Chemistry:Ropivacaine

Short description: Local anaesthetic drug

Ropivacaine

Clinical data
Trade names	Naropin, Rocaine
AHFS/Drugs.com	Monograph
Pregnancy category	AU: B1
Routes of administration	Parenteral
ATC code	N01BB09 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)
Pharmacokinetic data
Bioavailability	87%–98% (epidural)
Metabolism	Liver (CYP1A2-mediated)
Elimination half-life	1.6–6 hours (varies with administration route)
Excretion	Kidney 86%
Identifiers
IUPAC name (S)-N-(2,6-dimethylphenyl)- 1-propylpiperidine-2-carboxamide
CAS Number	84057-95-4 Y
PubChem CID	175805
IUPHAR/BPS	7602
DrugBank	DB00296 Y
ChemSpider	153165 Y
UNII	7IO5LYA57N
KEGG	D08490 Y as HCl: D04048 Y
ChEBI	CHEBI:8890 Y
ChEMBL	ChEMBL1077896 Y
Chemical and physical data
Formula	C17H26N2O
Molar mass	274.408 g·mol−1
3D model (JSmol)	Interactive image
Melting point	144 to 146 °C (291 to 295 °F)
SMILES O=C(Nc1c(cccc1C)C)[C@H]2N(CCC)CCCC2
InChI 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 Y Key:ZKMNUMMKYBVTFN-HNNXBMFYSA-N Y
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Ropivacaine (rINN) /roʊˈpɪvəkeɪn/ 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.

External links

• "Ropivacaine". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/ropivacaine. 
• "Ropivacaine hydrochloride". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/ropivacaine%20hydrochloride.