<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2783</id>
  <title>T3D2741</title>
  <common-name>Ropivacaine</common-name>
  <description>Ropivacaine is only found in individuals that have used or taken this drug. It 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. 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 depolarization and consequent action potentials. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers.</description>
  <cas>84057-95-4</cas>
  <pubchem-id>175805</pubchem-id>
  <chemical-formula>C17H26N2O</chemical-formula>
  <weight>274.204510</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>57.6 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Epidural.Bioavailability is 87%-98% following epidural administration.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>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 depolarization and consequent action potentials. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers.</mechanism-of-toxicity>
  <metabolism>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.</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Used in obstetric anesthesia and regional anesthesia for surgery. 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.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Systemic exposure to excessive quantities of lidocaine mainly result in central nervous system (CNS) and cardiovascular effects. CNS effects may include CNS excitation(nervousness, tingling around the mouth) followed by depression. [Wikipedia]</health-effects>
  <symptoms> 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.</symptoms>
  <treatment>The first step in the management of systemic toxic reactions consists of immediate attention to the establishment and maintenance of a patent airway  and effective assisted or controlled ventilation with 100% oxygen with a delivery system capable of permitting immediate positive airway pressure by mask. Circulation  should be assisted as necessary. If necessary, use drugs to control convulsions. Intravenous barbiturates, anticonvulsant agents, or muscle relaxants should only be administered by those familiar with their use. Immediately after the institution of these ventilatory measures, the adequacy of the circulation should be evaluated. Supportive treatment of circulatory depression may require administration of intravenous fluids, and, when appropriate, a vasopressor dictated by the clinical situation (such as ephedrine or epinephrine to enhance myocardial contractile force). (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:26:31Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:25:15Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Ropivacaine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07532</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>8890</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Ropivacaine</stitch-id>
  <drugbank-id>DB00296</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C</moldb-smiles>
  <moldb-formula>C17H26N2O</moldb-formula>
  <moldb-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</moldb-inchi>
  <moldb-inchikey>ZKMNUMMKYBVTFN-HNNXBMFYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">274.4011</moldb-average-mass>
  <moldb-mono-mass type="decimal">274.204513464</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.9</logp>
  <hmdb-id>HMDB14441</hmdb-id>
  <chembl-id>CHEMBL1077896</chembl-id>
  <chemspider-id>153165</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Peter Jaksch, &amp;#8220;Process for the preparation of ropivacaine hydrochloride monohydrate.&amp;#8221; U.S. Patent US5959112, issued February, 1970.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002163</chemdb-id>
  <dsstox-id>DTXSID4040187</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00001426</susdat-id>
  <iupac>(2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide</iupac>
  <moldb-polar-surface-area>32.34</moldb-polar-surface-area>
  <moldb-refractivity>85.5923</moldb-refractivity>
  <moldb-polarizability>32.665408838794555</moldb-polarizability>
  <moldb-rotatable-bond-count>4</moldb-rotatable-bond-count>
  <moldb-acceptor-count>2</moldb-acceptor-count>
  <moldb-donor-count>1</moldb-donor-count>
  <moldb-pka-strongest-acidic>13.623525622831593</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>7.818046257329233</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>2.91</moldb-alogps-logp>
  <moldb-alogps-logs>-3.04</moldb-alogps-logs>
  <moldb-alogps-solubility>2.53e-01 g/l</moldb-alogps-solubility>
</compound>
