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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:37 UTC
HMDB IDHMDB0014441
Secondary Accession Numbers
  • HMDB14441
Metabolite Identification
Common NameRopivacaine
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. [Wikipedia ]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.
Structure
Data?1582753179
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 Weight274.4011
Monoisotopic Molecular Weight274.204513464
IUPAC Name(2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
Traditional Nameropivacaine
CAS Registry Number84057-95-4
SMILES
CCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C
InChI Identifier
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
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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.25 g/LNot Available
LogP3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.39431661259
DarkChem[M-H]-164.02131661259
DeepCCS[M+H]+170.83730932474
DeepCCS[M-H]-168.47930932474
DeepCCS[M-2H]-201.36530932474
DeepCCS[M+Na]+176.9330932474
AllCCS[M+H]+167.932859911
AllCCS[M+H-H2O]+164.532859911
AllCCS[M+NH4]+171.132859911
AllCCS[M+Na]+172.032859911
AllCCS[M-H]-171.332859911
AllCCS[M+Na-2H]-171.832859911
AllCCS[M+HCOO]-172.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RopivacaineCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C2640.0Standard polar33892256
RopivacaineCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C2241.1Standard non polar33892256
RopivacaineCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C2192.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ropivacaine,1TMS,isomer #1CCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C2084.9Semi standard non polar33892256
Ropivacaine,1TMS,isomer #1CCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C2147.0Standard non polar33892256
Ropivacaine,1TMS,isomer #1CCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C2779.2Standard polar33892256
Ropivacaine,1TBDMS,isomer #1CCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2307.7Semi standard non polar33892256
Ropivacaine,1TBDMS,isomer #1CCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2372.7Standard non polar33892256
Ropivacaine,1TBDMS,isomer #1CCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2878.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ropivacaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-8920000000-73e85079216552ba91a92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ropivacaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropivacaine 10V, Positive-QTOFsplash10-00b9-0970000000-5c1a64ae27aff997890c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropivacaine 20V, Positive-QTOFsplash10-00fr-2900000000-672e3b8722fe16738c242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropivacaine 40V, Positive-QTOFsplash10-0006-9200000000-082eb7de53612f8e41d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropivacaine 10V, Negative-QTOFsplash10-00di-0290000000-0bab56be469e7bd6a5072016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropivacaine 20V, Negative-QTOFsplash10-00di-0960000000-9f382933eb477808418c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropivacaine 40V, Negative-QTOFsplash10-00xr-6900000000-85680fbf3993e3ad0b262016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropivacaine 10V, Negative-QTOFsplash10-00di-0090000000-f65ed1883e2d820878542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropivacaine 20V, Negative-QTOFsplash10-00di-0590000000-0e618e825ce0a7c6f8942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropivacaine 40V, Negative-QTOFsplash10-00yi-2910000000-3a2ddfb03e07c24ab3b32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropivacaine 10V, Positive-QTOFsplash10-004i-0190000000-5ca58a328a550062ca9f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropivacaine 20V, Positive-QTOFsplash10-004i-2910000000-0b84aebef101786ad64a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ropivacaine 40V, Positive-QTOFsplash10-004j-5900000000-12d6c869d1aa71a3e37b2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00296 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00296 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00296
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID153165
KEGG Compound IDC07532
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRopivacaine
METLIN IDNot Available
PubChem Compound175805
PDB IDNot Available
ChEBI ID8890
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. [PubMed:12772136 ]
  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. [PubMed:16430560 ]
  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. [PubMed:16810015 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Arlander E, Ekstrom G, Alm C, Carrillo JA, Bielenstein M, Bottiger Y, Bertilsson L, Gustafsson LL: Metabolism of ropivacaine in humans is mediated by CYP1A2 and to a minor extent by CYP3A4: an interaction study with fluvoxamine and ketoconazole as in vivo inhibitors. Clin Pharmacol Ther. 1998 Nov;64(5):484-91. [PubMed:9834040 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
Molecular weight:
220623.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Liu BG, Zhuang XL, Li ST, Xu GH: The effects of ropivacaine on sodium currents in dorsal horn neurons of neonatal rats. Anesth Analg. 2000 May;90(5):1034-8. [PubMed:10781449 ]