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リドカイン

リドカイン 化学構造式
137-58-6
CAS番号.
137-58-6
化学名:
リドカイン
别名:
リドカイン;ズンカイン;オリベス;ユーパッチ;2-(ジエチルアミノ)-N-(2,6-ジメチルフェニル)アセトアミド;イシカイナ;ペンレス;マリカイン;フリードカイン;リグノカイン;メドカイン;ソルカイン;2-ジエチルアミノ-2',6'-ジメチルアセトアニリド;キシロシチン;ルカイナ;リオカイン;レオステシン;パートラン;プロリフェロール;アネトカイン
英語化学名:
Lidocaine
英語别名:
Xilina;Xllina;Xyline;Rucaina;Solcain;Xycaine;Xylotox;Anbesol;L-Caine;Mesocain
CBNumber:
CB9128024
化学式:
C14H22N2O
分子量:
234.34
MOL File:
137-58-6.mol

リドカイン 物理性質

融点 :
66-69°C
沸点 :
bp4 180-182°; bp2 159-160°
比重(密度) :
0.9944 (rough estimate)
屈折率 :
1.5110 (estimate)
闪点 :
9℃
貯蔵温度 :
Store at RT
溶解性:
ethanol: 4 mg/mL
外見 :
powder
酸解離定数(Pka):
pKa 7.88(H2O)(Approximate)
色:
White to slightly yellow
水溶解度 :
practically insoluble
Merck :
14,5482
安定性::
Stable. Incompatible with strong oxidizing agents.
InChIKey:
NNJVILVZKWQKPM-UHFFFAOYSA-N
CAS データベース:
137-58-6(CAS DataBase Reference)
NISTの化学物質情報:
Lidocaine(137-58-6)
EPAの化学物質情報:
Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)- (137-58-6)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xn,T,F
Rフレーズ  22-39/23/24/25-23/24/25-11
Sフレーズ  22-26-36-45-36/37-16-7
RIDADR  3249
WGK Germany  3
RTECS 番号 AN7525000
国連危険物分類  6.1(b)
容器等級  III
HSコード  29242990
有毒物質データの 137-58-6(Hazardous Substances Data)
毒性 LD50 oral in rat: 317mg/kg
化審法 (3)-273, (9)-1510
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H225 引火性の高い液体および蒸気 引火性液体 2 危険 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H302 飲み込むと有害 急性毒性、経口 4 警告 P264, P270, P301+P312, P330, P501
H370 臓器の障害 特定標的臓器有害性、単回暴露 1 危険 P260, P264, P270, P307+P311, P321,P405, P501
注意書き
P210 熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。
P260 粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ と。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P301+P310 飲み込んだ場合:直ちに医師に連絡すること。
P311 医師に連絡すること。

リドカイン 価格 もっと(37)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01COBQA-3221 リドカイン
Lidocaine
137-58-6 5g ¥3600 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01COBQA-3221 リドカイン
Lidocaine
137-58-6 25g ¥7200 2021-03-23 購入
東京化成工業 L0156 リドカイン >99.0%(HPLC)(T)
Lidocaine >99.0%(HPLC)(T)
137-58-6 25g ¥5100 2021-03-23 購入
東京化成工業 L0156 リドカイン >99.0%(HPLC)(T)
Lidocaine >99.0%(HPLC)(T)
137-58-6 100g ¥14300 2021-03-23 購入
関東化学株式会社(KANTO) 13725-1A 2‐(ジエチルアミノ)‐N‐(2,6‐ジメチルフェニル)アセトアミド 97.5%
2‐(Diethylamino)‐N‐(2,6‐dimethylphenyl)acetamide 97.5%
137-58-6 10g ¥4600 2021-03-23 購入

リドカイン MSDS


Xylocaine

リドカイン 化学特性,用途語,生産方法

外観

白色〜わずかにうすい黄色, 結晶〜結晶性粉末

溶解性

エタノール、クロロホルムに易溶、エーテル、オリーブ油、ゴマ油に可溶。水に不溶。

解説

2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide.C14H22N2O(234.34).リグノカインともいう.2,6-ジメチルアニリンにモノクロロ酢酸クロリド,ジエチルアミンを順次縮合させて合成する."融点68~69 ℃,沸点159~160 ℃(266 Pa).水に不溶,エタノールに可溶.表面麻酔および脊椎麻酔作用があり,プロカインの数倍の強さを示す.塩酸塩(融点127~129 ℃)は作用発現が迅速で持続時間も長いことから,注射用局所麻酔に使用される.LD50 292 mg/kg(マウス,経口).[CAS 137-58-6]
森北出版「化学辞典(第2版)

