Compound Detail

CHEMBL1751

DIGOXIN

💊 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]5C[C@@H](O)[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	CHEMBL1751
Name	DIGOXIN
Phase	Approved
Structure Type	MOL
InChI Key	LTMHDMANZUZIPE-PUGKRICDSA-N
Therapeutic	✓ Yes

Known Names

Digamex Digoxin Digoxin pediatric Digoxina Digoxine Digoxinum Dynamos Fargoxin Lanocardin Lanoxicaps Lanoxin Lanoxin pediatric +9 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

781.0

MW (Da)

2.22

ALogP

HBA

HBD

203.1

PSA (Å²)

0.16

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1975
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Natural Product

USAN Stem

-oxin

Extended Properties

Molecular Formula	C41H64O14
MW	780.95
Aromatic Rings	0
Heavy Atoms	55
NP-Likeness	2.30

Mechanism of Action

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

Indications

Atrial Fibrillation Cardiovascular Diseases Heart Failure Heart Failure Arrhythmias, Cardiac Tachycardia, Supraventricular Arthritis, Rheumatoid Breast Neoplasms Breast Neoplasms Carcinoma, Non-Small-Cell Lung Keratosis, Actinic Non-alcoholic Fatty Liver Disease Pancreatic Neoplasms Pancreatic Neoplasms Prostatic Neoplasms, Castration-Resistant Sarcoma, Kaposi Angioedemas, Hereditary Cytomegalovirus Infections Depressive Disorder Depressive Disorder, Major

