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| {{SB}} Digox, Digoxin, Lanoxin | | {{SB}} Digox, Digoxin, Lanoxin |
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| ==='''[[Digoxin tablet ]]'''=== | | ==='''''[[Digoxin tablet ]]'''''=== |
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| ==='''[[Digoxin injection]]'''=== | | ==='''''[[Digoxin injection]]'''''=== |
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| ==='''[[Digoxin solution]]'''=== | | ==='''''[[Digoxin solution]]'''''=== |
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| ==Overview== | | ==Overview== |
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| Cardiac glycoside | | Cardiac glycoside |
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| {{Distinguish|Dioxin|Digitoxin}}
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| {{drugbox | Watchedfields = changed
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| | verifiedrevid = 459476549
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| | IUPAC_name = <small>4-[(3''S'',5''R'',8''R'',9''S'',10''S'',12''R'',13''S'',14''S'')-3-[(2''S'',4''S'',5''R'',6''R'')-5-[(2''S'',4''S'',5''R'',6''R'')-5-[(2''S'',4''S'',5''R'',6''R'')-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]-5''H''-furan-2-one</small>
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| | image = Digoxin structure 2.png
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| | width = 300px
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| | image2 = Digon ball-and-stick.png
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| <!--Clinical data-->
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| | tradename = Lanoxin
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| | Drugs.com = {{drugs.com|monograph|digoxin}}
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| | MedlinePlus = a682301
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| | pregnancy_category = A <small>([[Australia|Au]])</small>, C <small>([[United States|U.S.]])</small>
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| | legal_status = S4 <small>(Au)</small>, POM <small>([[United Kingdom|UK]])</small>, ℞-only <small>(U.S.)</small>
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| | routes_of_administration = [[Route of administration#Enteral|Oral]], [[Intravenous therapy|Intravenous]]
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| <!--Pharmacokinetic data-->
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| | bioavailability = 60 to 80% (Oral)
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| | protein_bound = 25%
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| | metabolism = [[Liver|Hepatic]] (16%)
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| | elimination_half-life = 36 to 48 [[hour]]s <br /><small>(patients with normal [[renal function]])</small><br />3.5 to 5 [[day]]s <br><small>(patients with impaired renal function)</small>
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| | excretion = [[Renal]]
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| <!--Identifiers-->
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| | CASNo_Ref = {{cascite|correct|CAS}}
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| | CAS_number_Ref = {{cascite|correct|??}}
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| | CAS_number = 20830-75-5
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| | ATC_prefix = C01
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| | ATC_suffix = AA05
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| | ATC_supplemental =
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| | 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
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| | PubChem = 2724385
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| | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| | DrugBank = DB00390
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| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| | ChemSpiderID = 2006532
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| | UNII_Ref = {{fdacite|correct|FDA}}
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| | UNII = 73K4184T59
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| | KEGG_Ref = {{keggcite|correct|kegg}}
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| | KEGG = D00298
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| | ChEBI_Ref = {{ebicite|correct|EBI}}
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| | ChEBI = 4551
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| | ChEMBL_Ref = {{ebicite|correct|EBI}}
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| | ChEMBL = 1751
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| <!--Chemical data-->
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| | C=41 | H=64 | O=14
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| | molecular_weight = 780.938 [[Gram|g]]/[[Mole (unit)|mol]]
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| | 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
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| | InChI = 1/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
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| | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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| | StdInChIKey = LTMHDMANZUZIPE-PUGKRICDSA-N
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| | melting_point = 249.3
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| | solubility = 0.0648
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| }}
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| ==References== | | ==References== |
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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,[1] 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
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
Template:Cardiac glycosides
Template:Antiarrhythmic agents