Ropivacaine (CHEM002163)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2009-07-21 20:26:31 UTC
Update Date2026-05-14 16:25:15 UTC
Accession NumberCHEM002163
Identification
Common NameRopivacaine
ClassSmall Molecule
DescriptionRopivacaine 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Anesthetic
  • Anesthetic, Local
  • Drug
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-1-Propyl-2',6'-dimethyl-2-piperidylcarboxyanilideChEBI
(-)-1-Propyl-2',6'-pipecoloxylidideChEBI
(S)-(-)-1-Propyl-2',6'-pipecoloxylidideChEBI
L-N-N-Propylpipecolic acid-2,6-xylidideChEBI
RopivacainaChEBI
RopivacainumChEBI
NaropinKegg
L-N-N-Propylpipecolate-2,6-xylidideGenerator
S-RopivacaineHMDB
LEA-103HMDB
NaropeineHMDB
Ropivacaine hydrochlorideHMDB
Ropivacaine monohydrochlorideHMDB
Ropivacaine monohydrochloride, (S)-isomerHMDB
1-Propyl-2',6'-pipecoloxylidideHMDB
LEA 103HMDB
1 Propyl 2',6' pipecoloxylidideHMDB
Chemical FormulaC17H26N2O
Average Molecular Mass274.401 g/mol
Monoisotopic Mass274.205 g/mol
CAS Registry Number84057-95-4
IUPAC Name(2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
Traditional Nameropivacaine
SMILESCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C
InChI IdentifierInChI=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
InChI KeyZKMNUMMKYBVTFN-HNNXBMFYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • 2-piperidinecarboxamide
  • Piperidinecarboxamide
  • Anilide
  • M-xylene
  • Xylene
  • N-arylamide
  • Monocyclic benzene moiety
  • Benzenoid
  • Piperidine
  • Carboxamide group
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility57.6 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP2.91ALOGPS
logP4.07ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)7.82ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity85.59 m³·mol⁻¹ChemAxon
Polarizability32.67 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-8920000000-73e85079216552ba91a9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00b9-0970000000-5c1a64ae27aff997890cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-2900000000-672e3b8722fe16738c24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-082eb7de53612f8e41d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-0bab56be469e7bd6a507Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0960000000-9f382933eb477808418cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-6900000000-85680fbf3993e3ad0b26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-f65ed1883e2d82087854Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0590000000-0e618e825ce0a7c6f894Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00yi-2910000000-3a2ddfb03e07c24ab3b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0190000000-5ca58a328a550062ca9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2910000000-0b84aebef101786ad64aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-5900000000-12d6c869d1aa71a3e37bSpectrum
Toxicity Profile
Route of ExposureEpidural. Bioavailability is 87%-98% following epidural administration.
Mechanism of ToxicityLocal 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.
MetabolismHepatic 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.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed 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.
Minimum Risk LevelNot Available
Health EffectsSystemic 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]
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.
TreatmentThe 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). (5)
Concentrations
Not Available
DrugBank IDDB00296
HMDB IDHMDB0014441
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRopivacaine
Chemspider ID153165
ChEBI ID8890
PubChem Compound ID175805
Kegg Compound IDC07532
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Peter Jaksch, “Process for the preparation of ropivacaine hydrochloride monohydrate.” U.S. Patent US5959112, issued February, 1970.

MSDSLink
General References
1. 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.
2. Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9.
3. 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.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19586686