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Identification
NameDigoxin
Accession NumberDB00390  (APRD00098)
TypeSmall Molecule
GroupsApproved
Description

A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone digoxigenin. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666)

Structure
Thumb
Synonyms
12beta-Hydroxydigitoxin
12β-hydroxydigitoxin
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
Digazolan
Digossina
Digoxin
Digoxina
Digoxine
Digoxinum
Lanadicor
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Digoxinsolution.05 mg/mLoralRoxane Laboratories, Inc2004-08-26Not applicableUs
Digoxintablet.25 mg/1oralPar Pharmaceutical Inc.2014-01-14Not applicableUs
Digoxintablet.25 mg/1oralAvera Mc Kennan Hospital2015-03-09Not applicableUs
Digoxinsolution.05 mg/mLoralPrecision Dose Inc.2012-05-04Not applicableUs
Digoxintablet.125 mg/1oralCardinal Health2014-01-14Not applicableUs
Digoxintablet.125 mg/1oralAvera Mc Kennan Hospital2015-03-02Not applicableUs
Digoxintablet.125 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2014-01-14Not applicableUs
Digoxintablet.125 mg/1oralState of Florida DOH Central Pharmacy2014-11-01Not applicableUs
Digoxinsolution.05 mg/mLoralAtlantic Biologicals Corps2004-08-26Not applicableUs
Digoxintablet.125 mg/1oralPar Pharmaceutical Inc.2014-01-14Not applicableUs
Digoxin Injection C.S.D.liquid0.25 mgintramuscular; intravenousSandoz Canada Incorporated1994-12-31Not applicableCanada
Lanoxintablet.0625 mg/1oralConcordia Pharmaceuticals Inc.2012-09-30Not applicableUs
Lanoxintablet125 ug/1oralREMEDYREPACK INC.2013-03-042016-03-31Us
Lanoxintablet.125 mg/1oralConcordia Pharmaceuticals Inc.2012-09-30Not applicableUs
Lanoxintablet250 ug/1oralPd Rx Pharmaceuticals, Inc.1984-07-02Not applicableUs
Lanoxininjection, solution100 ug/mLintramuscular; intravenousCovis Pharmaceuticals, Inc.2013-01-14Not applicableUs
Lanoxintablet.25 mg/1oralCardinal Health2012-09-30Not applicableUs
Lanoxininjection, solution250 ug/mLintramuscular; intravenousCovis Pharmaceuticals, Inc.2013-02-15Not applicableUs
Lanoxintablet.125 mg/1oralCardinal Health2012-09-30Not applicableUs
Lanoxintablet.25 mg/1oralCovis Pharmaceuticals, Inc.2012-09-30Not applicableUs
Lanoxintablet125 ug/1oralCardinal Health1997-09-30Not applicableUs
Lanoxintablet250 ug/1oralCardinal Health1997-09-30Not applicableUs
Lanoxintablet.1875 mg/1oralCovis Pharmaceuticals, Inc.2012-09-30Not applicableUs
Lanoxintablet0.25 mgoralPharmascience Inc2001-03-16Not applicableCanada
Lanoxintablet125 ug/1oralRx Pak Division Of Mc Kesson Corporation1984-09-14Not applicableUs
Lanoxininjection, solution250 ug/mLintramuscular; intravenousCardinal Health1985-10-01Not applicableUs
Lanoxintablet.125 mg/1oralCovis Pharmaceuticals, Inc.2012-09-30Not applicableUs
Lanoxintablet.25 mg/1oralConcordia Pharmaceuticals Inc.2012-09-30Not applicableUs
Lanoxintablet125 ug/1oralCardinal Health1997-09-30Not applicableUs
Lanoxintablet.0625 mg/1oralCovis Pharmaceuticals, Inc.2012-09-30Not applicableUs
Lanoxintablet0.125 mgoralPharmascience Inc2001-03-16Not applicableCanada
Lanoxintablet0.0625 mgoralPharmascience Inc2001-06-22Not applicableCanada
Lanoxintablet.1875 mg/1oralConcordia Pharmaceuticals Inc.2012-09-30Not applicableUs
Lanoxin Elx 0.05mg/ml Pediatricliquid.05 mgoralGlaxo Wellcome Inc.1956-12-312003-07-31Canada
Lanoxin Inj 0.05mg/ml Pediatricliquid.05 mgintramuscular; intravenousGlaxo Wellcome Inc.1963-12-312001-08-02Canada
Lanoxin Inj 0.25mg/mlliquid.25 mgintramuscular; intravenousGlaxo Wellcome Inc.1955-12-312001-08-02Canada
Lanoxin Tab 0.0625mgtablet.0625 mgoralGlaxo Wellcome Inc.1987-12-312001-08-02Canada
Lanoxin Tab 0.125mgtablet.125 mgoralGlaxo Wellcome Inc.1971-12-312001-08-02Canada
Lanoxin Tab 0.25mgtablet.25 mgoralGlaxo Wellcome Inc.1936-12-312001-08-02Canada
Novo-digoxin Tab 0.25mgtablet.25 mgoralNovopharm Limited1966-12-312004-11-05Canada
Pediatric Digoxin Injection C.S.D.liquid0.05 mgintramuscular; intravenousSandoz Canada Incorporated1994-12-31Not applicableCanada
PMS-digoxintablet0.25 mgoralPharmascience Inc2006-06-21Not applicableCanada
PMS-digoxintablet0.125 mgoralPharmascience Inc2006-06-21Not applicableCanada
PMS-digoxintablet0.0625 mgoralPharmascience Inc2006-06-21Not applicableCanada
Toloxintablet0.125 mgoralPendopharm Division Of De Pharmascience Inc2009-12-23Not applicableCanada
Toloxinsolution0.05 mgoralPendopharm Division Of De Pharmascience Inc2001-06-01Not applicableCanada
Toloxintablet0.250 mgoralPendopharm Division Of De Pharmascience Inc2009-12-23Not applicableCanada
Toloxintablet0.0625 mgoralPendopharm Division Of De Pharmascience Inc2009-12-23Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-digoxintablet0.25 mgoralApotex Inc2006-06-22Not applicableCanada
Apo-digoxintablet0.0625 mgoralApotex Inc2006-06-22Not applicableCanada
Apo-digoxintablet0.125 mgoralApotex Inc2006-06-22Not applicableCanada
Digitektablet.125 mg/1oralMylan Institutional Inc.2015-06-18Not applicableUs
Digitektablet.25 mg/1oralMylan Institutional Inc.2015-06-18Not applicableUs
Digitektablet.25 mg/1oralMylan Pharmaceuticals Inc.2014-11-17Not applicableUs
Digitektablet.125 mg/1oralMylan Pharmaceuticals Inc.2014-11-17Not applicableUs
Digoxtablet250 ug/1oralREMEDYREPACK INC.2015-12-30Not applicableUs
Digoxtablet250 ug/1oralSt Marys Medical Park Pharmacy2014-05-23Not applicableUs
Digoxtablet125 ug/1oralMc Kesson Contract Packaging2012-09-28Not applicableUs
Digoxtablet.125 mg/1oralSt Marys Medical Park Pharmacy2013-05-02Not applicableUs
Digoxtablet250 ug/1oralUnit Dose Services2002-07-26Not applicableUs
Digoxtablet250 ug/1oralLannett Company, Inc.2002-07-26Not applicableUs
