Digitoxin

Digitoxin

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Encyclopedia
Digitoxin is a cardiac glycoside
Cardiac glycoside
Cardiac glycosides are drugs used in the treatment of congestive heart failure and cardiac arrhythmia. These glycosides are found as secondary metabolites in several plants, but also in some animals, such as the milkweed butterflies. -Function:...

. It has similar structure and effects to digoxin
Digoxin
Digoxin INN , also known as digitalis, is a purified cardiac glycoside and extracted from the foxglove plant, Digitalis lanata. Its corresponding aglycone is digoxigenin, and its acetyl derivative is acetyldigoxin...

 (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.

Toxicity


Digitoxin exhibits similar toxic effects to the more-commonly used digoxin
Digoxin
Digoxin INN , also known as digitalis, is a purified cardiac glycoside and extracted from the foxglove plant, Digitalis lanata. Its corresponding aglycone is digoxigenin, and its acetyl derivative is acetyldigoxin...

, 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.

History


The first description of the use of foxglove dates back to 1775. For quite some time the active compound was not isolated. It took until 1875 when Oswald Schmiedeberg
Oswald Schmiedeberg
Oswald Schmiedeberg was a Baltic German pharmacologist.Schmiedeberg was born at Gut Laidsen in the Imperial Russian province of Courland. In 1866 he earned his medical doctorate from the University of Dorpat with a thesis concerning the measurement of chloroform in blood. Afterwards he was an...

 was able to obtain a pure sample. The first structural analysis was done by Adolf Otto Reinhold Windaus
Adolf Otto Reinhold Windaus
Adolf Otto Reinhold Windaus was a German chemist who won a Nobel Prize in Chemistry in 1928 for his work on sterols and their relation to vitamins. He was the doctoral advisor of Adolf Butenandt who also won a Nobel Prize in Chemistry in 1939.Adolf Windaus was born in Berlin. His interest in...

 in 1925 but the full structure with an exact determination of the sugar groups had to wait until 1962.

Use in fiction


Used as the murder weapon in Agatha Christie
Agatha Christie
Dame Agatha Christie DBE was a British crime writer of novels, short stories, and plays. She also wrote romances under the name Mary Westmacott, but she is best remembered for her 66 detective novels and 14 short story collections , and her successful West End plays.According to...

's Appointment with Death
Appointment with Death
Appointment with Death is a work of detective fiction by Agatha Christie and first published in the UK by the Collins Crime Club on May 2, 1938 and in the US by Dodd, Mead and Company later in the same year...

.

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
The Decemberists
The Decemberists are an indie folk rock band from Portland, Oregon, United States, fronted by singer/songwriter Colin Meloy. The other members of the band are Chris Funk , Jenny Conlee , Nate Query , and John Moen .The band's...

's song, "The Rake's Song" off of the The Hazards of Love
The Hazards of Love
The Hazards of Love, released March 24, 2009, is the fifth album by The Decemberists. The album was inspired by an Anne Briggs EP titled The Hazards of Love. According to the band, frontman Colin Meloy set out to write a song with the album's title—eventually leading to an entire album...

album, the narrator murders his daughter by feeding her foxglove.

External links