Digoxin

Digoxin
Clinical data
Pronunciation	/dɪˈdʒɒksɪn/
Trade names	Lanoxin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682301
License data	US DailyMed: Digoxin;
Pregnancy; category	AU: A;
Routes of; administration	By mouth, intravenous
ATC code	C01AA05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	60 to 80% (by mouth)
Protein binding	25%
Metabolism	Liver (16%)
Elimination half-life	36 to 48 hours ; (normal kidney function); 3.5 to 5 days ; (impaired kidney function)
Excretion	Kidney
Identifiers
	IUPAC name 3β-[(O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-12β,14-dihydroxy-5β-card-20(22)-enolide;
CAS Number	20830-75-5 ;
PubChem CID	2724385;
IUPHAR/BPS	4726;
DrugBank	DB00390 ;
ChemSpider	2006532 ;
UNII	73K4184T59;
KEGG	D00298 ;
ChEBI	CHEBI:4551 ;
ChEMBL	ChEMBL1751 ;
PDB ligand	DGX (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID5022934 ;
ECHA InfoCard	100.040.047
Chemical and physical data
Formula	C41H64O14
Molar mass	780.949 g·mol−1
3D model (JSmol)	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 ; Key:LTMHDMANZUZIPE-PUGKRICDSA-N ;
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Digoxin (better known as Digitalis), 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 one of the oldest medications used in the field of cardiology. It works by increasing myocardial contractility, increasing stroke volume and blood pressure, reducing heart rate, and somewhat extending the time frame of the contraction. Digoxin is taken by mouth or by injection into a vein. Digoxin has a half life of approximately 36 hours given at average doses in patients with normal renal function. It is excreted mostly unchanged in the urine.

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 whether use during pregnancy is safe.

Digoxin is in the cardiac glycoside family of medications. It was first isolated in 1930 from the foxglove plant, Digitalis lanata. It is on the World Health Organization's List of Essential Medicines. In 2021, it was the 241st most commonly prescribed medication in the United States, with more than 1 million prescriptions.

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