Digoxtablet250 ug/1oralCarilion Materials Management2002-07-26Not applicableUs
Digoxtablet125 ug/1oralLannett Company, Inc.2002-07-26Not applicableUs
Digoxtablet125 ug/1oralCarilion Materials Management2002-07-26Not applicableUs
Digoxtablet250 ug/1oralAidarex Pharmaceuticals LLC2002-07-26Not applicableUs
Digoxtablet250 ug/1oralUnit Dose Services2002-07-26Not applicableUs
Digoxtablet250 ug/1oralPd Rx Pharmaceuticals, Inc.2002-07-26Not applicableUs
Digoxtablet125 ug/1oralLake Erie Medical DBA Quality Care Products LLC2002-07-26Not applicableUs
Digoxtablet250 ug/1oralREMEDYREPACK INC.2013-03-052016-04-05Us
Digoxtablet125 ug/1oralTYA Pharmaceuticals2002-07-26Not applicableUs
Digoxintablet250 ug/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Digoxintablet.25 mg/301oralNorthwind Pharmaceuticals2014-05-16Not applicableUs
Digoxintablet125 ug/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2002-07-26Not applicableUs
Digoxintablet125 ug/1oralWest Ward Pharmaceuticals Corp2007-10-30Not applicableUs
Digoxintablet125 ug/1oralbryant ranch prepack2007-10-30Not applicableUs
Digoxintablet125 ug/1oralCardinal Health2009-12-01Not applicableUs
Digoxintablet250 ug/1oralState of Florida DOH Central Pharmacy2013-01-01Not applicableUs
Digoxintablet250 ug/1oralbryant ranch prepack2007-10-30Not applicableUs
Digoxintablet125 ug/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Digoxintablet250 ug/1oralJerome Stevens Pharmaceuticals, Inc.2002-07-26Not applicableUs
Digoxintablet.125 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-10-30Not applicableUs
Digoxininjection.25 mg/mLintramuscular; intravenousCardinal Health2011-06-28Not applicableUs
Digoxintablet125 ug/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Digoxintablet125 ug/1oralJerome Stevens Pharmaceuticals, Inc.2002-07-26Not applicableUs
Digoxintablet250 ug/1oralMajor Pharmaceuticals2009-06-10Not applicableUs
Digoxintablet250 ug/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-10-30Not applicableUs
Digoxintablet250 ug/1oralCardinal Health2011-07-01Not applicableUs
Digoxintablet125 ug/1oralMc Kesson Contract Packaging2011-10-11Not applicableUs
Digoxintablet125 ug/1oralDEPT HEALTH CENTRAL PHARMACY2008-05-01Not applicableUs
Digoxintablet125 ug/1oralMajor Pharmaceuticals2009-06-10Not applicableUs
Digoxintablet250 ug/1oralSun Pharmaceutical Industries, Inc.2015-02-17Not applicableUs
Digoxintablet125 ug/1oralCardinal Health2011-07-01Not applicableUs
Digoxintablet125 ug/1oralREMEDYREPACK INC.2014-10-08Not applicableUs
Digoxininjection, solution250 ug/mLintramuscular; intravenous; parenteralSandoz Inc2003-08-21Not applicableUs
Digoxintablet125 ug/1oralSun Pharmaceutical Industries, Inc.2015-02-17Not applicableUs
Digoxintablet125 ug/1oralPhysicians Total Care, Inc.1992-09-22Not applicableUs
Digoxintablet250 ug/1oralImpax Generics2009-07-20Not applicableUs
Digoxininjection.25 mg/mLintramuscular; intravenousWest Ward Pharmaceuticals Corp.1975-10-24Not applicableUs
Digoxintablet250 ug/1oralPhysicians Total Care, Inc.2000-08-21Not applicableUs
Digoxintablet125 ug/1oralImpax Generics2009-07-20Not applicableUs
Digoxintablet250 ug/1oralAmerican Health Packaging2014-09-22Not applicableUs
Digoxininjection250 ug/mLintramuscular; intravenousGeneral Injecatables & Vaccines, Inc2010-07-01Not applicableUs
Digoxintablet125 ug/1oralPd Rx Pharmaceuticals, Inc.2002-07-26Not applicableUs
Digoxintablet250 ug/1oralA S Medication Solutions Llc2007-10-30Not applicableUs
Digoxintablet125 ug/1oralAmerican Health Packaging2014-09-23Not applicableUs
Digoxintablet125 ug/1oralREMEDYREPACK INC.2014-01-302016-04-05Us
Digoxininjection.25 mg/mLintramuscular; intravenousWest Ward Pharmaceuticals Corp.1975-10-24Not applicableUs
Digoxintablet.125 mg/301oralNorthwind Pharmaceuticals2014-05-16Not applicableUs
Digoxintablet.125 mg/1oralREMEDYREPACK INC.2011-07-20Not applicableUs
Digoxintablet250 ug/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2002-07-26Not applicableUs
Digoxintablet250 ug/1oralWest Ward Pharmaceuticals Corp2007-10-30Not applicableUs
Digoxintablet125 ug/1oralCardinal Health2009-06-10Not applicableUs
Digoxintablet125 ug/1oralA S Medication Solutions Llc2007-10-30Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AgoxinAristopharma
CardiacinCenter
CardiogoxinMedipharma
CardioxinOboi
CardoxinNot Available
CeloxinCelon
CentoxinOpsonin
Digacinmibe
Digocard-GKlonal
DigoxinaGlaxoSmithKline
EudigoxTeofarma
LanacordinKern
LanacristNot Available
LanicorRoche
LanoxicapsNot Available
LenoxinGlaxoSmithKline
Brand mixturesNot Available
SaltsNot Available
Categories
UNII73K4184T59
CAS number20830-75-5
WeightAverage: 780.9385
Monoisotopic: 780.429606756
Chemical FormulaC41H64O14
InChI KeyInChIKey=LTMHDMANZUZIPE-PUGKRICDSA-N
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
IUPAC Name
4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one
SMILES
[H][C@]12CC[C@]3([H])[C@]([H])(C[C@@H](O)[C@]4(C)[[email protected]](CC[C@]34O)C3=CC(=O)OC3)[C@@]1(C)CC[C@@H](C2)O[[email protected]]1C[[email protected]](O)[[email protected]](O[[email protected]]2C[[email protected]](O)[[email protected]](O[[email protected]]3C[[email protected]](O)[[email protected]](O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cardenolide glycosides and derivatives. These are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentCardenolide glycosides and derivatives
Alternative Parents
Substituents
  • Cardanolide-glycoside
  • Steroidal glycoside
  • Oligosaccharide
  • Hydroxysteroid
  • 12-hydroxysteroid
  • Oxane
  • Saccharide
  • 2-furanone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Dihydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure.
