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Levobupivacaine HCl Sodium Channel inhibitor

Cat.No.S4061

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 Sodium Channel inhibitor Chemical Structure

Chemical Structure

Molecular Weight: 324.89

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Quality Control

Batch: S406101 DMSO]64 mg/mL]false]Water]64 mg/mL]false]Ethanol]57 mg/mL]false Purity: 99.61%
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99.61

Solubility

In vitro
Batch:

DMSO : 64 mg/mL (196.98 mM)
(Moisture-contaminated DMSO may reduce solubility. Use fresh, anhydrous DMSO.)

Water : 64 mg/mL

Ethanol : 57 mg/mL

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In vivo
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Chemical Information, Storage & Stability

Molecular Weight 324.89 Formula

C18H28N2O.HCl

 Storage (From the date of receipt)
CAS No. 27262-48-2 Download SDF Storage of Stock Solutions

Synonyms (S)-(-)-Bupivacaine HCl Smiles CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl

Mechanism of Action

Targets/IC50/Ki
Sodium Channel
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. 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. 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. 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.
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.
References
  • [4] https://pubmed.ncbi.nlm.nih.gov/15992136/

Clinical Trial Information

(data from https://clinicaltrials.gov, updated on 2024-05-22)

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT04221568 Unknown status
Labor Pain
Assiut University
 March 1 2020 Phase 1
NCT03258697 Unknown status
Arthropathy
Chang Gung Memorial Hospital
 October 17 2017 Not Applicable

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