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Compound Detail

CHEMBL254219

DIGITOXIN
💊 Approved Drug
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💊 Approved Drug
C[C@H]1O[C@@H](O[C@H]2[C@@H](O)C[C@H](O[C@H]3[C@@H](O)C[C@H](O[C@H]4CC[C@@]5(C)[C@H](CC[C@@H]6[C@@H]5CC[C@]5(C)[C@@H](C7=CC(=O)OC7)CC[C@]65O)C4)O[C@@H]3C)O[C@@H]2C)C[C@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL254219
Name DIGITOXIN
Phase Approved
Structure Type MOL
InChI Key WDJUZGPOPHTGOT-XUDUSOBPSA-N
Therapeutic ✓ Yes

Known Names

Cristapurat CRYSTODIGIN Digimerck Digitalin, crystalline Digitophyllin Digitoxin Digitoxina Digitoxine Digitoxinum Glucodigin Lanatoxin Nativelle digitaline +3 more
32
Targets
53
Activities
4
Assay Types
7
PK Parameters
20
Publications
15
Known Names
2
Indications
1
Mechanisms

Molecular Properties

765.0
MW (Da)
3.25
ALogP
13
HBA
5
HBD
182.8
PSA (Ų)
0.19
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -oxin

Extended Properties

Molecular Formula C41H64O13
MW 764.95
Aromatic Rings 0
Heavy Atoms 54
NP-Likeness 2.20

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Sodium/potassium-transporting ATPase inhibitor INHIBITOR Sodium/potassium-transporting ATPase ✓ ✓

Indications

Cardiovascular Diseases Cystic Fibrosis

ATC Classification

C01AA04
digitoxin
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY

Activity Summary

IC50 44 meas. best 8.49
Ki 6 meas. best 10.0
Kd 2 meas. best 9.22
EC50 1 meas. best 7.63