用途

ナトリウム透過性抑制作用を 示します。

用途

ナトリウム透過性抑制作用を 示します。

用途

局所麻酔剤、抗不整脈剤

用途

神経化学研究用。

用途

薬理・生理作用研究用。

効能

表面麻酔薬, 抗不整脈薬, ナトリウムチャネル遮断薬

商品名

ペンレス (日東電工)

説明

Lidocaine [2-(diethylamino)-N-(2, 6-dimethylphenyl) acetamide monohydrochloride] is the most commonly used amino amide-type local anesthetic. Lidocaine is very lipid soluble and, thus, has a more rapid onset and a longer duration of action than most amino ester-type local anesthetics, such as procaine and tetracaine. It can be administered parenterally (with or without epinephrine) or topically either by itself or in combination with prilocaine or etidocaine as a eutectic mixture that is very popular with pediatric patients. The use of lidocaine–epinephrine mixtures should be avoided, however, in areas with limited vascular supply to prevent tissue necrosis. Lidocaine also frequently is used as a class IB antiarrhythmic agent for the treatment of ventricular arrhythmias, both because it binds and inhibits sodium channels in the cardiac muscle and because of its longer duration of action than amino ester-type local anesthetics.
Central nervous system changes are the most frequently observed systemic toxicities of lidocaine. The initial manifestations are restlessness, vertigo, tinnitus, slurred speech, and eventually, seizures. Subsequent manifestations include CNS depression with a cessation of convulsions and the onset of unconsciousness and respiratory depression or cardiac arrest. This biphasic effect occurs because local anesthetics initially block the inhibitory GABAergic pathways, resulting in stimulation, and eventually block both inhibitory and excitatory pathways (i.e., block the sodium channels associated with the NMDA receptors, resulting in overall CNS inhibition).

化学的特性

solid

Originator

Xylocaine,Astra,US,1949

使用

Lidocaine is used in creams and lotions to soothe areas of inflamed skin or for example in hemorrhoid preparations to reduce discomfort; used by doctors to anesthetise areas prior to surgery, often avoiding the need for a general anesthetie; used by injection after a heart attack to treat some rhythm disturbances.

使用

Lidocaine (Alphacaine)is a selective inverse peripheral histamine H1-receptor agonist with an IC50 of >32 μM. [1] Histamine is responsible for many features of allergic reactions. Lidocaine (Alphacaine)is a second-generation antihistamine agent closely st

使用

Antiarrhythmic Agents, Anesthetics;Anticonvulsant;antihypertensive

定義

ChEBI: The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.

適応症

Experimentally, lidocaine has been found to prevent VF arising during myocardial ischemia or infarction by preventing the fragmentation of organized largewavefronts into heterogeneous wavelets. Although lidocaine is of proven benefit in preventing VF early after clinical myocardial infarction, there is no evidence that it reduces mortality. To the contrary, lidocaine may increase mortality after myocardial infarction by approximately 40% to 60%.There are no controlled studies of lidocaine in secondary prevention of recurrence of VT or VF.
Lidocaine terminates organized monomorphic spontaneous VT or induced sustained VT in only approximately 20% of cases and is less effective than many other antiarrhythmic drugs. In a blinded, randomized study of intravenous lidocaine versus intravenous amiodarone in out-of-hospital VF resistant to defibrillation, lidocaine was associated with half the likelihood of survival to hospital admission compared with amiodarone.

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.)

brand name

Alphacaine (Carlisle); Lidoderm (Teikoku); Xylocaine (AstraZeneca).

Therapeutic Function

Local anesthetic, Antiarrhythmic

一般的な説明

Lidocaine was the first amino amide synthesized in 1948and has become the most widely used local anesthetic. Thetertiary amine has a pKa of 7.8 and it is formulated as thehydrochloride salt with a pH between 5.0 and 5.5. When lidocaineis formulated premixed with epinephrine the pH ofthe solution is adjusted to between 2.0 and 2.5 to prevent the hydrolysis of the epinephrine. Lidocaine is also availablewith or without preservatives. Some formulations of lidocainecontain a methylparaben preservative that maycause allergic reactions in PABA-sensitive individuals. Thelow pKa and medium water solubility provide intermediateduration of topical anesthesia of mucous membranes.Lidocaine can also be used for infiltration, peripheral nerveand plexus blockade, and epidural anesthesia.

