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Identification
NameMepivacaine
Accession NumberDB00961  (APRD01094)
TypeSmall Molecule
GroupsApproved, Vet Approved
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
(+-)-1-Methyl-2',6'-pipecoloxylidide
1-methyl-2',6'-pipecoloxylidide
Carbocaine
DL-Mepivacaine
Mepivacaina
Mepivacainum
N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide
N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamide
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
3% Polocaine Dentalliquid30 mgblock/infiltrationDentsply Canada Limited2009-10-19Not applicableCanada
Carbocaineinjection, solution10 mg/mLepidural; infiltrationHospira, Inc.1960-03-15Not applicableUs
Carbocaineinjection, solution20 mg/mLinfiltrationHospira, Inc.1960-03-15Not applicableUs
Carbocaineinjection, solution20 mg/mLepidural; infiltrationHospira, Inc.1960-03-15Not applicableUs
Carbocaineinjection, solution15 mg/mLepidural; infiltrationHospira, Inc.1960-03-15Not applicableUs
Carbocaineinjection, solution10 mg/mLinfiltrationHospira, Inc.1960-03-15Not applicableUs
Carbocaine Liq 2%liquid20 mgintracaudal; epiduralSanofi Canada, Inc.1959-12-312001-08-10Canada
Carbocaine 1%solution1 %block/infiltrationHospira Healthcare Corporation2001-07-15Not applicableCanada
Carbocaine 1%solution1 %intracaudal; epiduralHospira Healthcare Corporation2001-06-01Not applicableCanada
Carbocaine 2%solution20 mgintracaudal; epiduralHospira Healthcare Corporation2001-07-15Not applicableCanada
Carbocaine 3%solution30 mgblock/infiltrationKodak Canada Inc.1993-12-312008-07-14Canada
Carbocaine 3%solution30 mgblock/infiltrationCarestream Health Canada Company2005-11-21Not applicableCanada
Carbocaine Inj Liq 10mg/mlliquid10 mgintracaudal; epiduralSterling Winthrop Inc.1992-12-311996-09-10Canada
Carbocaine Inj Liq 20mg/mlliquid20 mgintraspinalSterling Winthrop Inc.1992-12-311996-09-10Canada
Carbocaine Liq 1%liquid1 %block/infiltrationSanofi Canada, Inc.1959-12-312001-08-10Canada
Carbocaine Liq 1%liquid1 %intracaudal; epiduralSanofi Canada, Inc.1959-12-312001-08-10Canada
Isocaine HCl Inj 3%solution30 mgsubcutaneousNovocol Pharmaceutical Of Canada Inc1977-12-31Not applicableCanada
Mepivicaine Hydrochloride Injection, USP 3%solution30 mgblock/infiltrationDentsply Canada Limited1989-12-312012-07-19Canada
Scandonest 3% Plain Injliquid30 mgblock/infiltrationSeptodont1980-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Carbocaineinjection, solution30 mg/mLsubcutaneousCaresteam Health, Inc.2011-01-01Not applicableUs
Iq Dental Mepivacaineinjection, solution30 mg/mLsubcutaneousIq Dental2012-08-15Not applicableUs
Isocaineinjection, solution30 mg/mLsubcutaneousNovocol Pharmaceutical of Canada, Inc.2010-08-20Not applicableUs
Mepivacaineinjection, solution30 mg/mLsubcutaneousBenco Dental2011-01-01Not applicableUs
Mepivacaineinjection, solution30 mg/mLsubcutaneousDarby Dental Supply, LLC2011-01-14Not applicableUs
Mepivacaineinjection, solution30 mg/mLsubcutaneousNovocol Pharmaceutical of Canada, Inc.2013-07-31Not applicableUs
Mepivacaineinjection, solution30 mg/mLsubcutaneousPatterson Dental Supply, Inc.2011-01-01Not applicableUs
Mepivacaineinjection, solution30 mg/mLsubcutaneousNDC, Inc.2015-04-10Not applicableUs
Mepivacaine Hydrochlorideinjection, solution30 mg/mLsubcutaneousSafco Dental Supply Co.2011-01-01Not applicableUs
Mepivacaine Hydrochlorideinjection, solution30 mg/mLdental; infiltrationHospira, Inc.2008-04-28Not applicableUs
Pearson Mepivacaineinjection, solution30 mg/mLsubcutaneousPearson Dental2012-05-15Not applicableUs
Polocaineinjection, solution30 mg/mLsubcutaneousDentsply Pharmaceutical1984-10-10Not applicableUs
Polocaineinjection, solution20 mg/mLinfiltrationAPP Pharmaceuticals, LLC2009-07-20Not applicableUs
Polocaineinjection, solution10 mg/mLinfiltrationAPP Pharmaceuticals, LLC2009-07-20Not applicableUs
Polocaine-mpfinjection, solution20 mg/mLepidural; infiltrationAPP Pharmaceuticals, LLC2009-07-21Not applicableUs
Polocaine-mpfinjection, solution15 mg/mLepidural; infiltrationAPP Pharmaceuticals, LLC2009-07-21Not applicableUs
Polocaine-mpfinjection, solution10 mg/mLepidural; infiltrationAPP Pharmaceuticals, LLC2009-07-20Not applicableUs
Scandonest Plaininjection, solution30 mg/mLsubcutaneousNovocol Pharmaceutical of Canada, Inc.2013-06-26Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ScandicaineNot Available
Brand mixtures
NameLabellerIngredients
2% Polocaine Dental With Levonordefrin 1:20,000Dentsply Canada Limited
Carbocaine 2% With Neo-cobefrinCarestream Health Canada Company
Carbocaine With Neo-cobefrinCaresteam Health, Inc.
Isocaine HCl Inj 2%Novocol Pharmaceutical Of Canada Inc
Mepivacaine Hydrochloride and LevonordefrinDarby Dental Supply, LLC
Mepivacaine With LevonordefrinPatterson Dental Supply, Inc.
Scandonest 2% Special InjSeptodont
Scandonest 2% With LevonordefrinNovocol Pharmaceutical Of Canada Inc
Scandonest LNovocol Pharmaceutical Of Canada, Inc
Salts
Name/CASStructureProperties
Mepivacaine Hydrochloride
1722-62-9
Thumb
  • InChI Key: RETIMRUQNCDCQB-UHFFFAOYNA-N
  • Monoisotopic Mass: 282.149891075
  • Average Mass: 282.809
DBSALT000478
Categories
UNIIB6E06QE59J
CAS number96-88-8
WeightAverage: 246.348
Monoisotopic: 246.173213336
Chemical FormulaC15H22N2O
InChI KeyInChIKey=INWLQCZOYSRPNW-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.
Related Articles
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 inhibitorNon-inhibitor0.933
CYP450 2D6 inhibitorInhibitor0.6146
CYP450 2C19 inhibitorNon-inhibitor0.9387
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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, 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
Liquidintracaudal; epidural20 mg
Solutionblock/infiltration1 %
Solutionintracaudal; epidural1 %
Solutionintracaudal; epidural20 mg
Solutionblock/infiltration30 mg
Liquidintracaudal; epidural10 mg
Liquidintraspinal20 mg
Liquidblock/infiltration1 %
Liquidintracaudal; epidural1 %
Injection, solutionsubcutaneous
Solutionblock/infiltration
Solutionsubcutaneous30 mg
Injection, solutiondental; infiltration30 mg/mL
Liquidblock/infiltration
Liquidblock/infiltration30 mg
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)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-6a3d80d214452a24ab62View in MoNA
References
Synthesis Reference

DrugSyn.org

US2799679
General ReferencesNot Available
External Links
ATC CodesN01BB03N01BB53
AHFS Codes
  • 72:00.00
PDB EntriesNot Available
FDA labelDownload (180 KB)
MSDSDownload (73.2 KB)
Interactions
Drug Interactions
Drug
AcebutololThe serum concentration of Mepivacaine can be increased when it is combined with Acebutolol.
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Mepivacaine.
AmitriptylineAmitriptyline may increase the activities of Mepivacaine.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Mepivacaine.
AtenololThe serum concentration of Mepivacaine can be increased when it is combined with Atenolol.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Mepivacaine.
BetaxololThe serum concentration of Mepivacaine can be increased when it is combined with Betaxolol.
BisoprololThe serum concentration of Mepivacaine can be increased when it is combined with Bisoprolol.
CabergolineCabergoline may increase the hypertensive activities of Mepivacaine.
CarteololThe serum concentration of Mepivacaine can be increased when it is combined with Carteolol.
CarvedilolThe serum concentration of Mepivacaine can be increased when it is combined with Carvedilol.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Mepivacaine.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Mepivacaine.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Mepivacaine.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Mepivacaine.
DoxofyllineThe risk or severity of adverse effects can be increased when Mepivacaine is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Mepivacaine.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Mepivacaine.
EsmololThe serum concentration of Mepivacaine can be increased when it is combined with Esmolol.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Mepivacaine.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Mepivacaine.
HyaluronidaseThe risk or severity of adverse effects can be increased when Hyaluronidase is combined with Mepivacaine.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Mepivacaine.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Mepivacaine.
LabetalolThe serum concentration of Mepivacaine can be increased when it is combined with Labetalol.
LevobunololThe serum concentration of Mepivacaine can be increased when it is combined with Levobunolol.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Mepivacaine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Mepivacaine.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Mepivacaine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Mepivacaine.
MetipranololThe serum concentration of Mepivacaine can be increased when it is combined with Metipranolol.
MetoprololThe serum concentration of Mepivacaine can be increased when it is combined with Metoprolol.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Mepivacaine.
NadololThe serum concentration of Mepivacaine can be increased when it is combined with Nadolol.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Mepivacaine.
NebivololThe serum concentration of Mepivacaine can be increased when it is combined with Nebivolol.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Mepivacaine.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Mepivacaine.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Mepivacaine.
PenbutololThe serum concentration of Mepivacaine can be increased when it is combined with Penbutolol.
PhenelzinePhenelzine may increase the hypertensive activities of Mepivacaine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Mepivacaine.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Mepivacaine.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Mepivacaine.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Mepivacaine.
PindololThe serum concentration of Mepivacaine can be increased when it is combined with Pindolol.
PrazosinPrazosin may decrease the vasoconstricting activities of Mepivacaine.
PropranololThe serum concentration of Mepivacaine can be increased when it is combined with Propranolol.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Mepivacaine.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Mepivacaine.
SotalolThe serum concentration of Mepivacaine can be increased when it is combined with Sotalol.
Technetium Tc-99m tilmanoceptMepivacaine may decrease effectiveness of Technetium Tc-99m tilmanocept as a diagnostic agent.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Mepivacaine.
TimololThe serum concentration of Mepivacaine can be increased when it is combined with Timolol.
TranylcypromineTranylcypromine may increase the hypertensive activities of Mepivacaine.
VenlafaxineVenlafaxine may increase the tachycardic activities of Mepivacaine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
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. 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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:24