Digitoxin: Difference between revisions

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Digitoxin
Clinical data
ATC code	C01AA04 (WHO) ;
Identifiers
	IUPAC name 5β,20(22)-Cardenolide-3β,14-diol-3-; (O-2,6-dideoxy-β-D-ribo-hexopyranosyl-; [1→4]-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-; [1→4]-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy;
CAS Number	71-63-6;
PubChem CID	3061;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C41H64O13
Molar mass	764.939 g/mol

VisualWikitext

Revision as of 14:16, 23 July 2014

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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

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

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]

References

↑ 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.
↑ 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.
↑ Withering, William (1785). An Account of the Foxglove and Some of its Medical Uses: With Practical Remarks on Dropsy and other Diseases.
↑ PMID 18127991 (PMID 18127991)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
↑ Sneader, Walter (2005). Drug discovery: A history. p. 107. ISBN 978-0-471-89980-8.

Johansson, S.; Lindholm, P.; Gullbo, J.; Larsson, R.; Bohlin, L.; Claeson, P. (2001). "Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells". Anticancer Drugs. 12 (5): 475–483. doi:10.1097/00001813-200106000-00009. PMID 11395576.
Hippius, M.; Humaid, B.; Sicker, T.; Hoffmann, A.; Göttler, M.; Hasford, J. (2001). "Adverse drug reaction monitoring--digitoxin overdosage in the elderly". International Journal of Clinical Pharmacology and Therapeutics. 39 (8): 336–343. PMID 11515708.
Haux, J.; Klepp, O.; Spigset, O.; Tretli, S. (2001). "Digitoxin medication and cancer; case control and internal dose-response studies" (pdf). BMC Cancer. 1: 11. doi:10.1186/1471-2407-1-11. PMC 48150. PMID 11532201.
Srivastava, M.; Eidelman, O.; Zhang, J.; Paweletz, C.; Caohuy, H.; Yang, Q.; Jacobson, K. A.; Heldman, E.; Huang, W.; Jozwik, C.; Pollard, B. S.; Pollard, H. B. (2004). "Digitoxin mimics gene therapy with CFTR and suppresses hypersecretion of IL-8 from cystic fibrosis lung epithelial cells". Proceedings of the National Academy of Science of the United States of America. 101 (20): 7693–7698. doi:10.1073/pnas.0402030101. PMC 419668. PMID 15136726.

Template:Glycosides Template:Cardiac glycosides

Template:WikiDoc Sources

[Belz-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.

[Kurowsky-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] PMID 18127991 (PMID 18127991)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand

[5] Sneader, Walter (2005). Drug discovery: A history. p. 107. ISBN 978-0-471-89980-8.

[1]

[2]

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[4]

