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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:52 UTC
HMDB IDHMDB0015137
Secondary Accession Numbers
  • HMDB15137
Metabolite Identification
Common NameLevobupivacaine
DescriptionLevobupivacaine is an amino-amide local anaesthetic drug belonging to the family of n-alkylsubstituted. pipecoloxylidide. It is the S-enantiomer of bupivacaine. Levobupivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Chirocaine. Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is approximately 13 per cent less potent (by molarity) than racemic bupivacaine.Levobupivacaine is indicated for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children. Adverse drug reactions (ADRs) are rare when it is administered correctly. Most ADRs relate to administration technique (resulting in systemic exposure) or pharmacological effects of anesthesia, however allergic reactions can rarely occur. [Wikipedia ]
Structure
Data?1582753262
Synonyms
ValueSource
(-)-BupivacaineChEBI
(S)-1-Butyl-2',6'-pipecoloxylidideChEBI
(S)-BupivacaineChEBI
L-(-)-BupivacaineChEBI
L-(-)-1-Butyl-2',6'-pipecoloxylidideChEBI
NovabupiKegg
Levobupivacaine hydrochlorideHMDB
ChirocaineHMDB
Chemical FormulaC18H28N2O
Average Molecular Weight288.4277
Monoisotopic Molecular Weight288.220163528
IUPAC Name(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
Traditional Name(-)-bupivacaine
CAS Registry Number27262-47-1
SMILES
CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C
InChI Identifier
InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1
InChI KeyLEBVLXFERQHONN-INIZCTEOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as piperidinecarboxamides. Piperidinecarboxamides are compounds containing a piperidine ring substituted with a carboxamide functional group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPiperidinecarboxylic acids and derivatives
Direct ParentPiperidinecarboxamides
Alternative Parents
Substituents
  • 2-piperidinecarboxamide
  • Piperidinecarboxamide
  • M-xylene
  • Xylene
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboximidic acid
  • Carboximidic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
  • 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide (CHEBI:6149 )
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.098 g/LNot Available
LogP3.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.098 g/LALOGPS
logP3.31ALOGPS
logP4.52ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity90.19 m³·mol⁻¹ChemAxon
Polarizability34.45 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]+169.96931661259
DarkChem[M-H]-169.79731661259
DeepCCS[M+H]+175.67730932474
DeepCCS[M-H]-173.31930932474
DeepCCS[M-2H]-206.20530932474
DeepCCS[M+Na]+181.7730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LevobupivacaineCCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C2737.3Standard polar33892256
LevobupivacaineCCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C2332.1Standard non polar33892256
LevobupivacaineCCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C2286.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Levobupivacaine,1TMS,isomer #1CCCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C2150.7Semi standard non polar33892256
Levobupivacaine,1TMS,isomer #1CCCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C2238.5Standard non polar33892256
Levobupivacaine,1TMS,isomer #1CCCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C2871.2Standard polar33892256
Levobupivacaine,1TBDMS,isomer #1CCCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2375.4Semi standard non polar33892256
Levobupivacaine,1TBDMS,isomer #1CCCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2459.3Standard non polar33892256
Levobupivacaine,1TBDMS,isomer #1CCCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C2969.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Levobupivacaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-6920000000-20e4e8d5c09a52a31c752017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levobupivacaine 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 - Levobupivacaine 10V, Positive-QTOFsplash10-0079-0970000000-e665f05dc8da9fafd8f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levobupivacaine 20V, Positive-QTOFsplash10-00dl-2900000000-6396ddc6fc9d5e9b6c642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levobupivacaine 40V, Positive-QTOFsplash10-0ac0-9200000000-befeaee90e72918d68b32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levobupivacaine 10V, Negative-QTOFsplash10-000i-0290000000-e01610a30f93d9c5ec2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levobupivacaine 20V, Negative-QTOFsplash10-00ri-0970000000-e26949f880557c6da8152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levobupivacaine 40V, Negative-QTOFsplash10-00xr-3900000000-56dfe5d9cd7f629f17e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levobupivacaine 10V, Negative-QTOFsplash10-000i-0090000000-e83ab5b70775090159b72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levobupivacaine 20V, Negative-QTOFsplash10-000i-0690000000-6ff0193988455d2867262021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levobupivacaine 40V, Negative-QTOFsplash10-00xr-1920000000-87f1897c4a60793791d52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levobupivacaine 10V, Positive-QTOFsplash10-000i-0190000000-23ffc5622396245151832021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levobupivacaine 20V, Positive-QTOFsplash10-000g-3920000000-6aaf7d8f5f0149cec33e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levobupivacaine 40V, Positive-QTOFsplash10-0007-8900000000-e62af4b8065c6c1caf012021-10-11Wishart 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 DB01002 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01002 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 IDDB01002
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID83289
KEGG Compound IDC07887
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevobupivacaine
METLIN IDNot Available
PubChem Compound92253
PDB IDNot Available
ChEBI ID6149
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. Burlacu CL, Buggy DJ: Update on local anesthetics: focus on levobupivacaine. Ther Clin Risk Manag. 2008 Apr;4(2):381-92. [PubMed:18728849 ]
  2. Leone S, Di Cianni S, Casati A, Fanelli G: Pharmacology, toxicology, and clinical use of new long acting local anesthetics, ropivacaine and levobupivacaine. Acta Biomed. 2008 Aug;79(2):92-105. [PubMed:18788503 ]

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:
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. 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. Ueta K, Sugimoto M, Suzuki T, Uchida I, Mashimo T: In vitro antagonism of recombinant ligand-gated ion-channel receptors by stereospecific enantiomers of bupivacaine. Reg Anesth Pain Med. 2006 Jan-Feb;31(1):19-25. [PubMed:16418020 ]
  4. Vladimirov M, Nau C, Mok WM, Strichartz G: Potency of bupivacaine stereoisomers tested in vitro and in vivo: biochemical, electrophysiological, and neurobehavioral studies. Anesthesiology. 2000 Sep;93(3):744-55. [PubMed:10969308 ]
  5. Brau ME, Branitzki P, Olschewski A, Vogel W, Hempelmann G: Block of neuronal tetrodotoxin-resistant Na+ currents by stereoisomers of piperidine local anesthetics. Anesth Analg. 2000 Dec;91(6):1499-505. [PubMed:11094008 ]