Acetyldigitoxin

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Acetyldigitoxin
Acetyldigitoxin.png
Clinical data
ATC code
Identifiers
  • [(2R,3R,4S,6S)-3-Hydroxy-6-[(2R,4S,6S)-4-hydroxy-6-[(2R,3S,4S,6R)-4-hydroxy-6-[ [(5R,8R,9S,10S,13R,14S,17R')-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-2-methyloxan-3-yl]oxy-2-methyloxan-3-yl]oxy-2-methyloxan-4-yl] acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.042.660 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C43H66O14
Molar mass 806.987 g·mol−1
3D model (JSmol)
  • O=C\1OC/C(=C/1)[C@H]2CC[C@@]8(O)[C@]2(C)CC[C@H]7[C@H]8CC[C@H]6[C@]7(C)CC[C@H](O[C@@H]5O[C@@H]([C@@H](O[C@@H]4O[C@@H]([C@@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@H](OC(=O)C)C3)[C@@H](O)C4)C)[C@@H](O)C5)C)C6
  • InChI=1S/C43H66O14/c1-21-38(48)33(54-24(4)44)19-37(51-21)57-40-23(3)53-36(18-32(40)46)56-39-22(2)52-35(17-31(39)45)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(47)50-20-25/h15,21-23,26-33,35-40,45-46,48-49H,7-14,16-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29+,30-,31+,32+,33+,35+,36+,37+,38-,39-,40-,41+,42-,43+/m1/s1 Yes check.svgY
  • Key:HPMZBILYSWLILX-UMDUKNJSSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Acetyldigitoxin is a cardiac glycoside. It is an acetyl derivative of digitoxin, found in the leaves of Digitalis species. [1] It is used to treat cardiac failure, particularly that associated with tachycardia. [2]

Related Research Articles

<span class="mw-page-title-main">Cardiac glycoside</span> Class of organic compounds

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.

<i>Digitalis</i> Genus of flowering plants in the family Plantaginaceae

Digitalis is a genus of about 20 species of herbaceous perennial plants, shrubs, and biennials, commonly called foxgloves.

<span class="mw-page-title-main">Digoxin</span> Plant-derived medication used in certain heart conditions

Digoxin, sold under the brand name Lanoxin among others, is a medication used to treat various heart conditions. Most frequently it is used for atrial fibrillation, atrial flutter, and heart failure. Digoxin is one of the oldest medications used in the field of cardiology. It works by increasing myocardial contractility, increasing stroke volume and blood pressure, reducing heart rate, and somewhat extending the time frame of the contraction. Digoxin is taken by mouth or by injection into a vein. Digoxin has a half life of approximately 36 hours given at average doses in patients with normal renal function. It is excreted mostly unchanged in the urine.

<span class="mw-page-title-main">Digitoxin</span> Chemical compound

Digitoxin is a cardiac glycoside used for the treatment of heart failure and certain kinds of heart arrhythmia. It is a phytosteroid and is similar in structure and effects to digoxin, though the effects are longer-lasting. Unlike digoxin, which is eliminated from the body via the kidneys, it is eliminated via the liver, and so can be used in patients with poor or erratic kidney function. While several controlled trials have shown digoxin to be effective in a proportion of patients treated for heart failure, the evidence base for digitoxin is not as strong, although it is presumed to be similarly effective.

<i>Digitalis purpurea</i> Toxic flowering plant in the family Plantaginaceae

Digitalis purpurea, the foxglove or common foxglove, is a poisonous species of flowering plant in the plantain family Plantaginaceae, native to and widespread throughout most of temperate Europe. It has also naturalised in parts of North America and some other temperate regions. The plant is a popular garden subject, with many cultivars available. It is the original source of the heart medicine digoxin. This biennial plant grows as a rosette of leaves in the first year after sowing, before flowering and then dying in the second year. It generally produces enough seeds, however, so that new plants will continue to grow in a garden setting.

<span class="mw-page-title-main">Phytochemistry</span> Study of phytochemicals, which are chemicals derived from plants

Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.

<span class="mw-page-title-main">Digitonin</span> Chemical compound

Digitonin is a steroidal saponin (saraponin) obtained from the foxglove plant Digitalis purpurea. Its aglycone is digitogenin, a spirostan steroid. It has been investigated as a detergent, as it effectively water-solubilizes lipids. As such, it has several potential membrane-related applications in biochemistry, including solubilizing membrane proteins, precipitating cholesterol, and permeabilizing cell membranes.

<span class="mw-page-title-main">Bernard Lown</span> American inventor and cardiologist (1921–2021)

Bernard Lown was a Lithuanian-American cardiologist and inventor. Lown was the original developer of the direct current defibrillator for cardiac resuscitation, and the cardioverter for correcting rapid disordered heart rhythms. He introduced a new use for the drug lidocaine to control heartbeat disturbances.

