Lidocainhydrochlorid

Bezeichnung:Lidocainhydrochlorid

CAS-Nr73-78-9

Englisch Name:Lidocaine hydrochloride

CBNumberCB4117973

SummenformelC14H23ClN2O

Molgewicht270.8

MOL-Datei73-78-9.mol

Synonyma

Lidocainhydrochlorid

Lidocainhydrochlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	80-82°C
storage temp.	Inert atmosphere,2-8°C
Aggregatzustand	Solid
Farbe	White to off-white
Wasserlöslichkeit	Water : ≥ 36 mg/mL (132.94 mM)
InChI	InChI=1S/C14H22N2O.ClH/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4;/h7-9H,5-6,10H2,1-4H3,(H,15,17);1H
InChIKey	IYBQHJMYDGVZRY-UHFFFAOYSA-N
SMILES	C(NC1=C(C)C=CC=C1C)(=O)CN(CC)CC.[H]Cl
LogP	2.359 (est)
CAS Datenbank	73-78-9(CAS DataBase Reference)
EPA chemische Informationen	Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)-, monohydrochloride (73-78-9)

Sicherheit

RIDADR	3249
HazardClass	6.1(b)
PackingGroup	III
Toxizität	LD50 oral in mouse: 220mg/kg

Gefahreninformationscode (GHS)

Lidocaine hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
White to Off-White Solid
Originator
Xylocaine,Astra,US,1949
Verwenden
Apply to affected site 5 to 10 minutes before procedure. Duration of anesthesia is relatively short (<1 hour).
Verwenden
Local anesthesic;Na+ channel blocker
Verwenden
Anesthetic (local); antiarrhythmic (class IB). Long-acting, membrane stabilizing agent against ventricular arrhythmia. Originally developed as a local anesthetic.
Definition
ChEBI: Lidocaine hydrochloride is the anhydrous form of the hydrochloride salt of lidocaine. It functions as both a local anesthetic and cardiac depressant, and is commonly used as an antiarrhythmic agent. Its potency is higher and its effects last longer than those of procaine, but its duration of action is shorter than that of bupivacaine or prilocaine.
Manufacturing Process
One mol of 2,6-xylidine is dissolved in 800 ml glacial acetic acid. The mixture is cooled to 10°C, after which 1.1 mol chloracetyl chloride is added at one time. The mixture is stirred vigorously during a few moments after which 1,000 ml half-saturated sodium acetate solution, or other buffering or alkalizing substance, is added at one time. The reaction mixture is shaken during half an hour. The precipitate formed which consists of ω-chloro-2,6- dimethyl-acetanilide is filtered off, washed with water and dried. The product is sufficiently pure for further treatment. The yield amounts to 70 to 80% of the theoretical amount.
One mole of the chloracetyl xylidide thus prepared and 2.5 to 3 mols diethyl amine are dissolved in 1,000 ml dry benzene. The mixture is refluxed for 4 to 5 hours. The separated diethyl amine hydrochloride is filtered off. The benzene solution is shaken out two times with 3N hydrochloric acid, the first time with 800 ml and the second time with 400 ml acid. To the combined acid extracts is added an approximately 30% solution of sodium hydroxide until the precipitate does not increase.
The precipitate, which sometimes is an oil, is taken up in ether. The ether solution is dried with anhydrous potassium carbonate after which the ether is driven off. The remaining crude substance is purified by vacuum distillation. During the distillation practically the entire quantity of the substance is carried over within a temperature interval of 1° to 2°C. The yield approaches the theoretical amount. MP 68° to 69°C. BP 180° to 182°C at 4 mm Hg; 159° to 160°C at 2 mm Hg. (Procedure is from US Patent 2,441,498.)
Trademarks
Alpha caine Hydrochloride (Carlisle); Anestacon (Polymedica); Laryng-O-Jet (International Medication); Lidocaton (Phar maton); Lidopen (Meridian); Xylocaine (Abraxis); Xylo caine (AstraZeneca); Xylocaine (Dentsply).
Therapeutic Function
Local anesthetic, Antiarrhythmic
Biologische Funktion
Lidocaine hydrochloride (Xylocaine) is the most commonly used local anesthetic. It is well tolerated, and in addition to its use in infiltration and regional nerve blocks, it is commonly used for spinal and topical anesthesia and as an antiarrhythmic agent. Lidocaine has a more rapidly occurring, more intense, and more prolonged duration of action than does procaine.
Allgemeine Beschreibung
Lidocaine hydrochloride,2-(diethylamino)-2 ,6 -acetoxylidide monohydrochloride(Xylocaine), was conceived as a derivative of gramine(3-dimethylaminomethylindole) and introduced as a localanesthetic. It is now being used intravenously as a standardparenteral agent for suppression of arrhythmias associatedwith acute myocardial infarction and cardiac surgery.It isthe drug of choice for the parenteral treatment of prematureventricular contractions.
Mechanism of action
Lidocaine can block Na+ and K+ ion channels and regulate intracellular and extracellular calcium concentrations through other ligand-gated ion channels. Lidocaine was the first sodium channel blocker to be identified. Its main mechanism of action is blocking voltage-gated Na+ channels (VGSC/NaVs).
Clinical Use
Lidocaine hydrochloride is a class IB antiarrhythmicagent with a different effect on the electrophysiologicalproperties of myocardial cells from that of procainamideand quinidine. It binds with equal affinity to the active (A)and inactive (I) Na⁺ ion channels. It depresses diastolic depolarizationand automaticity in the Purkinje fiber networkand increases the functional refractory period relative toaction potential duration, as do procainamide and quinidine.It differs from the latter two drugs, however, in that it doesnot decrease, and may even enhance, conduction velocity and increase membrane responsiveness to stimulation.There are fewer data available on the subcellular mechanismsresponsible for the antiarrhythmic actions of lidocainethan on the more established drug quinidine. It has been proposedthat lidocaine has little effect on membrane cation exchangeof the atria. Sodium ion entrance into ventricularcells during excitation is not influenced by lidocaine becauseit does not alter conduction velocity in this area.Lidocaine hydrochloride does depress Na⁺ influx duringdiastole, as do all other antiarrhythmic drugs, to diminishautomaticity in myocardial tissue. It also alters membraneresponsiveness in Purkinje fibers, allowing increased conductionvelocity and ample membrane potential at the timeof excitation.
Sicherheitsprofil
Poison by ingestion, intraperitoneal, intravenous, subcutaneous, intramuscular, and intratracheal routes. Human systemic effects: somnolence, respiratory depression, low blood pressure, cardiomyopathy includmg infarction, pulse rate increase. An experimental teratogen. Other experimental reproductive effects. A skin and eye irritant. An anesthetic. When heated to decomposition it emits very toxic fumes of NOx and HCl.
Lager
Store in a tightly closed container at room temperature away from light and moisture. Do not store in the bathroom. Do not freeze. Keep all medications away from children and pets.

Lidocaine hydrochloride Upstream-Materialien And Downstream Produkte

Lidocainhydrochlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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