Digitoxin


Digitoxin
Digitoxin
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
Pregnancy cat.  ?
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
SMILES eMolecules & PubChem
 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 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]

Contents

Toxicity

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]

History

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]

Use in fiction

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.

References

  1. ^ Belz GG, Breithaupt-Grögler K, Osowski U (2001). "Treatment of congestive heart failure—current status of use of digitoxin". Eur. J. Clin. Invest. 31 (Suppl 2): 10–7. doi:10.1046/j.1365-2362.2001.0310s2010.x. PMID 11525233. http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0014-2972&date=2001&volume=31&issue=&spage=10. 
  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 Med 18 (7): 439–42. 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. http://books.google.com/books?id=tORsAAAAMAAJ. 
  4. ^ . PMC 2598854. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2598854. 
  5. ^ Sneader, Walter (2005). Drug discovery: A history. pp. 107. ISBN 9780471899808. http://books.google.com/books?id=mYQxRY9umjcC&pg=PA107. 

External links


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Look at other dictionaries:

  • digitoxin — dig i*tox in (d[i^]j [i^]*t[o^]k s[i^]n), n. (Chem.) A steroid glycoside, one of the cardiotonic chemical substances which is extracted from the foxglove. It is a white, crystalline substance ({C41H64O13}), and is a 3 substituted triglucoside of… …   The Collaborative International Dictionary of English

  • Digitoxīn — Digitoxīn, s. Digitalin …   Meyers Großes Konversations-Lexikon

  • digitoxin — [dij΄i täk′sin] n. [ DIGI(TALIS) + TOXIN] a glycoside, C41H64O13, extracted from digitalis leaves, like digitalis in physiological action, but more potent …   English World dictionary

  • Digitoxin — Strukturformel Allgemeines Freiname Digitoxin Andere Namen …   Deutsch Wikipedia

  • digitoxin — A cardioactive glycoside obtained from the leaves of Digitalis purpurea; it is more completely absorbed from the gastrointestinal tract than is digitalis. Largely eliminated by hepatic metabolism. SYN: crystalline digitalin. * * * dig·i·tox·in… …   Medical dictionary

  • digitoxin — noun Etymology: International Scientific Vocabulary, blend of New Latin Digitalis and International Scientific Vocabulary toxin Date: circa 1883 a poisonous cardiotonic glycoside C41H64O13 that is the most active constituent of digitalis; …   New Collegiate Dictionary

  • digitoxin — /dij i tok sin/, n. Pharm. a white, crystalline, water insoluble cardiac glycoside, C41H64O13, or a mixture of cardiac glycosides of which this is the chief constituent, obtained from digitalis and used in the treatment of congestive heart… …   Universalium

  • digitoxin — noun A toxic cardiac glycoside, obtained from digitalis, related to cardenolide …   Wiktionary

  • Digitoxin — Di|gi|to|xin 〈n. 11; unz.; Pharm.〉 Glykosid, das aus den Digitalisblättern gewonnen wird u. insbesondere zur Behandlung von Herzkrankheiten eingesetzt wird [<Digi(talis) + Toxin] * * * Di|gi|to|xin [nlat. Digitalis = Fingerhut (Bot.); ↑ Toxin] …   Universal-Lexikon

  • Digitoxin — Di|gi|to|xin 〈n.; Gen.: s; Pl.: unz.; Pharm.〉 Glykosid, das aus den Digitalisblättern gewonnen wird und insbesondere zur Behandlung von Herzkrankheiten eingesetzt wird [Etym.: <Digitalis + Toxin] …   Lexikalische Deutsches Wörterbuch