Lanatoside C

Last updated
Lanatoside C
Lanatoside C.svg
Clinical data
Other names[6-[6-[6-[[12,14-dihydroxy- 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]- 4-hydroxy- 2-methyloxan- 3-yl]oxy- 4-hydroxy- 2-methyloxan-3-yl]oxy- 2-methyl- 3-[3,4,5-trihydroxy- 6-(hydroxymethyl)oxan-2-yl]oxyoxan- 4-yl] acetate
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral, intravenous
ATC code
Identifiers
  • (3β,5β,12β)- 3-{[β-D- glucopyranosyl- (1→4)- 3-O-acetyl- 2,6-dideoxy- β-D-ribo- hexopyranosyl- (1→4)- 2,6-dideoxy- β-D- ribo- hexopyranosyl- (1→4)- 2,6-dideoxy- β-D- ribo- hexopyranosyl]oxy}- 12,14-dihydroxycard- 20(22)- enolide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.037.754 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C49H76O20
Molar mass 985.127 g·mol−1
3D model (JSmol)
  • C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3C[C@H]([C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)O)C)O)O[C@H]7C[C@@H]([C@@H]([C@H](O7)C)O[C@H]8C[C@@H]([C@@H]([C@H](O8)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)OC(=O)C)O
  • InChI=1S/C49H76O20/c1-21-43(67-38-17-32(53)44(22(2)62-38)68-39-18-33(64-24(4)51)45(23(3)63-39)69-46-42(58)41(57)40(56)34(19-50)66-46)31(52)16-37(61-21)65-27-9-11-47(5)26(14-27)7-8-29-30(47)15-35(54)48(6)28(10-12-49(29,48)59)25-13-36(55)60-20-25/h13,21-23,26-35,37-46,50,52-54,56-59H,7-12,14-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29-,30+,31+,32+,33+,34-,35-,37+,38+,39+,40-,41+,42-,43-,44-,45-,46+,47+,48+,49+/m1/s1 Yes check.svgY
  • Key:JAYAGJDXJIDEKI-PTGWOZRBSA-N Yes check.svgY
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Lanatoside C (or isolanid) is a cardiac glycoside, a type of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia (irregular heartbeat). Lanatoside C can be used orally [1] or by the intravenous route. [2] It is marketed in a number of countries and is also available in generic form. [3] Its main indications are rapid response atrial fibrilation and paroxysmal supraventricular tachycardia,[ citation needed ] two common types of arrhythmia.

It is found in Digitalis lanata . [4]

Chemistry

The substance is composed of four monosaccharides (glucose, 3-acetyldigitoxose and two digitoxoses) and an aglycon named digoxigenin. [5]

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">Lidocaine</span> Local anesthetic

Lidocaine, also known as lignocaine and sold under the brand name Xylocaine among others, is a local anesthetic of the amino amide type. It is also used to treat ventricular tachycardia. When used for local anaesthesia or in nerve blocks, lidocaine typically begins working within several minutes and lasts for half an hour to three hours. Lidocaine mixtures may also be applied directly to the skin or mucous membranes to numb the area. It is often used mixed with a small amount of adrenaline (epinephrine) to prolong its local effects and to decrease bleeding.

<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.

<span class="mw-page-title-main">Quinidine</span> Antiarrythmic medication

Quinidine is a class IA antiarrhythmic agent used to treat heart rhythm disturbances. It is the enantiomer of antimalarial agent quinine, originally derived from the bark of the cinchona tree. The drug causes increased action potential duration, as well as a prolonged QT interval. As of 2019, its IV formulation is no longer being manufactured for use in the United States.

<span class="mw-page-title-main">Amiodarone</span> Antiarrhythmic medication used for various types of irregular heartbeats

Amiodarone is an antiarrhythmic medication used to treat and prevent a number of types of cardiac dysrhythmias. This includes ventricular tachycardia (VT), ventricular fibrillation (VF), and wide complex tachycardia, as well as atrial fibrillation and paroxysmal supraventricular tachycardia. Evidence in cardiac arrest, however, is poor. It can be given by mouth, intravenously, or intraosseously. When used by mouth, it can take a few weeks for effects to begin.

<span class="mw-page-title-main">Flecainide</span> Antiarrhythmic medication used to prevent and treat tachyarrhythmias

Flecainide is a medication used to prevent and treat abnormally fast heart rates. This includes ventricular and supraventricular tachycardias. Its use is only recommended in those with dangerous arrhythmias or when significant symptoms cannot be managed with other treatments. Its use does not decrease a person's risk of death. It is taken by mouth or injection into a vein.

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

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

Digoxigenin (DIG) is a steroid found exclusively in the flowers and leaves of the plants Digitalis purpurea, Digitalis orientalis and Digitalis lanata (foxgloves), where it is attached to sugars, to form the glycosides.

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

Acecainide is an antiarrhythmic drug. Chemically, it is the N-acetylated metabolite of procainamide. It is a Class III antiarrhythmic agent, whereas procainamide is a Class Ia antiarrhythmic drug. It is only partially as active as procainamide; when checking levels, both must be included in the final calculation.

<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.

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">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.

<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">Mephentermine</span> Adrenergic and dopaminergic cardiac stimulant

Mephentermine is a cardiac stimulant.

<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">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.

References

  1. Lypka A, Lazowski J (September 1979). "[Comparative study of blood serum concentrations of digoxin and lanatoside C after single oral administration]" [Comparative study of blood serum concentrations of digoxin and lanatoside C after single oral administration]. Wiadomosci Lekarskie (in Polish). 32 (18): 1277–81. PMID   506267.
  2. Tàmmaro AE, Baldoli C (January 1967). "[On some immediate effects of the intravenous administration of desacetyl-lanatoside C in aged subjects]" [On some immediate effects of the intravenous administration of desacetyl-lanatoside C in aged subjects]. La Clinica Terapeutica (in Italian). 40 (2): 157–61. PMID   5600177.
  3. "Lanatoside C". International Drug Names. Drugs.com.
  4. Ikeda Y, Fujii Y, Yamazaki M (June 1992). "Determination of Lanatoside C and Digoxin in Digitalis lanata by HPLC and its Application to Analysis of the Fermented Leaf Powder". Journal of Natural Products. 55 (6): 748–52. doi:10.1021/np50084a007.
  5. Desai UR (2005). "Cardiac Glycosides". VCU School of Pharmacy.