Levobupivacaine hydrochloride

SKU: orb1300653

Description

Levobupivacaine hydrochloride is the pure S(-)-enantiomer of bupivacaine, functioning as a long-acting local anesthetic via reversible sodium channel blockade. It is widely used in research for in vivo pain models and in vitro electrophysiological studies of neuronal signaling.

Research Area

Cell Biology, Pharmacology & Drug Discovery

Key Properties

• CAS Number: 27262-48-2
• MW: 324.89
• Purity: 99.93% (May vary between batches)
• Formula: C₁₈H₂₈N₂O·HCl
• SMILES: Cl.CCCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C
• Target: Ferroptosis,Sodium Channel
• Solubility: Ethanol:53 mg/mL (163.13 mM);H2O:59 mg/mL (181.6 mM);DMSO:50 mg/mL (153.9 mM);10% DMSO+40% PEG300+5% Tween 80+45% Saline:2.5 mg/mL (7.69 mM)

Bioactivity

• 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.
• 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 (1 mM) 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 39 μM. 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.

Storage & Handling

• Storage: Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

CYP450, CNS toxicity, (S)-(-)-Bupivacaine HCl, (S)-(-)-Bupivacaine monohydrochloride, cardiac toxicity, Bupivacaine Monohydrochloride, Bupivacaine, Bupivacaine HCl, analgesic, anaesthetic, inhibit, NMDA, Na+ channels, Na channels, Ferroptosis, Erastin, Levobupivacaine, Levobupivacaine HCl, Levobupivacaine Hydrochloride, Levobupivacaine hydrochloride, Inhibitor, gastric cancer, SodiumChannel, Sodium Channel

Compound Identifiers

PubChem CID

117965