ATC Classification

C01AA05

digoxin

Level 1: CARDIOVASCULAR SYSTEM

Level 2: CARDIAC THERAPY

Activity Summary

IC50 74 meas. best 8.26

Ki 8 meas. best 9.1

EC50 7 meas. best 7.52

Kd 2 meas. best 8.51

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Monoclonal antibody (mAb) CHEMBL613294	Ki	9.1	9.01	0.8	2
Monoclonal antibody (mAb) CHEMBL613294	Kd	8.51	8.51	3.1	1
N+/K+ ATPase alpha-4/beta-1 CHEMBL4106165	IC50	8.26	8.26	5.5	1
D283 Med CHEMBL614476	IC50	8.0	8.0	10.0	1
TK-10 CHEMBL614056	IC50	7.84	7.84	14.6	1
MCF7 CHEMBL387	IC50	7.62	6.44	24.1	3
K562 CHEMBL385	IC50	7.55	7.55	28.2	1
UACC-62 CHEMBL614610	IC50	7.53	7.53	29.5	1
Unchecked CHEMBL612545	EC50	7.52	7.4633	30.0	3
Solute carrier organic anion transporter family member 1A4 CHEMBL1781860	Ki	7.43	6.835	37.0	2
ADMET CHEMBL612558	IC50	7.4	5.86	40.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.4	6.848	40.0	5
Sodium/potassium-transporting ATPase subunit alpha-2/beta-3 CHEMBL6066562	Ki	7.37	7.37	42.8	1
A549 CHEMBL392	IC50	7.3	7.3	50.0	1
BT-549 CHEMBL614072	IC50	7.29	7.29	51.0	1
Sodium/potassium-transporting ATPase subunit alpha-2/beta-2 CHEMBL6066561	Ki	7.24	7.24	58.0	1
Sodium/potassium-transporting ATPase subunit alpha-2/beta-1 CHEMBL6066560	Ki	7.23	7.23	58.7	1
Hs-578T CHEMBL614645	IC50	7.16	5.93	69.0	3
PC-3 CHEMBL390	IC50	7.12	7.12	75.0	1
Kasumi 1 CHEMBL613988	IC50	7.03	7.03	93.0	1
OVCAR-3 CHEMBL614213	IC50	7.0	7.0	100.0	1
Unchecked CHEMBL612545	IC50	6.97	6.0938	106.0	8
MV4-11 CHEMBL613835	IC50	6.96	6.96	111.0	1
Nuclear receptor ROR-gamma CHEMBL1741186	Kd	6.96	6.96	109.0	1
CAL-51 CHEMBL1075411	IC50	6.89	6.89	130.0	1
Sodium/potassium-transporting ATPase CHEMBL2095186	IC50	6.8	6.59	160.0	3
MDA-MB-435 CHEMBL614697	IC50	6.77	6.77	170.0	1
SARS-CoV-2 CHEMBL4303835	IC50	6.72	6.72	190.0	1
Sodium/potassium-transporting ATPase subunit alpha-2/alpha-3 CHEMBL3885640	IC50	6.66	6.66	220.0	1
MDA-MB-453 CHEMBL614334	IC50	6.64	6.64	230.0	1
MDA-MB-468 CHEMBL614335	IC50	6.64	6.64	230.0	1
Vaccinia virus CHEMBL613493	EC50	6.6	6.6	250.0	1
SK-MEL-28 CHEMBL614919	IC50	6.58	6.58	266.0	1
Sodium/potassium-transporting ATPase subunit alpha-1/beta-1 CHEMBL6066559	Ki	6.57	6.57	268.0	1
HCT-116 CHEMBL394	IC50	6.57	6.57	270.0	1
SUM185PE CHEMBL4632331	IC50	6.55	6.55	280.0	1
HCC1806 CHEMBL1075457	IC50	6.55	6.55	280.0	1
HT-29 CHEMBL384	IC50	6.55	6.2733	280.0	3
Sodium/potassium-transporting ATPase subunit alpha-1 CHEMBL1807	IC50	6.54	6.54	290.0	1
MDA-MB-231 CHEMBL400	IC50	6.51	6.415	310.0	2
Cavia porcellus CHEMBL369	EC50	6.42	6.4133	380.0	3
NCI-H1299 CHEMBL612255	IC50	6.34	6.34	460.0	2
Sodium/potassium-transporting ATPase subunit alpha-1 CHEMBL4838	IC50	6.3	6.3	500.0	2
HCC1937 CHEMBL1075458	IC50	6.26	6.26	550.0	1
HCC70 CHEMBL1075461	IC50	6.19	6.19	640.0	1
T47D CHEMBL614361	IC50	6.18	6.18	660.0	1
SK-BR-3 CHEMBL613834	IC50	5.97	5.97	1080.0	1
Nuclear receptor ROR-gamma CHEMBL1741186	IC50	5.75	5.2522	1800.0	9
Signal transducer and activator of transcription 3 CHEMBL4026	IC50	5.73	5.73	1862.0	1
Nuclear receptor ROR-gamma CHEMBL1293231	IC50	5.7	5.7	2000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	1.7	mL.min-1.kg-1	Homo sapiens
CL	1.7	mL.min-1.kg-1	Homo sapiens
CL	-	mL.min-1.kg-1	Homo sapiens
CL	1.7	mL.min-1.kg-1	Homo sapiens
CL	2.68	mL.min-1.kg-1	Canis lupus familiaris
CL	1.313	mL.min-1.kg-1	Canis lupus familiaris
CL	4.329	mL.min-1.kg-1	Rattus norvegicus
CL	3.03	mL.min-1.kg-1	Rattus norvegicus
CL	2.279	mL.min-1.kg-1	Homo sapiens
CL	1.595	mL.min-1.kg-1	Homo sapiens
CL	0.0036	mL.min-1.g-1	Homo sapiens
CL	0.00188	mL.min-1.g-1	Homo sapiens
CL	0.00453	mL.min-1.g-1	Homo sapiens
CL	0.00406	mL.min-1.g-1	Homo sapiens
CL	0.00188	mL.min-1.g-1	Homo sapiens
F	95.0	%	Homo sapiens
F	70.0	%	Homo sapiens
Fu	0.7	-	Homo sapiens
Fu	0.7	-	Homo sapiens
Fu	0.583	-	Rattus norvegicus
