Levobupivacaine

Levobupivacaine

Systematic (IUPAC) name
(S)-1-butyl-N-(2,6-dimethylphenyl) piperidine-2-carboxamide
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy cat.	B3(AU)
Legal status	Prescription Only (S4) (AU)
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 Y
ATC code	N01BB10
PubChem	CID 92253
DrugBank	APRD00110
ChemSpider	83289 Y
UNII	A5H73K9U3W Y
ChEBI	CHEBI:6149 N
ChEMBL	CHEMBL1201193 N
Chemical data
Formula	C18H28N2O
Mol. mass	288.43 g/mol
SMILES	eMolecules & PubChem
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 Y Key:LEBVLXFERQHONN-INIZCTEOSA-N Y
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Levobupivacaine (rINN) ( /liːvoʊbjuːˈpɪvəkeɪn/) 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

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

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

Contraindications

Levobupivacaine is contraindicated for IV regional anaesthesia (IVRA).

Adverse effects

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.^[3]

References

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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2504073. 
2. ^ Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
3. ^ Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3