Product Name

Levobupivacaine (Bupivacaine)

CAS Number

2180 92 9

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Product Name:
Levobupivacaine (Bupivacaine)
CAS Number:
2180 92 9
Indication:
For the production of local or regional anesthesia for surgery and obstetrics, and for post-operative pain management.
Mode of Action:

Local anesthetics such as Levobupivacaine block the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers. Specifically, the drug binds to the intracellular portion of sodium channels and blocks sodium influx into nerve cells, which prevents depolarization.

Pharmacodynamics:

Levobupivacaine, a local anesthetic agent, is indicated for the production of local or regional anesthesia or analgesia for surgery, for oral surgery procedures, for diagnostic and therapeutic procedures, and for obstetrical procedures.

Metabolism:

Levobupivacaine is extensively metabolized with no unchanged levobupivacaine detected in urine or feces. In vitro studies using [14 C] levobupivacaine showed that CYP3A4 isoform and CYP1A2 isoform mediate the metabolism of levobupivacaine to desbutyl levobupivacaine and 3-hydroxy levobupivacaine, respectively. In vivo, the 3-hydroxy levobupivacaine appears to undergo further transformation to glucuronide and sulfate conjugates. Metabolic inversion of levobupivacaine to R(+)-bupivacaine was not evident both in vitro and in vivo.

Toxicity:

LD50: 5.1mg/kg in rabbit, intravenous; 18mg/kg in rabbit, oral; 207mg/kg in rabbit, parenteral; 63mg/kg in rat, subcutaneous (Archives Internationales de Pharmacodynamie et de Therapie. Vol. 200, Pg. 359, 1972.) Levobupivacaine appears to cause less myocardial depression than both bupivacaine and ropivacaine, despite being in higher concentrations.

IUPAC:
(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
ATC:
N01BB10 — Levobupivacaine
PubChem:
46505295
DrugBank:
DB01002
Formula:
C18-H28-N2O
Molecular Mass:
288.4277
Synonyms:
(-)-bupivacaine (S)-1-butyl-2′,6′-pipecoloxylidide (S)-bupivacaine L-(-)-1-Butyl-2′,6′-pipecoloxylidide L-(−)-bupivacaine Levobupivacaína Levobupivacaine
SMILES:
CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C
InChi:
InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1
General Reference:
General Reference:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Ueta K, Sugimoto M, Suzuki T, Uchida I, Mashimo T: In vitro antagonism of recombinant ligand-gated ion-channel receptors by stereospecific enantiomers of bupivacaine. Reg Anesth Pain Med. 2006 Jan-Feb;31(1):19-25. [PubMed:16418020]
Vladimirov M, Nau C, Mok WM, Strichartz G: Potency of bupivacaine stereoisomers tested in vitro and in vivo: biochemical, electrophysiological, and neurobehavioral studies. Anesthesiology. 2000 Sep;93(3):744-55. [PubMed:10969308]
Brau ME, Branitzki P, Olschewski A, Vogel W, Hempelmann G: Block of neuronal tetrodotoxin-resistant Na+ currents by stereoisomers of piperidine local anesthetics. Anesth Analg. 2000 Dec;91(6):1499-505. [PubMed:11094008]

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