生物活性

Anasthetic and class Ib antiarrhythmic agent.? Blocks voltage-gated sodium channels in the inactivated state.

接触アレルゲン

Lidocaine is an anesthetic of the amide group, like articaine or bupivacaine. Immediate-type IgE-dependent reactions are rare, and delayed-type contact dermatitis is exceptional. Cross-reactivity between the different amide anesthetics is not systematic.

Biochem/physiol Actions

Na+ channel blocker; class IB antiarrhythmic that is rapidly absorbed after parenteral administration.

薬物動態学

Lidocaine is administered intravenously because extensive first-pass transformation by the liver prevents clinically effective plasma concentrations orally. The drug is dealkylated and eliminated almost entirely by the liver; therefore, dosage adjustments are necessary in the presence of hepatic disease or dysfunction. Lidocaine clearance exhibits the time dependency common to high-clearance agents. With a continuous infusion lasting more than 24 hours, there is a decrease in total lidocaine clearance and an increase in elimination half-life compared with a single dose. Lidocaine free plasma levels can vary in certain patients owing to binding with albumin and the acutephase reactant a1-acid glycoprotein. Levels of a1-acid glycoprotein are increased in patients after surgery or acute myocardial infarction, whereas levels of both a1-acid glycoprotein and serum albumin are decreased in chronic hepatic disease or heart failure and in those who are malnourished. This is an essential consideration because it is the unbound fraction that is pharmacologically active.

臨床応用

The metabolism of lidocaine is typical of the amino amideanesthetics . The liver is responsiblefor most of the metabolism of lidocaine and any decreasein liver function will decrease metabolism. Lidocaineis primarily metabolized by de-ethylation of the tertiary nitrogento form monoethylglycinexylidide (MEGX). At lowlidocaine concentrations, CYP1A2 is the enzyme responsiblefor most MEGX formation. At high lidocaine concentrations,both CYP1A2 and CYP3A4 are responsible for the formationof MEGX.

副作用

Central nervous system side effects such as drowsiness, slurred speech, paresthesias, agitation, and confusion predominate. These symptoms may progress to convulsions and respiratory arrest with higher plasma concentrations. A rare adverse effect is malignant hyperthermia.
Cimetidine significantly reduces the systemic clearance of lidocaine as well as the volume of distribution at steady state and the degree of plasma protein binding. Beta blockers also reduce lidocaine clearance owing to a decrease in hepatic blood flow. For the same reason, clearance is reduced in congestive heart failure or low-output states.
Amiodarone may also influence the pharmacokinetics of lidocaine. In patients receiving amiodarone, single doses of intravenous lidocaine do not influence the pharmacokinetics of either agent. When amiodarone treatment is started in patients who are already receiving lidocaine infusion, there is a decrease in lidocaine clearance, which can result in toxic lidocaine levels.

安全性プロファイル

Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human systemic effects: blood pressure lowering, changes in heart rate, coma, convulsions, dlstorted perceptions, dyspnea, excitement, hallucinations, muscle contraction or spasticity, pulse rate, respiratory depression, toxic psychosis. An experimental teratogen. Other experimental reproductive effects. A local anesthetic. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Chemical Synthesis

Lidocaine, 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide (2.2.2), is synthesized from 2,6-dimethylaniline upon reaction with chloroacetic acid chloride, which gives α-chloro-2,6-dimethylacetanilide (2.1.1), and its subsequent reaction with diethylamine [11].

Veterinary Drugs and Treatments

Besides its use as a local and topical anesthetic agent, lidocaine is used to treat ventricular arrhythmias, principally ventricular tachycardia and ventricular premature complexes in all species. Cats may be more sensitive to the drug and some clinicians feel that it should not be used in this species as an antiarrhythmic, but this remains controversial. In horses, lidocaine may be useful to prevent postoperative ileus and reperfusion injury.

電気生理学的効果

Experimentally, lidocaine has been found to prevent VF arising during myocardial ischemia or infarction by preventing the fragmentation of organized largewavefronts into heterogeneous wavelets. Although lidocaine is of proven benefit in preventing VF early after clinical myocardial infarction, there is no evidence that it reduces mortality. To the contrary, lidocaine may increase mortality after myocardial infarction by approximately 40% to 60%.There are no controlled studies of lidocaine in secondary prevention of recurrence of VT or VF.
Lidocaine terminates organized monomorphic spontaneous VT or induced sustained VT in only approximately 20% of cases and is less effective than many other antiarrhythmic drugs. In a blinded, randomized study of intravenous lidocaine versus intravenous amiodarone in out-of-hospital VF resistant to defibrillation, lidocaine was associated with half the likelihood of survival to hospital admission compared with amiodarone.

