Ropivacaine

Ropivacaine

Clinical data
AHFS/Drugs.com	Consumer Drug Information
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	Hepatic (CYP1A2-mediated)
Biological half-life	1.6–6 hours (varies with administration route)
Excretion	Renal 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 Y
KEGG	D08490 Y
ChEBI	CHEBI:8890 Y
ChEMBL	CHEMBL1077896 Y
ECHA InfoCard	100.128.244
Chemical and physical data
Formula	C17H26N2O
Molar mass	274.4 g/mol
3D model (Jmol)	Interactive image
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

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 trade name Naropin.

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.

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.

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.