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Mesylate Esters
In organosulfur chemistry, a mesylate is any salt or ester of methanesulfonic acid (). In salts, the mesylate is present as the anion. When modifying the international nonproprietary name of a pharmaceutical substance containing the group or anion, the spelling used is sometimes mesilate (as in ''imatinib mesilate'', the mesylate salt of imatinib). Mesylate esters are a group of organic compounds that share a common functional group with the general structure , abbreviated , where R is an organic substituent. Mesylate is considered a leaving group in nucleophilic substitution reactions. Preparation Mesylate esters are generally prepared by treating an alcohol and methanesulfonyl chloride in the presence of a base, such as triethylamine. Mesyl Related to mesylate is the mesyl (Ms) or methanesulfonyl () functional group. The shortened term itself was coined by Helferich et al. in 1938 similarly to tosyl adopted earlier. Methanesulfonyl chloride is often referred to as mesy ...
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Base (chemistry)
In chemistry, there are three definitions in common use of the word "base": '' Arrhenius bases'', '' Brønsted bases'', and '' Lewis bases''. All definitions agree that bases are substances that react with acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis ...s, as originally proposed by Guillaume-François Rouelle, G.-F. Rouelle in the mid-18th century. In 1884, Svante Arrhenius proposed that a base is a substance which dissociates in aqueous solution to form hydroxide ions OH−. These ions can react with Hydron (chemistry), hydrogen ions (H+ according to Arrhenius) from the dissociation of acids to form water in an acid–base reaction. A base was therefore a metal hydroxide such as NaOH or Calcium hydroxide, Ca(OH)2. Such aqueous hydroxide solutions were also described by ...
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Dronedarone
Dronedarone, sold under the brand name Multaq, is a class III antiarrhythmic medication developed by Sanofi-Aventis. It was approved by the US Food and Drug Administration (FDA) in July 2009. Besides being indicated in arrhythmias, it was recommended as an alternative to amiodarone for the treatment of atrial fibrillation and atrial flutter in people whose hearts have either returned to normal rhythm or who undergo drug therapy or electric shock treatment i.e. direct current cardioversion (DCCV) to maintain normal rhythm. It is a class III antiarrhythmic drug. The FDA label includes a claim for reducing hospitalization, but not for reducing mortality, as a reduction in mortality was not demonstrated in the clinical development program. A trial of the drug in heart failure was stopped as an interim analysis showed a possible increase in heart failure deaths, in people with moderate to severe congestive heart failure. The FDA label for dronedarone includes a boxed warning, statin ...
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Sematilide
Sematilide is an antiarrhythmic agent. It is the same structure as for procainamide, differing only by the placement of a mesyl sulfonamide moiety to the anilino nitrogen. Synthesis Sematilide can be synthesized from benzocaine (1).David D. Davey, William C. Lumma, Jr., Ronald A. Wohl, (1985 to Schering A.G.) Reaction with mesyl chloride, followed by saponification and removal of the water from the reaction mixture, gives sodium 4- methylsulfonyl)aminoenzoate (2). Chlorination with thionyl chloride Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately Volatility (chemistry), volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a Halogenation, chlorinating reagen ... gives 4- methylsulfonyl)aminoenzoyl chloride. Amide formation with ''N'',''N''-diethylethylenediamine (3) then concludes the synthesis of sematilide (4). References {{Reflist Sulfonamides Antiarrhythmic agents Benzamides Diethyl ...
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Ibutilide
Ibutilide is a Class III antiarrhythmic agent that is indicated for acute cardioconversion of atrial fibrillation and atrial flutter of a recent onset to sinus rhythm. It exerts its antiarrhythmic effect by induction of slow inward sodium current, which prolongs action potential and refractory period of myocardial cells. Because of its Class III antiarrhythmic activity, there should not be concomitant administration of Class Ia and Class III agents. Ibutilide is marketed as Corvert by Pfizer. Administration resulted in successful heart rhythm control in 31–44% of patients within 90 minutes, with sustained polymorphic ventricular tachycardia in 0.9–2.5% of patients. It appears to show better results in atrial flutter as compared to atrial fibrillation. Mechanism of action Ibutilide, like other class III antiarrhythmic drugs, blocks delayed rectified potassium current. It does have action on the slow sodium channel and promotes the influx of sodium through these slow channe ...
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Sotalol
Sotalol, sold under the brand name Betapace among others, is a medication used to treat and prevent abnormal heart rhythms. Evidence does not support a decreased risk of death with long term use. It is taken by mouth or given by injection into a vein. Common side effects include a slow heart rate, chest pain, low blood pressure, feeling tired, dizziness, shortness of breath, problems seeing, vomiting, and swelling. Other serious side effects may include QT prolongation, heart failure, or bronchospasm. Sotalol is a non-selective β-adrenergic receptor blocker which has both class II and class III antiarrhythmic properties. Sotalol was first described in 1964 and came into medical use in 1974. It is available as a generic medication. In 2020, it was the 296th most commonly prescribed medication in the United States, with more than 1million prescriptions. Medical uses According to the U.S. Food and Drug Administration (FDA), sotalol can be validly used to maintain a nor ...
