Digoxin: Difference between revisions

Digoxin
	File:Digoxin structure 2.svg
Clinical data
Trade names	Lanoxin
AHFS/Drugs.com	Monograph
MedlinePlus	a682301
Pregnancy; category	A (Au), C (U.S.);
Routes of; administration	Oral, Intravenous
ATC code	C01AA05 (WHO) ;
Legal status
Legal status	S4 (Au), POM (UK), ℞-only (U.S.);
Pharmacokinetic data
Bioavailability	60 to 80% (Oral)
Protein binding	25%
Metabolism	Hepatic (16%)
Elimination half-life	36 to 48 hours ; (patients with normal renal function); 3.5 to 5 days ; (patients with impaired renal function)
Excretion	Renal
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 ;
PubChem CID	2724385;
DrugBank	DB00390 ;
ChemSpider	2006532 ;
UNII	73K4184T59;
KEGG	D00298 ;
ChEBI	CHEBI:4551 ;
ChEMBL	ChEMBL1751 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C41H64O14
Molar mass	780.938 g/mol
3D model (JSmol)	Interactive image;
Melting point	249.3 °C (480.74 °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 ;
(verify)

VisualWikitext

Revision as of 14:42, 20 March 2014

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Abdurahman Khalil, M.D. [2]

Synonyms / Brand Names:'''Lanoxin^®, Digoxin^®, Digox^®.

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.

Prescribing Information

Lanoxin (digoxin) tablet

Lanoxin injection

Digoxin solution

References

↑ Hollman A (1996). "Digoxin comes from Digitalis lanata". British Medical Journal. 312 (7035): 912.

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

[1] Hollman A (1996). "Digoxin comes from Digitalis lanata". British Medical Journal. 312 (7035): 912.

[1]

