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Ropivacaine
Local anaesthetic drug
Local anaesthetic drug
| Field | Value | |||
|---|---|---|---|---|
| verifiedrevid | 464383595 | |||
| image | Ropivacaine.svg | |||
| image_class | skin-invert-image | |||
| image2 | Ropivacaine-from-xtal-3D-bs-17.png | |||
| image_class2 | bg-transparent | |||
| pronounce | ||||
| tradename | Naropin, Rocaine | |||
| Drugs.com | ||||
| DailyMedID | ||||
| pregnancy_AU | B1 | |||
| routes_of_administration | Parenteral | |||
| ATC_prefix | N01 | |||
| ATC_suffix | BB09 | |||
| legal_AU | S4 | |||
| legal_BR | ||||
| legal_CA | Rx-only | |||
| legal_CA_comment | ||||
| legal_DE | ||||
| legal_NZ | ||||
| legal_UK | ||||
| legal_US | ||||
| legal_UN | ||||
| legal_status | ||||
| bioavailability | 87%–98% (epidural) | |||
| metabolism | Liver (CYP1A2-mediated) | |||
| elimination_half-life | 1.6–6 hours (varies with administration route) | |||
| excretion | Kidney 86% | |||
| index2_label | as HCl | |||
| CAS_number_Ref | ||||
| CAS_number | 84057-95-4 | |||
| PubChem | 175805 | |||
| IUPHAR_ligand | 7602 | |||
| DrugBank_Ref | ||||
| DrugBank | DB00296 | |||
| ChemSpiderID_Ref | ||||
| ChemSpiderID | 153165 | |||
| UNII_Ref | ||||
| UNII | 7IO5LYA57N | |||
| KEGG_Ref | ||||
| KEGG | D08490 | |||
| KEGG2_Ref | ||||
| KEGG2 | D04048 | |||
| ChEBI_Ref | ||||
| ChEBI | 8890 | |||
| ChEMBL_Ref | ||||
| ChEMBL | 1077896 | |||
| IUPAC_name | (S)-N-(2,6-dimethylphenyl)- | |||
| 1-propylpiperidine-2-carboxamide | ||||
| C | 17 | H=26 | N=2 | O=1 |
| SMILES | O=C(Nc1c(cccc1C)C)[C@H]2N(CCC)CCCC2 | |||
| StdInChI_Ref | ||||
| StdInChI | 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 | |||
| StdInChIKey_Ref | ||||
| StdInChIKey | ZKMNUMMKYBVTFN-HNNXBMFYSA-N | |||
| melting_point | 144 | |||
| melting_high | 146 |
| Drugs.com =
| elimination_half-life = 1.6–6 hours (varies with administration route)
1-propylpiperidine-2-carboxamide
Ropivacaine (rINN) 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 brand name Naropin.
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) can be used, because they have less cardiovascular and central nervous system toxicity than racemic bupivacaine.
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.
Postarthroscopic glenohumeral chondrolysis
Ropivacaine is toxic to cartilage and their intra-articular infusions can lead to Postarthroscopic glenohumeral chondrolysis.
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 and in humans in a process called lipid rescue.
References
References
- (28 July 2017). "Naropin Product information".
- (Basic of Anesthesia, Robert Stoelting, page 289)
- Rossi S, editor. [[Australian Medicines Handbook]] 2006. Adelaide: Australian Medicines Handbook; 2006. {{ISBN. 0-9757919-2-3
- (December 2015). "Articular cartilage and local anaesthetic: A systematic review of the current literature". Journal of Orthopaedics.
- (2003). "Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity". Regional Anesthesia and Pain Medicine.
- (February 2006). "Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob". Anaesthesia.
- (July 2006). "Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest". Anesthesiology.
- (August 2006). "Successful resuscitation of a patient with ropivacaine-induced asystole after axillary plexus block using lipid infusion". Anaesthesia.
This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.
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