薬物相互作用

The concurrent administration of lidocaine with cimetidine but not ranitidine may cause an increase (15%) in the plasma concentration of lidocaine. This effect is a manifestation of cimetidine reducing the clearance and volume of distribution of lidocaine. The myocardial depressant effect of lidocaine is enhanced by phenytoin administration.

代謝

Lidocaine is extensively metabolized in the liver by N-dealkylation and aromatic hydroxylations catalyzed by CYP1A2 isozymes. Lidocaine also possesses a weak inhibitory activity toward the CYP1A2 isozymes and, therefore, may interfere with metabolism of other medications.

Toxicity evaluation

The potency of lidocaine depends on various factors including age of the subject, weight, physique including obesity, vascularity of the site, and indication for use, as this would determine the absorption and excretion rate. Physiologically, lidocaine blocks neuronal transmission by interfering with the flow of sodium across excitable membranes. A single lidocaine molecule binds to a single voltage-gated sodium channel impeding the movement of sodium ions across neuronal membranes. Consequently repolarization is prevented and further depolarization is not possible. Toxicity is dose related and results from excessive quantities of lidocaine.

予防処置

Contraindications include hypersensitivity to local anesthetics of the amide type (a very rare occurrence), severe hepatic dysfunction, a history of grand mal seizures due to lidocaine, and age 70 or older. Lidocaine is contraindicated in the presence of second- or thirddegree heart block, since it may increase the degree of block and can abolish the idioventricular pacemaker responsible for maintaining the cardiac rhythm.

リドカイン 上流と下流の製品情報

原材料

準備製品


リドカイン 生産企業

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137-58-6(リドカイン)キーワード:


  • 137-58-6
  • 2-(Diethylamino)-2',6'-acetoxylidide
  • 2-(diethylamino)-2’,6’-acetoxylidide
  • 2-(diethylamino)-n-(2,6-dimethylphenyl)-acetamid
  • 2',6'-Acetoxylidide, 2-(diethylamino)-
  • 6’-acetoxylidide,2-(diethylamino)-2
  • Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)-
  • Ligoncaine
  • Maricaine
  • Mesocain
  • N-Di-ethylaminoacetyl-2,6-dimethylaniline
  • Alphacaine
  • Lidocaine solution
  • omega-Diethylamino-2,6-dimethylacetanilide
  • Remicaine
  • Rucaina
  • Solarcaine aloe extra burn relief cream
  • Solcain
  • Xilina
  • Xilocaina
  • Xllina
  • Xycaine
  • Xylestesin
  • Xyline
  • Xylocain
  • Xylocitin
  • Xyloneural (free base)
  • Xylotox
  • BULK DRUGS. LIDOCAINE USP
  • Lidocaine base BP98 USP24
  • IN STOCK LIDOCAINE CAS 137-58-6
  • リドカイン
  • ズンカイン
  • オリベス
  • ユーパッチ
  • 2-(ジエチルアミノ)-N-(2,6-ジメチルフェニル)アセトアミド
  • イシカイナ
  • ペンレス
  • マリカイン
  • フリードカイン
  • リグノカイン
  • メドカイン
  • ソルカイン
  • 2-ジエチルアミノ-2',6'-ジメチルアセトアニリド
  • キシロシチン
  • ルカイナ
  • リオカイン
  • レオステシン
  • パートラン
  • プロリフェロール
  • アネトカイン
  • N-(2,6-ジメチルフェニル)-Nα,Nα-ジエチルグリシンアミド
  • イシカイン
  • キシロカイン
  • キシカイン
  • N-(2,6-ジメチルフェニル)-2-(ジエチルアミノ)アセトアミド
  • グラボカイン
  • キシロカインビスカス
  • キシレステシン
  • 2-ジエチルアミノ-N-(2,6-ジメチルフェニル)アセトアミド
  • 2‐(ジエチルアミノ)‐N‐(2,6‐ジメチルフェニル)アセトアミド
  • N1-(2,6-ジメチルフェニル)-N2,N2-ジエチルグリシンアミド
  • リドカイン, 結晶
  • リドカイン (JP17)
  • 生化学
  • 薬理研究用試薬
  • 医薬農薬成分(その他)
  • 歯科用薬
  • 局所麻酔薬
  • 抗不整脈薬
  • 口腔用薬
  • 眼科用薬
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