Bupivacaine Hydrochloride

Bupivacaine Hydrochloride

Cat Number
API0231667
CAS Number
14252-80-3

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CAS Number
14252-80-3
EINECS
241-917-8
Synonyms
Bupivacaine hydrochloride; Bupivacaine HCl; Marcaine; Sensorcaine
Molecular Formula
C18H29ClN2O
Molecular Weight
324.9
Smiles
CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl
Appearance
White crystalline powder
Melting Point
249-251℃
Boiling Point
423.4℃
General Description
Bupivacaine hydrochloride is the hydrochloride salt formulation of bupivacaine, a potent amide-type local anesthetic widely used for surgical anesthesia and pain management. It appears as a white crystalline powder that is freely soluble in water and alcohol, making it suitable for injectable solutions.
Mechanism of Action
Bupivacaine hydrochloride produces anesthesia by reversibly blocking voltage-gated sodium channels on neuronal cell membranes, thereby preventing the propagation of action potentials along nerve fibers. The hydrochloride salt dissociates in tissues to release the lipophilic bupivacaine base, which penetrates the nerve sheath and axonal membrane to reach its intracellular binding site. This results in a stable, prolonged sensory and motor blockade due to the drug's slow dissociation from sodium channels, particularly in cardiac tissue.
Application
Bupivacaine hydrochloride is indicated for local infiltration, peripheral nerve blocks, epidural anesthesia, and spinal anesthesia for surgical procedures and postoperative pain control. It is particularly valued for prolonged analgesia in obstetrics and orthopedic surgery due to its extended duration of action.

Chen H, et al. investigated whether bupivacaine, a local anesthetic associated with cardiotoxicity, inhibits small-conductance calcium-activated potassium type 2 (SK2) channels, which are expressed in cardiac tissue and contribute to physiological function. The half-maximal inhibitory concentration (IC50) for bupivacaine was 16.5 μM, indicating it is a more potent inhibitor than ropivacaine (46.5 μM) or lidocaine (77.8 μM). The extent of inhibition was also dependent on intracellular calcium concentrations.

Fig. 1 Inhibitory effect of bupivacaine on SK2 currents was reversible. (Chen H, <i>et al</i>., 2017) Fig. 1 Inhibitory effect of bupivacaine on SK2 currents was reversible. (Chen H, et al., 2017)

References

  1. Chen H, et al. Bupivacaine inhibits a small conductance calcium-activated potassium type 2 channel in human embryonic kidney 293 cells. BMC Pharmacol Toxicol. 2021;22(1):15.

Pedoto A, et al. compared the analgesic efficacy of liposomal bupivacaine versus standard bupivacaine hydrochloride for intercostal nerve blockade in 60 patients undergoing minimally invasive thoracic surgery lobectomy. All patients received multimodal analgesia including intravenous patient-controlled analgesia postoperatively. No statistically significant differences were observed between groups in perioperative opioid consumption, pain scores at any time point, Richmond Agitation-Sedation Scale scores, or lengths of post-anesthesia care unit and hospital stay.

Fig. 2 Postoperative total morphine equivalents (intravenous plus oral) use at 12-h intervals for 72 h. B-HCl, bupivacaine hydrochloride; Lipo-B, liposomal bupivacaine. (Pedoto A, <i>et al</i>, 2021) Fig. 2 Postoperative total morphine equivalents (intravenous plus oral) use at 12-h intervals for 72 h. B-HCl, bupivacaine hydrochloride; Lipo-B, liposomal bupivacaine. (Pedoto A, et al, 2021)

References

  1. Pedoto A, et al. Liposomal Bupivacaine Versus Bupivacaine Hydrochloride for Intercostal Nerve Blockade in Minimally Invasive Thoracic Surgery. J Cardiothorac Vasc Anesth. 2021;35(5):1393-1398.

Can Bupivacaine Hydrochloride be stored in plastic containers?

The solid API is stable in approved pharmaceutical-grade plastic containers. For solutions, we recommend glass or specific polymers to avoid leaching or adsorption issues.

Does Bupivacaine Hydrochloride retain stability under tropical climate conditions?

Yes, it exhibits good intrinsic stability. For shipments to tropical zones, we use insulated packaging to mitigate any risk of thermal degradation during transit.

What is the pH range of a typical Bupivacaine Hydrochloride solution?

A 1% aqueous solution of our Bupivacaine Hydrochloride typically has a pH between 4.5 and 6.0, which is optimal for maintaining chemical stability and patient comfort.

How is the absence of related impurities verified in Bupivacaine Hydrochloride?

We employ a high-resolution HPLC method to quantify the 2,6-dimethylaniline impurity, a key degradation marker, ensuring it is consistently below pharmacopoeial limits.
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