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
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
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
Title | Date | PubMed |
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[Cardiac arrhythmia in old age caused by digitalis intoxication]. | 1967 Apr 27 |
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[On the treatment of the digitalis-induced atrial tachycardia with AV conduction disorder. Experiences with sodium-magnesium aspartate]. | 1968 Mar 29 |
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Digitoxin induced cardiac necrosis and its inhibition. | 1969 |
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[Spironolactone protection against experimental cardiopathy due to digitoxin, disodium phosphate and oil]. | 1970 Feb |
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Possible mechanism of the prevention of digitoxin toxicity by spironolactone in the mouse. | 1971 Jan |
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Protection by spironolactone and oxandrolone against chronic digitoxin or indomethacin intoxication. | 1971 Mar |
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His bundle electrocardiography during bidirectional tachycardia. | 1973 Jul |
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Reversal of advanced digitoxin toxicity and modification of pharmacokinetics by specific antibodies and Fab fragments. | 1977 Dec |
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Digitalis delirium: a reminder. | 1980 Mar |
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Effects of atropine on the cardiac arrest induced by propranolol and digitoxin in dogs. | 1982 |
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[Digitoxin poisoning: reversing ventricular fibrillation with Fab fragments of anti-digoxin antibody]. | 1982 Dec 25 |
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Reversal of digitalis-induced mesenteric vasospasm by sodium nitroprusside. | 1982 Feb |
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Effect of age, clonidine or propranolol on behavioral toxicity induced with digitoxin in mice. | 1982 Sep |
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Effect of long-term administration of digoxin on exercise performance in chronic airflow obstruction. | 1985 Apr |
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Effect of digitoxin on cardiac arrhythmias in hemodialysis patients. | 1987 Nov 16 |
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[Digitoxin-induced thrombocytopenia]. | 1993 |
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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 |
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Chronic hypertension induced by ouabain but not digoxin in the rat: antihypertensive effect of digoxin and digitoxin. | 2000 Sep |
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Digitoxin medication and cancer; case control and internal dose-response studies. | 2001 |
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Digitoxin mimics gene therapy with CFTR and suppresses hypersecretion of IL-8 from cystic fibrosis lung epithelial cells. | 2004 May 18 |
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Ouabain, a cardiac glycoside, inhibits the Fanconi anemia/BRCA pathway activated by DNA interstrand cross-linking agents. | 2013 |
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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
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 862.3300
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WHO-VATC |
QC01AA04
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FDA ORPHAN DRUG |
205005
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FDA ORPHAN DRUG |
149601
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NCI_THESAURUS |
C471
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NCI_THESAURUS |
C78322
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WHO-ATC |
C01AA04
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admin on Tue Oct 22 00:46:29 UTC 2019 , Edited by admin on Tue Oct 22 00:46:29 UTC 2019
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LIVERTOX |
306
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admin on Tue Oct 22 00:46:29 UTC 2019 , Edited by admin on Tue Oct 22 00:46:29 UTC 2019
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FDA ORPHAN DRUG |
149701
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Code System | Code | Type | Description | ||
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71-63-6
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3403
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M4452
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PRIMARY | Merck Index | ||
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1547
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DB01396
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71-63-6
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admin on Tue Oct 22 00:46:29 UTC 2019 , Edited by admin on Tue Oct 22 00:46:29 UTC 2019
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DIGITOXIN
Created by
admin on Tue Oct 22 00:46:29 UTC 2019 , Edited by admin on Tue Oct 22 00:46:29 UTC 2019
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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. | ||
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71-63-6
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admin on Tue Oct 22 00:46:29 UTC 2019 , Edited by admin on Tue Oct 22 00:46:29 UTC 2019
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CHEMBL254219
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441207
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C2634
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D004074
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200-760-5
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admin on Tue Oct 22 00:46:29 UTC 2019 , Edited by admin on Tue Oct 22 00:46:29 UTC 2019
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DIGITOXIN
Created by
admin on Tue Oct 22 00:46:29 UTC 2019 , Edited by admin on Tue Oct 22 00:46:29 UTC 2019
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6782
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SUB07133MIG
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ACTIVE MOIETY