Gitoformate
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Gitoformate
Gitoformate (International Nonproprietary Name, INN, or pentaformylgitoxin, trade name Dynocard) is a cardiac glycoside, a type of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia (irregular heartbeat). Produced by Madaus, it is not available in the US, and does not seem to be available in Europe either. Chemistry Gitoformate is a derivative of the glycoside gitoxin, with five of the six free hydroxyl groups formylated, one on the aglycon and four on the sugar. Gitoxin, a cardiac glycoside from the woolly foxglove (''Digitalis lanata''), has an aglycon of the cardenolide type named gitoxigenin, which is also the aglycon of lanatoside B, another ''Digitalis lanata'' glycoside. References

Cardenolides Formate esters Tertiary alcohols {{cardiovascular-drug-stub ...
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Cardiac Glycoside
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 defensive poisons in several plant genera such as ''Digitalis'' (the foxgloves) and '' Asclepias'' (the milkweeds), these compounds nevertheless have a diverse range of biochemical effects regarding cardiac cell function and have also been suggested for use in cancer treatment. Classification General structure The general structure of a cardiac glycoside consists of a steroid molecule attached to a sugar (glycoside) and an R group. The steroid nucleus consists of four fused rings to which other functional groups such as methyl, hydroxyl, and aldehyde groups can be attached to influence th ...
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Congestive Heart Failure
Heart failure (HF), also known as congestive heart failure (CHF), is a syndrome caused by an impairment in the heart's ability to fill with and pump blood. Although symptoms vary based on which side of the heart is affected, HF typically presents with shortness of breath, excessive fatigue, and bilateral leg swelling. The severity of the heart failure is mainly decided based on ejection fraction and also measured by the severity of symptoms. Other conditions that have symptoms similar to heart failure include obesity, kidney failure, liver disease, anemia, and thyroid disease. Common causes of heart failure include coronary artery disease, heart attack, high blood pressure, atrial fibrillation, valvular heart disease, excessive alcohol consumption, infection, and cardiomyopathy. These cause heart failure by altering the structure or the function of the heart or in some cases both. There are different types of heart failure: right-sided heart failure, which affect ...
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Cardiac Arrhythmia
Arrhythmias, also known as cardiac arrhythmias, are irregularities in the heartbeat, including when it is too fast or too slow. Essentially, this is anything but normal sinus rhythm. A resting heart rate that is too fast – above 100 beats per minute in adults – is called tachycardia, and a resting heart rate that is too slow – below 60 beats per minute – is called bradycardia. Some types of arrhythmias have no symptoms. Symptoms, when present, may include palpitations or feeling a pause between heartbeats. In more serious cases, there may be lightheadedness, passing out, shortness of breath, chest pain, or decreased level of consciousness. While most cases of arrhythmia are not serious, some predispose a person to complications such as stroke or heart failure. Others may result in sudden death. Arrhythmias are often categorized into four groups: extra beats, supraventricular tachycardias, ventricular arrhythmias and bradyarrhythmias. Extra beats incl ...
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Glycoside
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 enzymatic, 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. In formal terms, a glycoside is any molecule in which a sugar group is bonded through its anomeric carbon to another group via a glycosidic bond. Glycosides can be linked by an O- (an ''O-glycoside''), N- (a ''glycosylamine''), S-(a ''thioglycoside''), or C- (a ''C-glycoside'') glycosidic bond. Accord ...
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Hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anion , called hydroxide, and the neutral radical , known as the hydroxyl radical, consist of an unbonded hydroxy group. According to IUPAC definitions, the term ''hydroxyl'' refers to the hydroxyl radical () only, while the functional group is called a ''hydroxy group''. Properties Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack thi ...
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Aglycon
An aglycone (aglycon or genin) is the chemical compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid molecule. Detection A way to identify aglycone is proposed to extract it from Agave spp. by using H-NMR and Heteronuclear multiple bond correlation (HMBC) experiments. The HMBC experiment can be combined with other techniques such as mass spectrometry to further examine the structure and the function of aglycone. Samples of glycones and glycosides from limonoids can be simultaneously quantified through a high performance liquid chromatography (HPLC) method, where a binary solvent system and a diode array detector separate and detect them at a sensitivity of 0.25-0.50 μg. Clinical significance A study on molecular markers in human aortic endothelial cells published that aglycone stopped cell migration but not monocyte adhesion, which is the initial step of atheroscl ...
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Woolly Foxglove
''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. Description ''Digitalis lanata'' is a biennial or perennial growing from a woody, horizontal rootstock. There is a tidy rosette before the spike goes up, and it is neatly arranged around the purple-tinged stems. The plant commonly forms a single, upright, more or less uniformly leafy stem that is partly ascending at the base. The plant send up these stems and flowers usually in its second year. The stems are 0.3 to 0.6 meters in height, or about 13 to 26 inches. The l ...
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Cardenolide
A cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides (cardenolides that contain structural groups derived from sugars). Cardenolide glycosides are often toxic; specifically, they are cardiac arrest, heart-arresting. Cardenolides are toxic to animals through inhibition of the enzyme Na+/K+-ATPase, Na+/K+-ATPase, which is responsible for maintaining the sodium and Potassium in biology, potassium ion gradients across the cell membranes. Etymology The term derives from ''card-'' "heart" (from Greek language, Greek καρδία ''kardiā'') and the suffix , referring to the lactone ring with double bond at C17. Cardenolides are a class of steroids (or aglycones if viewed as cardiac glycoside constituents), and cardenolides are a subtype of this class (see Wikipedia:MeSH D04#MeSH D04.808.155 --- cardenolides, MeSH D codes list). Structure Cardenolides are C(23)-steroids with methyl ...
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