Substance
ID:181
Names and Identifiers
Brand Name
Naropin
Synonyms
Ropivacaina [Spanish]Ropivacaina [INN-Spanish]Ropivacaine [INN]S-RopivacaineRopivacainum [INN-Latin]Ropivacaine
IUPAC Traditional name
@ropivacaine
IUPAC name
(2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
Registration numbers
CAS Number
Properties
Physical Property
Solubility
57.6 mg/L
Hydrophobicity(logP)
3
Molecule Details
Drug Groups
approved
Description
Ropivacaine 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. [Wikipedia]
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.
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
Biotransformation
Hepatic
Absorption
Bioavailability is 87%–98% following epidural administration.
Half Life
Approximately 4.2 hours.
Protein Binding
94%, mainly to a1-acid glycoprotein
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.
Clearance
* 387?+/- 107 mL/min
* unbound plasma clearance=7.2 +/- 1.6 L/min
* unbound plasma clearance=7.2 +/- 1.6 L/min
References
•
Weinberg G, Ripper R, Feinstein DL, Hoffman W: Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity. Reg Anesth Pain Med. 2003 May-Jun;28(3):198-202.
[Pubmed]
•
Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9.
[Pubmed]
•
Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB: Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology. 2006 Jul;105(1):217-8.
[Pubmed]
External Links
Molecular Spectra
No Data Available
Click here to submit data
References
• Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB: Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology. 2006 Jul;105(1):217-8. Pubmed
• Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9. Pubmed
• Weinberg G, Ripper R, Feinstein DL, Hoffman W: Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity. Reg Anesth Pain Med. 2003 May-Jun;28(3):198-202. Pubmed