| Systematic (IUPAC) name | |
|---|---|
| (3β,5β)-3-[(O-2,6-dideoxy- β-D-ribo-hexapyranosyl-(1->4)- 2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]- 14-hydroxycard-20(22)-enolide |
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| Clinical data | |
| Trade names | Digitaline |
| Pregnancy cat. | ? |
| Legal status | ? |
| Pharmacokinetic data | |
| Bioavailability | 95% (Oral) |
| Metabolism | Liver |
| Half-life | 5~7 days |
| Identifiers | |
| CAS number | 71-63-6 |
| ATC code | C01AA04 |
| PubChem | CID 441207 |
| DrugBank | DB01396 |
| ChemSpider | 389987 |
| UNII | E90NZP2L9U |
| KEGG | D00297 |
| ChEBI | CHEBI:28544 |
| ChEMBL | CHEMBL254219 |
| Chemical data | |
| Formula | C41H64O13 |
| Mol. mass | 764.939 g/mol |
| SMILES | eMolecules & PubChem |
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Digitoxin is a cardiac glycoside. It has similar 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, so could be used in patients with poor or erratic kidney function. However, it is now rarely used in current Western 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.[1]
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Digitoxin exhibits similar toxic effects to the more-commonly used digoxin, namely: anorexia, nausea, vomiting, diarrhea, confusion, visual disturbances, and cardiac arrhythmias. Anti-digoxin antibody fragments, the specific treatment for digoxin poisoning, are also effective in serious digitoxin toxicity.[2]
The first description of the use of foxglove dates back to 1775.[3] For quite some time the active compound was not isolated. It took until 1875 when Oswald Schmiedeberg was able to obtain a pure sample. The first structural analysis was done by Adolf Otto Reinhold Windaus in 1925 but the full structure with an exact determination of the sugar groups had to wait until 1962.[4][5]
Used as the murder weapon in Agatha Christie's Appointment with Death.
Used as a murder weapon in Elizabeth Peters' Die For Love.
Used as murder weapon with crop duster in CSI, Season 9 Episode 19: "The Descent of Man".
Digoxin used as a poison in "Uneasy Lies the Crown" Columbo 1990[Season 9, Episode 5]
Used as murder weapon in "Affair of the Heart" McMillan and Wife 1977 [Season 6, Episode 5].
Used as murder weapon in Murder 101: college can be a murder.
In the The Decemberists's song, "The Rake's Song" off of the The Hazards of Love album, the narrator murders his daughter by feeding her foxglove.
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