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
Molecular Formula | C41H64O13 |
Molecular Weight | 764.9391 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | |
Defined Stereocenters | 20 / 20 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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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Influence of drugs, implanted into the hypothalamus, on the water consumption of rats. | 1968 Jan |
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Atrial dissociation due to digitalis toxicity. | 1968 Jun |
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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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[Acute digitalic poisoning]. | 1970 Feb |
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The clinical value of serum digitalis glycoside concentrations in the evaluation of drug toxicity. | 1971 Jul 6 |
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Protection by spironolactone and oxandrolone against chronic digitoxin or indomethacin intoxication. | 1971 Mar |
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Effect of microsomal enzyme inducers on the biliary excretion of cardiac glycosides. | 1974 Nov |
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Transient global amnesia associated with cardiac arrhythmia and digitalis intoxication. | 1975 Sep-Oct |
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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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Effects of atropine on the cardiac arrest induced by propranolol and digitoxin in dogs. | 1982 |
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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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Study of the factors influencing cardiac growth. II. Digitoxin treatment and isoproterenol-induced cardiac hypertrophy in the rat. | 1985 |
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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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Hepatorenal syndrome in cirrhotic patients: terlipressine is a safe and efficient treatment; propranolol and digitalic treatments: precipitating and preventing factors? | 2000 Oct |
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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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Treatment of congestive heart failure--current status of use of digitoxin. | 2001 |
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Adverse drug reaction monitoring--digitoxin overdosage in the elderly. | 2001 Aug |
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Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. | 2001 Jun |
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Bidirectional tachycardia: two cases and a review. | 2002 Aug |
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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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Bidirectional ventricular tachycardia due to digitalis intoxication. | 2005 Feb |
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Iatrogenic sick sinus syndrome. | 2007 May |
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Heart failure drug digitoxin induces calcium uptake into cells by forming transmembrane calcium channels. | 2008 Feb 19 |
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Digitoxin elicits anti-inflammatory and vasoprotective properties in endothelial cells: Therapeutic implications for the treatment of atherosclerosis? | 2009 Oct |
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Antiherpes activity of glucoevatromonoside, a cardenolide isolated from a Brazilian cultivar of Digitalis lanata. | 2011 Oct |
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Digitoxin and a synthetic monosaccharide analog inhibit cell viability in lung cancer cells. | 2012 Jan 1 |
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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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Interaction of digitalis-like compounds with p-glycoprotein. | 2013 Feb |
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A novel cell-based high-throughput screen for inhibitors of HIV-1 gene expression and budding identifies the cardiac glycosides. | 2014 Apr |
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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
Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Oct 22 00:46:29 UTC 2019
by
admin
on
Tue Oct 22 00:46:29 UTC 2019
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Record UNII |
E90NZP2L9U
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Record Status |
Validated (UNII)
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Record Version |
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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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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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PRIMARY | RxNorm | ||
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M4452
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PRIMARY | Merck Index | ||
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1547
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PRIMARY | |||
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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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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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DIGITOXIN
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6782
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SUB07133MIG
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METABOLIC ENZYME -> SUBSTRATE |
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ACTIVE MOIETY |