Levobupivacaine HCl 27262-48-2

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Molecular Weight:

324.89 Levobupivacaine HCl, the pure S(-)-enantiomer of bupivacaine, is a reversible neuronal Sodium Channel Inhibitor, used as a long-acting local anesthetic.

Biological Activity

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.


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.

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Product Categories : Transmembrane Transporters > Sodium Channel Inhibitor