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Levobupivacaine

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	AU: B3
Routes of administration	Parenteral
ATC code	N01BB10 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)
Pharmacokinetic data
Bioavailability	n/a
Metabolism	Hepatic
Elimination half-life	2–2.6 hours
Excretion	Renal 70%, faecal 24%
Identifiers
IUPAC name (S)-1-butyl-N-(2,6-dimethylphenyl) piperidine-2-carboxamide
CAS Number	27262-47-1
PubChem CID	92253
DrugBank	APRD00110
ChemSpider	83289
UNII	A5H73K9U3W
ChEBI	CHEBI:6149
ChEMBL	ChEMBL1201193
CompTox Dashboard (EPA)	DTXSID8048496
Chemical and physical data
Formula	C18H28N2O
Molar mass	288.43 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C(Nc1c(cccc1C)C)2N(CCCC)CCCC2
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 Key:LEBVLXFERQHONN-INIZCTEOSA-N
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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.

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

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.

References

1. Burlacu CL, Buggy DJ (2008). "Update on local anesthetics: focus on levobupivacaine". Ther Clin Risk Manag. 4 (2): 381–92. PMC 2504073. PMID 18728849. {{cite journal}}: Unknown parameter |month= ignored (help)
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

• Ill-formatted IPAc-en transclusions
• Local anesthetics
• Enantiopure drugs
• Piperidines
• Anilides