Identification

Summary

Mepivacaine is a local anesthetic used for local or regional analgesia or anesthesia.

Brand Names
Carbocaine, Carbocaine With Neo-cobefrin, Carbocaine With Neocobefrin, Isocaine, Isocaine With Levonordefrin, Polocaine, Scandonest, Scandonest L, Scandonest Plain
Generic Name
Mepivacaine
DrugBank Accession Number
DB00961
Background

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)

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 246.348
Monoisotopic: 246.173213336
Chemical Formula
C15H22N2O
Synonyms
  • (+-)-1-Methyl-2',6'-pipecoloxylidide
  • 1-methyl-2',6'-pipecoloxylidide
  • DL-Mepivacaine
  • Mepivacaina
  • Mepivacaine
  • Mepivacainum
  • N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide
  • N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamide

Pharmacology

Indication

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.

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Mepivicaine is an amide local anesthetic. 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 action

Local 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.

TargetActionsOrganism
ASodium channel protein type 10 subunit alpha
inhibitor
Humans
Absorption

Absorbed 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 distribution

Not Available

Protein binding

Mepivacaine 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 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.

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

The 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.

Pathways
PathwayCategory
Mepivacaine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Mepivacaine is combined with 1,2-Benzodiazepine.
AbacavirMepivacaine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcebutololThe serum concentration of Mepivacaine can be increased when it is combined with Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Mepivacaine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Mepivacaine which could result in a higher serum level.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Mepivacaine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Mepivacaine.
AcetophenazineThe risk or severity of adverse effects can be increased when Mepivacaine is combined with Acetophenazine.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Mepivacaine which could result in a higher serum level.
AclidiniumMepivacaine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Mepivacaine hydrochloride4VFX2L7EM51722-62-9RETIMRUQNCDCQB-UHFFFAOYSA-N
International/Other Brands
Scandicaine
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
3% Polocaine DentalLiquid30 mg / mLInfiltrationDentsply Pharmaceutical2009-10-19Not applicableCanada flag
CarbocaineInjection, solution20 mg/1mLInfiltrationHospira, Inc.2006-09-27Not applicableUS flag
CarbocaineInjection, solution10 mg/1mLEpidural; InfiltrationHospira, Inc.2006-03-23Not applicableUS flag
CarbocaineInjection, solution20 mg/1mLEpidural; InfiltrationHospira, Inc.2007-01-31Not applicableUS flag
CarbocaineInjection, solution10 mg/1mLInfiltrationHospira, Inc.2007-10-10Not applicableUS flag
CarbocaineInjection, solution15 mg/1mLEpidural; InfiltrationHospira, Inc.2006-04-28Not applicableUS flag
Carbocaine 1%Solution10 mg / mLEpidural; IntracaudalPfizer Canada Ulc2001-06-01Not applicableCanada flag
Carbocaine 1%Solution10 mg / mLInfiltrationPfizer Canada Ulc2001-07-15Not applicableCanada flag
Carbocaine 2%Solution20 mg / mLEpidural; IntracaudalPfizer Canada Ulc2001-07-15Not applicableCanada flag
Carbocaine 3%Solution30 mg / mLInfiltrationCarestream Health Inc.2005-11-212018-09-06Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CarbocaineInjection, solution30 mg/1mLSubcutaneousSeptodont, Inc.2018-06-21Not applicableUS flag
CarbocaineInjection, solution30 mg/1mLSubcutaneousCaresteam Health, Inc.2011-01-01Not applicableUS flag
IQ Dental MepivacaineInjection, solution30 mg/1mLSubcutaneousIq Dental2012-08-15Not applicableUS flag
IsocaineInjection, solution30 mg/1mLSubcutaneousNovocol Inc.2010-08-20Not applicableUS flag
MepivacaineInjection, solution30 mg/1mLSubcutaneousNDC, Inc.2015-04-10Not applicableUS flag
MepivacaineInjection, solution30 mg/1mLSubcutaneousBenco Dental2011-01-01Not applicableUS flag
MepivacaineInjection, solution30 mg/1mLSubcutaneousPatterson Dental Supply, Inc.2011-01-01Not applicableUS flag
MepivacaineInjection, solution30 mg/1mLSubcutaneousDarby Dental Supply, LLC2011-01-14Not applicableUS flag
MepivacaineInjection, solution30 mg/1mLSubcutaneousNovocol Inc.2013-07-31Not applicableUS flag
Mepivacaine HydrochlorideInjection, solution30 mg/1mLSubcutaneousHenry Schein Inc.2011-01-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
2% Polocaine Dental With Levonordefrin 1:20,000Mepivacaine hydrochloride (20 mg / mL) + Levonordefrin (0.05 mg / mL)SolutionInfiltrationDentsply Pharmaceutical1990-12-312011-08-04Canada flag
Carbocaine 2% With Neo-cobefrinMepivacaine hydrochloride (20 mg / mL) + Levonordefrin (0.05 mg / mL)SolutionInfiltrationNovocol Inc.2019-07-30Not applicableCanada flag
Carbocaine 2% With Neo-cobefrinMepivacaine hydrochloride (20 mg / mL) + Levonordefrin (0.05 mg / mL)SolutionInfiltrationCarestream Health Inc.2006-09-012018-09-06Canada flag
Carbocaine 2% With Neo-cobefrinMepivacaine hydrochloride (20 mg / mL) + Levonordefrin (0.05 mg / mL)SolutionInfiltrationKodak Canada Inc.2005-04-222008-07-14Canada flag
Carbocaine with Neo-CobefrinMepivacaine hydrochloride (30 mg/1mL) + Levonordefrin (0.05 mg/1mL)Injection, solutionSubcutaneousSeptodont, Inc.2018-11-19Not applicableUS flag
Carbocaine with Neo-CobefrinMepivacaine hydrochloride (20 mg/1mL) + Levonordefrin (0.05 mg/1mL)Injection, solutionSubcutaneousCaresteam Health, Inc.2011-01-01Not applicableUS flag
Isocaine HCl Inj 2%Mepivacaine hydrochloride (20 mg / mL) + Levonordefrin (0.05 mg / mL)SolutionInfiltrationNovocol Inc.1977-12-31Not applicableCanada flag
Isocaine with LevonordefrinMepivacaine hydrochloride (20 mg/1mL) + Levonordefrin (0.05 mg/1mL)Injection, solutionSubcutaneousNovocol Pharmaceutical of Canada Inc.2006-04-14Not applicableUS flag
Mepivacaine Hydrochloride and LevonordefrinMepivacaine hydrochloride (20 mg/1mL) + Levonordefrin (0.05 mg/1mL)Injection, solutionSubcutaneousDarby Dental Supply Llc2011-01-14Not applicableUS flag
Mepivacaine Hydrochloride with LevonordefrinMepivacaine hydrochloride (20 mg/1mL) + Levonordefrin (0.05 mg/1mL)Injection, solutionSubcutaneousHenry Schein Inc.2011-01-012016-05-24US flag

