading
- External links
Digitoxin is a cardiac glycoside used for the treatment of heart failure and certain kinds of heart arrhythmia. It is a phytosteroid and is similar in structure and effects to digoxin, though the effects are longer-lasting. Unlike digoxin, which is eliminated from the body via the kidneys, it is eliminated via the liver, and so can be used in patients with poor or erratic kidney function. While several controlled trials have shown digoxin to be effective in a proportion of patients treated for heart failure, the evidence base for digitoxin is not as strong, although it is presumed to be similarly effective.
==Medical uses== Digitoxin is used for the treatment of heart failure, especially in people with impaired kidney function. It is also used to treat certain kinds of heart arrhythmia, such as atrial fibrillation.