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Monoclonal antibody (mAb)
CHEMBL613294
 Ki 10.0 9.85 0.1 2
Monoclonal antibody (mAb)
CHEMBL613294
 Kd 9.22 9.22 0.6 1
TK-10
CHEMBL614056
 IC50 8.49 8.49 3.2 1
K562
CHEMBL385
 IC50 8.19 8.19 6.4 1
Sodium/potassium-transporting ATPase
CHEMBL2095186
 IC50 8.1 8.1 8.0 1
Sodium/potassium-transporting ATPase subunit alpha-1
CHEMBL4838
 IC50 8.1 8.1 8.0 1
MCF7
CHEMBL387
 IC50 7.99 7.35 10.2 3
Unchecked
CHEMBL612545
 IC50 7.96 6.9 11.0 8
Human betaherpesvirus 5
CHEMBL371
 EC50 7.63 7.63 23.3 1
Sodium/potassium-transporting ATPase subunit alpha-2/beta-3
CHEMBL6066562
 Ki 7.54 7.54 28.8 1
Sodium/potassium-transporting ATPase subunit alpha-2/beta-1
CHEMBL6066560
 Ki 7.53 7.53 29.5 1
UACC-62
CHEMBL614610
 IC50 7.47 7.47 33.5 1
Sodium/potassium-transporting ATPase subunit alpha-2/beta-2
CHEMBL6066561
 Ki 7.39 7.39 40.7 1
MDA-MB-435
CHEMBL614697
 IC50 7.37 7.365 43.0 2
HT-29
CHEMBL384
 IC50 7.17 6.5767 67.6 3
OVCAR-8
CHEMBL612555
 IC50 7.15 7.15 71.5 1
Sodium/potassium-transporting ATPase subunit alpha-1/beta-1
CHEMBL6066559
 Ki 7.05 7.05 89.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.0 6.5833 100.0 3
OVCAR-3
CHEMBL614213
 IC50 6.93 6.925 117.1 2
Solute carrier organic anion transporter family member 4C1
CHEMBL2073690
 IC50 6.92 6.92 120.0 1
OVCAR-5
CHEMBL614214
 IC50 6.49 6.49 321.0 1
NCI-H460
CHEMBL396
 IC50 6.45 6.405 357.0 2
OVCAR-4
CHEMBL614051
 IC50 6.37 6.37 425.6 1
SK-OV-3
CHEMBL614925
 IC50 6.36 6.36 440.0 1
SF-268
CHEMBL613977
 IC50 6.36 6.36 440.0 1
NCI/ADR-RES
CHEMBL613829
 IC50 6.36 6.36 440.0 1
DU-145
CHEMBL613508
 IC50 6.36 6.36 440.0 1
A549
CHEMBL392
 IC50 6.36 6.36 440.0 1
HCT-116
CHEMBL394
 IC50 6.36 6.245 440.0 2
MDA-MB-231
CHEMBL400
 IC50 6.32 6.32 480.0 2
Signal transducer and activator of transcription 3
CHEMBL4026
 IC50 6.16 6.16 700.0 1
KURAMOCHI
CHEMBL2366119
 IC50 5.23 5.23 5911.0 1
Unchecked
CHEMBL612545
 Kd 4.55 4.55 28000.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.51 4.51 31000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.043 mL.min-1.kg-1 Homo sapiens
F 88.5 % Homo sapiens
Fu 0.066 - Homo sapiens
MRT 170.0 hr Homo sapiens
T1/2 0.245 hr -
T1/2 0.7183 hr -
T1/2 180.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Monoclonal antibody (mAb) Ki = 0.1 nM 10.0 Binding affinity against Monoclonal antibody mAB-1B3 using [3H]digoxin as radiol... 12109909
Monoclonal antibody (mAb) Ki = 0.2 nM 9.7 Binding affinity against Monoclonal antibody mAB-1B3 using [3H]digitoxin as radi... 12109909
Monoclonal antibody (mAb) Kd = 0.6 nM 9.22 Kinetic parameter against Monoclonal antibody mAB-1B3 12109909
TK-10 IC50 = 3.2 nM 8.49 Cytotoxicity against human TK10 cells after 48 hrs by SRB assay 16309315
K562 IC50 = 6.4 nM 8.19 Cytotoxicity against human K562 cells by XTT assay 16309315
Sodium/potassium-transporting ATPase IC50 = 8.0 nM 8.1 Inhibition of [3H]- ouabain binding to digitalis receptor 8421289
Sodium/potassium-transporting ATPase subunit alpha-1 IC50 = 8.0 nM 8.1 Inhibition of [3H]ouabain binding to Digitalis receptor in dog heart microsomes 9154966
MCF7 IC50 = 10.2 nM 7.99 Cytotoxicity against human MCF7 cells after 48 hrs by SRB assay 16309315
Unchecked IC50 = 11.0 nM 7.96 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
MCF7 IC50 = 20.0 nM 7.7 Antiproliferative activity against human MCF7 cells assessed as cell viability t... 21421322
Human betaherpesvirus 5 EC50 = 23.3 nM 7.63 Antiviral activity against Human cytomegalovirus Towne infected in HFF assessed ... 24900847
Sodium/potassium-transporting ATPase subunit alpha-2/beta-3 Ki = 28.8 nM 7.54 Selective Inhibition Assays of Isolated Na,K-ATPase: To screen for isoform selec... -
Sodium/potassium-transporting ATPase subunit alpha-2/beta-1 Ki = 29.5 nM 7.53 Selective Inhibition Assays of Isolated Na,K-ATPase: To screen for isoform selec... -
UACC-62 IC50 = 33.5 nM 7.47 Cytotoxicity against human UACC62 cells after 48 hrs by SRB assay 16309315
Sodium/potassium-transporting ATPase subunit alpha-2/beta-2 Ki = 40.7 nM 7.39 Selective Inhibition Assays of Isolated Na,K-ATPase: To screen for isoform selec... -
MDA-MB-435 IC50 = 43.0 nM 7.37 Cytotoxicity against human MDA-MB-435 cells after 72 hrs by CellTiter 96 Aqueous... 32096998
MDA-MB-435 IC50 = 43.3 nM 7.36 Antiproliferative activity against human MDA-MB-435 cells after 72 hrs by CellTi... 28234008
Unchecked IC50 = 48.4 nM 7.32 Antiproliferative activity against human IOSE-80 cells after 72 hrs by CellTiter... 28234008
HT-29 IC50 = 68.0 nM 7.17 Cytotoxicity against human HT-29 cells after 72 hrs by CellTiter 96 Aqueous One ... 32096998
HT-29 IC50 = 67.6 nM 7.17 Antiproliferative activity against human HT-29 cells after 72 hrs by CellTiter 9... 28234008

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 526
28234008 10.1021/acs.jnatprod.6b01150 Unchecked 15
12109909 10.1021/jm0102811 Monoclonal antibody (mAb) 8
28234008 10.1021/acs.jnatprod.6b01150 OVCAR-3 6
24900847 10.1021/ml400529q HFF 6
24900847 10.1021/ml400529q Human betaherpesvirus 5 5
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
19894733 10.1021/np900210m HT-29 4
19894733 10.1021/np900210m NON-PROTEIN TARGET 4
16309315 10.1021/np050226l TK-10 4
20014752 10.1021/tx900326k Hepatotoxicity 3
19894733 10.1021/np900210m HCT-116 3
16309315 10.1021/np050226l DNA topoisomerase 2-beta 3
16309315 10.1021/np050226l DNA topoisomerase 2-alpha 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
7143360 10.1021/jm00352a025 ADMET 2
141522 10.1021/jm00216a022 Unchecked 2
21643465 10.1021/ml100219d NCI-H460 2
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] A 2

Data from ChEMBL 36 via Core Engine