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@@ Line 25: / Line 25: @@
 ==Overview==
-'''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 UK 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. <ref name=Belz> Treatment of congestive heart failure--current status of use of digitoxin. Belz GG, Breithaupt-Grogler K and Osowski U.  ''Eur J Clin Invest.'' 2001;31 Suppl 2:10-7.  [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=11525233&query_hl=13&itool=pubmed_DocSum PMID: 11525233 (accessed 20 Sep 2006)]</ref>
+'''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.<ref name=Belz>{{cite journal | author = Belz, G. G.; Breithaupt-Grögler, K.; Osowski, U. | title = Treatment of congestive heart failure—current status of use of digitoxin | journal = European Journal of Clinical Investigation | year = 2001 | volume = 31 | issue = Suppl 2 | pages = 10–17 | doi = 10.1046/j.1365-2362.2001.0310s2010.x | pmid = 11525233 | url = http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0014-2972&date=2001&volume=31&issue=&spage=10 }}</ref>
-== Toxicity==
+==Toxicity==
-Digitoxin exhibits similar toxic effects to the more-commonly used [[digoxin]], namely: anorexia, nausea, vomiting, diarrhoea, confusion, visual disturbances, and cardiac [[arrhythmias]].  Anti-digoxin antibody fragments, the specific treatment for digoxin poisoning, are also effective in serious digitoxin toxicity.<ref name=Kurowsky> Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies. Kurowski V, Iven H and Djonlagic H.  ''Intensive Care Med'' 1992;18(7):439-42. [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?itool=abstractplus&db=pubmed&cmd=Retrieve&dopt=abstractplus&list_uids=1469187 PMID: 1469187 (accessed 19 Sep 2006]</ref>
+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.<ref name=Kurowsky>{{cite journal | author = Kurowski, V.; Iven, H.; Djonlagic, H. | title = Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies | journal = Intensive Care Medicine | volume = 18 | issue = 7 | pages = 439–442 | year = 1992 | pmid = 1469187 | doi = 10.1007/BF01694351 }}</ref>
+==History==
+The first description of the use of [[Digitalis purpurea|foxglove]] dates back to 1775.<ref>{{cite book | url = http://books.google.com/books?id=tORsAAAAMAAJ | title = An Account of the Foxglove and Some of its Medical Uses: With Practical Remarks on Dropsy and other Diseases | author1 = Withering, William | year = 1785 }}</ref> 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.<ref>{{cite pmid | 18127991 }}</ref><ref>{{cite book | url = http://books.google.com/books?id=mYQxRY9umjcC&pg=PA107 | pages = 107 | title = Drug discovery: A history | isbn = 978-0-471-89980-8 | author1 = Sneader, Walter | year = 2005}}</ref>
 ==References==
-<references/>
+{{reflist|2}}
+{{refbegin}}
-==External links==
+* {{cite journal | author = Johansson, S.; Lindholm, P.; Gullbo, J.; Larsson, R.; Bohlin, L.; Claeson, P. | title = Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells | journal = Anticancer Drugs | year = 2001 | volume = 12 | issue = 5 | pages = 475–483 | pmid = 11395576 | doi = 10.1097/00001813-200106000-00009 }}
-* [http://www.medscape.com/viewarticle/410488 "Comparing the Toxicity of Digoxin and Digitoxin in a Geriatric Population: Should an Old Drug Be Rediscovered?"]
+* {{cite journal | author = Hippius, M.; Humaid, B.; Sicker, T.; Hoffmann, A.; Göttler, M.; Hasford, J. | title = Adverse drug reaction monitoring--digitoxin overdosage in the elderly | journal = International Journal of Clinical Pharmacology and Therapeutics | year = 2001 | volume = 39 | issue = 8 | pages = 336–343 | pmid = 11515708 }}
-* {{cite journal | author = Johansson S, Lindholm P, Gullbo J, Larsson R, Bohlin L, Claeson P | title = Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. | journal = Anticancer Drugs | volume = 12 | issue = 5 | pages = 475-83 | year = 2001 | id = PMID 11395576}}
+* {{cite journal | author = Haux, J.; Klepp, O.; Spigset, O.; Tretli, S. | title = Digitoxin medication and cancer; case control and internal dose-response studies | journal = BMC Cancer | year = 2001 | volume = 1 | pages = 11 | pmid = 11532201 | doi = 10.1186/1471-2407-1-11 | pmc = 48150 | url = http://www.ncbi.nlm.nih.gov/pmc/articles/PMC48150/pdf/1471-2407-1-11.pdf | format = pdf }}
-* {{cite journal | author = Hippius M, Humaid B, Sicker T, Hoffmann A, Göttler M, Hasford J | title = Adverse drug reaction monitoring--digitoxin overdosage in the elderly. | journal = Int J Clin Pharmacol Ther | volume = 39 | issue = 8 | pages = 336-43 | year = 2001 | id = PMID 11515708}}
+* {{cite journal | author = Srivastava, M.; Eidelman, O.; Zhang, J.; Paweletz, C.; Caohuy, H.; Yang, Q.; Jacobson, K. A.; Heldman, E.; Huang, W.; Jozwik, C.; Pollard, B. S.; Pollard, H. B. | title = Digitoxin mimics gene therapy with CFTR and suppresses hypersecretion of IL-8 from cystic fibrosis lung epithelial cells | journal = Proceedings of the National Academy of Science of the United States of America | year = 2004 | volume = 101 | issue = 20 | pages = 7693–7698 | pmid = 15136726 | doi = 10.1073/pnas.0402030101 | pmc = 419668 }}
-* {{cite journal | author = Belz G, Breithaupt-Grögler K, Osowski U | title = Treatment of congestive heart failure--current status of use of digitoxin. | journal = Eur J Clin Invest | volume = 31 Suppl 2 | issue = | pages = 10-7 | year = | id = PMID 11525233}}
+{{refend}}
-* {{cite journal | author = Haux J, Klepp O, Spigset O, Tretli S | title = Digitoxin medication and cancer; case control and internal dose-response studies. | journal = BMC Cancer | volume = 1 | issue = | pages = 11 | year = | id = PMID 11532201}}
-* {{cite journal | author = Srivastava M, Eidelman O, Zhang J, Paweletz C, Caohuy H, Yang Q, Jacobson K, Heldman E, Huang W, Jozwik C, Pollard B, Pollard H | title = Digitoxin mimics gene therapy with CFTR and suppresses hypersecretion of IL-8 from cystic fibrosis lung epithelial cells. | journal = Proc Natl Acad Sci U S A | volume = 101 | issue = 20 | pages = 7693-8 | year = 2004 | id = PMID 15136726}}
-http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/D5878
 {{Glycosides}}