PharmacodynamicsDigoxin, a cardiac glycoside similar to digitoxin, is used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation.
Mechanism of actionDigoxin inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium. The sodium calcium exchanger (NCX)in turn tries to extrude the sodium and in so doing, pumps in more calcium. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Digoxin also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.
Related Articles
AbsorptionAbsorption of digoxin from the elixir pediatric formulation has been demonstrated to be 70% to 85% complete (90% to 100% from the capsules, and 60% to 80% for tablets).
Volume of distributionNot Available
Protein binding25%
Metabolism

Hepatic (but not dependent upon the cytochrome P-450 system). The end metabolites, which include 3 b-digoxigenin, 3-keto-digoxigenin, and their glucuronide and sulfate conjugates, are polar in nature and are postulated to be formed via hydrolysis, oxidation, and conjugation.

SubstrateEnzymesProduct
Digoxin
Not Available
3 b-digoxigeninDetails
Digoxin
Not Available
3-keto-digoxigeninDetails
Route of eliminationFollowing intravenous administration to healthy volunteers, 50% to 70% of a digoxin dose is excreted unchanged in the urine.
Half life3.5 to 5 days
ClearanceNot Available
ToxicityToxicity includes ventricular tachycardia or ventricular fibrillation, or progressive bradyarrhythmias, or heart block. LD50 = 7.8 mg/kg (orally in mice).
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.941
Blood Brain Barrier-0.7241
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.8586
P-glycoprotein inhibitor INon-inhibitor0.5325
P-glycoprotein inhibitor IINon-inhibitor0.6209
Renal organic cation transporterNon-inhibitor0.8621
CYP450 2C9 substrateNon-substrate0.855
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7366
CYP450 1A2 substrateNon-inhibitor0.9261
CYP450 2C9 inhibitorNon-inhibitor0.9196
CYP450 2D6 inhibitorNon-inhibitor0.9359
CYP450 2C19 inhibitorNon-inhibitor0.9385
CYP450 3A4 inhibitorNon-inhibitor0.9279
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9279
Ames testNon AMES toxic0.9233
CarcinogenicityNon-carcinogens0.9668
BiodegradationNot ready biodegradable0.9555
Rat acute toxicity4.4721 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9818
hERG inhibition (predictor II)Inhibitor0.8051
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline llc
  • Roxane laboratories inc
  • Abraxis pharmaceutical products
  • Baxter healthcare corp anesthesia and critical care
  • Hospira inc
  • Sandoz canada inc
  • Wyeth ayerst laboratories
  • Actavis totowa llc
  • Caraco pharmaceutical laboratories ltd
  • Impax laboratories inc
  • Jerome stevens pharmaceuticals inc
  • West ward pharmaceutical corp
  • Smithkline beecham corp dba glaxosmithkline
Packagers
Dosage forms
FormRouteStrength
Tabletoral.125 mg/1
Tabletoral.25 mg/1
Injectionintramuscular; intravenous.25 mg/mL
Injectionintramuscular; intravenous250 ug/mL
Injection, solutionintramuscular; intravenous; parenteral250 ug/mL
Solutionoral.05 mg/mL
Tabletoral.125 mg/301
Tabletoral.25 mg/301
Tabletoral125 ug/1
Tabletoral250 ug/1
Liquidintramuscular; intravenous0.25 mg
Injection, solutionintramuscular; intravenous100 ug/mL
Injection, solutionintramuscular; intravenous250 ug/mL
Tabletoral.0625 mg/1
Tabletoral.1875 mg/1
Tabletoral0.0625 mg
Tabletoral0.125 mg
Tabletoral0.25 mg
Liquidoral.05 mg
Liquidintramuscular; intravenous.05 mg
Liquidintramuscular; intravenous.25 mg
Tabletoral.0625 mg
Tabletoral.125 mg
Tabletoral.25 mg
Liquidintramuscular; intravenous0.05 mg
Solutionoral0.05 mg
Tabletoral0.250 mg
Prices
Unit descriptionCostUnit
Digibind 38 mg vial727.91USD vial
Digifab 40 mg vial615.6USD vial
Digoxin powder450.28USD g
Digoxin 0.05 mg/ml Solution 60ml Bottle36.99USD bottle
Lanoxin ped 0.1 mg/ml ampul6.91USD ml
Digoxin Pediatric 0.05 mg/ml6.79USD ml
Digoxin 0.25 mg/ml2.91USD ml
Lanoxin 0.25 mg/ml ampul1.44USD ml
Lanoxin 0.125 mg tablet0.73USD tablet
Lanoxin 0.25 mg tablet0.66USD tablet
Digoxin 0.125 mg tablet0.64USD tablet
Digoxin 0.25 mg tablet0.62USD tablet
Digoxin 0.25 mg/ml ampul0.61USD ml
Lanoxin Pediatric 0.05 mg/ml Elixir0.41USD ml
Lanoxicaps 0.1 mg capsule0.4USD capsule
Lanoxin 125 mcg tablet0.3USD tablet
Lanoxin 250 mcg tablet0.3USD tablet
Digitek 125 mcg tablet0.28USD tablet
Digitek 250 mcg tablet0.28USD tablet
Lanoxicaps 0.05 mg capsule0.28USD capsule
Toloxin 0.0625 mg Tablet0.27USD tablet
Toloxin 0.125 mg Tablet0.27USD tablet
Toloxin 0.25 mg Tablet0.27USD tablet
Digoxin 125 mcg tablet0.22USD tablet
Digoxin 250 mcg tablet0.22USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point217-221Stoll, A .and Kreis, W.; US.Patent 2,776,963; January 8,1957;assigned to Sandoz, AG, Switzerland.
water solubility64.8 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.26SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.127 mg/mLALOGPS
logP1.04ALOGPS
logP2.37ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.15ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area203.06 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity193.23 m3·mol-1ChemAxon
Polarizability84.8 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Wolfgang Voigtlander, Fritz Kaiser, Wolfgang Schaumann, Kurt Stach, “Preparation of C22-alkyl derivative of digoxin.” U.S. Patent US3981862, issued October, 1972.

