Bupivacaine HCl

Catalog No.S2454

Bupivacaine HCl  Chemical Structure

Molecular Weight(MW): 324.89

Bupivacaine HCl binds to the intracellular portion of voltage-gated sodium channels and blocks sodium influx into nerve cells, used for treating cardiac arrhythmias.

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In DMSO USD 130 In stock
USD 97 In stock
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Biological Activity

Description Bupivacaine HCl binds to the intracellular portion of voltage-gated sodium channels and blocks sodium influx into nerve cells, used for treating cardiac arrhythmias.
Targets
Sodium channel [4]
In vitro

Bupivacaine solution is cytotoxic to bovine articular chondrocytes and articular cartilage in vitro after only 15 to 30 minutes exposure. [1] Bupivacaine acts in isolated mitochondria, as uncouplers between oxygen consumption and phosphorylation of adenosine diphosphate. [2] Bupivacaine causes a concentration-dependent mitochondrial depolarization and pyridine nucleotide oxidation in isolated mitochondria, which are matched by an increased oxygen consumption at bupivacaine concentrations of 1.5 mm or less at pH 7.4, whereas respiration is inhibited at higher concentrations. Bupivacaine causes the opening of the permeability transition pore (PTP), a cyclosporin A-sensitive inner membrane channel that plays a key role in many forms of cell death. Bupivacaine causes mitochondrial depolarization and pyridine nucleotides oxidation that are matched by increased concentrations of cytosolic free Ca(2+), release of cytochrome c, and eventually, hypercontracture in intact flexor digitorum brevis fibers. [3] Bupivacaine inhibits GIRK channels within seconds of application, regardless of whether channels are activated through the muscarinic receptor or directly via coexpressed G protein G(beta)gamma subunits. Bupivacaine also inhibits alcohol-induced GIRK currents in the absence of functional pertussis toxin-sensitive G proteins. [4] Bupivacaine HCl also potently inhibits cAMP production with an IC50 of 2.3 μM.[6]

In vivo Bupivacaine does not only induce Ca2+ release from the sarcoplasmic reticulum (SR) in rats, but also inhibits Ca2+ uptake by the SR, which is mainly regulated by SR Ca2+ adenosine triphosphatase activity. [5]

Protocol

Solubility (25°C)

In vitro DMSO 65 mg/mL (200.06 mM)
Ethanol 65 mg/mL (200.06 mM)
Water 23 mg/mL (70.79 mM)

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 324.89
Formula

C18H28N2O.HCl

CAS No. 18010-40-7
Storage powder
in solvent
Synonyms N/A

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Clinical Trial Information

NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT03553576 Not yet recruiting Drug: Low volume bolus|Drug: High volume bolus Pain|Anesthesia|Labor Pain Northwestern University December 1 2019 Phase 4
NCT04083768 Not yet recruiting Device: 15° and 30° wedge sponges Elective Cesarean Section|Spinal Anesthesia Xuzhou Medical University October 1 2019 Not Applicable
NCT03920904 Recruiting Other: Collection of blood samples Pharmacokinetics Centre hospitalier de l''Université de Montréal (CHUM) July 29 2019 --

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Sodium Channel Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID