Quinidine sulfate dihydrate

Bezeichnung:Quinidine sulfate dihydrate

CAS-Nr6591-63-5

Englisch Name:Quinidine sulfate dihydrate

CBNumberCB2471189

SummenformelC20H26N2O6S

Molgewicht422.5

MOL-Datei6591-63-5.mol

Quinidine sulfate dihydrate physikalisch-chemischer Eigenschaften

Schmelzpunkt	212-214 °C (dec.)(lit.)
alpha	[α]D20 +260～+270° (c=5, dil. HCl.10min)
Brechungsindex	275 ° (C=2, 0.1mol/L HCl)
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit	Slightly soluble in water, soluble in boiling water and in ethanol (96 per cent), practically insoluble in acetone.
Farbe	White to Off-White
Wasserlöslichkeit	Soluble in chloroform, water (11 mg/ml at 20°C), alcohol, and ethanol (50 mg/ml).
Sensitive	Light Sensitive
Merck	14,8060
InChIKey	AKYHKWQPZHDOBW-ZAXYGKDDNA-N
SMILES	[C@@H]([C@@]1([H])C[C@@H]2CC[N@]1C[C@@H]2C=C)(C1=CC=NC2=CC=C(OC)C=C12)O.S(O)(O)(=O)=O \|&1:0,1,4,7,9,r\|
CAS Datenbank	6591-63-5(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-20/21/22
S-Sätze:	13-36
RIDADR	UN 2811 6.1/PG III
WGK Germany	3
RTECS-Nr.	VA5605000
TSCA	Yes
HazardClass	6.1
PackingGroup	III
HS Code	2939200050

Gefahreninformationscode (GHS)

Quinidine sulfate dihydrate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S13:Von Nahrungsmitteln, Getränken und Futtermitteln fernhalten.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Quinidine sulfate dihydrate is a diastereomer of quinine and a Na+ channel blocker. Also a class I antiarrhythmic drug. Quinidine sulfate dihydrate is a white, odorless crystalline substance that has a bitter flavor. It has limited solubility in water and alcohol but dissolves easily in chloroform and ether. This compound is effective against bacteria resistant to erythromycin, including staphylococci and streptococci, and works by inhibiting cellular ATPases.
Chemische Eigenschaften
Quinidine sulfate dihydrate is white to light yellow crystal powde
Verwenden
Quinidine sulfate dihydrate (cas# 6591-63-5) is the hydrated, sulfate salt of Quinidine (Q685000), a dextrorotatory stereoisomer of Quinine. Antiarrhythmic (class IA). Antimalarial.
Verwenden
antiarrhythmic, antimalarial
Application
Quinidine sulfate salt dihydrate has been used as an antiarrhythmic drug to study its effects on phosphorylation and mutations in the cardiac sodium channel Nav1.5.
Trademarks
Cin-Quin (Solvay Pharmaceuticals); Quinidex (Wyeth); Quinora (Schering).
Allgemeine Beschreibung
Quinidine sulfate dihydrate is the sulfateof an alkaloid obtained from various species ofCinchona and their hybrids. It is a dextrorotatory diastereoisomerof quinine. The salt crystallizes from wateras the dihydrate, in the form of fine, needlelike, white crystals.Quinidine sulfate contains a hydroxymethyl groupthat serves as a link between a quinoline ring and a quinuclidinemoiety. The structure contains two basic nitrogens,of which the quinuclidine nitrogen is the stronger base(pKa 10). Quinidine sulfate dihydrate is bitter and light sensitive.Quinidine sulfate dihydrates are nearly neutral or slightly alkaline. Itis soluble to the extent of 1% in water and more highly solublein alcohol or chloroform.
Hazard
Quinidine sulfate dihydrate is acutely toxic and photosensitising. The photosensitisation reaction to quinidine sulphate was reproducible in the photopic test and after oral administration plus ultraviolet A (UVA) irradiation. Eczematous dermatitis was induced after intradermal injection of quinidine sulfate dihydrate irradiated by UVA in vitro only in the presence of the patient's serum. Three workers exposed to quinidine sulphate developed allergic reactions within a short period of time (2-3 months).
Biochem/physiol Actions
Class IA antiarrhythmic; potassium channel blocker.
Clinical Use
Quinidine sulfate is the prototype of antiarrhythmicdrugs and a class IA antiarrhythmic agent according to theVaughan Williams classification. It reduces Na⁺ current bybinding the open ion channels (i.e., state A). The decreasedNa⁺entry into the myocardial cell depresses phase 4 diastolicdepolarization and shifts the intracellular threshold potentialtoward zero. These combined actions diminish thespontaneous frequency of pacemaker tissues, depress theautomaticity of ectopic foci, and, to a lesser extent, reduceimpulse formation in the SA node. This last action results inbradycardia. During the spike action potential, quinidinesulfate decreases transmembrane permeability to passiveinflux of Na⁺, thus slowing the process of phase 0 depolarization,which decreases conduction velocity. This is shownas a prolongation of the QRS complex of electrocardiograms.Quinidine sulfate also prolongs action potential duration,which results in a proportionate increase in the QTinterval. It is used to treat supraventricular and ventricularectopic arrhythmias, such as atrial and ventricular prematurebeats, atrial and ventricular tachycardia, atrial flutter, andatrial fibrillation.

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