27262-47-1

• 常用中文名：左布比卡因
• 常用英文名：Levobupivacaine
• CAS号：27262-47-1
• 分子式：C₁₈H₂₈N₂O
• 分子量：288.428
• 相关类别： 信号通路 细胞凋亡 Ferroptosis
• 发布时间：2018-02-23 08:00:00
• 更新时间：2024-01-03 12:13:33
• 左旋布比卡因((S)-(-)-布比卡因)是一种长效酰胺类局部麻醉剂。左旋布比卡因通过可逆阻断神经元钠通道发挥麻醉和镇痛作用。左布比卡因可抑制心血管和其他组织中的脉冲传递和传导,具有一定的心脏和中枢神经系统毒性。左布比卡因在体内由肝细胞色素P450(CYP450)酶代谢。左旋布比卡因还可通过miR-489-3p/SLC7A11信号在胃癌中诱导铁下垂[1][2][3]。

名称

• 中文名: 左布比卡因
• 英文名: levobupivacaine
• 中文别名: 1-丁基-N-(2,6-二甲基苯基)-哌啶-2-甲酰胺; LEVOBUPIVACAINE 左布比卡因; 左旋布比卡因; 左布比咔因
• 英文别名: 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (2S)-; (2S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide; L-(-)-Bupivacaine; 2',6'-Pipecoloxylidide,1-butyl-,L-(-); 1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide; (-)-Bupivacaine; Levobupivacaine; 1-butyl-piperidine-2-carboxylic acid-(2,6-dimethyl-anilide); (S)-(-)-Bupivacaine; (S)-Bupivacaine; (2S)-1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide

物化性质

• 密度: 1.0±0.1 g/cm3
• 沸点: 423.4±45.0 °C at 760 mmHg
• 熔点: 254ºC (dec.)(lit.)
• 分子式: C₁₈H₂₈N₂O
• 分子量: 288.428
• 闪点: 209.9±28.7 °C
• 精确质量: 288.220154
• PSA: 32.34000
• LogP: 3.64
• 外观性状: 白色固体
• 蒸汽压: 0.0±1.0 mmHg at 25°C
• 折射率: 1.547
• 储存条件: 库房通风低温干燥,与食品原料类分开存放

生物活性

• 描述: 左旋布比卡因((S)-(-)-布比卡因)是一种长效酰胺类局部麻醉剂。左旋布比卡因通过可逆阻断神经元钠通道发挥麻醉和镇痛作用。左布比卡因可抑制心血管和其他组织中的脉冲传递和传导,具有一定的心脏和中枢神经系统毒性。左布比卡因在体内由肝细胞色素P450(CYP450)酶代谢。左旋布比卡因还可通过miR-489-3p/SLC7A11信号在胃癌中诱导铁下垂[1][2][3]。
• 相关类别:
  信号通路 >> 跨膜转运 >> 钠通道
  研究领域 >> 癌症
  信号通路 >> 细胞凋亡 >> Ferroptosis
  研究领域 >> 神经疾病
• 靶点:

  Sodium channels, Ferroptosis[1][2]

• 体外研究: 左旋布比卡因(0-4 mM；24小时)不影响GES-1细胞的存活率,但抑制HGC27和SGC7901细胞的存活[2]。左旋布比卡因(2mM；24、48或72小时)增强Erastin诱导的对HGC27和SGC7901细胞活性的抑制作用；诱导Fe2+、铁和脂质ROS的水平[2]。左旋布比卡因(2mM；24h)增强HGC27和SGC7901细胞中miR-489-3p的表达,增加Fe2+和铁的水平[2]。细胞活力测定[2]细胞系：GES-1、HGC27和SGC790浓度：0、0.5、1、2和4 mM孵育时间：24 h结果：不影响正常胃上皮GES-2细胞系的活力,但以剂量依赖性方式抑制HGC27与SGC7901细胞的活力。细胞存活率测定[2]细胞系：HGC27和SGC7901(与5μM erastin孵育)浓度：2mM孵育时间：24、48或72小时结果：erastin对HGC27及SGC791细胞存活率的抑制作用增强；诱导Fe2+、铁和脂质ROS的水平。RT-PCR[2]细胞系：HGC27和SGC7901(与5μM erastin孵育)浓度：2mM孵育时间：24h结果：增强了HGC27细胞和SGC79 01细胞中miR-489-3p的表达,增加了Fe2+和铁的水平。
• 体内研究: 左旋布比卡因(40μmol/kg；IP；每天一次,持续25天)显著抑制SGC7901细胞生长,并增强脂质ROS的积累[2]。左旋布比卡因(5或36 mg/kg；IP；单剂量)增加部分癫痫发作的潜伏期,并在低剂量下防止全身性癫痫发作的发生；降低N-甲基-d-天冬氨酸(NMDA)诱导癫痫发作的潜伏期,并在高剂量下增加癫痫发作的严重程度[3]。动物模型：CD1小鼠(30-35g；通过注射NMDA诱导癫痫发作)[3]剂量：5或36mg/kg给药：IP；单剂量结果：5mg/kg增加了部分癫痫发作的潜伏期,并防止了全身性癫痫发作的发生；降低NMDA诱发癫痫的潜伏期,并增加36mg/kg时的癫痫严重程度。动物模型：SCID裸鼠(6-8周；皮下注射5×106 SGC7901细胞)[2]剂量：40μmol/kg给药：IP；结果：显著抑制SGC7901细胞生长,增强脂质ROS积累。
• 参考文献:

  [1]. Sanford M, et al. Levobupivacaine: a review of its use in regional anaesthesia and pain management. Drugs. 2010 Apr 16;70(6):761-91.

  [2]. Mao SH, et al. Levobupivacaine Induces Ferroptosis by miR-489-3p/SLC7A11 Signaling in Gastric Cancer. Front Pharmacol. 2021 Jun 9;12:681338.

  [3]. Marganella C, et al. Comparative effects of levobupivacaine and racemic bupivacaine on excitotoxic neuronal death in culture and N-methyl-D-aspartate-induced seizures in mice. Eur J Pharmacol. 2005 Aug 22;518(2-3):111-5.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : TK6090000 CHEMICAL NAME : 2',6'-Pipecoloxylidide, 1-butyl-, L-(-)- CAS REGISTRY NUMBER : 27262-47-1 LAST UPDATED : 199112 DATA ITEMS CITED : 7 MOLECULAR FORMULA : C18-H28-N2-O MOLECULAR WEIGHT : 288.48 WISWESSER LINE NOTATION : T6NTJ A4 BVMR B1 F1 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 52 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,273,1972 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 7200 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,273,1972 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 100 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,273,1972 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 9600 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,273,1972 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 9700 ug/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold REFERENCE : APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,273,1972 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Parenteral SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : >120 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 26,78,1976 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intratracheal SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 14 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 26,78,1976

安全

• 危害码 (欧洲): Xn: Harmful;T+: Very toxic;
• 危险品运输编码: UN 2811 6
• 海关编码: 2933399090

海关

海关编码	2933399090
中文概述	2933399090. 其他结构含非稠合吡啶环的化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%
申报要素	品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期
Summary	2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%