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CAS 752-61-4

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Digitalin

Description:
Digitalin is a cardiac glycoside derived from the leaves of the Digitalis plant, commonly known as foxglove. It is primarily used in the treatment of heart conditions, particularly heart failure and atrial fibrillation, due to its ability to increase the force of heart contractions and regulate heart rhythm. The compound exhibits a complex structure characterized by a steroid nucleus with multiple sugar moieties, which contribute to its solubility and biological activity. Digitalin acts by inhibiting the Na+/K+ ATPase enzyme, leading to an increase in intracellular sodium and calcium concentrations, ultimately enhancing cardiac contractility. Its pharmacokinetics can vary based on factors such as formulation and patient metabolism, and it has a narrow therapeutic window, necessitating careful monitoring of blood levels to avoid toxicity. Common side effects may include gastrointestinal disturbances, visual changes, and arrhythmias. As with other cardiac glycosides, the use of digitalin requires caution, particularly in patients with renal impairment or electrolyte imbalances.
Formula:C36H56O14
InChI:InChI=1S/C36H56O14/c1-16-30(50-32-28(42)27(41)26(40)23(14-37)49-32)31(45-4)29(43)33(47-16)48-19-7-9-34(2)18(12-19)5-6-21-20(34)8-10-35(3)25(17-11-24(39)46-15-17)22(38)13-36(21,35)44/h11,16,18-23,25-33,37-38,40-44H,5-10,12-15H2,1-4H3/t16-,18-,19+,20+,21-,22+,23-,25+,26-,27+,28-,29-,30+,31-,32+,33+,34+,35-,36+/m1/s1
InChI key:InChIKey=CKNOLMVLQUPVMU-YMMLYESFSA-N
SMILES:O[C@@]12[C@@](C)([C@H]([C@@H](O)C1)C=3COC(=O)C3)CC[C@]4([C@]2(CC[C@]5([C@]4(C)CC[C@H](O[C@H]6[C@H](O)[C@@H](OC)[C@@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@@H](C)O6)C5)[H])[H])[H]
Synonyms:
  • Glucostrospeside
  • Digitalin
  • (3β,5β,16β)-3-[(6-Deoxy-4-O-β-D-glucopyranosyl-3-O-methyl-β-D-galactopyranosyl)oxy]-14,16-dihydroxycard-20(22)-enolide
  • Digitalin (glycoside)
  • Card-20(22)-enolide, 3-[(6-deoxy-4-O-β-D-glucopyranosyl-3-O-methyl-β-D-galactopyranosyl)oxy]-14,16-dihydroxy-, (3β,5β,16β)-
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