U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C41H64O13
Molecular Weight 764.9391
Optical Activity UNSPECIFIED
Defined Stereocenters 20 / 20
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIGITOXIN

SMILES

C[C@H]1O[C@H](C[C@H](O)[C@@H]1O)O[C@H]2[C@@H](O)C[C@H](O[C@H]3[C@@H](O)C[C@H](O[C@H]4CC[C@@]5(C)[C@H](CC[C@@H]6[C@@H]5CC[C@]7(C)[C@H](CC[C@]67O)C8=CC(=O)OC8)C4)O[C@@H]3C)O[C@@H]2C

InChI

InChIKey=WDJUZGPOPHTGOT-XUDUSOBPSA-N
InChI=1S/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1

HIDE SMILES / InChI

Description

Digoxin is a cardiac glycoside derived from the purple foxglove flower. In 1785, the English chemist, botanist, and physician Sir William Withering published his findings that Digitalis purpurea could be used to treat cardiac dropsy (congestive heart failure; CHF). Digoxin has been in use for many years, but was not approved by the FDA for treatment of heart failure (HF) until the late 1990s. Another FDA indication for digoxin is atrial fibrillation (AF). Digoxin also has numerous off-label uses, such as in fetal tachycardia, supra-ventricular tachycardia, cor pulmonale, and pulmonary hypertension. Digitoxin inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Digoxin also has Para sympathomimetic properties. By increasing vagal tone in the sinoatrial and atrioventricular (AV) nodes, it slows the heart rate and AV nodal conduction.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
[Cardiac arrhythmia in old age caused by digitalis intoxication].
1967 Apr 27
Influence of drugs, implanted into the hypothalamus, on the water consumption of rats.
1968 Jan
Atrial dissociation due to digitalis toxicity.
1968 Jun
[On the treatment of the digitalis-induced atrial tachycardia with AV conduction disorder. Experiences with sodium-magnesium aspartate].
1968 Mar 29
Digitoxin induced cardiac necrosis and its inhibition.
1969
[Acute digitalic poisoning].
1970 Feb
[Spironolactone protection against experimental cardiopathy due to digitoxin, disodium phosphate and oil].
1970 Feb
Possible mechanism of the prevention of digitoxin toxicity by spironolactone in the mouse.
1971 Jan
The clinical value of serum digitalis glycoside concentrations in the evaluation of drug toxicity.
1971 Jul 6
Protection by spironolactone and oxandrolone against chronic digitoxin or indomethacin intoxication.
1971 Mar
His bundle electrocardiography during bidirectional tachycardia.
1973 Jul
Effect of microsomal enzyme inducers on the biliary excretion of cardiac glycosides.
1974 Nov
Transient global amnesia associated with cardiac arrhythmia and digitalis intoxication.
1975 Sep-Oct
Hypotensive and antiarrhythmic effects of a new alkaloid, the 13-hydroxylupanine-2-pyrrolcarbonic acid ester, from the Madagascan plant Cadia ellisiana.
1976
Reversal of advanced digitoxin toxicity and modification of pharmacokinetics by specific antibodies and Fab fragments.
1977 Dec
Digitalis delirium: a reminder.
1980 Mar
Effects of atropine on the cardiac arrest induced by propranolol and digitoxin in dogs.
1982
[Digitoxin poisoning: reversing ventricular fibrillation with Fab fragments of anti-digoxin antibody].
1982 Dec 25
Reversal of digitalis-induced mesenteric vasospasm by sodium nitroprusside.
1982 Feb
Effect of age, clonidine or propranolol on behavioral toxicity induced with digitoxin in mice.
1982 Sep
Study of the factors influencing cardiac growth. II. Digitoxin treatment and isoproterenol-induced cardiac hypertrophy in the rat.
1985
Effect of long-term administration of digoxin on exercise performance in chronic airflow obstruction.
1985 Apr
Effect of digitoxin on cardiac arrhythmias in hemodialysis patients.
1987 Nov 16
Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies.
1992
[Digitoxin-induced thrombocytopenia].
1993
Synthesis of 20-hydroxy-, 20-amino-, and 20-nitro-14-hydroxy-21-nor-5 beta,14 beta-pregnane C-3 glycosides and related derivatives: structure-activity relationships of pregnanes that bind to the digitalis receptor.
1993 Jan 8
Hepatorenal syndrome in cirrhotic patients: terlipressine is a safe and efficient treatment; propranolol and digitalic treatments: precipitating and preventing factors?
2000 Oct
Chronic hypertension induced by ouabain but not digoxin in the rat: antihypertensive effect of digoxin and digitoxin.
2000 Sep
Digitoxin medication and cancer; case control and internal dose-response studies.
2001
Treatment of congestive heart failure--current status of use of digitoxin.
2001
Adverse drug reaction monitoring--digitoxin overdosage in the elderly.
2001 Aug
Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells.
2001 Jun
Bidirectional tachycardia: two cases and a review.
2002 Aug
Posterior encephalopathy with vasospasm: MRI and angiography.
2003 Dec
Digitoxin mimics gene therapy with CFTR and suppresses hypersecretion of IL-8 from cystic fibrosis lung epithelial cells.
