Digoxin

Digoxin

Clinical data
Pronunciation	/dᵻˈdʒɒksᵻn/, with a soft gee
Trade names	Lanoxin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682301
Pregnancy category	A (Au), C (U.S.)
Routes of administration	by mouth, intravenous
ATC code	C01AA05 (WHO)
Legal status
Legal status	S4 (Au), POM (UK), ℞-only (U.S.)
Pharmacokinetic data
Bioavailability	60 to 80% (by mouth)
Protein binding	25%
Metabolism	liver (16%)
Biological half-life	36 to 48 hours (normal kidney function) 3.5 to 5 days (impaired kidney function)
Excretion	kidney
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
IUPHAR/BPS	4726
DrugBank	DB00390 Y
ChemSpider	2006532 Y
UNII	73K4184T59 Y
KEGG	D00298 Y
ChEBI	CHEBI:4551 Y
ChEMBL	CHEMBL1751 Y
ECHA InfoCard	100.040.047
Chemical and physical data
Formula	C41H64O14
Molar mass	780.949 g/mol
3D model (Jmol)	Interactive image
Melting point	249.3 °C (480.7 °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

Digoxin, sold under the brand name Lanoxin among others, is a medication used to treat various heart conditions. Most frequently it is used for atrial fibrillation, atrial flutter, and heart failure. Digoxin is taken by mouth or by injection into a vein.

Common side effects include breast enlargement with other side effects generally due to an excessive dose. These side effects may include loss of appetite, nausea, trouble seeing, confusion, and an irregular heartbeat. Greater care is required in older people and those with poor kidney function. It is unclear if use during pregnancy is safe. Digoxin is in cardiac glycoside family of medications.

Digoxin was first isolated in 1930 from the foxglove plant, Digitalis lanata. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 0.21 to 6.6 USD a month. In the United States it generally costs less than 25 USD per month as of 2015.

The most common indications for digoxin are atrial fibrillation and atrial flutter with rapid ventricular response, though beta blockers and/or calcium channel blockers are often preferred.

There is tentative evidence that digoxin may increase the risk of death, though another meta-analysis reports no change in mortality.