US3981862
General References
  1. Thompson DF, Carter JR: Drug-induced gynecomastia. Pharmacotherapy. 1993 Jan-Feb;13(1):37-45. [PubMed:8094898 ]
  2. Doering W, Konig E, Sturm W: [Digitalis intoxication: specifity and significance of cardiac and extracardiac symptoms. part I: Patients with digitalis-induced arrhythmias (author's transl)]. Z Kardiol. 1977 Mar;66(3):121-8. [PubMed:857452 ]
  3. Kaplanski J, Weinhouse E, Topaz M, Genchik G: Verapamil and digoxin: interactions in the rat. Res Commun Chem Pathol Pharmacol. 1983 Dec;42(3):377-88. [PubMed:6665298 ]
  4. Flanagan RJ, Jones AL: Fab antibody fragments: some applications in clinical toxicology. Drug Saf. 2004;27(14):1115-33. [PubMed:15554746 ]
External Links
ATC CodesC01AA05
AHFS Codes
  • 24:04.08
  • 80:04.00
PDB EntriesNot Available
FDA labelDownload (563 KB)
MSDSDownload (74.6 KB)
Interactions
Drug Interactions
Drug
AcarboseThe serum concentration of Digoxin can be decreased when it is combined with Acarbose.
AcebutololAcebutolol may increase the bradycardic activities of Digoxin.
AdenosineThe risk or severity of adverse effects can be increased when Digoxin is combined with Adenosine.
AlfacalcidolAlfacalcidol may increase the arrhythmogenic activities of Digoxin.
AmikacinThe serum concentration of Digoxin can be decreased when it is combined with Amikacin.
AmilorideThe therapeutic efficacy of Digoxin can be decreased when used in combination with Amiloride.
AmiodaroneThe serum concentration of Digoxin can be increased when it is combined with Amiodarone.
Amphotericin BThe risk or severity of adverse effects can be increased when Amphotericin B is combined with Digoxin.
ArbekacinThe serum concentration of Digoxin can be decreased when it is combined with Arbekacin.
AtazanavirThe serum concentration of Digoxin can be increased when it is combined with Atazanavir.
AtenololAtenolol may increase the bradycardic activities of Digoxin.
AtorvastatinThe serum concentration of Digoxin can be increased when it is combined with Atorvastatin.
Atracurium besylateAtracurium besylate may increase the arrhythmogenic activities of Digoxin.
AzithromycinThe serum concentration of Digoxin can be increased when it is combined with Azithromycin.
BalsalazideThe serum concentration of Digoxin can be decreased when it is combined with Balsalazide.
BarnidipineThe risk or severity of adverse effects can be increased when Barnidipine is combined with Digoxin.
BatimastatThe serum concentration of Digoxin can be increased when it is combined with Batimastat.
BendroflumethiazideBendroflumethiazide may increase the bradycardic activities of Digoxin.
BepridilBepridil may increase the atrioventricular blocking (AV block) activities of Digoxin.
BetamethasoneBetamethasone may increase the arrhythmogenic activities of Digoxin.
BetaxololBetaxolol may increase the bradycardic activities of Digoxin.
BisoprololBisoprolol may increase the bradycardic activities of Digoxin.
BoceprevirThe serum concentration of Digoxin can be increased when it is combined with Boceprevir.
BretyliumBretylium may increase the bradycardic activities of Digoxin.
BrimonidineBrimonidine may increase the bradycardic activities of Digoxin.
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Digoxin.
CalcidiolThe serum concentration of Digoxin can be increased when it is combined with Calcidiol.
CalcipotriolCalcipotriol may increase the arrhythmogenic activities of Digoxin.
CalcitriolCalcitriol may increase the arrhythmogenic activities of Digoxin.
Calcium AcetateCalcium Acetate may increase the arrhythmogenic activities of Digoxin.
Calcium carbonateCalcium carbonate may increase the arrhythmogenic activities of Digoxin.
Calcium ChlorideCalcium Chloride may increase the arrhythmogenic activities of Digoxin.
Calcium citrateCalcium citrate may increase the arrhythmogenic activities of Digoxin.
Calcium gluconateCalcium gluconate may increase the arrhythmogenic activities of Digoxin.
CarbimazoleThe serum concentration of Digoxin can be increased when it is combined with Carbimazole.
CarteololCarteolol may increase the bradycardic activities of Digoxin.
CarvedilolDigoxin may increase the bradycardic activities of Carvedilol.
CelecoxibThe serum concentration of Digoxin can be increased when it is combined with Celecoxib.
CeritinibDigoxin may increase the bradycardic activities of Ceritinib.
ChloroquineThe serum concentration of Digoxin can be increased when it is combined with Chloroquine.
ChlorothiazideThe risk or severity of adverse effects can be increased when Chlorothiazide is combined with Digoxin.
ChlorthalidoneThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Digoxin.
CholecalciferolCholecalciferol may increase the arrhythmogenic activities of Digoxin.
CholestyramineCholestyramine can cause a decrease in the absorption of Digoxin resulting in a reduced serum concentration and potentially a decrease in efficacy.
Cisatracurium besylateCisatracurium besylate may increase the arrhythmogenic activities of Digoxin.
ClarithromycinThe serum concentration of Digoxin can be increased when it is combined with Clarithromycin.
ClonidineClonidine may increase the atrioventricular blocking (AV block) activities of Digoxin.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Digoxin.
ColesevelamColesevelam can cause a decrease in the absorption of Digoxin resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Digoxin resulting in a reduced serum concentration and potentially a decrease in efficacy.
ConivaptanThe serum concentration of Digoxin can be increased when it is combined with Conivaptan.
CyclosporineThe serum concentration of Digoxin can be increased when it is combined with Cyclosporine.
DaclatasvirThe serum concentration of Digoxin can be increased when it is combined with Daclatasvir.
DarunavirThe serum concentration of Digoxin can be increased when it is combined with Darunavir.
DaunorubicinDigoxin may decrease the cardiotoxic activities of Daunorubicin.
DiclofenacThe serum concentration of Digoxin can be increased when it is combined with Diclofenac.
DiflunisalThe serum concentration of Digoxin can be increased when it is combined with Diflunisal.
