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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H66O14
Molecular Weight 806.9757
Optical Activity UNSPECIFIED
Defined Stereocenters 20 / 20
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETYLDIGITOXIN

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](OC(C)=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=HPMZBILYSWLILX-UMDUKNJSSA-N
InChI=1S/C43H66O14/c1-21-38(48)33(54-24(4)44)19-37(51-21)57-40-23(3)53-36(18-32(40)46)56-39-22(2)52-35(17-31(39)45)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(47)50-20-25/h15,21-23,26-33,35-40,45-46,48-49H,7-14,16-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29+,30-,31+,32+,33+,35+,36+,37+,38-,39-,40-,41+,42-,43+/m1/s1

HIDE SMILES / InChI

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CRYSTODIGIN
Diagnostic
CRYSTODIGIN

Cmax

ValueDoseCo-administeredAnalytePopulation
1.76 ng/mL
0.25 mg 1 times / day steady-state, oral
DIGITOXIN plasma
Homo sapiens
1.32 ng/mL
0.25 mg 1 times / day steady-state, oral
DIGITOXIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
13.3 ng × h/mL
0.25 mg 1 times / day steady-state, oral
DIGITOXIN plasma
Homo sapiens
12.5 ng × h/mL
0.25 mg 1 times / day steady-state, oral
DIGITOXIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
9.5 day
0.5 mg single, intravenous
DIGITOXIN unknown
Homo sapiens
7.4 day
0.5 mg single, oral
DIGITOXIN unknown
Homo sapiens
9.7 day
0.5 mg single, oral
DIGITOXIN unknown
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
Unknown