2004 May 18
Bidirectional ventricular tachycardia due to digitalis intoxication.
2005 Feb
Iatrogenic sick sinus syndrome.
2007 May
Heart failure drug digitoxin induces calcium uptake into cells by forming transmembrane calcium channels.
2008 Feb 19
Digitoxin elicits anti-inflammatory and vasoprotective properties in endothelial cells: Therapeutic implications for the treatment of atherosclerosis?
2009 Oct
Antiherpes activity of glucoevatromonoside, a cardenolide isolated from a Brazilian cultivar of Digitalis lanata.
2011 Oct
Digitoxin and a synthetic monosaccharide analog inhibit cell viability in lung cancer cells.
2012 Jan 1
Ouabain, a cardiac glycoside, inhibits the Fanconi anemia/BRCA pathway activated by DNA interstrand cross-linking agents.
2013
Interaction of digitalis-like compounds with p-glycoprotein.
2013 Feb
A novel cell-based high-throughput screen for inhibitors of HIV-1 gene expression and budding identifies the cardiac glycosides.
2014 Apr
Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs.
2015 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Age Oral Loading Dose, mcg/kg Premature: 20 - 30; Full-Term 25 - 35; 1 to 24 months 35 - 60; 2 to 5 years 30 - 45; 5 to 10 years 20 - 35; Over 10 years 10 - 15
Route of Administration: Oral
Name Type Language
DIGITOXIN
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
TRADIGAL
Common Name English
CRYSTODIGIN
Code English
DIGIMERCK
Common Name English
DIGITOXINUM [HPUS]
Common Name English
UNIDIGIN
Common Name English
CARD-20(22)-ENOLIDE, 3-((O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-14-HYDROXY-, (3.BETA.,5.BETA.)-
Common Name English
DIGITOXIN [MART.]
Common Name English
(3.BETA.,5.BETA.)-3-((O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-14-HYDROXYCARD-20(22)-ENOLIDE
Common Name English
DIGITALIN, CRYSTALLINE
Common Name English
DIGITOXIN [WHO-IP]
Common Name English
DIGITOXIN [MI]
Common Name English
DIGITOXIN [JAN]
Common Name English
(3.BETA.,5.BETA.)-3-((O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXAPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-14-HYDROXYCARD-20(22)-ENOLIDE
Common Name English
DIGITOXOSIDE
Common Name English
DIGITOXIN [USP]
Common Name English
DIGITOPHYLLIN
Common Name English
DIGITOXINUM
HPUS   WHO-IP LATIN  
Common Name English
GLUCODIGIN
Common Name English
DIGITOXIN [ORANGE BOOK]
Common Name English
DIGITOXIN [HSDB]
Common Name English
DIGITOXIN [USP-RS]
Common Name English
DIGITOXIN [EP]
Common Name English
DIGITOXINUM [WHO-IP LATIN]
Common Name English
DIGITOXIN [VANDF]
Common Name English
DIGITOXIN [INN]
Common Name English
NSC-7529
Code English
PURPURID
Common Name English
DIGITOXIN [WHO-DD]
Common Name English
LANATOXIN
Common Name English
CRISTAPURAT
Common Name English
Classification Tree Code System Code
CFR 21 CFR 862.3300
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
WHO-VATC QC01AA04
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
WHO-ATC C01AA04
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
LIVERTOX 306
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
Code System Code Type Description
HSDB
71-63-6
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY
RXCUI
3403
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY RxNorm
MERCK INDEX
M4452
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY Merck Index
INN
1547
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY
DRUG BANK
DB01396
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY
EPA CompTox
71-63-6
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIGITOXIN
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY Description: A white or almost white, microcrystalline powder; odourless.Solubility: Practically insoluble in water; slightly soluble in ethanol (~750 g/l) TS.Category: Cardiotonic.Storage: Digitoxin should be kept in a well-closed container, protected from light.Additional information: CAUTION: Digitoxin is extremely poisonous and should be handled with care.Requirements: Definition. Digitoxin contains not less than 95.0% and not more than 105.0% of C41H64O13, calculated with reference to the dried substance.
CAS
71-63-6
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY
ChEMBL
CHEMBL254219
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY
PUBCHEM
441207
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY SWITZERF
NCI_THESAURUS
C2634
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY
MESH
D004074
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY
ECHA (EC/EINECS)
200-760-5
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY
WIKIPEDIA
DIGITOXIN
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY
IUPHAR
6782
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY
EVMPD
SUB07133MIG
Created by admin on Tue Mar 06 12:06:31 UTC 2018 , Edited by admin on Tue Mar 06 12:06:31 UTC 2018
PRIMARY