Levobupivacaine

From Wikipedia, the free encyclopedia - View original article

Levobupivacaine
Levobupivacaine.png
Systematic (IUPAC) name
(S)-1-butyl-N-(2,6-dimethylphenyl)
piperidine-2-carboxamide
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy cat.B3 (AU)
Legal statusPrescription Only (S4) (AU)
RoutesParenteral
Pharmacokinetic data
Bioavailabilityn/a
MetabolismHepatic
Half-life2–2.6 hours
ExcretionRenal 70%, faecal 24%
Identifiers
CAS number27262-47-1 YesY
ATC codeN01BB10
PubChemCID 92253
DrugBankDB01002
ChemSpider83289 YesY
UNIIA5H73K9U3W YesY
ChEBICHEBI:6149 YesY
ChEMBLCHEMBL1201193 N
Chemical data
FormulaC18H28N2O 
Mol. mass288.43 g/mol
 N (what is this?)  (verify)
 
Jump to: navigation, search
Levobupivacaine
Levobupivacaine.png
Systematic (IUPAC) name
(S)-1-butyl-N-(2,6-dimethylphenyl)
piperidine-2-carboxamide
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy cat.B3 (AU)
Legal statusPrescription Only (S4) (AU)
RoutesParenteral
Pharmacokinetic data
Bioavailabilityn/a
MetabolismHepatic
Half-life2–2.6 hours
ExcretionRenal 70%, faecal 24%
Identifiers
CAS number27262-47-1 YesY
ATC codeN01BB10
PubChemCID 92253
DrugBankDB01002
ChemSpider83289 YesY
UNIIA5H73K9U3W YesY
ChEBICHEBI:6149 YesY
ChEMBLCHEMBL1201193 N
Chemical data
FormulaC18H28N2O 
Mol. mass288.43 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.

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