Levobupivacaine

SKU: orb1225455

Description

Levobupivacaine is an amino-amide local anaesthetic drug belonging to the family of n-alkylsubstituted pipecoloxylidide. It is the S-enantiomer of bupivacaine. Levobupivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Chirocaine. Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is approximately 13 per cent less potent (by molarity) than racemic bupivacaine.Levobupivacaine is indicated for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children. Adverse drug reactions (ADRs) are rare when it is administered correctly. Most ADRs relate to administration technique (resulting in systemic exposure) or pharmacological effects of anesthesia, however allergic reactions can rarely occur. \n(In Vitro):Levobupivacaine (0-4 mM; 24 h) does not affect the viability of GES-1 cells but inhibits the viability of HGC27 and SGC7901 cells.Levobupivacaine (2 mM; 24, 48 or 72 h) enhances Erastin-induced inhibitory impact on HGC27 and SGC7901 cell viabilities; induces the levels of Fe2+, iron, and lipid ROS.Levobupivacaine (2 mM; 24 h) enhances the expression of miR-489-3p in HGC27 and SGC7901 cells, increases the levels of Fe2+ and iron.(In Vivo):Levobupivacaine (40 μmol/kg; IP; once daily for 25 days) significantly inhibits SGC7901 cell growth, and enhances the lipid ROS accumulation.Levobupivacaine (5 or 36 mg/kg; IP; single dosage) increases the latency to partial seizures and prevents the occurrence of generalized seizures at low dosage; reduces the latency to N-methyl-d-aspartate (NMDA)-induced seizures and increased seizure severity at high dosage.

Key Properties

• CAS Number: 27262-47-1
• MW: 288.43
• Purity: >98% (HPLC)
• Formula: C₁₈H₂₈N₂O
• SMILES: CCCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C
• Target: Sodium Channel
• Solubility: Soluble in DMSO

Bioactivity

• In Vivo:
  Levobupivacaine (40 μmol/kg; IP; once daily for 25 days) significantly inhibits SGC7901 cell growth, and enhances the lipid ROS accumulation. Levobupivacaine (5 or 36 mg/kg; IP; single dosage) increases the latency to partial seizures and prevents the occurrence of generalized seizures at low dosage; reduces the latency to N-methyl-d-aspartate (NMDA)-induced seizures and increased seizure severity at high dosage. Animal model: CD1 mice (30-35 g; induced epileptic seizures by injecting with NMDA). Dosage: 5 or 36 mg/kg. Administration: IP; single dosage. Result: Increased the latency to partial seizures and prevented the occurrence of generalized seizures at 5 mg/kg; reduced the latency to NMDA-induced seizures and increased seizure severity at 36 mg/kg. Animal model: SCID nude mice (6-8 weeks; subcutaneously injected with 5×106 SGC7901 cells). Dosage: 40 μmol/kg. Administration: IP; once daily for 25 days. Result: Significantly inhibited SGC7901 cell growth, and enhanced the lipid ROS accumulation.
• In Vitro:
  Levobupivacaine (0-4 mM; 24 h) does not affect the viability of GES-1 cells but inhibits the viability of HGC27 and SGC7901 cells. Levobupivacaine (2 mM; 24, 48 or 72 h) enhances Erastin-induced inhibitory impact on HGC27 and SGC7901 cell viabilities; induces the levels of Fe2+, iron, and lipid ROS. Levobupivacaine (2 mM; 24 h) enhances the expression of miR-489-3p in HGC27 and SGC7901 cells, increases the levels of Fe2+ and iron. Cell Viability Assay Cell line: GES-1, HGC27 and SGC790. Concentration: 0, 0.5, 1, 2 and 4 mM Incubation time: 24 h. Result: Did not affect the viability of normal gastric epithelial GES-1 cell lines but inhibited the viability of HGC27 and SGC7901 cells in a dose-dependent manner. Cell Viability Assay Cell line: HGC27 and SGC7901 (incubated with 5 μM erastin). Concentration: 2 mM. Incubation time: 24, 48 or 72 h. Result: Enhanced erastin-induced inhibitory impact on HGC27 and SGC7901 cell viabilities; induced the levels of Fe2+, iron, and lipid ROS. RT-PCR Cell line: HGC27 and SGC7901 (incubated with 5 μM erastin). Concentration: 2 mM. Incubation time: 24 h. Result: Enhanced the expression of miR-489-3p in HGC27 and SGC7901 cells, increased the levels of Fe2+ and iron.

Storage & Handling

• Storage: Storage temperature: -20°C. Stability: ≥ 2 years
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Quick Database Links

Gene Symbol

Sodium Channel