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Identification
NameMepivacaine
Accession NumberDB00961  (APRD01094)
TypeSmall Molecule
GroupsApproved
Description

A 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
SynonymLanguageCode
(+-)-1-Methyl-2',6'-pipecoloxylidideNot AvailableNot Available
1-methyl-2',6'-pipecoloxylidideNot AvailableNot Available
CarbocaineNot AvailableNot Available
DL-MepivacaineNot AvailableNot Available
MepivacainaSpanishINN
MepivacainumLatinINN
N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamideNot AvailableNot Available
N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamideNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Carbocaineinjection, solution10 mg/mLepidural; infiltrationHospira, Inc.2010-03-08Not AvailableUs
Carbocaineinjection, solution10 mg/mLinfiltrationHospira, Inc.2010-03-08Not AvailableUs
Carbocaineinjection, solution15 mg/mLepidural; infiltrationHospira, Inc.2010-03-08Not AvailableUs
Carbocaineinjection, solution20 mg/mLepidural; infiltrationHospira, Inc.2010-03-08Not AvailableUs
Carbocaineinjection, solution20 mg/mLinfiltrationHospira, Inc.2010-03-08Not AvailableUs
Polocaineinjection, solution30 mg/mLsubcutaneousDentsply Pharmaceutical1984-10-10Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mepivacaine Hydrochlorideinjection, solution30 mg/mLdental; infiltrationHospira, Inc.2009-11-09Not AvailableUs
Carbocaineinjection, solution30 mg/mLsubcutaneousCaresteam Health, Inc.2011-01-01Not AvailableUs
Mepivacaineinjection, solution30 mg/mLsubcutaneousPatterson Dental Supply, Inc.2011-01-01Not AvailableUs
Mepivacaineinjection, solution30 mg/mLsubcutaneousNovocol Pharmaceutical of Canada, Inc.2013-07-31Not AvailableUs
Scandonest Plaininjection, solution30 mg/mLsubcutaneousNovocol Pharmaceutical of Canada, Inc.2013-06-26Not AvailableUs
Isocaineinjection, solution30 mg/mLsubcutaneousNovocol Pharmaceutical of Canada, Inc.2010-08-20Not AvailableUs
Polocaineinjection, solution10 mg/mLinfiltrationAPP Pharmaceuticals, LLC2009-07-20Not AvailableUs
Polocaineinjection, solution20 mg/mLinfiltrationAPP Pharmaceuticals, LLC2009-07-20Not AvailableUs
Mepivacaineinjection, solution30 mg/mLsubcutaneousDarby Dental Supply, LLC2011-01-14Not AvailableUs
Mepivacaineinjection, solution30 mg/mLsubcutaneousBenco Dental2011-01-01Not AvailableUs
Mepivacaine Hydrochlorideinjection, solution30 mg/mLsubcutaneousSafco Dental Supply Co.2011-01-01Not AvailableUs
Over the Counter ProductsNot Available
International Brands
NameCompany
ScandicaineNot Available
Brand mixtures
Brand NameIngredients
2% Polocaine Dental with Levonordefrin 1:20,000Corbadrine + Mepivacaine Hydrochloride
Arestocaine Hcl 2% W Levonordefrin 1:20000Levonordefrin Hydrochloride + Mepivacaine Hydrochloride
Carbocaine 2% Neo-Cobefrin 1:20,000 LiqLevonordefrin Hydrochloride + Mepivacaine Hydrochloride
Carbocaine 2% with Neo-CobefrinCorbadrine + Mepivacaine Hydrochloride
Isocaine Hcl Inj 2%Levonordefrin Hydrochloride (Levonordefrin Hydrochloride) + Mepivacaine Hydrochloride
Mepivacaine Hcl 2% W Levonordefrin InjLevonordefrin Hydrochloride + Mepivacaine Hydrochloride
Scandonest 2% Special InjEpinephrine + Mepivacaine Hydrochloride
Salts
Name/CASStructureProperties
Mepivacaine Hydrochloride
1722-62-9
Thumb
  • InChI Key: RETIMRUQNCDCQB-UHFFFAOYNA-N
  • Monoisotopic Mass: 282.149891075
  • Average Mass: 282.809
DBSALT000478
Categories
CAS number96-88-8
WeightAverage: 246.348
Monoisotopic: 246.173213336
Chemical FormulaC15H22N2O
InChI KeyINWLQCZOYSRPNW-UHFFFAOYSA-N
InChI
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)
IUPAC Name
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
SMILES
CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C
Taxonomy
DescriptionThis compound 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
  • N-arylamide
  • Piperidinecarboxylic acid
  • Piperidinecarboxamide
  • 2-piperidinecarboxamide
  • Benzenoid
  • Piperidine
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor production of local or regional analgesia and anesthesia by local infiltration, peripheral nerve block techniques, and central neural techniques including epidural and caudal blocks.
PharmacodynamicsMepivicaine is a local anesthetic of the amide type. Mepivicaine as a reasonably rapid onset and medium duration and is known by the proprietary names as Carbocaine and Polocaine. Mepivicaine is used in local infiltration and regional anesthesia. Systemic absorption of local anesthetics produces effects on the cardiovascular and central nervous systems. At blood concentrations achieved with normal therapeutic doses, changes in cardiac conduction, excitability, refractoriness, contractility, and peripheral vascular resistance are minimal.
Mechanism of actionLocal 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.
AbsorptionAbsorbed 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.
Volume of distributionNot Available
Protein bindingMepivacaine is approximately 75% bound to plasma proteins. Generally, the lower the plasma concentration of drug, the higher the percentage of drug bound to plasma.
Metabolism

