Levobupivacaine

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Levobupivacaine
Levobupivacaine.png
Systematic (IUPAC) name
(S)-1-butyl-N-(2,6-dimethylphenyl)
piperidine-2-carboxamide
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy cat.
Legal status
Routes Parenteral
Pharmacokinetic data
Bioavailability n/a
Metabolism Hepatic
Half-life 2–2.6 hours
Excretion Renal 70%, faecal 24%
Identifiers
CAS number 27262-47-1 YesY
ATC code N01BB10
PubChem CID 92253
DrugBank DB01002
ChemSpider 83289 YesY
UNII A5H73K9U3W YesY
ChEBI CHEBI:6149 YesY
ChEMBL CHEMBL1201193 N
Chemical data
Formula C18H28N2O 
Mol. mass 288.43 g/mol
 N (what is this?)  (verify)

Levobupivacaine (rINN) /lvbjuːˈpɪvəkn/ is a local anaesthetic drug belonging to the amino amide group. It is the S-enantiomer of bupivacaine.[1]

Levobupivacaine hydrochloride is commonly marketed by Abbott under the trade name Chirocaine.[2]

Clinical use[edit]

Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is approximately 13 percent less potent (by molarity) than racemic bupivacaine and has a longer motor block onset time. [3]


Indications[edit]

Levobupivacaine is indicated for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children.

Contraindications[edit]

Levobupivacaine is contraindicated for IV regional anaesthesia (IVRA).

Adverse effects[edit]

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.

Systemic exposure to excessive quantities of bupivacaine mainly result in central nervous system (CNS) and cardiovascular effects – CNS effects usually occur at lower blood plasma concentrations and additional cardiovascular effects present at higher concentrations, though cardiovascular collapse may also occur with low concentrations. CNS effects may include CNS excitation (nervousness, tingling around the mouth, tinnitus, tremor, dizziness, blurred vision, seizures) followed by depression (drowsiness, loss of consciousness, respiratory depression and apnea). Cardiovascular effects include hypotension, bradycardia, arrhythmias, and/or cardiac arrest – some of which may be due to hypoxemia secondary to respiratory depression.[2]

References[edit]

  1. ^ Burlacu CL, Buggy DJ (April 2008). "Update on local anesthetics: focus on levobupivacaine". Ther Clin Risk Manag 4 (2): 381–92. PMC 2504073. PMID 18728849. 
  2. ^ a b Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
  3. ^ Gulec D (Apr 2014). "Intrathecal bupivacaine or levobupivacaine: which should be used for elderly patients?.". J Int Med Res 42 (2): 376–385. doi:10.1177/0300060513496737. PMID 24595149.