U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C41H64O14
Molecular Weight 780.94
Optical Activity UNSPECIFIED
Defined Stereocenters 21 / 21
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIGOXIN

SMILES

C[C@]1([H])[C@]([H])([C@]([H])(C[C@@]([H])(O1)O[C@]2([H])[C@@]([H])(C)O[C@]([H])(C[C@]2([H])O)O[C@]3([H])[C@@]([H])(C)O[C@]([H])(C[C@]3([H])O)O[C@@]4([H])CC[C@@]5(C)[C@]([H])(CC[C@]6([H])[C@]5([H])C[C@]([H])([C@]7(C)[C@]([H])(CC[C@]67O)C8=CC(=O)OC8)O)C4)O)O

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

HIDE SMILES / InChI

Molecular Formula C41H64O14
Molecular Weight 780.94
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 21 / 21
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: 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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL613820
0.100000000000000006 µM [IC50]
Target ID: P05370
Gene ID: 24377
Gene Symbol: G6pdx
Target Organism: Rattus norvegicus (Rat)
0.0899999999999999967 mM [IC50]
Target ID: P85968
Gene ID: 100360180
Gene Symbol: Pgd
Target Organism: Rattus norvegicus (Rat)
0.140000000000000013 mM [IC50]
0.220000000000000001 mM [IC50]
0.400000000000000022 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LANOXIN

Approved Use

LANOXIN 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 Date

-505008000000
Primary
LANOXIN

Approved Use

LANOXIN 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 Date

-505008000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.32 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
12.5 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
42 h
unknown, intravenous
DIGOXIN unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
75%
unknown, intravenous
DIGOXIN unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
22.5 mg single, oral
Overdose
Dose: 22.5 mg
Route: oral
Route: single
Dose: 22.5 mg
Sources:
healthy, 2
Health Status: healthy
Age Group: 2
Sex: F
Sources:
Disc. AE: Vomiting, Lethargy...
AEs leading to
discontinuation/dose reduction:
Vomiting
Lethargy
Tachycardia
Sources:
25 mg single, oral
Overdose
Dose: 25 mg
Route: oral
Route: single
Dose: 25 mg
Sources:
healthy, 26
Health Status: healthy
Age Group: 26
Sex: M
Sources:
Disc. AE: Blurred vision, Sinus bradycardia...
AEs leading to
discontinuation/dose reduction:
Blurred vision
Sinus bradycardia
Electrocardiogram ST segment depression
Heart block
Ventricular tachycardia
Ventricular fibrillation
Sources:
18 mg single, oral
Overdose
Dose: 18 mg
Route: oral
Route: single
Dose: 18 mg
Sources:
healthy, 41
Health Status: healthy
Age Group: 41
Sex: F
Sources:
Disc. AE: Hyperkalemia, Nausea...
AEs leading to
discontinuation/dose reduction:
Hyperkalemia
Nausea
Vomiting
Lethargy
Atrioventricular block
Sources:
AEs

