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QuickView for ropivacaine (compound)

Name: ropivacaine
PubChem Compound ID: 175804
Molecular formula: C17H27ClN2O
Molecular weight: 310.862 g/mol
C14004; Naropin; Ropivacaine hydrochloride; Ropivacaine monohydrochloride; Naropin (TN); 2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-propyl-, monohydrochloride, (S)-; D02225; Anapeine (TN); 98717-15-8; Anapeine
Name: ropivacaine
Name (isomeric): DB00296
Drug Type: small molecule
Ropivacaine [INN]; S-Ropivacaine; Ropivacainum [INN-Latin]; Ropivacaina [Spanish]; Ropivacaina [INN-Spanish]
Brand: Naropin
Category: Local Anesthetics, Anesthetics, Anesthetics, Local
CAS number: 84057-95-4
Indication: Used in obstetric anesthesia and regional anesthesia for surgery.
Pharmacology: Ropivacaine, a local anesthetic agent, is indicated for the production of local or regional anesthesia or analgesia for surgery, for oral surgery procedures, for diagnostic and therapeutic procedures, and for obstetrical procedures.
Mechanism of Action:
Local anesthetics such as Ropivacaine block the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. Specifically, they block the sodium-channel and decrease chances of...
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Absorption: Bioavailability is 87%–98% following epidural administration.
Protein binding: 94%, mainly to a1-acid glycoprotein
Biotransformation: Hepatic
Route of elimination: Ropivacaine is extensively metabolized in the liver, predominantly by aromatic hydroxylation mediated by cytochrome P4501A to 3-hydroxy ropivacaine. After a single IV dose approximately 37% of the total dose is excreted in the urine as both free and conjugated 3-hydroxy ropivacaine. In total, 86% of the ropivacaine dose is excreted in the urine after intravenous administration of which only 1% relates to unchanged drug.
Half Life: Approximately 4.2 hours.
Clearance: 387 +/- 107 mL/min unbound plasma clearance=7.2 +/- 1.6 L/min
Toxicity: 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.
Affected organisms: Humans and other mammals
Drug interaction:
FluvoxamineIncreases the effect and toxicity of ropivacaine