<i>Digitalis lanata</i> Species of flowering plant in the plantain family Plantaginaceae

Digitalis lanata, vernacularly often called woolly foxglove or Grecian foxglove, is a species of foxglove, a flowering plant in the plantain family Plantaginaceae. It gets its name due to the woolly indumentum of the leaves. D. lanata, like other foxglove species, is toxic in all parts of the plant. Symptoms of digitalis poisoning include nausea, vomiting, severe headache, dilated pupils, problems with eyesight, and convulsions at the worst level of toxicity. The plant is also harmful to other animals.

<span class="mw-page-title-main">Pulsus bigeminus</span>

Pulsus bigeminus is a cardiovascular phenomenon characterized by groups of two heartbeats close together followed by a longer pause. The second pulse is weaker than the first. Look for a pattern of what appears to be a relatively normal QRS complexes, each followed by a smaller, abnormal one. The smaller beat is palpated as either a missing or an extra beat, and on EKG resembles a PVC. These PVCs appearing every other beat are also called extrasystoles.

k-Strophanthidin Chemical compound

k-Strophanthidin is a cardenolide found in species of the genus Strophanthus. It is the aglycone of k-strophanthin, an analogue of ouabain. k-strophanthin is found in the ripe seeds of Strophanthus kombé and in the lily Convallaria.

<span class="mw-page-title-main">Dopexamine</span> Chemical compound

Dopexamine is a synthetic analogue of dopamine that is administered intravenously in hospitals to reduce exacerbations of heart failure and to treat heart failure following cardiac surgery. It is not used often, as more established drugs like epinephrine, dopamine, dobutamine, norepinephrine, and levosimendan work as well. It works by stimulating beta-2 adrenergic receptors and peripheral dopamine receptor D1 and dopamine receptor D2. It also inhibits the neuronal re-uptake of norepinephrine.

<span class="mw-page-title-main">Digoxin immune fab</span>

Digoxin immune fab or digoxin-specific antibody is an antidote for overdose of digoxin. It is made from immunoglobulin fragments from sheep that have already been immunized with a digoxin derivative, digoxindicarboxymethoxylamine (DDMA). Its brand names include Digibind (GlaxoSmithKline) and DigiFab.

<i>Digitalis grandiflora</i> Species of foxglove

Digitalis grandiflora, the yellow foxglove, big-flowered foxglove, or large yellow foxglove, is a species of flowering plant in the genus Digitalis, family Plantaginaceae. It is native to southern Europe and Asia. In mountains it grows on warm, bushy slopes or areas left after logging. The Latin specific epithet grandiflora means “large flowered”.

<span class="mw-page-title-main">Gitoformate</span>

Gitoformate is a cardiac glycoside, a type of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia. Produced by Madaus, it is not available in the US, and does not seem to be available in Europe either.

<span class="mw-page-title-main">Deslanoside</span>

Deslanoside is a cardiac glycoside, a type of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia. It is found in the leaves of Digitalis lanata, the Woolly Foxglove.

<span class="mw-page-title-main">Digoxin toxicity</span> Medical condition

Digoxin toxicity, also known as digoxin poisoning, is a type of poisoning that occurs in people who take too much of the medication digoxin or eat plants such as foxglove that contain a similar substance. Symptoms are typically vague. They may include vomiting, loss of appetite, confusion, blurred vision, changes in color perception, and decreased energy. Potential complications include an irregular heartbeat, which can be either too fast or too slow.

<span class="mw-page-title-main">Convallatoxin</span> Chemical compound

Convallatoxin is a glycoside extracted from Convallaria majalis.

<i>Digitalis obscura</i> Species of plant

Digitalis obscura, commonly called willow-leaved foxglove or dusty foxglove or spanish rusty foxglove, is a flowering plant native to regions in Spain and Morocco. It is also grown as an ornamental flower. This foxglove is a woody perennial plant belonging to the family Plantaginaceae. Along with the other foxgloves it used to be placed in the figwort family, Scrophulariaceae; however, recent genetic research has moved the genus Digitalis to a larger family. It is similar to many of the foxglove species in its high toxicity and medicinal use as a source for the heart-regulating drug digoxin. Its strikingly distinctive amber- to copper-coloured flowers give the species its name and help distinguish it from other members of the genus.

<span class="mw-page-title-main">Calotropin</span> Chemical compound

Calotropin is a toxic cardenolide found in plants in the family Asclepiadoideae. In extreme cases, calotropin poisoning can cause respiratory and cardiac failure. Accidental poisoning is common in livestock who have ingested milkweed. Calotropin is commonly stored as a defense mechanism by insects that eat milkweeds as their main food source.

References

  1. Kemertelidze ÉP, Gvazava LN (1979-11-01). "Odorobioside G from the leaves ofDigitalis ciliata". Chemistry of Natural Compounds. 15 (6): 779. doi: 10.1007/BF00565608 .
  2. Loffler W, Essellier AF, Forster G (June 1954). "Acetyl-digitoxin; clinical observations on the treatment of patients with advanced congestive heart failure". American Heart Journal. 47 (5): 898–911. doi:10.1016/0002-8703(54)90160-X. PMID   13158272.