AEs

AESignificanceDosePopulation
Lethargy Disc. AE
22.5 mg single, oral
Overdose
Dose: 22.5 mg
Route: oral
Route: single
Dose: 22.5 mg
Sources:
healthy, 2
Health Status: healthy
Age Group: 2
Sex: F
Sources:
Tachycardia Disc. AE
22.5 mg single, oral
Overdose
Dose: 22.5 mg
Route: oral
Route: single
Dose: 22.5 mg
Sources:
healthy, 2
Health Status: healthy
Age Group: 2
Sex: F
Sources:
Vomiting Disc. AE
22.5 mg single, oral
Overdose
Dose: 22.5 mg
Route: oral
Route: single
Dose: 22.5 mg
Sources:
healthy, 2
Health Status: healthy
Age Group: 2
Sex: F
Sources:
Blurred vision Disc. AE
25 mg single, oral
Overdose
Dose: 25 mg
Route: oral
Route: single
Dose: 25 mg
Sources:
healthy, 26
Health Status: healthy
Age Group: 26
Sex: M
Sources:
Electrocardiogram ST segment depression Disc. AE
25 mg single, oral
Overdose
Dose: 25 mg
Route: oral
Route: single
Dose: 25 mg
Sources:
healthy, 26
Health Status: healthy
Age Group: 26
Sex: M
Sources:
Heart block Disc. AE
25 mg single, oral
Overdose
Dose: 25 mg
Route: oral
Route: single
Dose: 25 mg
Sources:
healthy, 26
Health Status: healthy
Age Group: 26
Sex: M
Sources:
Sinus bradycardia Disc. AE
25 mg single, oral
Overdose
Dose: 25 mg
Route: oral
Route: single
Dose: 25 mg
Sources:
healthy, 26
Health Status: healthy
Age Group: 26
Sex: M
Sources:
Ventricular fibrillation Disc. AE
25 mg single, oral
Overdose
Dose: 25 mg
Route: oral
Route: single
Dose: 25 mg
Sources:
healthy, 26
Health Status: healthy
Age Group: 26
Sex: M
Sources:
Ventricular tachycardia Disc. AE
25 mg single, oral
Overdose
Dose: 25 mg
Route: oral
Route: single
Dose: 25 mg
Sources:
healthy, 26
Health Status: healthy
Age Group: 26
Sex: M
Sources:
Atrioventricular block Disc. AE
18 mg single, oral
Overdose
Dose: 18 mg
Route: oral
Route: single
Dose: 18 mg
Sources:
healthy, 41
Health Status: healthy
Age Group: 41
Sex: F
Sources:
Hyperkalemia Disc. AE
18 mg single, oral
Overdose
Dose: 18 mg
Route: oral
Route: single
Dose: 18 mg
Sources:
healthy, 41
Health Status: healthy
Age Group: 41
Sex: F
Sources:
Lethargy Disc. AE
18 mg single, oral
Overdose
Dose: 18 mg
Route: oral
Route: single
Dose: 18 mg
Sources:
healthy, 41
Health Status: healthy
Age Group: 41
Sex: F
Sources:
Nausea Disc. AE
18 mg single, oral
Overdose
Dose: 18 mg
Route: oral
Route: single
Dose: 18 mg
Sources:
healthy, 41
Health Status: healthy
Age Group: 41
Sex: F
Sources:
Vomiting Disc. AE
18 mg single, oral
Overdose
Dose: 18 mg
Route: oral
Route: single
Dose: 18 mg
Sources:
healthy, 41
Health Status: healthy
Age Group: 41
Sex: F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 1 uM]
yes [IC50 7.9 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
yes
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
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
[Digitalis intoxication: specifity and significance of cardiac and extracardiac symptoms. part I: Patients with digitalis-induced arrhythmias (author's transl)].
1977 Mar
Verapamil and digoxin: interactions in the rat.
1983 Dec
Drug-induced gynecomastia.
1993 Jan-Feb
26-10 Fab-digoxin complex: affinity and specificity due to surface complementarity.
1993 Nov 1
Structure and specificity of the anti-digoxin antibody 40-50.
1995 Apr 28
Fab antibody fragments: some applications in clinical toxicology.
2004
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Tablets:
Route of Administration: Other
Digoxin was effective against B. mandrillaris at 250uM
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:05:23 UTC 2021
Edited
by admin
on Fri Jun 25 21:05:23 UTC 2021
Record UNII
73K4184T59
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIGOXIN
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
DYNAMOS
Common Name English
DIGOXIN [IARC]
Common Name English
DIGOXIN [WHO-DD]
Common Name English
STILLACOR-
Common Name English
LANOCARDIN
Common Name English
DIGOXIN [WHO-IP]
Common Name English
DIGOXIN [MI]
Common Name English
TOLOXIN
Common Name English
MAPLUXIN
Common Name English
DIGOXIN [VANDF]
Common Name English
DIGOXIN [EP MONOGRAPH]
Common Name English
DIGOXIN [HSDB]
Common Name English
3.BETA.-((O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-12.BETA.,14-DIHYDROXY-5.BETA.-CARD-20(22)-ENOLIDE
Common Name English
DIGOXINUM [WHO-IP LATIN]
Common Name English
NATIGOXIN
Common Name English
DIGOXIN [INN]
Common Name English
DIGOXIN [USP-RS]
Common Name English
DIGOXIN [MART.]
Common Name English
DIGOXIN [JAN]
Common Name English
DIGOXIN [USP MONOGRAPH]
Common Name English
VANOXIN
Common Name English
CARD-20(22)-ENOLIDE, 3-((O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-12,14-DIHYDROXY-,(3.BETA.,5.BETA.,12.BETA.)-
Common Name English
NSC-95100
Code English
DIGOXIN [ORANGE BOOK]
Common Name English
LANOXIN
Brand Name English
ROUGOXIN
Common Name English
FARGOXIN
Common Name English
Classification Tree Code System Code
NDF-RT N0000175568
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
WHO-VATC QC01AA05
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 12.2
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
NCI_THESAURUS C823
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
LIVERTOX 307
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
NDF-RT N0000008157
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
NDF-RT N0000008157
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
CFR 21 CFR 862.3320
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 12.4
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
NCI_THESAURUS C78322
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
WHO-ATC C01AA05
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
244-068-1
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
HSDB
214
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
MERCK INDEX
M4456
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY Merck Index
EPA CompTox
20830-75-5
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
CAS
20830-75-5
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
EVMPD
SUB07135MIG
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
RXCUI
3407
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL1751
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
INN
389
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
WIKIPEDIA
DIGOXIN
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
LACTMED
Digoxin
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
DRUG CENTRAL
882
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
DRUG BANK
DB00390
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
NCI_THESAURUS
C28990
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
IUPHAR
4726
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
FDA UNII
73K4184T59
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
MESH
D004077
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
PUBCHEM
2724385
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIGOXIN
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
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.
USP_CATALOG
1200000
Created by admin on Fri Jun 25 21:05:23 UTC 2021 , Edited by admin on Fri Jun 25 21:05:23 UTC 2021
PRIMARY USP-RS
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