Ropivacaine

Ropivacaine (rINN) /rˈpɪvəkn/ is a local anaesthetic drug belonging to the amino amide group. The name ropivacaine refers to both the racemate and the marketed S-enantiomer. Ropivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Naropin.

Ropivacaine
Clinical data
AHFS/Drugs.comConsumer Drug Information
Pregnancy
category
    Routes of
    administration
    Parenteral
    ATC code
    Legal status
    Legal status
    • AU: S4 (Prescription only)
    Pharmacokinetic data
    Bioavailability87%–98% (epidural)
    MetabolismHepatic (CYP1A2-mediated)
    Elimination half-life1.6–6 hours (varies with administration route)
    ExcretionRenal 86%
    Identifiers
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard100.128.244
    Chemical and physical data
    FormulaC17H26N2O
    Molar mass274.4 g/mol g·mol−1
    3D model (JSmol)
    Melting point144 to 146 °C (291 to 295 °F)
      (verify)

    History

    Ropivacaine was developed after bupivacaine was noted to be associated with cardiac arrest, particularly in pregnant women. Ropivacaine was found to have less cardiotoxicity than bupivacaine in animal models.

    Clinical use

    Contraindications

    Ropivacaine is contraindicated for intravenous regional anaesthesia (IVRA). However, new data suggested both ropivacaine (1.2-1.8 mg/kg in 40ml) and levobupivacaine (40 ml of 0.125% solution) be used, because they have less cardiovascular and central nervous system toxicity than racemic bupivacaine.[1]

    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 ropivacaine 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]

    Postarthroscopic glenohumeral chondrolysis

    Ropivacaine is toxic to cartilage and their intra-articular infusions can lead to Postarthroscopic glenohumeral chondrolysis.[3]

    Treatment of overdose

    As for bupivacaine, Celepid, a commonly available intravenous lipid emulsion, can be effective in treating severe cardiotoxicity secondary to local anaesthetic overdose in animal experiments[4] and in humans in a process called lipid rescue.[5][6][7]

    References

    1. (Basic of Anesthesia, Robert Stoelting, page 289)
    2. Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
    3. Gulihar, Abhinav; Robati, Shibby; Twaij, Haider; Salih, Alan; Taylor, Grahame J.S. (December 2015). "Articular cartilage and local anaesthetic: A systematic review of the current literature". Journal of Orthopaedics. 12: S200–S210. doi:10.1016/j.jor.2015.10.005. PMC 4796530. PMID 27047224.
    4. Weinberg, G; Ripper, R; Feinstein, DL; Hoffman, W (2003). "Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity". Reg Anesth Pain Med. 28 (3): 198–202. doi:10.1053/rapm.2003.50041. PMID 12772136.
    5. Picard, J; Meek, T (2006). "Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob". Anaesthesia. 61 (2): 107–9. doi:10.1111/j.1365-2044.2005.04494.x. PMID 16430560.
    6. Rosenblatt, MA; Abel, M; Fischer, GW; Itzkovich, CJ; Eisenkraft, JB (2006). "Successful Use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest". Anesthesiology. 105 (1): 217–8. doi:10.1097/00000542-200607000-00033. PMID 16810015.
    7. Litz, RJ; Popp, M; Stehr, S N; Koch, T (2006). "Successful resuscitation of a patient with ropivacaine-induced asystole after axillary plexus block using lipid infusion". Anaesthesia. 61: 800–1. doi:10.1111/j.1365-2044.2006.04740.x. PMID 16867094.
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