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Ropivacaine

From Wikipedia, the free encyclopedia
Local anaesthetic drug

Pharmaceutical compound
Ropivacaine
Clinical data
Pronunciation/rˈpɪvəkn/
Trade namesNaropin, Rocaine
AHFS/Drugs.comMonograph
Pregnancy
category
Routes of
administration
Parenteral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability87%–98% (epidural)
MetabolismLiver (CYP1A2-mediated)
Eliminationhalf-life1.6–6 hours (varies with administration route)
ExcretionKidney 86%
Identifiers
  • (S)-N-(2,6-dimethylphenyl)-
    1-propylpiperidine-2-carboxamide
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.128.244Edit this at Wikidata
Chemical and physical data
FormulaC17H26N2O
Molar mass274.408 g·mol−1
3D model (JSmol)
Melting point144 to 146 °C (291 to 295 °F)
  • O=C(Nc1c(cccc1C)C)[C@H]2N(CCC)CCCC2
  • InChI=1S/C17H26N2O/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20)/t15-/m0/s1 checkY
  • Key:ZKMNUMMKYBVTFN-HNNXBMFYSA-N checkY
  (verify)

Ropivacaine (rINN) is alocal anaesthetic drug belonging to theaminoamide group. The name ropivacaine refers to both theracemate and the marketedS-enantiomer. Ropivacaine hydrochloride is commonly marketed byAstraZeneca under the brand nameNaropin.

History

[edit]

Ropivacaine was developed afterbupivacaine was noted to be associated withcardiac arrest, particularly in pregnant women. Ropivacaine was found to have lesscardiotoxicity than bupivacaine in animal models.

Clinical use

[edit]

Contraindications

[edit]

Ropivacaine is contraindicated forintravenous 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) can be used, because they have less cardiovascular and central nervous system toxicity than racemic bupivacaine.[2]

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, howeverallergic reactions can rarely occur.

Systemic exposure to excessive quantities of ropivacaine mainly result incentral nervous system (CNS) andcardiovascular effects – CNS effects usually occur at lowerblood 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 andapnea). Cardiovascular effects includehypotension,bradycardia,arrhythmias, and/orcardiac arrest – some of which may be due tohypoxemia secondary to respiratory depression.[3]

Postarthroscopic glenohumeral chondrolysis

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Ropivacaine is toxic tocartilage and their intra-articular infusions can lead toPostarthroscopic glenohumeral chondrolysis.[4]

Treatment of overdose

[edit]

As forbupivacaine,Celepid, a commonly available intravenous lipid emulsion, can be effective in treating severe cardiotoxicity secondary to local anaesthetic overdose in animal experiments[5] and in humans in a process calledlipid rescue.[6][7][8]

References

[edit]
  1. ^"Naropin Product information".health-products.canada.ca. 28 July 2017. Retrieved17 February 2025.
  2. ^(Basic of Anesthesia, Robert Stoelting, page 289)
  3. ^Rossi S, editor.Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006.ISBN 0-9757919-2-3
  4. ^Gulihar A, Robati S, Twaij H, Salih A, Taylor GJ (December 2015)."Articular cartilage and local anaesthetic: A systematic review of the current literature".Journal of Orthopaedics.12 (Suppl 2): S200-10.doi:10.1016/j.jor.2015.10.005.PMC 4796530.PMID 27047224.
  5. ^Weinberg G, Ripper R, Feinstein DL, Hoffman W (2003). "Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity".Regional Anesthesia and Pain Medicine.28 (3):198–202.doi:10.1053/rapm.2003.50041.PMID 12772136.S2CID 6247454.
  6. ^Picard J, Meek T (February 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.S2CID 29843241.
  7. ^Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB (July 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.S2CID 40214528.
  8. ^Litz RJ, Popp M, Stehr SN, Koch T (August 2006). "Successful resuscitation of a patient with ropivacaine-induced asystole after axillary plexus block using lipid infusion".Anaesthesia.61 (8):800–1.doi:10.1111/j.1365-2044.2006.04740.x.PMID 16867094.S2CID 43125067.
Esters by acid
Aminobenzoic
Benzoic
ArCO2- (not para-amino or Ph)
Amides
Combinations
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