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
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 |
|||
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 |
---|---|---|
Influence of drugs, implanted into the hypothalamus, on the water consumption of rats. | 1968 Jan |
|
[Acute digitalic poisoning]. | 1970 Feb |
|
[Digitoxin-induced thrombocytopenia]. | 1993 |
|
Digitoxin medication and cancer; case control and internal dose-response studies. | 2001 |
|
Adverse drug reaction monitoring--digitoxin overdosage in the elderly. | 2001 Aug |
|
Bidirectional tachycardia: two cases and a review. | 2002 Aug |
|
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 |
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
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
CFR |
21 CFR 862.3300
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
||
|
WHO-VATC |
QC01AA04
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
||
|
FDA ORPHAN DRUG |
205005
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
||
|
FDA ORPHAN DRUG |
149601
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
||
|
NCI_THESAURUS |
C471
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
||
|
NCI_THESAURUS |
C78322
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
||
|
WHO-ATC |
C01AA04
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
||
|
LIVERTOX |
306
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
||
|
FDA ORPHAN DRUG |
149701
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
215
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
3403
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | RxNorm | ||
|
m4452
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | Merck Index | ||
|
145796
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
881
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
1547
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
DB01396
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
DTXSID0022933
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
DIGITOXIN
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
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. | ||
|
E90NZP2L9U
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
71-63-6
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
CHEMBL254219
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
441207
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
100000092778
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
E90NZP2L9U
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
28544
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
C2634
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
D004074
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
200-760-5
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
7529
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
DIGITOXIN
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
6782
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
1199002
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY | |||
|
SUB07133MIG
Created by
admin on Fri Dec 15 16:39:41 UTC 2023 , Edited by admin on Fri Dec 15 16:39:41 UTC 2023
|
PRIMARY |
ACTIVE MOIETY