Levobupivacaine

Levobupivacaine
Clinical data
Pronunciation/liːvoʊbjuːˈpɪvəkeɪn/
Trade namesChirocaine
Other names(S)-bupivacaine

(-)-bupivacaine

L(-)-bupivacaine
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • AU: B3
Routes of
administration		Parenteral
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • EU: Rx-only
Pharmacokinetic data
Bioavailabilityn/a
Protein binding97%
MetabolismHepatic
Metabolites3-hydroxy-levobupivacaine desbutyl-levobupivacaine
Onset of actionWithin 15 minutes
Elimination half-life80 minutes
Duration of actionUp to 16 hours
ExcretionRenal 71%, faecal 24%
Identifiers
  • (S)-1-butyl-N-(2,6-dimethylphenyl)
    piperidine-2-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H28N2O
Molar mass288.435 g·mol−1
3D model (JSmol)
  • O=C([C@H]1N(CCCC1)CCCC)NC2=C(C)C=CC=C2C
  • 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 checkY
  • Key:LEBVLXFERQHONN-INIZCTEOSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Levobupivacaine (rINN) is a local anaesthetic drug indicated for minor and major surgical anaesthesia and pain management. It is a long-acting amide-type local anaesthetic that blocks nerve impulses by inhibiting sodium ion influx into the nerve cells.[1] Levobupivacaine is the S-enantiomer of racemic bupivacaine and therefore similar in pharmacological effects.[2] The drug typically starts taking effect within 15 minutes and can last up to 16 hours depending on factors such as site of administration and dosage.[1]

Levobupivacaine was designed, in the late 1970s, to be a safer and more effective alternative to bupivacaine, which had been associated with a higher risk of cardiotoxicity.[1][2] Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is approximately 13 per cent less potent (by molarity) than racemic bupivacaine and has a longer motor block onset time.[3] Ropivacaine is, next to levobupivacaine, another less cardiotoxic alternative to bupivacaine.[4]

Levobupivacaine hydrochloride is commonly marketed by AbbVie under the trade name Chirocaine.[5] In Europe, Chirocaine is available – prescription only – in concentrations ranging from 0.625 mg/mL to 7.5 mg/mL.[6]

  1. ^ a b c Heppolette CA, Brunnen D, Bampoe S, Odor PM (June 2020). "Clinical Pharmacokinetics and Pharmacodynamics of Levobupivacaine". Clinical Pharmacokinetics. 59 (6): 715–745. doi:10.1007/s40262-020-00868-0. PMID 32034727. S2CID 211061840.
  2. ^ a b Burlacu CL, Buggy DJ (April 2008). "Update on local anesthetics: focus on levobupivacaine". Therapeutics and Clinical Risk Management. 4 (2): 381–392. doi:10.2147/TCRM.S1433. PMC 2504073. PMID 18728849.
  3. ^ Gulec D, Karsli B, Ertugrul F, Bigat Z, Kayacan N (April 2014). "Intrathecal bupivacaine or levobupivacaine: which should be used for elderly patients?". The Journal of International Medical Research. 42 (2): 376–385. doi:10.1177/0300060513496737. PMID 24595149. S2CID 206506181.
  4. ^ Cada DJ, Baker DE, Levien T (December 1999). "Levobupivacaine". Hospital Pharmacy. 34 (12): 1441–1453. doi:10.1177/194512539903401211. ISSN 0018-5787. S2CID 261109078.
  5. ^ Rossi S (2006). AMH 2006 (7th ed.). Adelaide, S.A.: Australian Medicines Handbook Pty Ltd. ISBN 0-9757919-2-3. OCLC 1322357781.
  6. ^ "Levobupivacaine - List of nationally authorised medicinal products" (PDF). European Medicines Agency. 2018-09-06.