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.

Route of eliminationIt 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 lifeThe half-life of mepivacaine in adults is 1.9 to 3.2 hours and in neonates 8.7 to 9 hours.
ClearanceNot Available
ToxicityThe 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. The intravenous and subcutaneous LD 50 in mice is 23 mg/kg to 35 mg/kg and 280 mg/kg respectively.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Mepivacaine Action PathwayDrug actionSMP00399
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9568
Blood Brain Barrier+0.9749
Caco-2 permeable+0.6836
P-glycoprotein substrateSubstrate0.7866
P-glycoprotein inhibitor IInhibitor0.6872
P-glycoprotein inhibitor IINon-inhibitor0.8665
Renal organic cation transporterNon-inhibitor0.5878
CYP450 2C9 substrateNon-substrate0.7853
CYP450 2D6 substrateSubstrate0.7423
CYP450 3A4 substrateSubstrate0.7726
CYP450 1A2 substrateNon-inhibitor0.7996
CYP450 2C9 substrateNon-inhibitor0.933
CYP450 2D6 substrateInhibitor0.6146
CYP450 2C19 substrateNon-inhibitor0.9387
CYP450 3A4 substrateNon-inhibitor0.5395
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7497
Ames testNon AMES toxic0.8252
CarcinogenicityNon-carcinogens0.9333
BiodegradationNot ready biodegradable0.939
Rat acute toxicity1.7237 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.908
hERG inhibition (predictor II)Inhibitor0.6936
Pharmacoeconomics
Manufacturers
  • Solvay pharmaceuticals
  • Eastman kodak co
  • Hospira inc
  • Novocol pharmaceutical inc
  • Graham chemical co
  • International medication system
  • Watson laboratories inc
  • App pharmaceuticals llc
  • Dentsply pharmaceutical
  • Deproco inc
Packagers
Dosage forms
FormRouteStrength
Injection, solutiondental; infiltration30 mg/mL
Injection, solutionepidural; infiltration10 mg/mL
Injection, solutionepidural; infiltration15 mg/mL
Injection, solutionepidural; infiltration20 mg/mL
Injection, solutioninfiltration10 mg/mL
Injection, solutioninfiltration20 mg/mL
Injection, solutionsubcutaneous30 mg/mL
Prices
Unit descriptionCostUnit
Mepivacaine hcl powder318.33USD g
Mepivacaine hcl 3% cartridge0.46USD ml
Carbocaine 1% vial0.26USD ml
Polocaine 1% vial0.25USD ml
Polocaine 2% vial0.24USD ml
Carbocaine 2% vial0.19USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point150.5 °CPhysProp
water solubility7000 mg/L (at 23 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.95HANSCH,C ET AL. (1995)
logS-1.55ADME Research, USCD
pKa7.7SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.621 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.32 m3·mol-1ChemAxon
Polarizability28.61 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.1 KB)
SpectraMS
References
Synthesis Reference

DrugSyn.org

US2799679
General ReferenceNot Available
External Links
ATC CodesN01BB03
AHFS Codes
  • 72:00.00
PDB EntriesNot Available
FDA labelDownload (180 KB)
MSDSDownload (73.2 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Sodium channel protein type 10 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium channel protein type 10 subunit alpha Q9Y5Y9 Details

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
  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
  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. Epub 2010 Jan 4. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:24