Proscillaridin

Last updated
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
  • 5-[(3S,8R,9S,10R,13R,14S,17R)-14-Hydroxy- 10,13-dimethyl-3-((2R,3R,4R,5R,6R)-3,4,5-trihydroxy- 6-methyltetrahydro-2H-pyran-2-yloxy)-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro- 1H-cyclopenta[a]phenanthren-17-yl]-2H-pyran-2-one
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 530.658 g·mol−1
3D model (JSmol)
  • O=C1OC=C([C@H]2CC[C@]3([C@@]2(CC[C@H]4[C@H]3CCC5=C[C@H](CC[C@@]54C)O[C@@H]6O[C@@H](C)[C@@H]([C@H]([C@H]6O)O)O)C)O)C=C1
  • InChI=1S/C30H42O8/c1-16-24(32)25(33)26(34)27(37-16)38-19-8-11-28(2)18(14-19)5-6-22-21(28)9-12-29(3)20(10-13-30(22,29)35)17-4-7-23(31)36-15-17/h4,7,14-16,19-22,24-27,32-35H,5-6,8-13H2,1-3H3/t16-,19-,20+,21-,22+,24-,25+,26+,27-,28-,29+,30-/m0/s1 Yes check.svgY
  • Key:MYEJFUXQJGHEQK-ALRJYLEOSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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

<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 include 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 and milkweed 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.

<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.

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

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

Scilla is a genus of about 30 to 80 species of bulb-forming perennial herbaceous plants in the family Asparagaceae, subfamily Scilloideae. Sometimes called the squills in English, they are native to woodlands, subalpine meadows, and seashores throughout Europe, Africa and the Middle East. A few species are also naturalized in Australasia 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.

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

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

Cerberin is a type of cardiac glycoside, found in the seeds of the dicotyledonous angiosperm genus Cerbera; including the suicide tree and the sea mango. As a cardiac glycoside, cerberin disrupts the function of the heart by blocking its sodium and potassium ATPase. Cerberin can be used as a treatment for heart failure and arrhythmia.

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.

<i>Cerbera manghas</i> Species of plant

Cerbera manghas, commonly known as the sea mango, tangena or bintaro is a small evergreen coastal tree growing up to 12 metres (39 ft) tall. It is native to coastal areas in Africa, Asia, Australasia, and the Pacific islands. It is classified as one of the three species in the genus Cerbera that constitute mangroves.

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

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.

<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.

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

<span class="mw-page-title-main">Lanatoside C</span> 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.

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

Oleandrin is a cardiac glycoside found in the poisonous plant oleander. As a main phytochemical of oleander, oleandrin is associated with the toxicity of oleander sap, and has similar properties to digoxin.

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

Arenobufagin is a cardiotoxic bufanolide steroid secreted by the Argentine toad Bufo arenarum. It has effects similar to digitalis, blocking the Na+/K+ pump in heart tissue.

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

Antiarins are cardiac glycoside poisons produced by the upas tree. There are two closely related forms, α-antiarin and β-antiarin. The two share the same aglycone, antiarigenin, but differ in the sugar group that is attached to it.

The molecular formula C30H42O8 may refer to:

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

Bufanolide is a C24 steroid and, indirectly, a parent structure of bufadienolide. Its derivatives was found in Bufo and Scilla, as an aglycone of cardiac glycosides and is usually toxic.

<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.