Categories

ATC Codes
N01BB53 — Mepivacaine, combinationsN01BB03 — Mepivacaine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as piperidinecarboxamides. These are compounds containing a piperidine ring substituted with a carboxamide functional group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Piperidinecarboxylic acids and derivatives
Direct Parent
Piperidinecarboxamides
Alternative Parents
m-Xylenes / Trialkylamines / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Hydrocarbon derivatives
Substituents
2-piperidinecarboxamide / Amine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carboximidic acid / Carboximidic acid derivative / Hydrocarbon derivative / M-xylene / Monocyclic benzene moiety
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidinecarboxamide (CHEBI:6759)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
B6E06QE59J
CAS number
96-88-8
InChI Key
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

References

Synthesis Reference
US2799679
General References
Not Available
Human Metabolome Database
HMDB0015096
KEGG Drug
D08181
KEGG Compound
C07528
PubChem Compound
4062
PubChem Substance
46507857
ChemSpider
3922
BindingDB
50417964
RxNav
6759
ChEBI
6759
ChEMBL
CHEMBL1087
Therapeutic Targets Database
DAP001232
PharmGKB
PA164748741
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Mepivacaine
FDA label
Download (180 KB)
MSDS
Download (73.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceCancer of Bladder1
4CompletedSupportive CareAnkle Fusion / Intraoperative Hypertension / Total Ankle Arthroplasty / Tourniquet Hypertension1
4CompletedSupportive CarePain1
4CompletedTreatmentAmbulatory Surgical Procedures / Arthroplasties, Replacement, Knee / Early Ambulation / Pain Management / Spinal Anaesthesia1
4CompletedTreatmentAnaesthesia therapy / Pain / Surgery / Varicosities of the great saphenous vein1
4CompletedTreatmentArrhythmia1
4CompletedTreatmentArthritis of the Knee Joint1
4CompletedTreatmentHip Arthroplasty1
4CompletedTreatmentOrthopedic Surgical Procedures / Postoperative pain1
4CompletedTreatmentOsteoarthritis in the Hip Joint1

