Editing Digoxin (section)

{{Short description|Plant-derived medication}}
{{Distinguish|Dioxin|Digitoxin}}
{{About||the genus of plants with the same name|Digitalis}}
{{drugbox
| Watchedfields = changed
| verifiedrevid = 459476549
| image = Digoxin.svg
| image_class = skin-invert-image
| width = 300
| alt =
| image2 = Digon ball-and-stick.png
| image_class2 = bg-transparent
| alt2 =

<!--Clinical data-->
| pronounce = {{IPAc-en|d|ᵻ|ˈ|dʒ|ɒ|k|s|ᵻ|n}}<ref name="oxforddict">{{cite dictionary |entry=Digoxin |entry-url=https://www.lexico.com/en/definition/digoxin |dictionary=Lexico |access-date=28 October 2019 |language=en |title=Digoxin &#124; Definition of Digoxin by Lexico |archive-date=27 October 2019 |archive-url=https://web.archive.org/web/20191027122438/https://www.lexico.com/en/definition/digoxin |url-status=dead }}</ref><ref>{{cite web |title=digoxin |website=WordReference |url=https://www.wordreference.com/definition/digoxin |access-date=28 October 2019 }}</ref>
| tradename = Lanoxin, others
| Drugs.com = {{drugs.com|monograph|digoxin}}
| MedlinePlus = a682301
| DailyMedID = Digoxin
| pregnancy_AU = A
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy" />
| pregnancy_category =
| routes_of_administration = [[Oral administration|By mouth]], [[Intravenous therapy|intravenous]]
| ATC_prefix = C01
| ATC_suffix = AA05
| ATC_supplemental =

| legal_AU = S4
| legal_UK = POM
| legal_US = Rx-only
| legal_status =

<!--Pharmacokinetic data-->
| bioavailability = 60 to 80% (by mouth)
| protein_bound = 25%
| metabolism = [[Liver]] (16%)
| elimination_half-life = 36 to 48 [[hour]]s <br />(normal [[kidney function]])<br />3.5 to 5 [[day]]s <br />(impaired kidney function)
| excretion = [[Kidney]]

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 20830-75-5
| PubChem = 2724385
| IUPHAR_ligand = 4726
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00390
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2006532
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 73K4184T59
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00298
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4551
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1751
| NIAID_ChemDB      =
| PDB_ligand        = DGX
| synonyms          =

<!--Chemical data-->
| 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
| C=41 | H=64 | O=14
| 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
| StdInChI = 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LTMHDMANZUZIPE-PUGKRICDSA-N
| melting_point = 249.3
| solubility = 0.0648
}}

<!-- Definition and medical uses -->
'''Digoxin''' (better known as '''digitalis'''), sold under the brand name '''Lanoxin''' among others, is a medication used to treat various [[heart disease|heart conditions]].<ref name=AHFS2016/> Most frequently it is used for [[atrial fibrillation]], [[atrial flutter]], and [[heart failure]].<ref name=AHFS2016/> 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 [[Muscle contraction|contraction]].<ref name="sciencedirect.com">{{cite journal | vauthors = Patocka J, Nepovimova E, Wu W, Kuca K | title = Digoxin: Pharmacology and toxicology-A review | journal = Environmental Toxicology and Pharmacology | volume = 79 | pages = 103400 | date = October 2020 | pmid = 32464466 | doi = 10.1016/j.etap.2020.103400 | s2cid = 218950180 | url = https://www.sciencedirect.com/science/article/pii/S1382668920300764 | url-access = subscription }}</ref> Digoxin is taken by mouth or by [[intravenous|injection into a vein]].<ref name=AHFS2016>{{cite web|title=Digoxin|url=https://www.drugs.com/monograph/digoxin.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161221004328/https://www.drugs.com/monograph/digoxin.html|archive-date=21 December 2016}}</ref> 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.

<!-- Side effects -->
Common side effects include [[gynecomastia|breast enlargement]] with other side effects generally due to an excessive dose.<ref name=AHFS2016/><ref name=WHO2008/> These side effects may include loss of appetite, nausea, trouble seeing, confusion, and an [[Heart arrhythmia|irregular heartbeat]].<ref name=WHO2008/> Greater care is required in older people and those with poor [[kidney function]].<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | hdl-access=free | page=270 }}</ref> It is unclear whether use during [[pregnancy]] is safe.<ref name="Drugs.com pregnancy">{{cite web|title=Digoxin Use During Pregnancy |url=https://www.drugs.com/pregnancy/digoxin.html|website=Drugs.com|access-date=14 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161221004656/https://www.drugs.com/pregnancy/digoxin.html|archive-date=21 December 2016}}</ref>

<!-- Class, history, use -->
Digoxin is in the [[cardiac glycoside]] family of medications.<ref name=AHFS2016/> It was first isolated in 1930 from the [[foxglove]] plant, ''[[Digitalis lanata]]''.<ref name=cartwright>{{cite book| vauthors = Cartwright AC |title=The British Pharmacopoeia, 1864 to 2014: Medicines, International Standards and the State|date=2016|publisher=Routledge|isbn=9781317039792|page=183|url=https://books.google.com/books?id=gI21CwAAQBAJ&pg=PA183|language=en|url-status=live|archive-url=https://web.archive.org/web/20170908135429/https://books.google.com/books?id=gI21CwAAQBAJ&pg=PA183|archive-date=2017-09-08}}</ref><ref name=hollman>{{cite journal | vauthors = Hollman A | title = Drugs for atrial fibrillation. Digoxin comes from Digitalis lanata | journal = BMJ | volume = 312 | issue = 7035 | pages = 912 | date = April 1996 | pmid = 8611904 | pmc = 2350584 | doi = 10.1136/bmj.312.7035.912 }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> In 2021, it was the 241st most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Digoxin - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Digoxin | access-date = 14 January 2024}}</ref>