View source for Digitoxin

{{Drugbox|
| IUPAC_name = (3β,5β)-3-[(O-2,6-dideoxy-<br/>β-D-ribo-hexapyranosyl-(1->4)-<br/>2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-<br/>14-hydroxycard-20(22)-enolide
| image = Digitoxin.png
| InChI = {{InChIwrap|1/C41H64O13/c1-20-36(46) 29(42)16-34(49-20)53-38-22(3)5 1-35(18-31(38)44)54-37-21(2)50 -33(17-30(37)43)52-25-8-11-39( 4)24(15-25)6-7-28-27(39)9-12-4 0(5)26(10-13-41(28,40)47)23-14 -32(45)48-19-23/h14,20-22,24-3 1,33-38,42-44,46-47H,6-13,15-1 9H2,1-5H3/t20-,21-,22-,24-,25+ ,26-,27+,28-,29+,30+,31+,33+,3 4+,35+,36-,37-,38-,39+,40-,41+ /m1/s1}}
| StdInChI = {{InChIwrap|1S/C41H64O13/c1-20-36(46 )29(42)16-34(49-20)53-38-22(3) 51-35(18-31(38)44)54-37-21(2)5 0-33(17-30(37)43)52-25-8-11-39 (4)24(15-25)6-7-28-27(39)9-12- 40(5)26(10-13-41(28,40)47)23-1 4-32(45)48-19-2 3/h14,20-22,24 -31,33-38,42-44,46-47H,6-13,15 -19H2,1-5H3/t20-,21-,22-,24-,2 5+,26-,27+,28-,29+,30+,31+,33+ ,34+,35+,36-,37-,38-,39+,40-,4 1+/m1/s1}}
| InChIKey = WDJUZGPOPHTGOT-XUDUSOBPBI
| StdInChIKey = WDJUZGPOPHTGOT-XUDUSOBPSA-N
| CASNo = 71-63-6
|   CASNo_Ref = {{cascite}}
| EC-number = 200-760-5
| ChemSpiderID = 389987
| ATC_prefix = C01
| ATC_suffix = AA04
| ATC_supplemental =
| PubChem = 11968425
| DrugBank =
| C=41 | H=64 | O=13
| molecular_weight = 764.94 g/mol
| bioavailability= 95% (Oral)
| metabolism = Liver
| elimination_half-life= 5–7 days
| excretion = 
| pregnancy_category =
| legal_status =
| routes_of_administration=
}}

'''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">{{citation | last1 = Belz | first1 = G. | last2 = Breithaupt-Grögler | first2 = K. | last3 = Osowski | first3 = U. | title = Treatment of congestive heart failure – current status of use of digitoxin | journal = Eur. J. Clin. Invest. | volume = 31 | issue = Suppl 2 | pages = 10–7 | year = 2001 | pmid = 11525233}}.</ref>

== 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.<ref name="Kurowski">{{citation | title = Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies | last1 = Kurowski | first1 = V. | last2 = Iven | first2 = H. | last3 = Djonlagic | first3 = H. | journal = Intensive Care Med. | year = 1992 | volume = 18 | issue = 7 | pages = 439–42 | pmid = 1469187}}.</ref>

==References==
{{reflist}}

==Further reading==
* {{citation | last1 = Johansson | first1 = S. | last2 = Lindholm | first2 = P. | last3 = Gullbo | first3 = J. | last4 = Larsson | first4 = R. | last5 = Bohlin | first5 = L. | last6 = Claeson | first6 = 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 | pmid = 11395576 | doi = 10.1097/00001813-200106000-00009}}.
* {{citation | last1 = Hippius | first1 = M. | last2 = Humaid | first2 = B. | last3 = Sicker | first3 = T. | last4 = Hoffmann | first4 = A. | last5 = Göttler | first5 = M. | last6 = Hasford  | first6 = 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 | pmid = 11515708}}.
* {{citation | last1 = Haux | first1 = J. | last2 = Klepp | first2 = O. | last3 = Spigset | first3 = O. | last4 = Tretli | first4 = S. | title = Digitoxin medication and cancer; case control and internal dose-response studies | journal = BMC Cancer | volume = 1 | issue = | pages = 11 | year = 2001 | pmid = 11532201 | doi = 10.1186/1471-2407-1-11}}.
* {{citation | last1 = Srivastava | first1 = M. | last2 = Eidelman | first2 = O. | last3 = Zhang | first3 = J. | last4 = Paweletz | first4 = C. | last5 = Caohuy | first5 = H. | last6 = Yang | first6 = Q. | last7 = Jacobson | first7 = K. | last8 = Heldman | first8 = E. | last9 = Huang | first9 = W. | last10 = Jozwik | first10 = C. | last11 = Pollard | first11 = B. | last12 = Pollard | first12 = 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. USA | volume = 101 | issue = 20 | pages = 7693–98 | year = 2004 | pmid = 15136726 | doi = 10.1073/pnas.0402030101}}.

==External links==
* [http://www.medscape.com/viewarticle/410488 "Comparing the Toxicity of Digoxin and Digitoxin in a Geriatric Population: Should an Old Drug Be Rediscovered?"]

[[Category:Cardiac glycosides]]
[[Category:Cardanolide steroids]]

{{Imported from Wikipedia|name=Digitoxin|id=297417192}}