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Digoxin

Not to be confused with Dioxin or Digitoxin.
For the genus of plants with the same name, see Digitalis.
Digoxin
Clinical data
Pronunciation/dɪˈdʒɒksɪn/[1][2]
Trade namesLanoxin, others
AHFS/Drugs.comMonograph
MedlinePlusa682301
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability60 to 80% (by mouth)
Protein binding25%
MetabolismLiver (16%)
Elimination half-life36 to 48 hours
(normal kidney function)
3.5 to 5 days
(impaired kidney function)
ExcretionKidney
Identifiers
  • 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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.040.047 Edit this at Wikidata
Chemical and physical data
FormulaC41H64O14
Molar mass780.949 g·mol−1
3D model (JSmol)
Melting point249.3 °C (480.7 °F)
Solubility in water0.0648 mg/mL (20 °C)
  • 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=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 checkY
  • Key:LTMHDMANZUZIPE-PUGKRICDSA-N checkY
  (verify)

Digoxin (better known as Digitalis), sold under the brand name Lanoxin among others, is a medication used to treat various heart conditions.[4] Most frequently it is used for atrial fibrillation, atrial flutter, and heart failure.[4] 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.[5] Digoxin is taken by mouth or by injection into a vein.[4] 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.[4][6] These side effects may include loss of appetite, nausea, trouble seeing, confusion, and an irregular heartbeat.[6] Greater care is required in older people and those with poor kidney function.[6] It is unclear whether use during pregnancy is safe.[3]

Digoxin is in the cardiac glycoside family of medications.[4] It was first isolated in 1930 from the foxglove plant, Digitalis lanata.[7][8] It is on the World Health Organization's List of Essential Medicines.[9] In 2021, it was the 241st most commonly prescribed medication in the United States, with more than 1 million prescriptions.[10][11]

  1. ^ "Digoxin". Digoxin | Definition of Digoxin by Lexico. Lexico. Archived from the original on 27 October 2019. Retrieved 28 October 2019.
  2. ^ "digoxin". WordReference. Retrieved 28 October 2019.
  3. ^ a b "Digoxin Use During Pregnancy". Drugs.com. Archived from the original on 21 December 2016. Retrieved 14 December 2016.
  4. ^ a b c d e "Digoxin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  5. ^ Patocka J, Nepovimova E, Wu W, Kuca K (October 2020). "Digoxin: Pharmacology and toxicology-A review". Environmental Toxicology and Pharmacology. 79: 103400. doi:10.1016/j.etap.2020.103400. PMID 32464466. S2CID 218950180.
  6. ^ a b c World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 270. hdl:10665/44053. ISBN 9789241547659.
  7. ^ Cartwright AC (2016). The British Pharmacopoeia, 1864 to 2014: Medicines, International Standards and the State. Routledge. p. 183. ISBN 9781317039792. Archived from the original on 2017-09-08.
  8. ^ Hollman A (April 1996). "Drugs for atrial fibrillation. Digoxin comes from Digitalis lanata". BMJ. 312 (7035): 912. doi:10.1136/bmj.312.7035.912. PMC 2350584. PMID 8611904.
  9. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  10. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  11. ^ "Digoxin - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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