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Sulfonamide
In organic chemistry, the sulfonamide functional group (also spelled sulphonamide) is an organosulfur group with the Chemical structure, structure . It consists of a sulfonyl group () connected to an amine group (). Relatively speaking this group is unreactive. Because of the rigidity of the functional group, sulfonamides are typically crystalline; for this reason, the formation of a sulfonamide is a classic method to convert an amine into a crystalline derivative which can be identified by its melting point. Many important drugs contain the sulfonamide group. A sulfonamide (compound) is a chemical compound that contains this group. The general formula is or , where each R is some organic group; for example, "methanesulfonamide" (where R = methane, R' = R" = hydrogen) is . Any sulfonamide can be considered as derived from a sulfonic acid by replacing a hydroxyl group () with an amine group. In medicine, the term "sulfonamide" is sometimes used as a synonym for Sulfonamide (m ...
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Antiarrhythmic
Antiarrhythmic agents, also known as cardiac dysrhythmia medications, are a class of drugs that are used to suppress abnormally fast rhythms (tachycardias), such as atrial fibrillation, supraventricular tachycardia and ventricular tachycardia. Many attempts have been made to classify antiarrhythmic agents. Many of the antiarrhythmic agents have multiple modes of action, which makes any classification imprecise. Action potential The cardiac myocyte has two general types of action potentials: conduction system and working myocardium. The action potential is divided into 5 phases and shown in the diagram. The sharp rise in voltage ("0") corresponds to the influx of sodium ions, whereas the two decays ("1" and "3", respectively) correspond to the sodium-channel inactivation and the repolarizing efflux of potassium ions. The characteristic plateau ("2") results from the opening of voltage-sensitive calcium channels. Each phase utilizes different channels and it is useful to compar ...
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Cardiac
The heart is a muscular organ found in humans and other animals. This organ pumps blood through the blood vessels. The heart and blood vessels together make the circulatory system. The pumped blood carries oxygen and nutrients to the tissue, while carrying metabolic waste such as carbon dioxide to the lungs. In humans, the heart is approximately the size of a closed fist and is located between the lungs, in the middle compartment of the chest, called the mediastinum. In humans, the heart is divided into four chambers: upper left and right atria and lower left and right ventricles. Commonly, the right atrium and ventricle are referred together as the right heart and their left counterparts as the left heart. In a healthy heart, blood flows one way through the heart due to heart valves, which prevent backflow. The heart is enclosed in a protective sac, the pericardium, which also contains a small amount of fluid. The wall of the heart is made up of three layers: epicardi ...
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Nitrogen
Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. It is a common element in the universe, estimated at Abundance of the chemical elements, seventh in total abundance in the Milky Way and the Solar System. At standard temperature and pressure, two atoms of the element chemical bond, bond to form N2, a colourless and odourless diatomic molecule, diatomic gas. N2 forms about 78% of Atmosphere of Earth, Earth's atmosphere, making it the most abundant chemical species in air. Because of the volatility of nitrogen compounds, nitrogen is relatively rare in the solid parts of the Earth. It was first discovered and isolated by Scottish physician Daniel Rutherford in 1772 and independently by Carl Wilhelm Scheele and Henry Cavendish at about the same time. The name was suggested by French chemist ...
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Hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis is the cleavage of Biomolecule, biomolecules where a water molecule is consumed to effect the separation of a larger molecule into component parts. When a carbohydrate is broken into its component sugar molecules by hydrolysis (e.g., sucrose being broken down into glucose and fructose), this is recognized as saccharification. Hydrolysis reactions can be the reverse of a condensation reaction in which two molecules join into a larger one and eject a water molecule. Thus hydrolysis adds water to break down, whereas condensation builds up by removing water. Types Usually hydrolysis is a chemical process in which a molecule of water is added to a substance. Sometimes this addition causes both the su ...
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Methanesulfonyl Chloride
Methanesulfonyl chloride (mesyl chloride) is an organosulfur compound with the formula . Using the organic pseudoelement symbol Ms for the methanesulfonyl (or mesyl) group –, it is frequently abbreviated MsCl in reaction schemes or equations. It is a colourless liquid that dissolves in polar organic solvents but is reactive toward water, alcohols, and many amines. The simplest organic sulfonyl chloride, it is used to make methanesulfonates and to generate the elusive molecule sulfene (methylenedioxosulfur(VI)).Valerie Vaillancourt, Michele M. Cudahy, Matthew M. Kreilein and Danielle L. Jacobs "Methanesulfonyl Chloride" in E-EROS Encyclopedia for Reagents in Organic Synthesis Preparation It is produced by the reaction of methane and sulfuryl chloride in a radical reaction: : Another method of production entails chlorination of methanesulfonic acid with thionyl chloride or phosgene: : : Reactions Methanesulfonyl chloride is a precursor to many compounds because it is highly rea ...
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