Digitoxin

Digitoxin
Clinical data
Trade names	Digalen, Digitaline, Digitmerck, others
Routes of; administration	By mouth, Intravenous injection
ATC code	C01AA04 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	98–100% (oral)
Protein binding	90–97%
Metabolism	Liver (CYP3A4)
Elimination half-life	7–8 days
Excretion	60% via urine, 40% via faeces
Identifiers
	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;
CAS Number	71-63-6 ;
PubChem CID	441207;
IUPHAR/BPS	6782;
DrugBank	DB01396 ;
ChemSpider	389987 ;
UNII	E90NZP2L9U;
KEGG	D00297 ;
ChEBI	CHEBI:28544 ;
ChEMBL	ChEMBL254219 ;
CompTox Dashboard (EPA)	DTXSID0022933 ;
ECHA InfoCard	100.000.691
Chemical and physical data
Formula	C41H64O13
Molar mass	764.950 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI InChI=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 ; Key:WDJUZGPOPHTGOT-XUDUSOBPSA-N ;
	(what is this?) (verify)

Digitoxin is a cardiac glycoside used for the treatment of heart failure and certain kinds of heart arrhythmia. It is a phytosteroid and is similar in 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.^[1]

^ Belz GG, 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): 10–7. doi:10.1046/j.1365-2362.2001.0310s2010.x (inactive 12 July 2025). PMID 11525233. Archived from the original on 2013-01-05.{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)

[Belz-1] Belz GG, 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): 10–7. doi:10.1046/j.1365-2362.2001.0310s2010.x (inactive 12 July 2025). PMID 11525233. Archived from the original on 2013-01-05.{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)

[1]