Fu	0.264	-	Rattus norvegicus
Fu	0.2	-	Homo sapiens
MRT	40.0	hr	Homo sapiens
T1/2	0.2033	hr	-
T1/2	0.3133	hr	-
T1/2	38.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Monoclonal antibody (mAb)	Ki	=	0.8	nM	9.1	Binding affinity against Monoclonal antibody mAB-1B3 using [3H]digitoxin as radi...	12109909
Monoclonal antibody (mAb)	Ki	=	1.2	nM	8.92	Binding affinity against Monoclonal antibody mAB-1B3 using [3H]digoxin as radiol...	12109909
Monoclonal antibody (mAb)	Kd	=	3.1	nM	8.51	Kinetic parameter against Monoclonal antibody mAB-1B3	12109909
N+/K+ ATPase alpha-4/beta-1	IC50	=	5.5	nM	8.26	Inhibition of recombinant rat Na+/K+-ATPase alpha4/beta1 expressed in baculoviru...	29291372
D283 Med	IC50	=	10.0	nM	8.0	Anticancer activity against human D283 Med cells assessed as reduction in cell v...	33636537
TK-10	IC50	=	14.6	nM	7.84	Cytotoxicity against human TK10 cells after 48 hrs by SRB assay	16309315
MCF7	IC50	=	24.1	nM	7.62	Cytotoxicity against human MCF7 cells after 48 hrs by SRB assay	16309315
K562	IC50	=	28.2	nM	7.55	Cytotoxicity against human K562 cells by XTT assay	16309315
UACC-62	IC50	=	29.5	nM	7.53	Cytotoxicity against human UACC62 cells after 48 hrs by SRB assay	16309315
Unchecked	EC50	=	30.0	nM	7.52	PUBCHEM_BIOASSAY: Luminescence Cell-Based HTS Dose Confirmation to Identify Inhi...	-
Unchecked	EC50	=	34.0	nM	7.47	PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response to Identify Inhibitors o...	-
Solute carrier organic anion transporter family member 1A4	Ki	=	37.0	nM	7.43	TP_TRANSPORTER: inhibition of E217betaG uptake in Oatp2-expressing LLC-PK1 cells	11408557
ADMET	IC50	=	40.0	nM	7.4	Cytotoxicity against human Hs578Bst cells after 72 hrs by CellTiter-Glo assay	22316168
NON-PROTEIN TARGET	IC50	=	40.0	nM	7.4	Cytotoxicity against human Hs683 cells after 3 days by MTT assay	23706005
Unchecked	EC50	=	40.0	nM	7.4	PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response to Identify Inhibitors o...	-
Sodium/potassium-transporting ATPase subunit alpha-2/beta-3	Ki	=	42.8	nM	7.37	Selective Inhibition Assays of Isolated Na,K-ATPase: To screen for isoform selec...	-
A549	IC50	=	50.0	nM	7.3	Cytotoxicity against human A549 cells after 3 days by MTT assay	23706005
BT-549	IC50	=	51.0	nM	7.29	Cytotoxicity against human BT-549 cells assessed as reduction in cell viability ...	32649211
Sodium/potassium-transporting ATPase subunit alpha-2/beta-2	Ki	=	58.0	nM	7.24	Selective Inhibition Assays of Isolated Na,K-ATPase: To screen for isoform selec...	-
Sodium/potassium-transporting ATPase subunit alpha-2/beta-1	Ki	=	58.7	nM	7.23	Selective Inhibition Assays of Isolated Na,K-ATPase: To screen for isoform selec...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	430
20926619	10.1124/dmd.110.034298	Hepatocyte	37
21051535	10.1124/dmd.110.034629	ADMET	15
21447733	10.1124/dmd.111.038075	ADMET	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
12699389	10.1021/jm021012t	ATP-dependent translocase ABCB1	13
24332858	10.1016/j.bmc.2013.11.037	MDCK	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
23382458	10.1124/dmd.112.050260	ADMET	11
32031812	10.1021/acs.jnatprod.9b00857	Danio rerio	9
33854703	10.1021/acsmedchemlett.1c00029	Nuclear receptor ROR-gamma	9
20926619	10.1124/dmd.110.034298	Solute carrier organic anion transporter family member 1B3	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
20070106	10.1021/jm901371v	Homo sapiens	8
12109909	10.1021/jm0102811	Monoclonal antibody (mAb)	8
37216676	10.1021/acs.jnatprod.3c00094	Unchecked	7
23073734	10.1124/dmd.112.048470	ADMET	6
32031803	10.1021/acs.jmedchem.9b02149	ADMET	6
22584255	10.1124/dmd.111.044008	ADMET	5
9108099	10.1073/pnas.94.8.4028	P-glycoprotein 1 and 3 (MDR1a/MDR1b)	5

Data from ChEMBL 36 via Core Engine