DihydrotachysterolDihydrotachysterol may increase the arrhythmogenic activities of Digoxin.
DiltiazemDiltiazem may increase the atrioventricular blocking (AV block) activities of Digoxin.
DoxercalciferolDoxercalciferol may increase the arrhythmogenic activities of Digoxin.
DoxorubicinDigoxin may decrease the cardiotoxic activities of Doxorubicin.
DronedaroneDigoxin may increase the atrioventricular blocking (AV block) activities of Dronedarone.
EdrophoniumEdrophonium may increase the atrioventricular blocking (AV block) activities of Digoxin.
EliglustatThe serum concentration of Digoxin can be increased when it is combined with Eliglustat.
EpirubicinDigoxin may decrease the cardiotoxic activities of Epirubicin.
EplerenoneThe therapeutic efficacy of Digoxin can be decreased when used in combination with Eplerenone.
EpoprostenolThe serum concentration of Digoxin can be increased when it is combined with Epoprostenol.
ErgocalciferolErgocalciferol may increase the arrhythmogenic activities of Digoxin.
ErythromycinThe serum concentration of Digoxin can be increased when it is combined with Erythromycin.
EsmololEsmolol may increase the bradycardic activities of Digoxin.
Etacrynic acidThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Digoxin.
EtodolacThe serum concentration of Digoxin can be increased when it is combined with Etodolac.
EtravirineThe serum concentration of Digoxin can be increased when it is combined with Etravirine.
FenoprofenThe serum concentration of Digoxin can be increased when it is combined with Fenoprofen.
FlecainideThe serum concentration of Digoxin can be increased when it is combined with Flecainide.
FlibanserinThe serum concentration of Digoxin can be increased when it is combined with Flibanserin.
FloctafenineThe serum concentration of Digoxin can be increased when it is combined with Floctafenine.
FlurbiprofenThe serum concentration of Digoxin can be increased when it is combined with Flurbiprofen.
FosamprenavirThe serum concentration of Digoxin can be increased when it is combined with Fosamprenavir.
FramycetinThe serum concentration of Digoxin can be decreased when it is combined with Framycetin.
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Digoxin.
GentamicinThe serum concentration of Digoxin can be decreased when it is combined with Gentamicin.
GlycopyrroniumThe serum concentration of Digoxin can be increased when it is combined with Glycopyrrolate.
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Hydrochlorothiazide is combined with Digoxin.
HydroxychloroquineThe serum concentration of Digoxin can be increased when it is combined with Hydroxychloroquine.
IbuprofenThe serum concentration of Digoxin can be increased when it is combined with Ibuprofen.
IdarubicinDigoxin may decrease the cardiotoxic activities of Idarubicin.
IndapamideThe risk or severity of adverse effects can be increased when Indapamide is combined with Digoxin.
IndinavirThe serum concentration of Digoxin can be increased when it is combined with Indinavir.
IndomethacinThe serum concentration of Digoxin can be increased when it is combined with Indomethacin.
InfliximabThe serum concentration of Digoxin can be increased when it is combined with Infliximab.
IsavuconazoniumThe serum concentration of Digoxin can be increased when it is combined with Isavuconazonium.
IsoflurophateThe serum concentration of Digoxin can be increased when it is combined with Isoflurophate.
ItraconazoleThe serum concentration of Digoxin can be increased when it is combined with Itraconazole.
IvabradineDigoxin may increase the bradycardic activities of Ivabradine.
KanamycinThe serum concentration of Digoxin can be decreased when it is combined with Kanamycin.
KaolinThe serum concentration of Digoxin can be decreased when it is combined with Kaolin.
KetoprofenThe serum concentration of Digoxin can be increased when it is combined with Ketoprofen.
KetorolacThe serum concentration of Digoxin can be increased when it is combined with Ketorolac.
LabetalolLabetalol may increase the bradycardic activities of Digoxin.
LacosamideDigoxin may increase the atrioventricular blocking (AV block) activities of Lacosamide.
LenalidomideThe serum concentration of Digoxin can be increased when it is combined with Lenalidomide.
LicoriceThe risk or severity of adverse effects can be increased when Licorice is combined with Digoxin.
LumacaftorThe serum concentration of Digoxin can be decreased when it is combined with Lumacaftor.
Mefenamic acidThe serum concentration of Digoxin can be increased when it is combined with Mefenamic acid.
MeloxicamThe serum concentration of Digoxin can be increased when it is combined with Meloxicam.
MesalazineThe serum concentration of Digoxin can be decreased when it is combined with Mesalazine.
MethimazoleThe serum concentration of Digoxin can be increased when it is combined with Methimazole.
MethyclothiazideThe risk or severity of adverse effects can be increased when Methyclothiazide is combined with Digoxin.
MetolazoneThe risk or severity of adverse effects can be increased when Metolazone is combined with Digoxin.
MetoprololMetoprolol may increase the bradycardic activities of Digoxin.
MidodrineDigoxin may increase the bradycardic activities of Midodrine.
MifepristoneThe serum concentration of Digoxin can be increased when it is combined with Mifepristone.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Digoxin.
MirabegronThe serum concentration of Digoxin can be increased when it is combined with Mirabegron.
MitoxantroneDigoxin may decrease the cardiotoxic activities of Mitoxantrone.
NabumetoneThe serum concentration of Digoxin can be increased when it is combined with Nabumetone.
NadololNadolol may increase the bradycardic activities of Digoxin.
NaproxenThe serum concentration of Digoxin can be increased when it is combined with Naproxen.
NebivololNebivolol may increase the bradycardic activities of Digoxin.
NefazodoneThe serum concentration of Digoxin can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Digoxin can be increased when it is combined with Nelfinavir.
NeomycinThe serum concentration of Digoxin can be decreased when it is combined with Neomycin.
NetilmicinThe serum concentration of Digoxin can be decreased when it is combined with Netilmicin.
NifedipineThe serum concentration of Digoxin can be increased when it is combined with Nifedipine.
OctreotideOctreotide may increase the bradycardic activities of Digoxin.
OlsalazineThe serum concentration of Digoxin can be decreased when it is combined with Olsalazine.
OxaprozinThe serum concentration of Digoxin can be increased when it is combined with Oxaprozin.
PancuroniumPancuronium may increase the arrhythmogenic activities of Digoxin.
Parathyroid hormoneThe risk or severity of adverse effects can be increased when Preotact is combined with Digoxin.
ParicalcitolThe risk or severity of adverse effects can be increased when Paricalcitol is combined with Digoxin.
PenbutololPenbutolol may increase the bradycardic activities of Digoxin.
