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Record Information
Version4.0
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-09-27 08:27:49 UTC
HMDB IDHMDB0015096
Secondary Accession Numbers
  • HMDB15096
Metabolite Identification
Common NameMepivacaine
DescriptionA local anesthetic that is chemically related to bupivacaine but pharmacologically related to lidocaine. It is indicated for infiltration, nerve block, and epidural anesthesia. Mepivacaine is effective topically only in large doses and therefore should not be used by this route. (From AMA Drug Evaluations, 1994, p168)
Structure
Thumb
Synonyms
ValueSource
(+-)-1-Methyl-2',6'-pipecoloxylidideChEBI
1-Methyl-2',6'-pipecoloxylidideChEBI
CarbocaineChEBI
DL-MepivacaineChEBI
MepivacainaChEBI
MepivacainumChEBI
N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamideChEBI
N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamideChEBI
Mepivacaine HCLHMDB
Mepivacaine hydrochlorideHMDB
MepivicaineHMDB
S-Ropivacaine mesylateHMDB
3m Brand OF mepivacaine hydrochlorideMeSH
AstraZeneca brand OF mepivacaine hydrochlorideMeSH
Inibsa brand OF mepivacaine hydrochlorideMeSH
IsogaineMeSH
Mepivacain injektopasMeSH
Mepivacaina braunMeSH
Monohydrochloride, mepivacaineMeSH
Pascoe brand OF mepivacaine hydrochlorideMeSH
ScandicaineMeSH
Astra brand OF mepivacaine hydrochlorideMeSH
Hexal brand OF mepivacaine hydrochlorideMeSH
Hydrochloride, mepivacaineMeSH
MepihexalMeSH
MepivastesinMeSH
Novocol brand OF mepivacaine hydrochlorideMeSH
PolocaineMeSH
Curasan brand OF mepivacaine hydrochlorideMeSH
Abbott brand OF mepivacaine hydrochlorideMeSH
Braun, mepivacainaMeSH
Clarben brand OF mepivacaine hydrochlorideMeSH
Dentsply brand OF mepivacaine hydrochlorideMeSH
MeaverinMeSH
MecainMeSH
Sanofi brand OF mepivacaine hydrochlorideMeSH
ScandinibsaMeSH
Aventis brand OF mepivacaine hydrochlorideMeSH
Braun brand OF mepivicaine hydrochlorideMeSH
CarbocaïneMeSH
IsocaineMeSH
Mepivacain-injektopasMeSH
Mepivacaine monohydrochlorideMeSH
ScandicainMeSH
ScandonestMeSH
Chemical FormulaC15H22N2O
Average Molecular Weight246.348
Monoisotopic Molecular Weight246.173213336
IUPAC NameN-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
Traditional Namemepivacaine
CAS Registry Number96-88-8
SMILES
CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C
InChI Identifier
InChI=1S/C15H22N2O/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18)
InChI KeyINWLQCZOYSRPNW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as piperidinecarboxamides. These are compounds containing a piperidine ring substituted with a carboxamide functional group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPiperidines
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Parenteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point150.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.62 g/LNot Available
LogP2.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP2.16ALOGPS
logP3.19ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)7.25ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.32 m³·mol⁻¹ChemAxon
Polarizability28.61 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0092-9200000000-a3a931af35da130669aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9040000000-3c0a89a13f39484eef97View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-9073826aa2631981fe72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-9b273b91b5148ef6a8faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-d541d397ca20f2f1a799View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-eda45d03ea77058a8429View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006t-9000000000-f42a147676c3c718e38fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-2890000000-4fd4344949c8e98d2d22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-9600000000-eccb3e339a3aafb57c83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9100000000-923210fdcbf3093cec8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0190000000-5c29854d995646f8e15fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fs-0960000000-75e4d525847b240eb8ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0g4i-6900000000-79da7c9893bedd422f3eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-6a3d80d214452a24ab62View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Mepivacaine PathwayPw000405Pw000405 greyscalePw000405 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00961 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00961 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-4 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00961
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3922
KEGG Compound IDC07528
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMepivacaine
METLIN IDNot Available
PubChem Compound4062
PDB IDNot Available
ChEBI ID6759
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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. Leffler A, Reckzeh J, Nau C: Block of sensory neuronal Na+ channels by the secreolytic ambroxol is associated with an interaction with local anesthetic binding sites. Eur J Pharmacol. 2010 Mar 25;630(1-3):19-28. doi: 10.1016/j.ejphar.2009.12.027. Epub 2010 Jan 4. [PubMed:20044988 ]