Ropivacaine

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Ropivacaine
Ropivacaine.png
Ropivacaine ball-and-stick.png
Systematic (IUPAC) name
(S)-N-(2,6-dimethylphenyl)-
1-propylpiperidine-2-carboxamide
Clinical data
AHFS/Drugs.com Consumer Drug Information
Pregnancy cat. B1 (AU)
Legal status Prescription Only (S4) (AU)
Routes Parenteral
Pharmacokinetic data
Bioavailability 87%–98% (epidural)
Metabolism Hepatic (CYP1A2-mediated)
Half-life 1.6–6 hours (varies with administration route)
Excretion Renal 86%
Identifiers
CAS number 84057-95-4 YesY
ATC code N01BB09
PubChem CID 175805
DrugBank DB00296
ChemSpider 153165 YesY
UNII 7IO5LYA57N YesY
KEGG D08490 YesY
ChEBI CHEBI:8890 YesY
ChEMBL CHEMBL1077896 YesY
Chemical data
Formula C17H26N2O 
Mol. mass 274.4 g/mol
 YesY (what is this?)  (verify)

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.

History[edit]

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[edit]

Indications[edit]

Ropivacaine is indicated for local anaesthesia including infiltration, nerve block, epidural and intrathecal anaesthesia in adults and children over 12 years. It is also indicated for peripheral nerve block and caudal epidural in children 1–12 years for surgical pain. It is also sometimes used for infiltration anaesthesia for surgical pain in children.

Ropivacaine is often coadministered with fentanyl for epidural analgesia, for example in pregnant women during labour.

Contraindications[edit]

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

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 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]

Treatment of overdose[edit]

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[3] and in humans in a process called lipid rescue.[4][5][6]

References[edit]

  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. ^ Weinberg, G, Ripper, R, Feinstein, DL, Hoffman W. Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity. Reg Anesth Pain Med 2003;28:198-202. doi:10.1053/rapm.2003.50041 PMID 12772136
  4. ^ Picard J, Meek T. Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia 2006;61:107-9. doi:10.1111/j.1365-2044.2005.04494.x PMID 16430560
  5. ^ Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB. Successful Use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology 2006;105:217-8. doi:10.1097/00000542-200607000-00033 PMID 16810015
  6. ^ Litz, RJ, Popp M, Stehr S N, Koch T. Successful resuscitation of a patient with ropivacaine-induced asystole after axillary plexus block using lipid infusion. Anaesthesia 2006;61:800-1.

External links[edit]