Bupivacaine

Name: Bupivacaine
SKU: B8261
Availability: InStock

Product ID B8261

Cas No. 38396-39-3

Purity ≥99%

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Description

Bupivacaine is an amino amide anesthetic that decreases current amplitude and inhibits whole cell K+ currents in Ca2+-activated (BK/SK) K+ channels and N-type voltage-gated (Kv1/shaker and Kv3 KCNA/KCNC) K+ channels. Bupivacaine also inhibits voltage-gated Na+ channels and tandem pore domain (TASK-2/KCNK-5) K+ channels. Bupivacaine may be neurotoxic at high doses, activating p38 MAPK, increasing levels of ROS and WDR53, and inducing apoptosis in neuroblastoma cells. In other cellular models, bupivacaine induces depolarization of the mitochondrial membrane potential, resulting in apoptosis.

Product Info

Cas No.	38396-39-3
Purity	≥99%
Formula	C₁₈H₂₈N₂O
Formula Wt.	288.43
Chemical Name	1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
IUPAC Name	1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
Melting Point	107-108°C
Solubility	DMF (30 mg/mL), DMSO (50 mg/mL) Ethanol (50mg/mL) Water: Insoluble
Appearance	White to off white powder

Shipping and Storage

Store Temp	Ambient
Ship Temp	Ambient

Downloads

MSDS	B8261 MSDS PDF
Info Sheet	B8261 Info Sheet PDF

References

Harato M, Huang L, Kondo F, et al. Bupivacaine-induced apoptosis independently of WDR35 expression in mouse neuroblastoma Neuro2a cells. BMC Neurosci. 2012 Dec 10;13:149. PMID: 23227925.

Martín P, Enrique N, Palomo AR, et al. Bupivacaine inhibits large conductance, voltage- and Ca2+- activated K+ channels in human umbilical artery smooth muscle cells. Channels (Austin). 2012 May-Jun;6(3):174-80. PMID: 22688134.

Lu J, Xu SY, Zhang QG, et al. Bupivacaine induces apoptosis via mitochondria and p38 MAPK dependent pathways. Eur J Pharmacol. 2011 Apr 25;657(1-3):51-8. PMID: 21315711.

Cela O, Piccoli C, Scrima R, et al. Bupivacaine uncouples the mitochondrial oxidative phosphorylation, inhibits respiratory chain complexes I and III and enhances ROS production: results of a study on cell cultures. Mitochondrion. 2010 Aug;10(5):487-96. PMID: 20546950.

Nilsson J, Madeja M, Elinder F, et al. Bupivacaine blocks N-type inactivating Kv channels in the open state: no allosteric effect on inactivation kinetics. Biophys J. 2008 Dec;95(11):5138-52. PMID: 18790854.

Kindler CH, Paul M, Zou H, et al. Amide local anesthetics potently inhibit the human tandem pore domain background K+ channel TASK-2 (KCNK5). J Pharmacol Exp Ther. 2003 Jul;306(1):84-92. PMID: 12660311.

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Bupivacaine

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