PenicillamineThe serum concentration of Digoxin can be decreased when it is combined with Penicillamine.
PindololPindolol may increase the bradycardic activities of Digoxin.
PiroxicamThe serum concentration of Digoxin can be increased when it is combined with Piroxicam.
Polyethylene glycolThe serum concentration of Digoxin can be decreased when it is combined with Polyethylene glycol.
Polystyrene sulfonateThe risk or severity of adverse effects can be increased when Polystyrene sulfonate is combined with Digoxin.
PosaconazoleThe serum concentration of Digoxin can be increased when it is combined with Posaconazole.
Potassium IodideThe serum concentration of Digoxin can be increased when it is combined with Potassium Iodide.
PrimaquineThe serum concentration of Digoxin can be increased when it is combined with Primaquine.
PropafenoneThe serum concentration of Digoxin can be increased when it is combined with Propafenone.
PropranololPropranolol may increase the bradycardic activities of Digoxin.
PropylthiouracilThe serum concentration of Digoxin can be increased when it is combined with Propylthiouracil.
QuinidineThe serum concentration of Digoxin can be increased when it is combined with Quinidine.
QuinineThe serum concentration of Digoxin can be increased when it is combined with Quinine.
RanolazineThe serum concentration of Digoxin can be increased when it is combined with Ranolazine.
RegorafenibRegorafenib may increase the bradycardic activities of Digoxin.
ReserpineThe risk or severity of adverse effects can be increased when Reserpine is combined with Digoxin.
RibostamycinThe serum concentration of Digoxin can be decreased when it is combined with Ribostamycin.
RitonavirThe serum concentration of Digoxin can be increased when it is combined with Ritonavir.
RocuroniumRocuronium may increase the arrhythmogenic activities of Digoxin.
RuxolitinibRuxolitinib may increase the bradycardic activities of Digoxin.
SaquinavirThe serum concentration of Digoxin can be increased when it is combined with Saquinavir.
SimeprevirThe serum concentration of Digoxin can be increased when it is combined with Simeprevir.
SitagliptinThe serum concentration of Digoxin can be increased when it is combined with Sitagliptin.
SotalolSotalol may increase the bradycardic activities of Digoxin.
SpectinomycinThe serum concentration of Digoxin can be decreased when it is combined with Spectinomycin.
SpiramycinThe serum concentration of Digoxin can be increased when it is combined with Spiramycin.
SpironolactoneThe serum concentration of Digoxin can be increased when it is combined with Spironolactone.
St. John's WortThe serum concentration of Digoxin can be decreased when it is combined with St. John's Wort.
StreptomycinThe serum concentration of Digoxin can be decreased when it is combined with Streptomycin.
SuccinylcholineSuccinylcholine may increase the arrhythmogenic activities of Digoxin.
SucralfateThe serum concentration of Digoxin can be decreased when it is combined with Sucralfate.
SulfisoxazoleThe serum concentration of Digoxin can be increased when it is combined with Sulfisoxazole.
SulindacThe serum concentration of Digoxin can be increased when it is combined with Sulindac.
SulpirideThe risk or severity of adverse effects can be increased when Sulpiride is combined with Digoxin.
TelaprevirThe serum concentration of Digoxin can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Digoxin can be increased when it is combined with Telithromycin.
TelmisartanThe serum concentration of Digoxin can be increased when it is combined with Telmisartan.
TesmilifeneThe serum concentration of Digoxin can be decreased when it is combined with Tesmilifene.
Tiaprofenic acidThe serum concentration of Digoxin can be increased when it is combined with Tiaprofenic acid.
TicagrelorThe serum concentration of Digoxin can be increased when it is combined with Ticagrelor.
TimololTimolol may increase the bradycardic activities of Digoxin.
TipranavirThe serum concentration of Digoxin can be increased when it is combined with Tipranavir.
TobramycinThe serum concentration of Digoxin can be decreased when it is combined with Tobramycin.
TofacitinibTofacitinib may increase the bradycardic activities of Digoxin.
TolmetinThe serum concentration of Digoxin can be increased when it is combined with Tolmetin.
TolvaptanThe serum concentration of Digoxin can be increased when it is combined with Tolvaptan.
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Digoxin.
TriamtereneThe therapeutic efficacy of Digoxin can be decreased when used in combination with Triamterene.
TrichlormethiazideThe risk or severity of adverse effects can be increased when Trichlormethiazide is combined with Digoxin.
TrimethoprimThe serum concentration of Digoxin can be increased when it is combined with Trimethoprim.
VandetanibThe serum concentration of Digoxin can be increased when it is combined with Vandetanib.
VecuroniumVecuronium may increase the arrhythmogenic activities of Digoxin.
VemurafenibThe serum concentration of Digoxin can be increased when it is combined with Vemurafenib.
VerapamilVerapamil may increase the atrioventricular blocking (AV block) activities of Digoxin.
VilazodoneThe serum concentration of Digoxin can be increased when it is combined with Vilazodone.
Food Interactions
  • Avoid avocado.
  • Avoid bran and high fiber foods within 2 hours of taking this medication.
  • Avoid excess salt/sodium unless otherwise instructed by your physician.
  • Avoid milk, calcium containing dairy products, iron, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication.
  • Avoid salt substitutes containing potassium.
