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Concept
Cardiac glycoside
Summary
Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses are as treatments for congestive heart failure and cardiac arrhythmias; however, their relative toxicity prevents them from being widely used. Most commonly found as secondary metabolites in several plants such as foxglove plants, these compounds nevertheless have a diverse range of biochemical effects regarding cardiac cell function and have also been suggested for use in cancer treatment.
The general structure of a cardiac glycoside consists of a steroid molecule attached to a sugar (glycoside) and an R group. The steroid nucleus consists of four fused rings to which other functional groups such as methyl, hydroxyl, and aldehyde groups can be attached to influence the overall molecule's biological activity. Cardiac glycosides also vary in the groups attached at either end of the steroid. Specifically, different sugar groups attached at the sugar end of the steroid can alter the molecule's solubility and kinetics; however, the lactone moiety at the R group end only serves a structural function.
In particular, the structure of the ring attached at the R end of the molecule allows it to be classified as either a cardenolide or bufadienolide. Cardenolides differ from bufadienolides due to the presence of an "enolide," a five-membered ring with a single double bond, at the lactone end. Bufadienolides, on the other hand, contain a "dienolide," a six-membered ring with two double bonds, at the lactone end. While compounds of both groups can be used to influence the cardiac output of the heart, cardenolides are more commonly used medicinally, primarily due to the widespread availability of the plants from which they are derived.
Cardiac glycosides can be more specifically categorized based on the plant they are derived from, as in the following list.
Official source
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