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PubChem
| Name: | levobupivacaine |
|---|---|
| PubChem Compound ID: | 117963 |
| Molecular formula: | C18H28N2O |
| Molecular weight: | 288.428 g/mol |
| Synonyms: |
D(+)-Bupivacaine; 2',6'-Pipecoloxylidide, 1-butyl-, D-(+)-; 27262-45-9
|
DrugBank
Identification
| Name: | levobupivacaine |
|---|---|
| Name (isomeric): | DB01002 |
| Drug Type: | small molecule |
| Synonyms: |
Levobupivacaine hydrochloride
|
| Brand: | Chirocaine |
| Category: | Anesthetics, Anesthetics, Local |
| CAS number: | 27262-47-1 |
Pharmacology
| Indication: | For the production of local or regional anesthesia for surgery and obstetrics, and for post-operative pain management |
|---|---|
| Pharmacology: | 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. |
| Mechanism 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 dia...
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| Absorption: | The plasma concentration of levobupivacaine following therapeutic administration depends on dose and also on route of administration, because absorption from the site of administration is affected by the vascularity of the tissue. Peak levels in blood were reached approximately 30 minutes after epidural administration, and doses up to 150 mg resulted in mean Cmax levels of up to 1.2 µg/mL. |
| Protein binding: | >97% |
| Biotransformation: | 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. |
| Route of elimination: | Following intravenous administration, recovery of the radiolabelled dose of levobupivacaine was essentially quantitative with a mean total of about 95% being recovered in urine and feces in 48 hours. Of this 95%, about 71% was in urine while 24% was in feces. |
| Half Life: | 3.3 hours |
| Clearance: | 39.06 ±13.29 L/h [after intravenous administration of 40 mg in healthy volunteers] |
| 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. |
| Affected organisms: | Humans and other mammals |
Targets
Enzymes