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
  • American Dental Cooperative Inc.
  • APP Pharmaceuticals
  • Ato Zizine Sarl
  • Benco Dental Co.
  • Cardent International Inc.
  • Carestream Health Inc.
  • Carlisle Laboratories Inc.
  • Darby Dental Supply Co. Inc.
  • DENTSPLY International
  • Eastman Kodak Co. Dental Products
  • H Meer Dental Supply Co.
  • Henry Schein Inc.
  • Hospira Inc.
  • Kent Dental
  • Les Laboratoires Medis S A
  • Novocol Pharmaceutical Canada
  • Patterson Dental Supply Inc.
  • Safco Dental Supply Co.
  • Septodont Inc.
  • Spectrum Pharmaceuticals
  • Veratex Corp.
Dosage Forms
FormRouteStrength
SolutionParenteral51 mg
SolutionParenteral30 mg
InjectionParenteral100 mg
InjectionParenteral200 mg
Injection, solution
SolutionEpidural; Intracaudal10 mg / mL
SolutionInfiltration10 mg / mL
SolutionEpidural; Intracaudal20 mg / mL
LiquidEpidural; Intracaudal10 mg / mL
LiquidIntraspinal20 mg / mL
LiquidEpidural; Intracaudal1 %
LiquidInfiltration1 %
LiquidEpidural; Intracaudal20 mg / mL
Injection, solution30 MG/ML
Injection, solutionDental30 mg/ml
InjectionSubcutaneous30 mg/mL
Injection, solutionInfiltration
SolutionSubcutaneous30 mg / mL
InjectionParenteral54 mg
Injection, solutionInfiltration
InjectionParenteral
Injection, solutionEpidural; Intradermal; Intramuscular; Perineural
Injection, solutionEpidural; Perineural
Injection, solutionParenteral
SolutionParenteral1000 mg
Injection, solution1 %
Injection, solution10 MG/ML
Injection, solution2 %
Injection, solution20 MG/ML
Injection, solution3 %
Injection, solutionParenteral20 MG/ML
Injection, solutionDental; Infiltration30 mg/1mL
SolutionParenteral200 mg
InjectionBuccal30 mg/ml
SolutionInfiltration30 mg / mL
SolutionParenteral10 mg
SolutionParenteral50 mg
SolutionParenteral20 mg
Injection, solutionParenteral
SolutionDental
SolutionInfiltration30 mg
InjectionDental30 mg/1mL
InjectionInfiltration10 mg/1mL
InjectionInfiltration15 mg/1mL
InjectionInfiltration20 mg/1mL
InjectionSubcutaneous
Injection, solutionInfiltration10 mg/1mL
Injection, solutionInfiltration20 mg/1mL
InjectionDental
Injection, solutionEpidural; Infiltration10 mg/1mL
Injection, solutionEpidural; Infiltration15 mg/1mL
Injection, solutionEpidural; Infiltration20 mg/1mL
Solution
Injection, solutionInfiltration; Perineural
SolutionInfiltration
LiquidInfiltration
InjectionIntramuscular18 mcg/1.8ml
Injection, solutionBuccal
LiquidInfiltration30 mg / mL
InjectionIntramuscular54 mg/1.8ml
Injection, solutionSubcutaneous
Injection, solutionSubcutaneous30 mg/1mL
SolutionInfiltration54 mg
SolutionParenteral
SolutionParenteral54 mg
Solution30 mg/1ml
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)150.5 °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 RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (7.1 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0002-9000000000-6a3d80d214452a24ab62
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-9040000000-3c0a89a13f39484eef97
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-9000000000-9073826aa2631981fe72
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-9000000000-9b273b91b5148ef6a8fa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-9000000000-d541d397ca20f2f1a799
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-9000000000-eda45d03ea77058a8429
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-006t-9000000000-f42a147676c3c718e38f

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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 acro...
Gene Name
SCN10A
Uniprot ID
Q9Y5Y9
Uniprot Name
Sodium channel protein type 10 subunit alpha
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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at November 28, 2021 11:56