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What is digoxin?

By Chelsie Vandaveer

November 8, 2002

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John Gerard's original herbal included two species he knew as Digitalis. He wrote this warning in 1597: "...they are bitter, are hot and drie, with a certaine kinde of clensing qualitie joined therewith; yet are they of no use, neither have they any place amongst medicines, according to the Antients." (The Herbal, 1633 ed.)

Today, there are nineteen recognized species in the genus, Digitalis Linnaeus; all are native to the Old World. And all contain
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Foxglove, which yields digitalis, is vital in the treatment of heart disease

Foxglove, which yields digitalis, is vital
in the treatment of heart disease

Sam Abell
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cardioactive glycosides to one degree or another.

Cardioactive glycosides are a family of related chemicals. The molecules consist of two or more parts, the glyco- or sugar moiety (part), and the remainder or aglycone, meaning the part without the sugar. These glycosides affect the function of the heart.

The Digitalis prescribed by William Withering in the late 1700s was the leaf of foxglove dried and probably powdered. The major problem with Digitalis was the narrow 'therapeutic window'; the amount that cured and the amount that killed were very close. The numerous glycosides present varied from plant to plant and with the season.

According to Mark S. Lesney, "By 1869, a French pharmacist, Claude-Adolphe Nativelle isolated a much-purified material he called 'digitalin', from foxglove. Six years later, German chemist, Oswald Schmiedeberg...isolated the first pure glycoside...which he called 'digitoxin'." ("Flowers for the Heart", Modern Drug Discovery, ACS Publications, 2002) It was the old convention to name extracted chemicals/drugs after their source, in this instance, Digitalis.

One of the most useful Digitalis extracts was discovered in 1957. By modern chemical convention, this extract is known as (3β,5β,12β)-3-[(O-2, 6-Dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxycard-20(22)-enolide. (Merck Index, 11th ed., 1989)

But for some reason, people prefer the heart medication's old-fashioned, 1957 name--digoxin.


The Rx List has more information about digoxin and its modern medical uses. To learn more about this plant extract, click on the link:

http://www.rxlist.com/cgi/generic/dig.htm

 

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Suggested Reading:

Did the queen of darkness cure dropsy? Herbal Folklore - June 23, 2003
How did foxes use these gloves? What's in a Name? - November 1, 2002
Who taught doctors how to cure dropsy? Plants that Changed History - October 29, 2002
How did we learn how to use digitalis? Plants that Changed History - November 5, 2002
What plant commemorates the death of a dragon? Herbal Folklore - March 11, 2002

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