Proscillaridin

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Proscillaridin
Proscillaridin structure.svg
Clinical data
Other names14β-Hydroxy-3β-[α-L-rhamnopyranosyl)oxy]bufa-4,20,22-trienolide
AHFS/Drugs.com International Drug Names
ATC code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.006.702 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C30H42O8
Molar mass 530.650 g·mol−1
3D model (JSmol)
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Proscillaridin is a cardiac glycoside, a kind of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia (irregular heartbeat). It is of the bufanolide type and can be obtained from plants of the genus Scilla and in Drimia maritima (Scilla maritima). [1]

The aglycone of proscillaridin is scillarenin.

Related Research Articles

Cardiac glycosides are a class of organic compounds that increase the output force of the heart and increase its rate of contractions by acting on 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 plants

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

Digitoxin chemical compound

Digitoxin is a cardiac glycoside. It is a phytosteroid and is similar in structure and effects to digoxin. Unlike digoxin, it is eliminated via the liver, so could be used in patients with poor or erratic kidney function. However, it is now rarely used in current Western medical practice. 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.

Squill is a common name for several lily-like plants and may refer to:

<i>Scilla</i> genus of plants

Scilla is a genus of about 50 to 80 bulb-forming perennial herbs in the family Asparagaceae, subfamily Scilloideae, native to woodlands, subalpine meadows, and seashores throughout Europe, Africa and the Middle-East. A few species are also naturalized in Australia, New Zealand and North America. Their flowers are usually blue, but white, pink, and purple types are known; most flower in early spring, but a few are autumn-flowering. Several Scilla species are valued as ornamental garden plants.

<i>Asclepias</i> Genus of flowering plants

Asclepias is a genus of herbaceous, perennial, flowering plants known as milkweeds, named for their latex, a milky substance containing cardiac glycosides termed cardenolides, exuded where cells are damaged. Most species are toxic to humans and many other species, primarily due to the presence of cardenolides, although, as with many such plants, there are species that feed upon them and from them. The genus contains over 200 species distributed broadly across Africa, North America, and South America. It previously belonged to the family Asclepiadaceae, which is now classified as the subfamily Asclepiadoideae of the dogbane family, Apocynaceae.

Glycoside molecule in which a sugar is bound to another functional group

In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

Scilloideae subfamily of plants

Scilloideae is a subfamily of bulbous plants within the family Asparagaceae. Scilloideae is sometimes treated as a separate family Hyacinthaceae, named after the genus Hyacinthus. Scilloideae or Hyacinthaceae include many familiar garden plants such as Hyacinthus (hyacinths), Hyacinthoides (bluebells), Muscari and Scilla and Puschkinia. Some are important as cut flowers.

Cerberin chemical compound

Cerberin is a type of cardiac glycoside, a steroidal class found in the seeds of the dicotyledonous angiosperm genus Cerbera; including the suicide tree and the sea mango. This class includes digitalis-like agents, channel-blockers that as a group have found historic uses as cardiac treatments, but which at higher doses are extremely toxic; in the case of cerberin, consumption of the C. odollam results in poisoning with presenting nausea, vomiting, and abdominal pain, often leading to death. The natural product has been structurally characterized, its toxicity is clear—it is often used as an intentional human poison in third-world countries, and accidental poisonings with fatalities have resulted from individuals even indirectly consuming the agent—but its potentially therapeutic pharmacologic properties are very poorly described.

NVC community H7 is one of the heath communities in the British National Vegetation Classification system. It is one of two communities categorised as maritime heaths.

British NVC community MC5 is one of the maritime cliff communities in the British National Vegetation Classification system. It is one of five communities categorised as maritime cliff crevice and ledge communities.

Bufadienolide chemical compound

Bufadienolide is a chemical compound with steroid structure. Its derivatives are collectively known as bufadienolides, including many in the form of bufadienolide glycosides. These are a type of cardiac glycoside, the other being the cardenolide glycosides. Both bufadienolides and their glycosides are toxic; specifically, they can cause an atrioventricular block, bradycardia, ventricular tachycardia, and possibly lethal cardiac arrest.

<i>Drimia maritima</i> Species of plant

Drimia maritima is a species of flowering plant in the family Asparagaceae, subfamily Scilloideae. This species is known by several common names, including squill, sea squill, sea onion, and maritime squill. It may also be called red squill, particularly a form which produces red-tinged flowers instead of white. It is native to southern Europe, western Asia, and northern Africa.

Gitoformate chemical compound

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.

Lanatoside C chemical compound

Lanatoside C is a cardiac glycoside, a type of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia. Lanatoside C can be used orally or by the intravenous route. It is marketed in a number of countries and is also available in generic form. Its main indications are rapid response atrial fibrilation and paroxysmal supraventricular tachycardia, two common types of arrhythmia.

Oleandrin chemical compound

Oleandrin is a toxic cardiac glycoside found in oleander. Along with conessine it is primarily responsible for the toxicity of the sap of oleander. Oleandrin has been used for many years in China and Russia for its properties as a cardiac glycoside, for both suicidal and therapeutic purposes as in treatment of cardiac insufficiency.

Antiarin concept amalgam in chemistry

Antiarins are cardiac glycoside poisons produced by the upas tree. There are two forms, α-antiarin and β-antiarin.

S. maritima may refer to:

<i>Barnardia japonica</i> Species of plant

Barnardia japonica, the Japanese jacinth, is a bulbous flowering plant in the family Asparagaceae, subfamily Scilloideae. It is one of the two species of the genus Barnardia, found in east China, Korea, Japan, Taiwan and East Russia.

Scillitoxin (scillaine) is a chemical substance found in daffodils. It is a cardiac glucoside. with effects similar to digitoxin. The first, 1889, edition of the Merck Index lists: "Scilli-toxin (Scillain)" under the heading of "Squill (Scilla) preparations". It was stated in 1929 that "Scillitoxin has not been chemically identified as a definite chemical entity".

References

  1. Kedra M, Kedrowa S (May 1968). "[Clinical evaluation of Proscillaridin A, a glycoside of Scilla maritima]". Polski Tygodnik Lekarski. 23 (19): 714–6. PMID   4876207.