Editing Digitoxin (section)

{{Short description|Chemical compound}}
{{Distinguish|Digoxin}}
{{Drugbox| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 297417192
| 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 structure.svg
| width = 250px
<!--Clinical data-->
| tradename = Digalen, Digitaline, Digitmerck, others
| pregnancy_category = 
| legal_status = Rx-only
| routes_of_administration = [[Oral administration|By mouth]], [[Intravenous injection]]
<!--Pharmacokinetic data-->
| bioavailability = 98–100% (oral)
| protein_bound = 90–97%
| metabolism = Liver ([[CYP3A4]])
| elimination_half-life = 7–8 days
| excretion = 60% via urine, 40% via faeces
<!--Identifiers-->
| IUPHAR_ligand = 6782
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 71-63-6
| ATC_prefix = C01
| ATC_suffix = AA04
| PubChem = 441207
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB01396
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 389987
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = E90NZP2L9U
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D00297
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 28544
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 254219
<!--Chemical data-->
| C=41 | H=64 | O=13
| smiles = O=C\1OC/C(=C/1)[C@H]2CC[C@@]8(O)[C@]2(C)CC[C@H]7[C@H]8CC[C@H]6[C@]7(C)CC[C@H](O[C@@H]5O[C@H](C)[C@@H](O[C@@H]4O[C@@H]([C@@H](O[C@@H]3O[C@@H]([C@@H](O)[C@@H](O)C3)C)[C@@H](O)C4)C)[C@@H](O)C5)C6
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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)50-33(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)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = WDJUZGPOPHTGOT-XUDUSOBPSA-N
}}

'''Digitoxin''' is a [[cardiac glycoside]] used for the treatment of [[heart failure]] and certain kinds of [[arrhythmia|heart arrhythmia]]. It is a [[phytosteroid]] and is similar in [[chemical structure|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, and so can be used in patients with poor or erratic kidney function. 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 | vauthors = Belz GG, Breithaupt-Grögler K, Osowski U | title = Treatment of congestive heart failure--current status of use of digitoxin | journal = European Journal of Clinical Investigation | volume = 31 | issue = Suppl 2 | pages = 10–7 | year = 2001 | pmid = 11525233 | doi = 10.1046/j.1365-2362.2001.0310s2010.x | doi-broken-date = 9 December 2024 | url = http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0014-2972&date=2001&volume=31&issue=&spage=10 | url-status = dead | archive-url = https://archive.today/20130105085338/http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0014-2972&date=2001&volume=31&issue=&spage=10 | archive-date = 2013-01-05 | url-access = subscription }}</ref>