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
[H][C@@]1(C[C@H](O)[C@H](O[C@@]2([H])C[C@H](O)[C@H](O[C@@]3([H])C[C@H](O)[C@H](O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1)O[C@H]4CC[C@@]5(C)[C@]([H])(CC[C@]6([H])[C@]5([H])CC[C@]7(C)[C@H](CC[C@]67O)C8=CC(=O)OC8)C4
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 | No |
Defined Stereocenters | 20 / 20 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.medscape.com/viewarticle/842364
Curator's Comment: description was created based on several sources, including
http://www.medscape.com/viewarticle/842364
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19751721 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CRYSTODIGIN Approved UseIn adults, digoxin is indicated for the treatment of mild to moderate heart failure and for the control of resting ventricular rate in patients with chronic atrial fibrillation. (1). In pediatric patients with heart failure, digoxin increases myocardial contractility |
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Diagnostic | CRYSTODIGIN Approved UseIn adults, digoxin is indicated for the treatment of mild to moderate heart failure and for the control of resting ventricular rate in patients with chronic atrial fibrillation. (1). In pediatric patients with heart failure, digoxin increases myocardial contractility |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.76 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18823299/ |
0.25 mg 1 times / day steady-state, oral dose: 0.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ETORICOXIB |
DIGITOXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1.32 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18823299/ |
0.25 mg 1 times / day steady-state, oral dose: 0.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DIGITOXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18823299/ |
0.25 mg 1 times / day steady-state, oral dose: 0.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ETORICOXIB |
DIGITOXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
12.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18823299/ |
0.25 mg 1 times / day steady-state, oral dose: 0.25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
DIGITOXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.5 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/914188/ |
0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
DIGITOXIN unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.4 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/914188/ |
0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIGITOXIN unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
9.7 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/914188/ |
0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIGITOXIN unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.1 mg 1 times / day multiple, oral Studied dose Dose: 0.1 mg, 1 times / day Route: oral Route: multiple Dose: 0.1 mg, 1 times / day Sources: |
healthy, 23 to 29 years n = 10 Health Status: healthy Age Group: 23 to 29 years Sex: M Population Size: 10 Sources: |
Other AEs: Color blindness acquired... |
0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Other AEs: Fatigue, Visual disorders NEC... Other AEs: Fatigue (53.1%) Sources: Visual disorders NEC (53.1%) Muscular weakness (45.8%) Nausea (45.2%) Anorexia (44.7%) Psychic disorder NOS (36.3%) Abdominal pain (36.3%) Dizziness (33%) Bad dreams (30.2%) Headache (25.1%) Diarrhoea (22.9%) Vomiting (22.3%) Pain retrosternal (5%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Color blindness acquired | 0.1 mg 1 times / day multiple, oral Studied dose Dose: 0.1 mg, 1 times / day Route: oral Route: multiple Dose: 0.1 mg, 1 times / day Sources: |
healthy, 23 to 29 years n = 10 Health Status: healthy Age Group: 23 to 29 years Sex: M Population Size: 10 Sources: |
|
Vomiting | 22.3% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Diarrhoea | 22.9% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Headache | 25.1% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Bad dreams | 30.2% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Dizziness | 33% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Abdominal pain | 36.3% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Psychic disorder NOS | 36.3% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Anorexia | 44.7% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Nausea | 45.2% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Muscular weakness | 45.8% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Pain retrosternal | 5% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Fatigue | 53.1% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Visual disorders NEC | 53.1% | 0.2 mg 2 times / day multiple, oral (mean) Studied dose Dose: 0.2 mg, 2 times / day Route: oral Route: multiple Dose: 0.2 mg, 2 times / day Co-administed with:: digoxin(0.05 mg; 2 tablets per day) Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: heart failure Age Group: adult Sex: M+F Population Size: 179 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 14.2 uM] | ||||
yes [IC50 36 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
[Spironolactone protection against experimental cardiopathy due to digitoxin, disodium phosphate and oil]. | 1970 Feb |
|
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 |
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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 |
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Reversal of advanced digitoxin toxicity and modification of pharmacokinetics by specific antibodies and Fab fragments. | 1977 Dec |
|
[Digitoxin poisoning: reversing ventricular fibrillation with Fab fragments of anti-digoxin antibody]. | 1982 Dec 25 |
|
Effect of age, clonidine or propranolol on behavioral toxicity induced with digitoxin in mice. | 1982 Sep |
|
Hepatorenal syndrome in cirrhotic patients: terlipressine is a safe and efficient treatment; propranolol and digitalic treatments: precipitating and preventing factors? | 2000 Oct |
|
Treatment of congestive heart failure--current status of use of digitoxin. | 2001 |
|
Bidirectional tachycardia: two cases and a review. | 2002 Aug |
|
Bidirectional ventricular tachycardia due to digitalis intoxication. | 2005 Feb |
|
Iatrogenic sick sinus syndrome. | 2007 May |
Patents
Sample Use Guides
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23858296
Curator's Comment: digitoxin inhibits interaction of NFAT1 with the proximal c-MYC promoter
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:39:41 GMT 2023
by
admin
on
Fri Dec 15 16:39:41 GMT 2023
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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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FDA ORPHAN DRUG |
149701
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215
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3403
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m4452
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145796
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881
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1547
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DB01396
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DTXSID0022933
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DIGITOXIN
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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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E90NZP2L9U
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71-63-6
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CHEMBL254219
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441207
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100000092778
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E90NZP2L9U
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28544
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C2634
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D004074
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200-760-5
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7529
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DIGITOXIN
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6782
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1199002
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SUB07133MIG
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
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ACTIVE MOIETY |