Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C41H64O14 |
Molecular Weight | 780.9385 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 21 / 21 |
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])C[C@@H](O)[C@]7(C)[C@H](CC[C@]67O)C8=CC(=O)OC8)C4
InChI
InChIKey=LTMHDMANZUZIPE-PUGKRICDSA-N
InChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25-,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1
Molecular Formula | C41H64O14 |
Molecular Weight | 780.9385 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 21 / 21 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB00390Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/digoxin.html
Sources: http://www.drugbank.ca/drugs/DB00390
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/digoxin.html
Digoxin, a cardiac glycoside similar to digitoxin, is used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation. Digoxin inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium. The sodium calcium exchanger (NCX) in turn tries to extrude the sodium and in so doing, pumps in more calcium. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Digoxin also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL613820 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26176875 |
0.1 µM [IC50] | ||
Target ID: P05370 Gene ID: 24377.0 Gene Symbol: G6pdx Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26820767 |
0.09 mM [IC50] | ||
Target ID: P85968 Gene ID: 1.00360176E8 Gene Symbol: Pgd Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26820767 |
0.14 mM [IC50] | ||
Target ID: CHEMBL3286088 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26820767 |
0.22 mM [IC50] | ||
Target ID: CHEMBL2095186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12904068 |
0.4 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LANOXIN Approved UseLANOXIN is a cardiac glycoside indicated for:
Treatment of mild to moderate heart failure in adults.
Increasing myocardial contractility in pediatric patients with heart failure.
Control of resting ventricular rate in adults with chronic atrial fibrillation. Launch Date1953 |
|||
Primary | LANOXIN Approved UseLANOXIN is a cardiac glycoside indicated for:
Treatment of mild to moderate heart failure in adults.
Increasing myocardial contractility in pediatric patients with heart failure.
Control of resting ventricular rate in adults with chronic atrial fibrillation. Launch Date1953 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.32 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18823299 |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIGOXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.5 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18823299 |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIGOXIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42 h |
unknown, intravenous |
DIGOXIN unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
75% |
unknown, intravenous |
DIGOXIN unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
22.5 mg single, oral Overdose Dose: 22.5 mg Route: oral Route: single Dose: 22.5 mg Sources: Page: p.901, 902 |
healthy, 2 n = 1 Health Status: healthy Age Group: 2 Sex: F Population Size: 1 Sources: Page: p.901, 902 |
Disc. AE: Vomiting, Lethargy... AEs leading to discontinuation/dose reduction: Vomiting Sources: Page: p.901, 902Lethargy Tachycardia |
25 mg single, oral Overdose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: Page: p.393 |
healthy, 26 n = 1 Health Status: healthy Age Group: 26 Sex: M Population Size: 1 Sources: Page: p.393 |
Disc. AE: Blurred vision, Sinus bradycardia... AEs leading to discontinuation/dose reduction: Blurred vision Sources: Page: p.393Sinus bradycardia Electrocardiogram ST segment depression Heart block Ventricular tachycardia Ventricular fibrillation |
18 mg single, oral Overdose Dose: 18 mg Route: oral Route: single Dose: 18 mg Sources: Page: p.2100 |
healthy, 41 n = 1 Health Status: healthy Age Group: 41 Sex: F Population Size: 1 Sources: Page: p.2100 |
Disc. AE: Hyperkalemia, Nausea... AEs leading to discontinuation/dose reduction: Hyperkalemia Sources: Page: p.2100Nausea Vomiting Lethargy Atrioventricular block |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Lethargy | Disc. AE | 22.5 mg single, oral Overdose Dose: 22.5 mg Route: oral Route: single Dose: 22.5 mg Sources: Page: p.901, 902 |
healthy, 2 n = 1 Health Status: healthy Age Group: 2 Sex: F Population Size: 1 Sources: Page: p.901, 902 |
Tachycardia | Disc. AE | 22.5 mg single, oral Overdose Dose: 22.5 mg Route: oral Route: single Dose: 22.5 mg Sources: Page: p.901, 902 |
healthy, 2 n = 1 Health Status: healthy Age Group: 2 Sex: F Population Size: 1 Sources: Page: p.901, 902 |
