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Quinidine

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CAS:56-54-2
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Products Intro: Product Name:(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
CAS:56-54-2
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CAS:56-54-2
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CAS:56-54-2
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Products Intro: Product Name:Quinidine
CAS:56-54-2
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Quinidine manufacturers

  • Quinidine
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  • Quinidine
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  • Quinidine
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  • 2024-10-25
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Quinidine Chemical Properties
Melting point 168-172 °C(lit.)
alpha 256 º (c=1, EtOH)
Boiling point 462.75°C (rough estimate)
density 1.1294 (rough estimate)
refractive index 1.5700 (estimate)
storage temp. Keep in dark place,Sealed in dry,2-8°C
solubility insoluble in H2O; ≥10.32 mg/mL in EtOH with ultrasonic; ≥11.95 mg/mL in DMSO
form Powder
pka5.4, 10.0(at 20℃)
color White to off-white
optical activity[α]20/D +265±5°, c = 0.8% in ethanol (dry matter)
Water Solubility 0.05 g/100 mL (20 ºC)
Sensitive Light Sensitive
Merck 14,8060
BRN 91866
BCS Class1
Stability:Stable. Incompatible with strong oxidizing agents.
LogP3.440
CAS DataBase Reference56-54-2(CAS DataBase Reference)
NIST Chemistry ReferenceQuinine(56-54-2)
EPA Substance Registry SystemQuinidine (56-54-2)
Safety Information
Hazard Codes Xn
Risk Statements 22-20/21/22
Safety Statements 36-22
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS VA4725000
8
TSCA Yes
HazardClass 6.1(b)
PackingGroup III
HS Code 29392000
Hazardous Substances Data56-54-2(Hazardous Substances Data)
ToxicityLD50 in rats (mg/kg): 30 i.v., 263 orally (Dietmann)
MSDS Information
Quinidine Usage And Synthesis
DescriptionQuinidine is a stereoisomer of the antimalarial agent quinine and a class Ia antiarrhythmic agent. Quinidine blocks the voltage-gated sodium (Nav) channel Nav1.5 in a use-dependent manner. It decreases the amplitude and duration of action potentials in isolated canine ventricular myocytes. It inhibits KKr, peak INa, and late INa (IC50s = 4.5, 11, and 12 μM, respectively) and can induce torsade de pointes in isolated rabbit hearts when used at a concentration of 1 μM. Quinidine induces QT prolongation in dogs. It also binds to M2 muscarinic acetylcholine receptors (Ki = 7.5 μM for human recombinant receptors expressed in HM2-B10 cells). Formulations containing quinidine have been used in the treatment of atrial fibrillation and ventricular arrhythmias.
DescriptionQuinidine is a commonly used class I antiarrhythmic drug. It is a stereoisomer of quinine, originally derived from the bark of the cinchona tree. It exerts its antiarrhythmic effects on the heart by interacting with the electrophysiology mechanisms that cause arrhythmias to modify the abnormalities in impulse initiation and conduction. Quinidine depresses normal automaticity in cardiac fibers that may act as ectopic pacemakers causing arrhythmias. Quinidine also blocks the slowly inactivating, tetrodotoxin-sensitive Na current, the slow inward calcium current (ICa), the rapid (IKr) and slow (IKs) components of the delayed potassium rectifier current, the inward potassium rectifier current (IKI), the ATP-sensitive potassium channel (IKATP) and Ito.
Chemical Propertieswhite to light yellow crystal powde
Physical propertiesAppearance: Quinidine is commonly used in its sulfate form with white needle-like crystal and bitter smell. It changes color easily when exposed to light. Solubility: It was soluble in ethanol and chloroform. Its water solubility is 0.05?g/100?mL (20?°C). Specific optical rotation: 256° (c?=?1, EtOH). Melting point: 168–172?°C.
HistoryIn 1820, the French chemists Pierre Pelletier and Joseph Caventou extracted some alkaloids from the cinchona bark, including quinine and quinidine. Subsequently, quinine was demonstrated to play a very important role in the treatment of malaria after a number of scientific researches. Quinidine is the dextroisomer of quinine and has the similar pharmacological properties as quinine, but quinidine’s effects are five to ten times stronger on the heart than quinine.
Usesantiarrhythmic, antimalarial
UsesA dextrorotatory stereoisomer of Quinine. Antiarrhythmic (class IA). Antimalarial
UsesQuinidine occurs in cinchona bark to about0.25–0.3% and also in cuprea bark. It is present in quinine sulfate mother liquor. Itis formed by isomerization of quinine. Itis used in the prevention of certain cardiacarrhythmias.
DefinitionChEBI: A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.
