Levobupivacaine HCl

Catalog No.S4061 Synonyms: (S)-(-)-Bupivacaine HCl

For research use only.

Levobupivacaine HCl ((S)-(-)-Bupivacaine), the pure S(-)-enantiomer of bupivacaine, is a reversible neuronal sodium channel inhibitor, used as a long-acting local anesthetic.

Levobupivacaine HCl Chemical Structure

CAS No. 27262-48-2

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Biological Activity

Description Levobupivacaine HCl ((S)-(-)-Bupivacaine), the pure S(-)-enantiomer of bupivacaine, is a reversible neuronal sodium channel inhibitor, used as a long-acting local anesthetic.
Targets
Sodium Channel [1]
In vitro

Levobupivacaine is an amide-type local anaesthetic. Levobupivacaine acts via blockade of voltage-sensitive ion channels in neuronal membranes, preventing transmission of nerve impulses. Localised and reversible anaesthesia is produced by interference with the opening of the sodium channel, which inhibits conduction of the action potential in nerves involved in sensory and motor activity and sympathetic activity. [1] Levobupivacaine displaces 3H-BTX from sodium channels of rat brain synaptosomes with IC50 of 2.9 μM and Hill coefficients of 1.2. When cell membrane is held at -80 mV, -70 mV, -60 mV or -100 mV, Levobupivacaine shows tonic inhibition of sodium channel in GH3 cells with IC50s of 132.1, 37.6, 21.6 and 264 μM, respectively. [2] Levobupivacaine depresses action potential of isolated axon in vitro. Levobupivacaine (1mM) depresses action potential amplitude and maximal rate of rise of action potential (dV/dtmax) in the crayfish giant axons with value of 88 and 81 respectively, after perfusion for 15 min. [3] Levobupivacaine also displays activity on cardiac ion channels. In isolated ventricular myocytes, the apparent affinity for inactivated state of the sodium channel is 4.8 μM for Levobupivacaine, with a calculated KD of 39μM. On inhibition of cardiac delayed rectifier potassium channels (hKv1.5), the steady-state block for Levobupivacaine (20 μM) is 31%, with a calculated KD of 27.3 μM. Levobupivacaine may also inhibit cardiac calcium channels. 10 μM Levobupivacaine produces a 50% decrease in contractile force of guinea-pig papillary muscles. [4]

In vivo Levobupivacaine has similar nerve blocking potency with bupivacaine. Levobupivacaine at a dose of 0.125%, inhibits motor and nocifensive pinch responses with maximum %MPE of 99 and 68 respectively, and inhibits the duration of deficits of motor and nocifensive pinch responses (60 and 30 , respectively) after sciatic nerve block. [4]

Protocol (from reference)

Solubility (25°C)

In vitro

DMSO 64 mg/mL
(196.98 mM)
Water 64 mg/mL
(196.98 mM)
Ethanol 57 mg/mL
(175.44 mM)

Chemical Information

Molecular Weight 324.89
Formula

C18H28N2O.HCl

CAS No. 27262-48-2
Storage 3 years -20°C powder
2 years -80°C in solvent
Smiles CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl

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Molarity Calculator

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Clinical Trial Information

NCT Number Recruitment Interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04221568 Unknown status Drug: Bupivacaine-fentanyl|Drug: levobupivacaine-fentanyl Labor Pain Assiut University March 1 2020 Phase 1
NCT03258697 Unknown status Drug: Levobupivacaine Hydrochloride Arthropathy Chang Gung Memorial Hospital October 17 2017 Not Applicable

(data from https://clinicaltrials.gov, updated on 2022-01-17)

Tech Support

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

Handling Instructions

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