@@ Line 1: / Line 1: @@
 __NOTOC__
-{{Digoxin}}
+{{Distinguish|Dioxin|Digitoxin}}
+{{drugbox | Watchedfields = changed
+| verifiedrevid = 459476549
+| 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>
+| image = Digoxin structure 2.svg
+| width = 300px
+| image2 = Digon ball-and-stick.png
+<!--Clinical data-->
+| tradename = Lanoxin
+| Drugs.com = {{drugs.com|monograph|digoxin}}
+| MedlinePlus = a682301
+| pregnancy_category = A <small>([[Australia|Au]])</small>, C <small>([[United States|U.S.]])</small>
+| legal_status = S4 <small>(Au)</small>, POM <small>([[United Kingdom|UK]])</small>, ℞-only <small>(U.S.)</small>
+| routes_of_administration = [[Route of administration#Enteral|Oral]], [[Intravenous therapy|Intravenous]]
+<!--Pharmacokinetic data-->
+| bioavailability = 60 to 80% (Oral)
+| protein_bound = 25%
+| metabolism = [[Liver|Hepatic]] (16%)
+| 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>
+| excretion = [[Renal]]
+<!--Identifiers-->
+| CASNo_Ref = {{cascite|correct|CAS}}
+| CAS_number_Ref = {{cascite|correct|??}}
+| CAS_number = 20830-75-5
+| ATC_prefix = C01
+| ATC_suffix = AA05
+| ATC_supplemental =
+| 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
+| PubChem = 2724385
+| 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
+<!--Chemical data-->
+| C=41 | H=64 | O=14
+| molecular_weight = 780.938 [[Gram|g]]/[[Mole (unit)|mol]]
+| 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 = 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
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = LTMHDMANZUZIPE-PUGKRICDSA-N
+| melting_point = 249.3
+| solubility = 0.0648
+}}
 {{CMG}}; {{AE}} {{AK}}
-'''''For patient information, click <u>[[Digoxin (patient information)|here]]'''''</u>.
+{{SB}}'''Lanoxin'''<sup>®</sup>, '''Digoxin'''<sup>®</sup>, '''Digox'''<sup>®</sup>.
 ==Overview==
 '''Digoxin''' [[International Nonproprietary Name|INN]] is a purified [[cardiac glycoside]] similar to [[Digitoxin]] extracted from the [[foxglove]] plant, ''[[Digitalis lanata]]'',<ref>{{cite journal | author = Hollman A | title = Digoxin comes from ''Digitalis lanata'' | journal = [[British Medical Journal]] | year = 1996 | volume = 312 | issue = 7035 | page = 912 | url = http://www.bmj.com/cgi/content/full/312/7035/912 }}</ref> 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 disease|heart conditions]], namely [[atrial fibrillation]], [[atrial flutter]] and sometimes [[heart failure]] that cannot be controlled by other [[medication]].
@@ Line 11: / Line 65: @@
 Cardiac [[glycosides]].
-==US Brand Names==
+==Prescribing Information==
-'''LANOXIN'''<sup>®</sup>, '''DIGOXIN'''<sup>®</sup>, '''DIGOX'''<sup>®</sup>.
-==FDA Package Insert==
-===DIGOXIN injection<sup>®</sup>===
-'''| [[DIGOXIN injection indications and usage|Indications and Usage]]'''
-'''| [[DIGOXIN injection dosage and administration|Dosage and Administration]]'''
-'''| [[DIGOXIN injection dosage forms and strengths|Dosage Forms and Strengths]]'''
-'''| [[DIGOXIN injection contraindications|Contraindications]]'''
-'''| [[DIGOXIN injection warnings and precautions|Warnings and Precautions]]'''
-'''| [[DIGOXIN injection adverse reactions|Adverse Reactions]]'''
-'''| [[DIGOXIN injection drug interactions|Drug Interactions]]'''
-'''| [[DIGOXIN injection use in specific populations|Use in Specific Populations]]'''
-'''| [[DIGOXIN injection overdosage|Overdosage]]'''
-'''| [[DIGOXIN injection description|Description]]'''
-'''| [[DIGOXIN injection clinical pharmacology|Clinical Pharmacology]]'''
-'''| [[DIGOXIN injection nonclinical toxicology|Nonclinical Toxicology]]'''
-'''| [[DIGOXIN injection clinical studies|Clinical Studies]]'''
-'''| [[DIGOXIN injection how supplied storage and handling|How Supplied/Storage and Handling]]'''
-'''| [[DIGOXIN injection patient counseling information|Patient Counseling Information]]'''
-'''| [[DIGOXIN injection labels and packages|Labels and Packages]]'''
-===DIGOXIN tablet<sup>®</sup>===
+=='''[[Lanoxin tablet|Lanoxin (digoxin) tablet ]]'''==
-'''| [[DIGOXIN tablet indications and usage|Indications and Usage]]'''
-'''| [[DIGOXIN tablet dosage and administration|Dosage and Administration]]'''
-'''| [[DIGOXIN tablet dosage forms and strengths|Dosage Forms and Strengths]]'''
-'''| [[DIGOXIN tablet contraindications|Contraindications]]'''
-'''| [[DIGOXIN tablet warnings and precautions|Warnings and Precautions]]'''
-'''| [[DIGOXIN tablet adverse reactions|Adverse Reactions]]'''
-'''| [[DIGOXIN tablet drug interactions|Drug Interactions]]'''
-'''| [[DIGOXIN tablet use in specific populations|Use in Specific Populations]]'''
-'''| [[DIGOXIN tablet overdosage|Overdosage]]'''
-'''| [[DIGOXIN tablet description|Description]]'''
-'''| [[DIGOXIN tablet clinical pharmacology|Clinical Pharmacology]]'''
-'''| [[DIGOXIN tablet nonclinical toxicology|Nonclinical Toxicology]]'''
-'''| [[DIGOXIN tablet clinical studies|Clinical Studies]]'''
-'''| [[DIGOXIN tablet how supplied storage and handling|How Supplied/Storage and Handling]]'''
-'''| [[DIGOXIN tablet patient counseling information|Patient Counseling Information]]'''
-'''| [[DIGOXIN tablet labels and packages|Labels and Packages]]'''
-==Mechanism of Action==
+=='''Lanoxin injection'''==
-All of digoxin’s actions are mediated through its effects on Na-K ATPase. This enzyme, the “sodium pump,” is responsible for maintaining the intracellular milieu throughout the body by moving sodium ions out of and potassium ions into cells. By inhibiting Na-K ATPase, digoxin
-*causes increased availability of intracellular calcium in the myocardium and conduction system, with consequent increased inotropy, increased automaticity, and reduced conduction velocity
-*indirectly causes parasympathetic stimulation of the autonomic nervous system, with consequent effects on the [[sinoatrial node|sino-atrial]] (SA) and [[atrioventricular nodes|atrioventricular (AV) nodes]]
-*reduces [[catecholamine ]]reuptake at nerve terminals, rendering blood vessels more sensitive to endogenous or exogenous catecholamines
-*increases [[baroreceptor ]]sensitization, with consequent increased carotid sinus nerve activity and enhanced sympathetic withdrawal for any given increment in mean arterial pressure
-*increases (at higher concentrations) [[sympathetic ]]outflow from the central nervous system (CNS) to both cardiac and peripheral sympathetic nerves
-allows (at higher concentrations) progressive efflux of intracellular [[potassium]], with consequent increase in serum potassium levels.
-The cardiologic consequences of these direct and indirect effects are an increase in the force and velocity of myocardial systolic contraction (positive inotropic action), a slowing of the heart rate (negative chronotropic effect), decreased conduction velocity through the AV node, and a decrease in the degree of activation of the sympathetic nervous system and renin-angiotensin system (neurohormonal deactivating effect).
+=='''Digoxin solution'''==
 ==References==
@@ Line 74: / Line 78: @@
 http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=41c16cff-b03e-405e-a617-d6f45d3ce2bd
+{{Cardiac glycosides}}
+{{Antiarrhythmic agents}}
 [[Category:Cardiovascular Drugs]]
 [[Category:Drugs]]