IndicationsQuinidine acts as a class I antiarrhythmic agent (Ia) in the heart. It was clinically applicable to the treatment of recurrent, documented, life-threatening ventricular arrhythmias .
Brand nameDuraquin (Warner Chilcott); Quinaglute (Berlex).
Biological FunctionsQuinidine is an alkaloid obtained from various species of Cinchona or its hybrids, from Remijia pedunculata, or from quinine. Quinidine is the dextrorotatory isomer of quinine.Quinidine (Quinidex) was one of the first clinically used antiarrhythmic agents. Because of the high incidence of ventricular proarrhythmia associated with its use and numerous other equally efficacious agents, quinidine is now used sparingly. Quinidine shares all of the pharmacological properties of quinine, including antimalarial, antipyretic, oxytocic, and skeletal muscle relaxant actions.
General DescriptionCrystals or white powder.
Air & Water ReactionsInsoluble in water.
HazardPoison.
Health HazardQuinidine is more potent than quinine in itsaction on the cardiovascular system. Overdosesmay cause lowering of blood pressure.Gastric effects are lower than quinine. Toxicityis lower relative to quinine; subcutaneouslethal dose in mice is 400 mg/kg against200 mg/kg for quinine.
Fire HazardFlash point data for Quinidine are not available. Quinidine is probably combustible.
Biochem/physiol ActionsClass IA antiarrhythmic; potassium channel blocker.
Mechanism of actionQuinidine generally is administered orally, although slow intravenous administration also is possible . Quinidine is the prototype of class I antiarrhythmics; therefore, substances in this group also are called “quinidine-like.”However, it differs, for example, from lidocaine by the following effects: it increases the duration of the action potential, in the ECG it increases QRS duration and Q– T interval, and the refractory period is markedly prolonged. Quinidine can accelerate the impulse conduction rate in the AV node (atropine-like effect).
PharmacologyQuinidine exhibits all of the pharmacological properties of quinine, including antimalarial, fever-reducing, and other properties. Quinidine is used in various forms of arrhythmia for preventing tachycardia and atrial fibrillation, and particularly for preventing ciliary fibrillation, paroxysmal supraventricular tachycardia, extrasystole, and ventricular tachycardia. However, it is a toxic drug and is used relatively rarely. It is also prescribed under the name cardioquin, duraquin, quinidex, and others.
Clinical UsePrimary indications for the use of quinidine include (1) abolition of premature complexes that have an atrial, A-V junctional, or ventricular origin; (2) restoration of normal sinus rhythm in atrial flutter and atrial fibrillation after controlling the ventricular rate with digitalis; (3) maintenance of normal sinus rhythm after electrical conversion of atrial arrhythmias; (4) prophylaxis against arrhythmias associated with electrical countershock; (5) termination of ventricular tachycardia; and (6) suppression of repetitive tachycardia associated with Wolff- Parkinson-White (WPW) syndrome.
Although quinidine often is successful in producing normal sinus rhythm, its administration in the presence of a rapid atrial rate (flutter and possibly atrial fibrillation) can lead to a further and dangerous increase in the ventricular rate secondary to inhibition of basal vagal tone upon the A-V node. For this reason, digitalis should be used before quinidine when one is attempting to convert atrial flutter or atrial fibrillation to normal sinus rhythm.
Side effectsThe most common adverse effects associated with quinidine administration are diarrhea (35%), upper gastrointestinal distress (25%), and light-headedness (15%). Other relatively common adverse effects include fatigue, palpitations, headache (each occurring with an incidence of 7%), anginalike pain, and rash. These adverse effects are generally dose related and reversible with cessation of therapy. In some patients, quinidine administration may bring on thrombocytopenia due to the formation of a plasma protein–quinidine complex that evokes a circulating antibody directed against the blood platelet. Although platelet counts return to normal on cessation of therapy, administration of quinidine or quinine at a later date can cause the reappearance of thrombocytopenia.
The cardiac toxicity of quinidine includes A-V and intraventricular block, ventricular tachyarrhythmias, and depression of myocardial contractility. Ventricular arrhythmia induced by quinidine leading to a loss of consciousness has been referred to as quinidine syncope. This devastating side effect is more common in women than in men and may occur at therapeutic or subtherapeutic plasma concentrations. Large doses of quinidine can produce a syndrome known as cinchonism, which is characterized by ringing in the ears, headache, nausea, visual disturbances or blurred vision, disturbed auditory acuity, and vertigo. Larger doses can produce confusion, delirium, hallucinations, or psychoses.Quinidine can decrease blood glucose concentrations, possibly by inducing insulin secretion.