  • Limit garlic, ginger, gingko, and horse chestnut.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular Weight:
112895.01 Da
References
  1. Ravikumar A, Arun P, Devi KV, Augustine J, Kurup PA: Isoprenoid pathway and free radical generation and damage in neuropsychiatric disorders. Indian J Exp Biol. 2000 May;38(5):438-46. [PubMed:11272406 ]
  2. Chen JJ, Wang PS, Chien EJ, Wang SW: Direct inhibitory effect of digitalis on progesterone release from rat granulosa cells. Br J Pharmacol. 2001 Apr;132(8):1761-8. [PubMed:11309248 ]
  3. Ke YS, Liu ZF, Yang H, Yang T, Huang JS, Rui SB, Cheng GH, Wang YX: Effect of anti-digoxin antiserum on endoxin and membrane ATPase activity in hypoxia-reoxygenation induced myocardial injury. Acta Pharmacol Sin. 2000 Apr;21(4):345-7. [PubMed:11324464 ]
  4. Kumar AR, Kurup PA: A hypothalamic digoxin mediated model for conscious and subliminal perception. J Neural Transm (Vienna). 2001;108(7):855-68. [PubMed:11515751 ]
  5. Aizman O, Uhlen P, Lal M, Brismar H, Aperia A: Ouabain, a steroid hormone that signals with slow calcium oscillations. Proc Natl Acad Sci U S A. 2001 Nov 6;98(23):13420-4. Epub 2001 Oct 30. [PubMed:11687608 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular Weight:
60101.87 Da
References
  1. Chen JJ, Wang PS, Chien EJ, Wang SW: Direct inhibitory effect of digitalis on progesterone release from rat granulosa cells. Br J Pharmacol. 2001 Apr;132(8):1761-8. [PubMed:11309248 ]
  2. Wang SW, Pu HF, Kan SF, Tseng CI, Lo MJ, Wang PS: Inhibitory effects of digoxin and digitoxin on corticosterone production in rat zona fasciculata-reticularis cells. Br J Pharmacol. 2004 Aug;142(7):1123-30. Epub 2004 Jul 12. [PubMed:15249423 ]
  3. Lin H, Wang SW, Tsai SC, Chen JJ, Chiao YC, Lu CC, Huang WJ, Wang GJ, Chen CF, Wang PS: Inhibitory effect of digoxin on testosterone secretion through mechanisms involving decreases of cyclic AMP production and cytochrome P450scc activity in rat testicular interstitial cells. Br J Pharmacol. 1998 Dec;125(8):1635-40. [PubMed:9886754 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Takara K, Tsujimoto M, Ohnishi N, Yokoyama T: Digoxin up-regulates MDR1 in human colon carcinoma Caco-2 cells. Biochem Biophys Res Commun. 2002 Mar 22;292(1):190-4. [PubMed:11890691 ]
  2. Takara K, Takagi K, Tsujimoto M, Ohnishi N, Yokoyama T: Digoxin up-regulates multidrug resistance transporter (MDR1) mRNA and simultaneously down-regulates steroid xenobiotic receptor mRNA. Biochem Biophys Res Commun. 2003 Jun 20;306(1):116-20. [PubMed:12788075 ]
  3. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389 ]
  4. Takara K, Tanigawara Y, Komada F, Nishiguchi K, Sakaeda T, Okumura K: Cellular pharmacokinetic aspects of reversal effect of itraconazole on P-glycoprotein-mediated resistance of anticancer drugs. Biol Pharm Bull. 1999 Dec;22(12):1355-9. [PubMed:10746169 ]
  5. Yamazaki M, Neway WE, Ohe T, Chen I, Rowe JF, Hochman JH, Chiba M, Lin JH: In vitro substrate identification studies for p-glycoprotein-mediated transport: species difference and predictability of in vivo results. J Pharmacol Exp Ther. 2001 Mar;296(3):723-35. [PubMed:11181899 ]
  6. Adachi Y, Suzuki H, Sugiyama Y: Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. [PubMed:11785684 ]
  7. Neuhoff S, Ungell AL, Zamora I, Artursson P: pH-dependent bidirectional transport of weakly basic drugs across Caco-2 monolayers: implications for drug-drug interactions. Pharm Res. 2003 Aug;20(8):1141-8. [PubMed:12948010 ]
  8. Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019 ]
  9. Dagenais C, Graff CL, Pollack GM: Variable modulation of opioid brain uptake by P-glycoprotein in mice. Biochem Pharmacol. 2004 Jan 15;67(2):269-76. [PubMed:14698039 ]
  10. Taipalensuu J, Tavelin S, Lazorova L, Svensson AC, Artursson P: Exploring the quantitative relationship between the level of MDR1 transcript, protein and function using digoxin as a marker of MDR1-dependent drug efflux activity. Eur J Pharm Sci. 2004 Jan;21(1):69-75. [PubMed:14706813 ]
  11. Tanigawara Y, Okamura N, Hirai M, Yasuhara M, Ueda K, Kioka N, Komano T, Hori R: Transport of digoxin by human P-glycoprotein expressed in a porcine kidney epithelial cell line (LLC-PK1). J Pharmacol Exp Ther. 1992 Nov;263(2):840-5. [PubMed:1359120 ]
  12. Fromm MF, Kim RB, Stein CM, Wilkinson GR, Roden DM: Inhibition of P-glycoprotein-mediated drug transport: A unifying mechanism to explain the interaction between digoxin and quinidine [seecomments]. Circulation. 1999 Feb 2;99(4):552-7. [PubMed:9927403 ]
  13. Soldner A, Christians U, Susanto M, Wacher VJ, Silverman JA, Benet LZ: Grapefruit juice activates P-glycoprotein-mediated drug transport. Pharm Res. 1999 Apr;16(4):478-85. [PubMed:10227700 ]
  14. Collett A, Tanianis-Hughes J, Hallifax D, Warhurst G: Predicting P-glycoprotein effects on oral absorption: correlation of transport in Caco-2 with drug pharmacokinetics in wild-type and mdr1a(-/-) mice in vivo. Pharm Res. 2004 May;21(5):819-26. [PubMed:15180340 ]
  15. Yamaguchi H, Yano I, Saito H, Inui K: Effect of cisplatin-induced acute renal failure on bioavailability and intestinal secretion of quinolone antibacterial drugs in rats. Pharm Res. 2004 Feb;21(2):330-8. [PubMed:15032316 ]
  16. Takara K, Sakaeda T, Kakumoto M, Tanigawara Y, Kobayashi H, Okumura K, Ohnishi N, Yokoyama T: Effects of alpha-adrenoceptor antagonist doxazosin on MDR1-mediated multidrug resistance and transcellular transport. Oncol Res. 2009;17(11-12):527-33. [PubMed:19806783 ]
  17. Jutabha P, Wempe MF, Anzai N, Otomo J, Kadota T, Endou H: Xenopus laevis oocytes expressing human P-glycoprotein: probing trans- and cis-inhibitory effects on [3H]vinblastine and [3H]digoxin efflux. Pharmacol Res. 2010 Jan;61(1):76-84. doi: 10.1016/j.phrs.2009.07.002. Epub 2009 Jul 21. [PubMed:19631272 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Organic anion transporter, capable of transporting pharmacological substances such as digoxin, ouabain, thyroxine, methotrexate and cAMP. May participate in the regulation of membrane transport of ouabain. Involved in the uptake of the dipeptidyl peptidase-4 inhibitor sitagliptin and hence may play a role in its transport into and out of renal proximal tubule cells. May be involved in the first...
