digitoxin
Trade name: Acylanid
Approved
Jun 1, 1954
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. — NCATS
Clinical trial activity
1 trials · 2 clinical orgs · 1 marketing orgs
Earliest trial started Aug 1, 2010 (NCT00782288)
Timeline
Indications
Approved for
Studied for
Mechanism of action
- Sodium/potassium-transporting ATPaseINHIBITOR
Sodium/potassium-transporting ATPase inhibitor
Alpha subunit is binding site
- Sodium/potassium-transporting ATPase subunit alpha-1 (ATP1A1) ↗
- Sodium/potassium-transporting ATPase subunit beta-2 (ATP1B2) ↗
- Sodium/potassium-transporting ATPase subunit beta-1 (ATP1B1) ↗
- Sodium/potassium-transporting ATPase subunit alpha-2 (ATP1A2) ↗
- Sodium/potassium-transporting ATPase subunit beta-3 (ATP1B3) ↗
- Sodium/potassium-transporting ATPase subunit alpha-3 (ATP1A3) ↗
- Sodium/potassium-transporting ATPase subunit alpha-4 (ATP1A4) ↗
- Sodium/potassium-transporting ATPase subunit gamma (FXYD2) ↗
- Sodium/potassium-transporting ATPase alpha-1 chain
- Sodium/potassium-transporting ATPase beta-3 chain
- Sodium/potassium-transporting ATPase subunit alpha-2/beta-1
- Sodium/potassium-transporting ATPase subunit alpha-1/beta-1
- Sodium/potassium-transporting ATPase subunit alpha-2/beta-3
- Sodium/potassium-transporting ATPase subunit alpha-2/beta-2
- Sodium/potassium-transporting ATPase beta-1 chain
Approval history
- approvedJun 1, 1954
Chemistry & pharmacology
SMILES
C[C@H]1O[C@H](C[C@H](O)[C@@H]1O)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@]7(C)[C@H](CC[C@]67O)C8=CC(=O)OC8)C4)O[C@@H]3C)O[C@@H]2C- Mol. weight
- 764.9391 g/mol
- Lipinski Ro5
- 2 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Discontinued
Oral
No
Parenteral
Yes
Topical
No
Sources
- WikipediaDigitoxin ↗
- NCATSE90NZP2L9U ↗
- ChEMBLCHEMBL254219 ↗
Also known as
- cardidigin
- cardigin
- carditoxin
- coramedan
- cristapurat
- crystodigin
- crystodigin
- crystodigin
- crystodigin
- crystodigin (tn)
- crystodigin (tn)
- digicor
- digimerck
- digimerck
- digipural
- digisidin
- digitoksin
- digitoksin
- digitophyllin
- digitoxigenin tridigitoxoside
- digitoxin
- digitoxin
- digitoxin
- digitoxin
- digitoxin
- digitoxin
- digitoxin
- digitoxin
- digitoxin
- digitoxin
- digitoxin
- digitoxinum
- digitoxinum
- digitoxoside
- digitoxoside
- digitoxoside
- digitoxoside
- myodigin
- nativelle digitaline
- purpurid
- tradigal
- unidigin
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT00782288 | Phase 2 | Aug 1, 2010 | Johns Hopkins University, University of Colorado, Denver |
Organizations
Research & Development (2)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Johns Hopkins University | Academic/Hospital | 1 | 0 | 1 | 2010 |
| University of Colorado, Denver | Academic/Hospital | 1 | 1 | 1 | 2010 |