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    Bupivacaine HCl (HSDB 7790)
    Bupivacaine HCl (HSDB 7790)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1642
    CAS #: 18010-40-7Purity ≥98%

    Description: Bupivacaine HCl (AH-250; HSDB 7790; SKY 0402) is a potent inhibitor of cAMP production that also binds to the intracellular portion of voltage-gated sodium channels and blocks sodium influx into nerve cells. Bupivacaine is a medication used to freeze tissue in a specific area. It is administered by injecting it into the area, around a nerve that supplies the area, or into the spinal canal's epidural space. It is available mixed with a small amount of epinephrine to make it last longer. Bupivacaine binds to the intracellular portion of voltage-gated sodium channels and blocks sodium influx into nerve cells, which prevents depolarization.

    References: Arthroscopy. 2006 Jul;22(7):693-9; Anesthesiology. 2002 Sep;97(3):710-6.

    Related CAS #: 18010-40-7 (HCl)   2180-92-9 (free base)  

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    Molecular Weight (MW)324.89
    FormulaC18H28N2O.HCl
    CAS No.18010-40-7
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 65 mg/mL (200.1 mM)
    Water: 23 mg/mL (70.8 mM)
    Ethanol: 65 mg/mL (200.1 mM)
    Other info

    Chemical Name: 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride

    InChi Key: SIEYLFHKZGLBNX-UHFFFAOYSA-N

    InChi Code: InChI=1S/C18H28N2O.ClH/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H

    SMILES Code: O=C(C1N(CCCC)CCCC1)NC2=C(C)C=CC=C2C

    Synonyms

    Marcaine; AH-250; AH 250; AH250; HSDB 7790; HSDB7790; HSDB-7790; SKY 0402; SKY0402, SKY-0402; Win-11318; Win 11318; Win11318


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    In Vitro

    In vitro activity:  Bupivacaine solution is cytotoxic to bovine articular chondrocytes and articular cartilage in vitro after only 15 to 30 minutes exposure. Bupivacaine acts in isolated mitochondria, as uncouplers between oxygen consumption and phosphorylation of adenosine diphosphate. 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.  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. Bupivacaine HCl also potently inhibits cAMP production with an IC50 of 2.3 μM.

    In VivoBupivacaine 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.
    Animal modelRats
    Formulation & Dosage
    References

    Arthroscopy. 2006 Jul;22(7):693-9; Anesthesiology. 2002 Sep;97(3):710-6.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

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