Digitoxin

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Digitoxin
Digitoxin.png
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
Clinical data
Trade names Digitaline
Legal status
?
Pharmacokinetic data
Bioavailability 95% (Oral)
Metabolism Liver
Half-life 5~7 days
Identifiers
CAS number 71-63-6 YesY
ATC code C01AA04
PubChem CID 441207
DrugBank DB01396
ChemSpider 389987 N
UNII E90NZP2L9U N
KEGG D00297 N
ChEBI CHEBI:28544 N
ChEMBL CHEMBL254219 N
Chemical data
Formula C41H64O13 
Mol. mass 764.939 g/mol
 N (what is this?)  (verify)

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 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.[1]

Toxicity[edit]

Digitoxin exhibits similar toxic effects to the more commonly used digoxin, namely: anorexia, nausea, vomiting, diarrhea, confusion, visual disturbances, and cardiac arrhythmias. Antidigoxin antibody fragments, the specific treatment for digoxin poisoning, are also effective in serious digitoxin toxicity.[2]

History[edit]

The first description of the use of foxglove dates back to 1775.[3] For quite some time, the active compound was not isolated. Oswald Schmiedeberg was able to obtain a pure sample in 1875. The modern therapeutic use of this molecule was made possible by the works of the pharmacist and the French chemist Claude-Adolphe Nativelle (1812-1889). 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 was not accomplished until 1962.[4][5]

Use in fiction[edit]

Digitoxin is used as the murder weapon in Agatha Christie's Appointment with Death, Elizabeth Peters' Die For Love and CSI, season 9, episode 19: "The Descent of Man". It was also used as a poison in "Uneasy Lies the Crown" on Columbo, season 9, episode 5 (1990), "Affair of the Heart" on McMillan and Wife, season 6, episode 5 (1977) and on Murder 101: "College can be a Murder". Also used in several episodes of Murder She Wrote.

In The Decemberists's song, "The Rake's Song" on the The Hazards of Love album, the narrator murders his daughter by feeding her foxglove.

References[edit]

  1. ^ Belz, G. G.; Breithaupt-Grögler, K.; Osowski, U. (2001). "Treatment of congestive heart failure—current status of use of digitoxin". European Journal of Clinical Investigation 31 (Suppl 2): 10–17. doi:10.1046/j.1365-2362.2001.0310s2010.x. PMID 11525233. 
  2. ^ Kurowski, V.; Iven, H.; Djonlagic, H. (1992). "Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies". Intensive Care Medicine 18 (7): 439–442. doi:10.1007/BF01694351. PMID 1469187. 
  3. ^ Withering, William (1785). An Account of the Foxglove and Some of its Medical Uses: With Practical Remarks on Dropsy and other Diseases. 
  4. ^ Diefenbach, W. C.; Meneely Jr, J. K. (1949). "Digitoxin; a critical review" (pdf). The Yale Journal of Biology and Medicine 21 (5): 421–431. PMC 2598854. PMID 18127991.  edit
  5. ^ Sneader, Walter (2005). Drug discovery: A history. p. 107. ISBN 978-0-471-89980-8. 

External links[edit]