Safety ProfilePoison by ingestion, subcutaneous, intravenous, intramuscular, and intraperitoneal routes. A skin irritant. Implicated in aplastic anemia. When heated to decomposition it emits toxic fumes of NOx.
Drug interactionsQuinidine can increase the plasma concentrations of digoxin, which may in turn lead to signs and symptoms of digitalis toxicity. Gastrointestinal, central nervous system (CNS), or cardiac toxicity associated with elevated digoxin concentrations may occur.Quinidine and digoxin can be administered concurrently; however, a downward adjustment in the digoxin dose may be required.
Drugs that have been associated with elevations in quinidine concentrations include acetazolamide, the antacids magnesium hydroxide and calcium carbonate, and the H2-receptor antagonist cimetidine. Cimetidine inhibits the hepatic metabolism of quinidine. Phenytoin, rifampin, and barbiturates increase the hepatic metabolism of quinidine and reduce its plasma concentrations.
MetabolismQuinidine's bioavailability appears to depend on a combination of metabolism and P-gp efflux. The bioavailabilities of quinidine sulfate and gluconate are 80 to 85% and 70 to 75%, respectively. Once absorbed, quinidine is subject to hepatic first-pass metabolism and is approximately 85% plasma protein bound, with an elimination half-life of approximately 6 hours. Quinidine is metabolized mainly in the liver, and renal excretion of unchanged drug also is significant (~10–50%). The metabolites are hydroxylated derivatives at either the quinoline ring through first-pass O-demethylation or at the quinuclidine ring through oxidation of the vinyl group. These metabolites possess only about one-third the activity of quinidine. Their contribution to overall therapeutic effect of quinidine is unclear. Recently, the clinical significance of the well-documented digoxin–quinidine interaction was described previously under digoxin–drug interactions. Apparently, quinidine (a P-gp substrate) inhibits the renal tubular secretion of digoxin via the P-gp efflux pump, resulting in increased plasma concentration for digoxin.
storageStore at -20°C
Purification MethodsCrystallise it from *C6H6 or dry CHCl3/pet ether (b 40-60o), discarding the initial, oily crop of crystals. Dry it under vacuum at 100o over P2O5. It has been used as a chiral catalyst [Wynberg & Staring J Am Chem Soc 104 166 1982, J Org Chem 50 1977 1985]. [Beilstein 23 H 506, 23 I 164, 23 II 414, 23 III/IV 3261, 23/13 V 395.]
PrecautionsOne of the few absolute contraindications for quinidine is complete A-V block with an A-V pacemaker or idioventricular pacemaker; this may be suppressed by quinidine, leading to cardiac arrest.
Persons with congenital QT prolongation may develop torsades de pointes tachyarrhythmia and should not be exposed to quinidine.
Owing to the negative inotropic action of quinidine, it is contraindicated in congestive heart failure and hypotension. Digitalis intoxication and hyperkalemia can accentuate the depression of conduction caused by quinidine.
Myasthenia gravis can be aggravated severely by quinidine’s actions at the neuromuscular junction. The use of quinidine and quinine should be avoided in patients who previously showed evidence of quinidine- induced thrombocytopenia.
ReferencesWit, Andrew L. "The Effects of Quinidine on the Cellular Electrophysiology of the Heart: A Brief Review." Journal of Cardiovascular Electrophysiology 3.5(2010):316-322.
Alloway, J. A., and M. P. Salata. "Quinidine-induced rheumatic syndromes. " Seminars in Arthritis & Rheumatism 24.5(1995):315-322.
Nakano, J, and M. C. R. Jr. "Effect of quinidine on cardiovascular dynamics." Arch Int Pharmacodyn Ther 168.2(1967):400-416.
Quinidine Preparation Products And Raw materials
Preparation ProductsQUININE SULFATE-->N-BENZYLQUINIDINIUM CHLORIDE
Tag:Quinidine(56-54-2) Related Product Information
VINYL PROPIONATE Quinidine sulfate dihydrate Quinoxaline QUINOLINE-4-CARBOXYLIC ACID Quinoline Quercetin dihydrate Quinic acid Quinazoline Quinoline-5-carboxylic acid HYDROQUINIDINE HYDROCHLORIDE QUINIDINE SULFATE,Quinidine sluphate,Quinidine hemisulfate HYDROQUINIDINE Quinidine cupric sulfate solution QUINIDINE GLUCONATE,QUINIDINE GLUCONATE SALT A-QUINIDINE,ALPHA-QUINIDINE (+)-Cinchonine, 98+%, cont. up to 3% quinidine/dihydroquinidine and 3% quinine/dihydroquinidine Quinine Quinidine monohydrate hydrochloride,QUINIDINE HYDROCHLORIDE,QUINIDINE HYDROCHLORIDE MONOHYDRATE