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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:47:32 UTC
HMDB IDHMDB0015096
Secondary Accession Numbers
  • HMDB15096
Metabolite Identification
Common NameMepivacaine
DescriptionMepivacaine, also known as carbocaine or carboplyin dental, belongs to the class of organic compounds known as piperidinecarboxamides. Piperidinecarboxamides are compounds containing a piperidine ring substituted with a carboxamide functional group. Mepivacaine is a drug which is used for production of local or regional analgesia and anesthesia by local infiltration, peripheral nerve block techniques, and central neural techniques including epidural and caudal blocks. In humans, mepivacaine is involved in the mepivacaine action pathway. Mepivacaine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Mepivacaine.
Structure
Data?1582753258
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
Carboplyin dentalKegg
Mepivacaine HCLHMDB
Mepivacaine hydrochlorideHMDB
MepivicaineHMDB
S-Ropivacaine mesylateHMDB
3m Brand OF mepivacaine hydrochlorideHMDB
AstraZeneca brand OF mepivacaine hydrochlorideHMDB
Inibsa brand OF mepivacaine hydrochlorideHMDB
IsogaineHMDB
Mepivacain injektopasHMDB
Mepivacaina braunHMDB
Monohydrochloride, mepivacaineHMDB
Pascoe brand OF mepivacaine hydrochlorideHMDB
ScandicaineHMDB
Astra brand OF mepivacaine hydrochlorideHMDB
Hexal brand OF mepivacaine hydrochlorideHMDB
Hydrochloride, mepivacaineHMDB
MepihexalHMDB
MepivastesinHMDB
Novocol brand OF mepivacaine hydrochlorideHMDB
PolocaineHMDB
Curasan brand OF mepivacaine hydrochlorideHMDB
Abbott brand OF mepivacaine hydrochlorideHMDB
Braun, mepivacainaHMDB
Clarben brand OF mepivacaine hydrochlorideHMDB
Dentsply brand OF mepivacaine hydrochlorideHMDB
MeaverinHMDB
MecainHMDB
Sanofi brand OF mepivacaine hydrochlorideHMDB
ScandinibsaHMDB
Aventis brand OF mepivacaine hydrochlorideHMDB
Braun brand OF mepivicaine hydrochlorideHMDB
CarbocaïneHMDB
IsocaineHMDB
Mepivacain-injektopasHMDB
Mepivacaine monohydrochlorideHMDB
ScandicainHMDB
ScandonestHMDB
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
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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point150.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.62 g/LNot Available
LogP2.2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM159.130932474
[M+H]+Not Available157.633http://allccs.zhulab.cn/database/detail?ID=AllCCS00000936
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP10(2.16) g/LALOGPS
logP10(3.19) g/LChemAxon
logS10(-2.6) g/LALOGPS
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
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]+159.531661259
DarkChem[M-H]-158.07131661259
DeepCCS[M+H]+161.74930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MepivacaineCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C2365.1Standard polar33892256
MepivacaineCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C2045.8Standard non polar33892256
MepivacaineCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C2046.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mepivacaine,1TMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)C1CCCCN1C)[Si](C)(C)C1955.5Semi standard non polar33892256
Mepivacaine,1TMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)C1CCCCN1C)[Si](C)(C)C1933.7Standard non polar33892256
Mepivacaine,1TMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)C1CCCCN1C)[Si](C)(C)C2507.0Standard polar33892256
Mepivacaine,1TBDMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)C1CCCCN1C)[Si](C)(C)C(C)(C)C2174.2Semi standard non polar33892256
Mepivacaine,1TBDMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)C1CCCCN1C)[Si](C)(C)C(C)(C)C2149.2Standard non polar33892256
Mepivacaine,1TBDMS,isomer #1CC1=CC=CC(C)=C1N(C(=O)C1CCCCN1C)[Si](C)(C)C(C)(C)C2627.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mepivacaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0092-9200000000-a3a931af35da130669aa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mepivacaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mepivacaine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-6a3d80d214452a24ab622014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine LC-ESI-QFT , positive-QTOFsplash10-0002-9040000000-3c0a89a13f39484eef972017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine LC-ESI-QFT , positive-QTOFsplash10-0002-9000000000-9073826aa2631981fe722017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine LC-ESI-QFT , positive-QTOFsplash10-0002-9000000000-9b273b91b5148ef6a8fa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine LC-ESI-QFT , positive-QTOFsplash10-0002-9000000000-d541d397ca20f2f1a7992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine LC-ESI-QFT , positive-QTOFsplash10-0002-9000000000-eda45d03ea77058a84292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine LC-ESI-QFT , positive-QTOFsplash10-006t-9000000000-f42a147676c3c718e38f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine 30V, Positive-QTOFsplash10-0002-9000000000-9073826aa2631981fe722021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine 45V, Positive-QTOFsplash10-0002-9000000000-9b273b91b5148ef6a8fa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine 15V, Positive-QTOFsplash10-0002-9040000000-3c0a89a13f39484eef972021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine 60V, Positive-QTOFsplash10-0002-9000000000-d541d397ca20f2f1a7992021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine 75V, Positive-QTOFsplash10-0002-9000000000-4b9a3b3048a6c1bbd6562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine 90V, Positive-QTOFsplash10-006t-9000000000-f42a147676c3c718e38f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mepivacaine 35V, Positive-QTOFsplash10-0002-9000000000-e7a7508a46c81f01a0f62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepivacaine 10V, Positive-QTOFsplash10-006t-2890000000-4fd4344949c8e98d2d222016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepivacaine 20V, Positive-QTOFsplash10-006t-9600000000-eccb3e339a3aafb57c832016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepivacaine 40V, Positive-QTOFsplash10-00di-9100000000-923210fdcbf3093cec8c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepivacaine 10V, Negative-QTOFsplash10-0002-0190000000-5c29854d995646f8e15f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepivacaine 20V, Negative-QTOFsplash10-00fs-0960000000-75e4d525847b240eb8dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepivacaine 40V, Negative-QTOFsplash10-0g4i-6900000000-79da7c9893bedd422f3e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepivacaine 10V, Positive-QTOFsplash10-0002-9380000000-6935f06f321d22f49f8f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepivacaine 20V, Positive-QTOFsplash10-0002-9630000000-fc9251019b6aa4d95ac02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepivacaine 40V, Positive-QTOFsplash10-0002-9000000000-64648fb1fd5128b768272021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepivacaine 10V, Negative-QTOFsplash10-0002-0090000000-4a0996a0879be85733ed2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepivacaine 20V, Negative-QTOFsplash10-00dj-0950000000-7a84cb81cb305d4c644e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mepivacaine 40V, Negative-QTOFsplash10-00xr-1910000000-dcbc91df93a09683c2612021-10-11Wishart 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 DB00961 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00961 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 IDDB00961
Phenol Explorer Compound IDNot Available
FooDB 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
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 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 ]