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メピバカイン

Mepivacaine

HCID 4062
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
96-88-8
標準SMILES
Cc1cccc(C)c1NC(=O)C1CCCCN1C
InChIKey
INWLQCZOYSRPNW-UHFFFAOYSA-N
分子式
C15H22N2O
平均分子量
246.35 g/mol
単同位体質量
246.17321332

概要

Mepivacaine is a piperidinecarboxamide in which N-methylpipecolic acid and 2,6-dimethylaniline have combined to form the amide bond. It is used as a local amide-type anaesthetic. It has a role as a local anaesthetic and a drug allergen.

名称と識別子

優先名称
Mepivacaine
IUPAC
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
現地名
メピバカイン
英語名
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
分子式
C15H22N2O
分子量
246.35

名称と別名

mepivacaine96-88-8N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamideDL-MepivacaineScandicaineMepivacainaMepivacainumtevacaine2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl-Carboplyin Dental2',6'-Pipecoloxylidide, 1-methyl-Mepisv
名称をさらに表示
スカンジカインN-(2,6-ジメチルフェニル)-1-メチルピペリジン-2-カルボキサミドN-(2,6-ジメチルフェニル)-1-メチル-2-ピペリジンカルボキサミド1-メチル-N-(2,6-ジメチルフェニル)-2-ピペリジンカルボアミドカルボカインN-(2,6-ジメチルフェニル)-1-メチル-2-ピペリジンカルボアミドメピバカインCarbocaineC07528CarbocainPolocaineMepicaineScandicainMepivacaine, 10 mM in DMSO
N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide(+-)-1-Methyl-2',6'-pipecoloxylidide1-METHYL-2',6'-PIPECOLOXYLIDIDEB6E06QE59JCHEBI:6759APF-135DTXSID90232595-22-01-00223 (Beilstein Handbook Reference)

物性

構造計算による物性

XLogP
1.9
極性表面積
32.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
2
重原子数
18
形式電荷
0
複雑度
282

実験および物理化学的性質

DrugsPharmaceuticals
LogP · 2 件

2.2

2.11

Solubility6.21e-01 g/L
Human Drugs · 2 件

Breast Feeding; Lactation; Anesthetics, Local

Pharmaceuticals

Melting Point150.5 °C
Physical DescriptionSolid
Dissociation Constants7.7
Collision Cross Section · 2 件

156.66 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

159.1 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

物理化学的性質

融点
150 · 150-151°
沸点
389.35 °C · 389.35°C (rough estimate)
比重(密度)
0.9978 · 0.9978 (rough estimate)
屈折率

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 3 (100%)

毒性情報

Treatment · 1 件

Treatment of a patient with toxic manifestations consists of assuring and maintaining a patient airway and supporting ventilation (respiration) as required. This usually will be sufficient in the management of most reactions. Should a convulsion persist despite ventilatory therapy, small increments of anticonvulsive agents may be given intravenously, such as benzodiazephine (e.g., diazepam) or ultrashort-acting barbiturates (e.g., thiopental or thiamylal) or short-acting barbiturates (e.g., pentobarbital or secobarbital). Cardiovascular depression may require circulatory assistance with intravenous fluids and/or vasopressor (e.g., Ephedrine) as dictated by the clinical situation. (L1712)

Exposure Routes · 1 件

Absorbed locally. The rate of systemic absorption of local anesthetics is dependent upon the total dose and concentration of drug administered, the route of administration, the vascularity of the administration site, and the presence or absence of epinephrine in the anesthetic solution. Subcutaneous, injection ; Infiltration

Toxicity Summary · 1 件

Local anesthetics block the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. In general, the progression of anesthesia is related to the diameter, myelination, and conduction velocity of affected nerve fibers. Clinically, the order of loss of nerve function is as follows: pain, temperature, touch, proprioception, and skeletal muscle tone.

化学と産業

薬理情報

ATC Code · 3 件

N01BB03

N - Nervous system

QN - Nervous system

Protein BindingMepivacaine is approximately 75% bound to plasma proteins. Generally, the lower the plasma concentration of drug, the higher the percentage of drug bound to plasma.
Pharmacodynamics · 1 件

Mepivicaine is an amide local anesthetic. Mepivicaine as a reasonably rapid onset and medium duration and is known by the proprietary names as Carbocaine and Polocaine. Mepivicaine is used in local infiltration and regional anesthesia. Systemic absorption of local anesthetics produces effects on the cardiovascular and central nervous systems. At blood concentrations achieved with normal therapeutic doses, changes in cardiac conduction, excitability, refractoriness, contractility, and peripheral vascular resistance are minimal.

