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Record Information
Version2.0
Creation Date2009-07-21 20:28:03 UTC
Update Date2014-12-24 20:25:53 UTC
Accession NumberT3D2942
Identification
Common NameMepivacaine
ClassSmall Molecule
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)
Compound Type
  • Amide
  • Amine
  • Anesthetic, Local
  • Drug
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(+-)-1-Methyl-2',6'-pipecoloxylidide
1-methyl-2',6'-pipecoloxylidide
Carbocaine
DL-Mepivacaine
Isocaine
Mepivacaina
Mepivacaine HCL
Mepivacaine hydrochloride
Mepivacainum
Mepivicaine
N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide
N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamide
Polocaine
S-Ropivacaine Mesylate
Scandicaine
Scandonest Plain
Chemical FormulaC15H22N2O
Average Molecular Mass246.348 g/mol
Monoisotopic Mass246.173 g/mol
CAS Registry Number96-88-8
IUPAC NameN-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
Traditional Namemepivacaine
SMILESCN1CCCCC1C(O)=NC1=C(C)C=CC=C1C
InChI IdentifierInChI=1/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 KeyInChIKey=INWLQCZOYSRPNW-UHFFFAOYNA-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Mepivacaine PathwayNot AvailableNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point150.5°C
Boiling PointNot Available
Solubility7000 mg/L (at 23°C)
LogP1.95
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 KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0092-9200000000-a3a931af35da130669aaJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9040000000-3c0a89a13f39484eef97JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-9073826aa2631981fe72JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-9b273b91b5148ef6a8faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-d541d397ca20f2f1a799JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-eda45d03ea77058a8429JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006t-9000000000-f42a147676c3c718e38fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-2890000000-4fd4344949c8e98d2d22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-9600000000-eccb3e339a3aafb57c83JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9100000000-923210fdcbf3093cec8cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0190000000-5c29854d995646f8e15fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fs-0960000000-75e4d525847b240eb8ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0g4i-6900000000-79da7c9893bedd422f3eJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-6a3d80d214452a24ab62JSpectraViewer | MoNA
Toxicity Profile
Route of ExposureAbsorbed locally. The rate of systemic absorption of local anesthetics is dependent upon the total dose and concentration of drug administered, the route of administration, the vascularity of the administration site, and the presence or absence of epinephrine in the anesthetic solution. Subcutaneous, injection ; Infiltration
Mechanism of ToxicityLocal anesthetics 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. In general, the progression of anesthesia is related to the diameter, myelination, and conduction velocity of affected nerve fibers. Clinically, the order of loss of nerve function is as follows: pain, temperature, touch, proprioception, and skeletal muscle tone.
MetabolismRapidly metabolized, with only a small percentage of the anesthetic (5 percent to 10 percent) being excreted unchanged in the urine. The liver is the principal site of metabolism, with over 50% of the administered dose being excreted into the bile as metabolites. Route of Elimination: It is rapidly metabolized, with only a small percentage of the anesthetic (5 percent to 10 percent) being excreted unchanged in the urine.The liver is the principal site of metabolism, with over 50% of the administered dose being excreted into the bile as metabolites. Half Life: The half-life of mepivacaine in adults is 1.9 to 3.2 hours and in neonates 8.7 to 9 hours.
Toxicity ValuesThe mean seizure dosage of mepivacaine in rhesus monkeys was found to be 18.8 mg/kg with mean arterial plasma concentration of 24.4 µg/mL. LD50: 23-35 mg/kg (Intravenous, Mouse) (1) LD50: 280 mg/kg (Subcutaneous, Mouse (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor production of local or regional analgesia and anesthesia by local infiltration, peripheral nerve block techniques, and central neural techniques including epidural and caudal blocks.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentTreatment of a patient with toxic manifestations consists of assuring and maintaining a patient airway and supporting ventilation (respiration) as required. This usually will be sufficient in the management of most reactions. Should a convulsion persist despite ventilatory therapy, small increments of anticonvulsive agents may be given intravenously, such as benzodiazephine (e.g., diazepam) or ultrashort-acting barbiturates (e.g., thiopental or thiamylal) or short-acting barbiturates (e.g., pentobarbital or secobarbital). Cardiovascular depression may require circulatory assistance with intravenous fluids and/or vasopressor (e.g., Ephedrine) as dictated by the clinical situation. (4)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00961
HMDB IDHMDB15096
PubChem Compound ID4062
ChEMBL IDCHEMBL1087
ChemSpider ID3922
KEGG IDC07528
UniProt IDNot Available
OMIM ID
ChEBI ID6759
BioCyc IDNot Available
CTD IDNot Available
Stitch IDMepivacaine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkMepivacaine
References
Synthesis Reference

DrugSyn.org

MSDSLink
General References
  1. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
  2. Driessen B, Reimann W: Interaction of the central analgesic, tramadol, with the uptake and release of 5-hydroxytryptamine in the rat brain in vitro. Br J Pharmacol. 1992 Jan;105(1):147-51. [1596676 ]
  3. AMA Drug Evaluations, 1994, p168.
  4. RxList: The Internet Drug Index (2009). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Voltage-gated sodium channel activity
Specific Function:
Tetrodotoxin-resistant channel that 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. Plays a role in neuropathic pain mechanisms.
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
Molecular Weight:
220623.605 Da
References
  1. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]