左布比卡因_用途_密度_熔点_左布比卡因CAS号【27262-47-1】

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]。

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[ 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.

[ 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

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

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[ 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%