Gene Name:
SLCO4C1
Uniprot ID:
Q6ZQN7
Molecular Weight:
78947.525 Da
References
  1. Mikkaichi T, Suzuki T, Onogawa T, Tanemoto M, Mizutamari H, Okada M, Chaki T, Masuda S, Tokui T, Eto N, Abe M, Satoh F, Unno M, Hishinuma T, Inui K, Ito S, Goto J, Abe T: Isolation and characterization of a digoxin transporter and its rat homologue expressed in the kidney. Proc Natl Acad Sci U S A. 2004 Mar 9;101(10):3569-74. Epub 2004 Mar 1. [PubMed:14993604 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [PubMed:10224140 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name:
SLCO2B1
Uniprot ID:
O94956
Molecular Weight:
76709.98 Da
References
  1. Nishio T, Adachi H, Nakagomi R, Tokui T, Sato E, Tanemoto M, Fujiwara K, Okabe M, Onogawa T, Suzuki T, Nakai D, Shiiba K, Suzuki M, Ohtani H, Kondo Y, Unno M, Ito S, Iinuma K, Nunoki K, Matsuno S, Abe T: Molecular identification of a rat novel organic anion transporter moat1, which transports prostaglandin D(2), leukotriene C(4), and taurocholate. Biochem Biophys Res Commun. 2000 Sep 7;275(3):831-8. [PubMed:10973807 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Transporter activity
Specific Function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular Weight:
146405.83 Da
References
  1. Lecureur V, Sun D, Hargrove P, Schuetz EG, Kim RB, Lan LB, Schuetz JD: Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein. Mol Pharmacol. 2000 Jan;57(1):24-35. [PubMed:10617675 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibited by the grapefruit juice component naringin.
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular Weight:
74144.105 Da
References
  1. Hagenbuch B, Adler ID, Schmid TE: Molecular cloning and functional characterization of the mouse organic-anion-transporting polypeptide 1 (Oatp1) and mapping of the gene to chromosome X. Biochem J. 2000 Jan 1;345 Pt 1:115-20. [PubMed:10600646 ]
  2. Noe B, Hagenbuch B, Stieger B, Meier PJ: Isolation of a multispecific organic anion and cardiac glycoside transporter from rat brain. Proc Natl Acad Sci U S A. 1997 Sep 16;94(19):10346-50. [PubMed:9294213 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Transporter activity
Specific Function:
Essential component of the Ost-alpha/Ost-beta complex, a heterodimer that acts as the intestinal basolateral transporter responsible for bile acid export from enterocytes into portal blood. Efficiently transports the major species of bile acids.
Gene Name:
SLC51A
Uniprot ID:
Q86UW1
Molecular Weight:
37734.575 Da
References
  1. Seward DJ, Koh AS, Boyer JL, Ballatori N: Functional complementation between a novel mammalian polygenic transport complex and an evolutionarily ancient organic solute transporter, OSTalpha-OSTbeta. J Biol Chem. 2003 Jul 25;278(30):27473-82. Epub 2003 Apr 28. [PubMed:12719432 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Transporter activity
Specific Function:
Essential component of the Ost-alpha/Ost-beta complex, a heterodimer that acts as the intestinal basolateral transporter responsible for bile acid export from enterocytes into portal blood. Efficiently transports the major species of bile acids. Modulates SLC51A glycosylation, membrane trafficking and stability activities.
Gene Name:
SLC51B
Uniprot ID:
Q86UW2
Molecular Weight:
14346.195 Da
References
  1. Seward DJ, Koh AS, Boyer JL, Ballatori N: Functional complementation between a novel mammalian polygenic transport complex and an evolutionarily ancient organic solute transporter, OSTalpha-OSTbeta. J Biol Chem. 2003 Jul 25;278(30):27473-82. Epub 2003 Apr 28. [PubMed:12719432 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Thyroid hormone transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate.
Gene Name:
SLCO4A1
Uniprot ID:
Q96BD0
Molecular Weight:
77192.505 Da
References
  1. Mikkaichi T, Suzuki T, Onogawa T, Tanemoto M, Mizutamari H, Okada M, Chaki T, Masuda S, Tokui T, Eto N, Abe M, Satoh F, Unno M, Hishinuma T, Inui K, Ito S, Goto J, Abe T: Isolation and characterization of a digoxin transporter and its rat homologue expressed in the kidney. Proc Natl Acad Sci U S A. 2004 Mar 9;101(10):3569-74. Epub 2004 Mar 1. [PubMed:14993604 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP). Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Molecular Weight:
77402.175 Da
References
  1. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [PubMed:11159893 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Thyroid hormone transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent high affinity transport of organic anions such as the thyroid hormones thyroxine (T4) and rT3. Other potential substrates, such as triiodothyronine (T3), 17-beta-glucuronosyl estradiol, estrone-3-sulfate and sulfobromophthalein (BSP) are transported with much lower efficiency. May play a signifiant role in regulating T4 flux into and out of the brain (By similarity).
Gene Name:
SLCO1C1
Uniprot ID:
Q9NYB5
Molecular Weight:
78695.625 Da
References
  1. Pizzagalli F, Hagenbuch B, Stieger B, Klenk U, Folkers G, Meier PJ: Identification of a novel human organic anion transporting polypeptide as a high affinity thyroxine transporter. Mol Endocrinol. 2002 Oct;16(10):2283-96. [PubMed:12351693 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular Weight:
76447.99 Da
References
  1. van Montfoort JE, Schmid TE, Adler ID, Meier PJ, Hagenbuch B: Functional characterization of the mouse organic-anion-transporting polypeptide 2. Biochim Biophys Acta. 2002 Aug 19;1564(1):183-8. [PubMed:12101011 ]
  2. Dagenais C, Ducharme J, Pollack GM: Uptake and efflux of the peptidic delta-opioid receptor agonist. Neurosci Lett. 2001 Apr 6;301(3):155-8. [PubMed:11257421 ]
  3. Sugiyama D, Kusuhara H, Shitara Y, Abe T, Meier PJ, Sekine T, Endou H, Suzuki H, Sugiyama Y: Characterization of the efflux transport of 17beta-estradiol-D-17beta-glucuronide from the brain across the blood-brain barrier. J Pharmacol Exp Ther. 2001 Jul;298(1):316-22. [PubMed:11408557 ]
  4. Hagenbuch N, Reichel C, Stieger B, Cattori V, Fattinger KE, Landmann L, Meier PJ, Kullak-Ublick GA: Effect of phenobarbital on the expression of bile salt and organic anion transporters of rat liver. J Hepatol. 2001 Jun;34(6):881-7. [PubMed:11451172 ]
  5. Gao B, Wenzel A, Grimm C, Vavricka SR, Benke D, Meier PJ, Reme CE: Localization of organic anion transport protein 2 in the apical region of rat retinal pigment epithelium. Invest Ophthalmol Vis Sci. 2002 Feb;43(2):510-4. [PubMed:11818398 ]
  6. Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [PubMed:11883641 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10