digitoxin

Trade name: Acylanid

Small moleculeapproved

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

Chemistry & pharmacology

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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

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 IDPhaseStart dateSponsor(s)
NCT00782288Phase 2Aug 1, 2010Johns Hopkins University, University of Colorado, Denver
Showing 1 of 1 trials
Page 1 / 1

Organizations

Research & Development (2)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Johns Hopkins UniversityAcademic/Hospital1012010
University of Colorado, DenverAcademic/Hospital1112010
2 organizations
Page 1 / 1

Marketing (2)

OrganizationOrg typeRelationshipDate
Eli LillyFor profitNDA
Eli LillyFor profitMKTGAug 28, 1978