Vomiting | Disc. AE | 22.5 mg single, oral Overdose Dose: 22.5 mg Route: oral Route: single Dose: 22.5 mg Sources: Page: p.901, 902 |
healthy, 2 n = 1 Health Status: healthy Age Group: 2 Sex: F Population Size: 1 Sources: Page: p.901, 902 |
Blurred vision | Disc. AE | 25 mg single, oral Overdose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: Page: p.393 |
healthy, 26 n = 1 Health Status: healthy Age Group: 26 Sex: M Population Size: 1 Sources: Page: p.393 |
Electrocardiogram ST segment depression | Disc. AE | 25 mg single, oral Overdose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: Page: p.393 |
healthy, 26 n = 1 Health Status: healthy Age Group: 26 Sex: M Population Size: 1 Sources: Page: p.393 |
Heart block | Disc. AE | 25 mg single, oral Overdose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: Page: p.393 |
healthy, 26 n = 1 Health Status: healthy Age Group: 26 Sex: M Population Size: 1 Sources: Page: p.393 |
Sinus bradycardia | Disc. AE | 25 mg single, oral Overdose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: Page: p.393 |
healthy, 26 n = 1 Health Status: healthy Age Group: 26 Sex: M Population Size: 1 Sources: Page: p.393 |
Ventricular fibrillation | Disc. AE | 25 mg single, oral Overdose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: Page: p.393 |
healthy, 26 n = 1 Health Status: healthy Age Group: 26 Sex: M Population Size: 1 Sources: Page: p.393 |
Ventricular tachycardia | Disc. AE | 25 mg single, oral Overdose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: Page: p.393 |
healthy, 26 n = 1 Health Status: healthy Age Group: 26 Sex: M Population Size: 1 Sources: Page: p.393 |
Atrioventricular block | Disc. AE | 18 mg single, oral Overdose Dose: 18 mg Route: oral Route: single Dose: 18 mg Sources: Page: p.2100 |
healthy, 41 n = 1 Health Status: healthy Age Group: 41 Sex: F Population Size: 1 Sources: Page: p.2100 |
Hyperkalemia | Disc. AE | 18 mg single, oral Overdose Dose: 18 mg Route: oral Route: single Dose: 18 mg Sources: Page: p.2100 |
healthy, 41 n = 1 Health Status: healthy Age Group: 41 Sex: F Population Size: 1 Sources: Page: p.2100 |
Lethargy | Disc. AE | 18 mg single, oral Overdose Dose: 18 mg Route: oral Route: single Dose: 18 mg Sources: Page: p.2100 |
healthy, 41 n = 1 Health Status: healthy Age Group: 41 Sex: F Population Size: 1 Sources: Page: p.2100 |
Nausea | Disc. AE | 18 mg single, oral Overdose Dose: 18 mg Route: oral Route: single Dose: 18 mg Sources: Page: p.2100 |
healthy, 41 n = 1 Health Status: healthy Age Group: 41 Sex: F Population Size: 1 Sources: Page: p.2100 |
Vomiting | Disc. AE | 18 mg single, oral Overdose Dose: 18 mg Route: oral Route: single Dose: 18 mg Sources: Page: p.2100 |
healthy, 41 n = 1 Health Status: healthy Age Group: 41 Sex: F Population Size: 1 Sources: Page: p.2100 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 1 uM] | ||||
yes [IC50 7.9 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 23.0 |
no | |||
yes | ||||
Page: 10.0 |
yes | yes (co-administration study) Comment: Many drug drug interactions. See https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020405s015lbl.pdf#page=11 Page: 10.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/17095614/ Page: 3.0 |
PubMed
Title | Date | PubMed |
---|---|---|
[Digitalis intoxication: specifity and significance of cardiac and extracardiac symptoms. part I: Patients with digitalis-induced arrhythmias (author's transl)]. | 1977 Mar |
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Verapamil and digoxin: interactions in the rat. | 1983 Dec |
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Drug-induced gynecomastia. | 1993 Jan-Feb |
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26-10 Fab-digoxin complex: affinity and specificity due to surface complementarity. | 1993 Nov 1 |
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Structure and specificity of the anti-digoxin antibody 40-50. | 1995 Apr 28 |
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Isolation and characterization of human monoclonal antibodies to digoxin. | 1999 Aug 15 |
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Structure-based design and synthesis of novel potent Na+,K+ -ATPase inhibitors derived from a 5alpha,14alpha-androstane scaffold as positive inotropic compounds. | 2003 Aug 14 |
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Fab antibody fragments: some applications in clinical toxicology. | 2004 |
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Effect of milk thistle (Silybum marianum) and black cohosh (Cimicifuga racemosa) supplementation on digoxin pharmacokinetics in humans. | 2006 Jan |
|
In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/digoxin.html
Tablets:
Initial: 500 to 750 mcg usually produces a detectable effect in 0.5 to 2 hours with a maximal effect in 2 to 6 hours. Additional doses of 125 to 375 mcg may be given at 6 to 8 hour intervals until clinical evidence of an adequate effect is noted. The usual amount of digoxin tablets that a 70 kg patient requires to achieve 8 to 12 mcg/kg peak body stores is 750 to 1250 mcg.
Injection:
Initial: 400 to 600 mcg of digoxin intravenously usually produces a detectable effect in 5 to 30 minutes with a maximal effect in 1 to 4 hours. Additional doses of 100 to 300 mcg may be given cautiously at 6 to 8 hour intervals until clinical evidence of an adequate effect is noted. The usual amount of digoxin injection that a 70 kg patient requires to achieve 8 to 12 mcg/kg peak body stores is 600 to 1000 mcg.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24726699
Digoxin was effective against B. mandrillaris at 250uM
Substance Class |
Chemical
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Record UNII |
73K4184T59
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Validated (UNII)
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175568
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WHO-VATC |
QC01AA05
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WHO-ESSENTIAL MEDICINES LIST |
12.2
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NCI_THESAURUS |
C823
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LIVERTOX |
307
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NDF-RT |
N0000008157
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NDF-RT |
N0000008157
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CFR |
21 CFR 862.3320
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WHO-ESSENTIAL MEDICINES LIST |
12.4
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NCI_THESAURUS |
C78322
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WHO-ATC |
C01AA05
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244-068-1
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214
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m4456
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DTXSID5022934
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20830-75-5
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100000091378
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SUB07135MIG
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3407
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145795
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CHEMBL1751
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389
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DIGOXIN
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95100
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Digoxin
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882
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DB00390
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C28990
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4726
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4551
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73K4184T59
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D004077
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1200000
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73K4184T59
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2724385
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DIGOXIN
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PRIMARY | Description: Colourless crystals or a white or almost white, crystalline powder; odourless.Solubility: Practically insoluble in water and ether R; freely soluble in pyridine R; slightly soluble in ethanol (~750 g/l) TS.Category: Cardiotonic.Storage: Digoxin should be kept in a well-closed container, protected from light.Additional information: CAUTION: Digoxin is extremely poisonous and should be handled with care.Requirements : Definition. Digoxin contains not less than 95.0% and not more than 103.0% of C41H64O14, calculated with reference to the driedsubstance. |
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE |
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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INHIBITOR -> TARGET |
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TRANSPORTER -> SUBSTRATE |
in vitro ER in the MDCK-MDR1 cell line from National Institutes of Health
EFFLUX RATIO
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PARENT -> METABOLITE |
Metabolite to parent drug ratio in non-uraemic human plasma.
The N-desmethyl metabolite has similar efficacy as the parent drug in the treatment of patients with petit mal epilepsy.
METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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