Mechanism of Action · 1 件

Local anesthetics block the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. In general, the progression of anesthesia is related to the diameter, myelination, and conduction velocity of affected nerve fibers. Clinically, the order of loss of nerve function is as follows: pain, temperature, touch, proprioception, and skeletal muscle tone.

Biological Half-LifeThe half-life of mepivacaine in adults is 1.9 to 3.2 hours and in neonates 8.7 to 9 hours.
Metabolism/Metabolites · 2 件

Rapidly metabolized, with only a small percentage of the anesthetic (5 percent to 10 percent) being excreted unchanged in the urine. The liver is the principal site of metabolism, with over 50% of the administered dose being excreted into the bile as metabolites.

Rapidly metabolized, with only a small percentage of the anesthetic (5 percent to 10 percent) being excreted unchanged in the urine. The liver is the principal site of metabolism, with over 50% of the administered dose being excreted into the bile as metabolites. Route of Elimination: It is rapidly metabolized, with only a small percentage of the anesthetic (5 percent to 10 percent) being excreted unchanged in the urine.The liver is the principal site of metabolism, with over 50% of the administered dose being excreted into the bile as metabolites. Half Life: The half-life of mepivacaine in adults is 1.9 to 3.2 hours and in neonates 8.7 to 9 hours.

関連反応

2 件
反応記録を作成
HRID 2273578 の反応式
HRID 2273578生成物としてuspto-grants-2015_09
HRID 2273579 の反応式
HRID 2273579生成物としてuspto-grants-2015_09

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
96-88-8
PubChem CID
4062
DTXSID
DTXSID9023259
ChEMBL
CHEMBL1087
ChEBI
CHEBI:6759
UNII
B6E06QE59J
EC Number
202-543-0
Nikkaji
J4.726K
1.628 · 1.6280 (estimate)
貯蔵温度
-20 °C · Store at -20°C
溶解性
30 mg/ml; · DMF: 30 mg/ml; DMSO: 25 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
外見
A crystalline solid
酸解離定数(Pka)
14.85 · 14.85±0.70(Predicted)
色
White to off-white
水溶解度
2.217 g/L · 2.217g/L(25℃)
EPAの化学物質情報
2 · 2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl- (96-88-8)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

mepivacaine

DILI Negative

Subcutaneous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataThe mean seizure dosage of mepivacaine in rhesus monkeys was found to be 18.8 mg/kg with mean arterial plasma concentration of 24.4 µg/mL. LD50: 23-35 mg/kg (Intravenous, Mouse) (A308) LD50: 280 mg/kg (Subcutaneous, Mouse (A308)

安全データ

tsca
TSCA listed
FDA Pharmacological Classification · 6 件

B6E06QE59J

MEPIVACAINE

Established Pharmacologic Class [EPC] - Amide Local Anesthetic

Chemical Structure [CS] - Amides

Physiologic Effects [PE] - Local Anesthesia

Mepivacaine is an Amide Local Anesthetic. The physiologic effect of mepivacaine is by means of Local Anesthesia.

MeSH Pharmacological Classification · 1 件

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.

Absorption, Distribution and Excretion · 2 件

Absorbed locally. The rate of systemic absorption of local anesthetics is dependent upon the total dose and concentration of drug administered, the route of administration, the vascularity of the administration site, and the presence or absence of epinephrine in the anesthetic solution.

It is rapidly metabolized, with only a small percentage of the anesthetic (5 percent to 10 percent) being excreted unchanged in the urine.The liver is the principal site of metabolism, with over 50% of the administered dose being excreted into the bile as metabolites.

Cellular LocationsExtracellular
Metabolite PathwaysMepivacaine Action Pathway

用途と製造

Uses · 2 件

Use (kg; approx.) in Germany (2009): >1000

For production of local or regional analgesia and anesthesia by local infiltration, peripheral nerve block techniques, and central neural techniques including epidural and caudal blocks.

Use ClassificationPharmaceuticals
General Manufacturing Information2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl-: ACTIVE

応用分野

解説メピバカイン.2,6-ジメチルアニリンとN-メチルピペコリン酸エチルとを縮合させてつくる.白色の結晶.融点150~151 ℃.味は苦く舌を麻ひさせる.塩酸塩は分解点262~264 ℃.水,メタノールに可溶.帝王切開手術などの局所麻酔剤で,0.5~3% 溶液が注射剤として用いられる.LD50 280 mg/kg(マウス,皮下).

使用Anesthetic (local).

上流・下流製品情報

上流原料

硝酸マグネシウム·6水和物4-ブロモ-2,6-ジメチルアニリン2,6-ジメチルアニリンブロモエタン

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補足説明

定義ChEBI: A piperidinecarboxamide in which N-methylpipecolic acid and 2,6-dimethylaniline have combined to form the amide bond. It is used as a local amide-type anaesthetic.