Digoxin

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Abdurahman Khalil, M.D. [2]

Synonyms / Brand Names: Digox, Digoxin, Lanoxin

Overview

Digoxin INN is a purified cardiac glycoside similar to Digitoxin extracted from the foxglove plant, Digitalis lanata, which was discovered by William Withering. Its corresponding aglycone is digoxigenin, and its acetyl derivative is acetyldigoxin. Digoxin is widely used in the treatment of various heart conditions, namely atrial fibrillation, atrial flutter and sometimes heart failure that cannot be controlled by other medication.

Category

Cardiac glycoside

Not to be confused with Dioxin or Digitoxin.

Digoxin

Clinical data
Trade names	Lanoxin
AHFS/Drugs.com	Monograph
MedlinePlus	a682301
Pregnancy category	A (Au), C (U.S.)
Routes of administration	Oral, Intravenous
ATC code	C01AA05 (WHO)
Legal status
Legal status	S4 (Au), POM (UK), ℞-only (U.S.)
Pharmacokinetic data
Bioavailability	60 to 80% (Oral)
Protein binding	25%
Metabolism	Hepatic (16%)
Elimination half-life	36 to 48 hours (patients with normal renal function) 3.5 to 5 days (patients with impaired renal function)
Excretion	Renal
Identifiers
IUPAC name 4-[(3S,5R,8R,9S,10S,12R,13S,14S)-3-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-4,5-dihydroxy-6-methyl-oxan-2-yl]oxy-4-hydroxy-6-methyl-oxan-2-yl]oxy-4-hydroxy-6-methyl-oxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-5H-furan-2-one
CAS Number	20830-75-5 Y
PubChem CID	2724385
DrugBank	DB00390 Y
ChemSpider	2006532 Y
UNII	73K4184T59
KEGG	D00298 Y
ChEBI	CHEBI:4551 Y
ChEMBL	ChEMBL1751 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C41H64O14
Molar mass	780.938 g/mol
3D model (JSmol)	Interactive image
Melting point	249.3 °C (480.74 °F)
Solubility in water	0.0648 mg/mL (20 °C)
SMILES O=C\1OC/C(=C/1)[C@H]2CC[C@@]8(O)[C@]2(C)[C@H](O)C[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/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25-,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1 Y Key:LTMHDMANZUZIPE-PUGKRICDSA-N Y
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References

http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=58f45aba-ff6f-43cc-bb88-be40a9f7beda

http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=41c16cff-b03e-405e-a617-d6f45d3ce2bd