DIGOXIN

Search structure
Trade Names:
Synonyms:
Status: Approved (1975)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C01AA05
UNII: 73K4184T59

Structure
InChI Key LTMHDMANZUZIPE-PUGKRICDSA-N
Smile 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]6C[C@@H](O)[C@]7(C)[C@@H](C8=CC(=O)OC8)CC[C@]7(O)[C@@H]6CC[C@@H]5C4)O[C@@H]3C)O[C@@H]2C)C[C@H](O)[C@@H]1O
InChI
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C41H64O14
Molecular Weight 780.95
AlogP 2.22
Hydrogen Bond Acceptor 14.0
Hydrogen Bond Donor 6.0
Number of Rotational Bond 7.0
Polar Surface Area 203.06
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 55.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Sodium/potassium-transporting ATPase inhibitor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 160-400 - 268
Enzyme Transferase
- - - - 13.79-18.32
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - 4.01-14.13
Ion channel Other ion channel Phospholemman family
- 160-400 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group F Nuclear hormone receptor subfamily 1 group F member 3
- 1800-85400 109 - -
Transcription factor
- 1800-85400 109 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- 13182.57 - 37-580 36-81.25
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 46.9
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 264100 - - 1
Transporter Primary active transporter P-type ATPase Sodium potassium ATPase
- 160-400 - 268 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Tachycardia, Supraventricular 3 D013617 ClinicalTrials
Arrhythmias, Cardiac 3 D001145 ClinicalTrials
Sarcoma, Kaposi 2 D012514 ClinicalTrials
Arthritis, Rheumatoid 2 D001172 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Non-alcoholic Fatty Liver Disease 2 D065626 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Keratosis, Actinic 2 D055623 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Substance-Related Disorders 1 D019966 ClinicalTrials
Head and Neck Neoplasms 1 D006258 ClinicalTrials
Nausea 1 D009325 ClinicalTrials
Myelodysplastic Syndromes 1 D009190 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Inflammation 1 D007249 ClinicalTrials
Influenza, Human 1 D007251 ClinicalTrials
Obesity 1 D009765 ClinicalTrials
Depressive Disorder, Major 1 D003865 ClinicalTrials
Pain 1 D010146 ClinicalTrials
Hepatitis C 1 D006526 ClinicalTrials
Depressive Disorder 1 D003866 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 1 D029424 ClinicalTrials
Infections 1 D007239 ClinicalTrials
Hepatitis B, Chronic 1 D019694 ClinicalTrials
Essential Hypertension 1 D000075222 ClinicalTrials
Diabetes Mellitus, Type 2 1 D003924 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials
Diabetes Mellitus 1 D003920 ClinicalTrials
Epilepsy 1 D004827 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Cytomegalovirus Infections 1 D003586 ClinicalTrials
von Hippel-Lindau Disease 1 D006623 ClinicalTrials
Angioedemas, Hereditary 1 D054179 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Abdominal pain
Cardiac disorders Dizziness 6.0
Gastrointestinal disorders Gastrointestinal pain
Cardiac disorders Dizziness
Cardiac disorders Dizziness 4.88
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
General disorders and administration site conditions Decreased appetite
Gastrointestinal disorders Diarrhoea 4.0
Cardiac disorders Dizziness
Nervous system disorders Headache
Nervous system disorders Headache 4.0
Gastrointestinal disorders Nausea 4.0
Cardiac disorders Palpitations
Gastrointestinal disorders Diarrhoea 3.25
Nervous system disorders Headache 3.25
Gastrointestinal disorders Nausea 3.25
General disorders and administration site conditions Decreased appetite
Nervous system disorders Headache
Cardiac disorders Palpitations
Skin and subcutaneous tissue disorders Dermatitis 2.0
Gastrointestinal disorders Nausea
Skin and subcutaneous tissue disorders Rash 2.0
Cardiac disorders Tachycardia 2.0
Gastrointestinal disorders Vomiting 2.0
Skin and subcutaneous tissue disorders Dermatitis 1.63
Skin and subcutaneous tissue disorders Rash 1.63
Cardiac disorders Tachycardia 1.63
Gastrointestinal disorders Vomiting 1.63
Gastrointestinal disorders Nausea
Cardiac disorders Cardiac arrest
Cardiac disorders Cardiac arrest 1.0
General disorders and administration site conditions Decreased appetite 1.0
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Diarrhoea
Cardiac disorders Palpitations 1.0
Skin and subcutaneous tissue disorders Rash
Cardiac disorders Tachycardia
Cardiac disorders Ventricular extrasystoles
Cardiac disorders Ventricular extrasystoles 1.0
Gastrointestinal disorders Vomiting
Cardiac disorders Cardiac arrest 0.813
General disorders and administration site conditions Decreased appetite 0.813
Cardiac disorders Palpitations 0.813
Cardiac disorders Ventricular extrasystoles 0.813
Cardiac disorders Cardiac arrest
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Diarrhoea
Skin and subcutaneous tissue disorders Rash
Cardiac disorders Tachycardia
Cardiac disorders Ventricular extrasystoles
Gastrointestinal disorders Vomiting

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Cardiac disorders
19.13
Injury, poisoning and procedural complications
13.57
General disorders and administration site conditions
10.54
Investigations
7.45
Nervous system disorders
7.33
Gastrointestinal disorders
6.24
Vascular disorders
6.2
Respiratory, thoracic and mediastinal disorders
5.34
Metabolism and nutrition disorders
4.26
Psychiatric disorders
3.54
Pregnancy, puerperium and perinatal conditions
3.48
Renal and urinary disorders
2.93

Cross References

Resources Reference
CAS NUMBER 20830-75-5
ChEBI 4551
ChEMBL CHEMBL1751
DrugBank DB00390
DrugCentral 882
EPA CompTox DTXSID5022934
FDA SRS 73K4184T59
Human Metabolome Database HMDB01917
Guide to Pharmacology 4726
KEGG C06956
PDB DGX
PubChem 2724385
SureChEMBL SCHEMBL20506
ZINC ZINC000242548690
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