Levobupivacaine  (Synonyms: (S)-(-)-Bupivacaine)

Levobupivacaine ((S)-(-)-Bupivacaine) is a long-acting amide local anaesthetic. Levobupivacaine exerts anaesthetic and analgesic effects through reversible blockade of neuronal sodium channel. Levobupivacaine can inhibit impulse transmission and conduction in cardiovascular and other tissues, possessing certain cardiac and CNS toxicity. Levobupivacaine is metabolized by hepatic cytochrome P450 (CYP450) enzymes in vivo. Levobupivacaine can also induce ferroptosis by miR-489-3p/SLC7A11 signaling in gastric cancer^[1][2][3].

Sodium channels, Ferroptosis^[1][2]

Levobupivacaine (0-4 mM; 24 h) does not affect the viability of GES-1 cells but inhibits the viability of HGC27 and SGC7901 cells^[2].
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^[2].
Levobupivacaine (2 mM; 24 h) enhances the expression of miR-489-3p in HGC27 and SGC7901 cells, increases the levels of Fe²⁺ and iron^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Levobupivacaine (40 μmol/kg; IP; once daily for 25 days) significantly inhibits SGC7901 cell growth, and enhances the lipid ROS accumulation^[2].
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^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

288.43

C₁₈H₂₈N₂O

27262-47-1

O=C([C@H]1N(CCCC)CCCC1)NC2=C(C)C=CC=C2C

Room temperature in continental US; may vary elsewhere.

Please store the product under the recommended conditions in the Certificate of Analysis.

• [1]. Sanford M, et al. Levobupivacaine: a review of its use in regional anaesthesia and pain management. Drugs. 2010 Apr 16;70(6):761-91.  [Content Brief]

  [2]. Mao SH, et al. Levobupivacaine Induces Ferroptosis by miR-489-3p/SLC7A11 Signaling in Gastric Cancer. Front Pharmacol. 2021 Jun 9;12:681338.  [Content Brief]

  [3]. Marganella C, et al. Comparative effects of levobupivacaine and racemic bupivacaine on excitotoxic neuronal death in culture and N-methyl-D-aspartate-induced seizures in mice. Eur J Pharmacol. 2005 Aug 22;518(2-3):111-5.  [Content Brief]