Identification

Name
Mepivacaine
Accession Number
DB00961  (APRD01094)
Type
Small Molecule
Groups
Approved, 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
  • DL-Mepivacaine
  • Mepivacaina
  • Mepivacaine
  • Mepivacainum
  • N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide
  • N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamide
Product Ingredients
IngredientUNIICASInChI Key
Mepivacaine Hydrochloride4VFX2L7EM51722-62-9RETIMRUQNCDCQB-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
3% Polocaine DentalLiquid30 mgInfiltrationDentsply Pharmaceutical2009-10-19Not applicableCanada
CarbocaineInjection, solution15 mg/1mLEpidural; InfiltrationHospira, Inc.2006-04-28Not applicableUs
CarbocaineInjection, solution20 mg/1mLInfiltrationHospira, Inc.2006-09-27Not applicableUs
CarbocaineInjection, solution20 mg/1mLEpidural; InfiltrationHospira, Inc.2007-01-31Not applicableUs
CarbocaineInjection, solution10 mg/1mLInfiltrationHospira, Inc.2007-10-10Not applicableUs
CarbocaineInjection, solution10 mg/1mLEpidural; InfiltrationHospira, Inc.2006-03-23Not applicableUs
Carbocaine 1%Solution1 %Epidural; IntracaudalPfizer2001-06-01Not applicableCanada
Carbocaine 1%Solution1 %InfiltrationPfizer2001-07-15Not applicableCanada
Carbocaine 2%Solution20 mgEpidural; IntracaudalPfizer2001-07-15Not applicableCanada
Carbocaine 3%Solution30 mgInfiltrationSeptodontNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CarbocaineInjection, solution30 mg/1mLSubcutaneousSeptodont2018-06-21Not applicableUs
CarbocaineInjection, solution30 mg/1mLSubcutaneousCaresteam Health, Inc.2011-01-01Not applicableUs
IQ Dental MepivacaineInjection, solution30 mg/1mLSubcutaneousIq Dental2012-08-15Not applicableUs
IsocaineInjection, solution30 mg/1mLSubcutaneousNovocol Inc.2010-08-20Not applicableUs
MepivacaineInjection, solution30 mg/1mLSubcutaneousDarby Dental Supply Llc2011-01-14Not applicableUs
MepivacaineInjection, solution30 mg/1mLSubcutaneousNDC, Inc.2015-04-10Not applicableUs
MepivacaineInjection, solution30 mg/1mLSubcutaneousNovocol Inc.2013-07-31Not applicableUs
MepivacaineInjection, solution30 mg/1mLSubcutaneousBenco Dental2011-01-01Not applicableUs
MepivacaineInjection, solution30 mg/1mLSubcutaneousPatterson Dental2011-01-01Not applicableUs
Mepivacaine HydrochlorideInjection, solution30 mg/1mLDental; InfiltrationHospira, Inc.2008-05-052012-06-01Us
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
2% Polocaine Dental With Levonordefrin 1:20,000Mepivacaine Hydrochloride (20 mg) + Levonordefrin (0.05 mg)SolutionInfiltrationDentsply Pharmaceutical1990-12-312011-08-04Canada
Carbocaine 2% With Neo-cobefrinMepivacaine Hydrochloride (20 mg) + Levonordefrin (0.05 mg)SolutionInfiltrationNovocol Inc.Not applicableNot applicableCanada
Carbocaine 2% With Neo-cobefrinMepivacaine Hydrochloride (20 mg) + Levonordefrin (0.05 mg)SolutionInfiltrationKodak Canada Inc.2005-04-222008-07-14Canada
Carbocaine 2% With Neo-cobefrinMepivacaine Hydrochloride (20 mg) + Levonordefrin (0.05 mg)SolutionInfiltrationCarestream Health Inc.2006-09-01Not applicableCanada
Carbocaine with Neo-CobefrinMepivacaine Hydrochloride (20 mg/1mL) + Levonordefrin (0.05 mg/1mL)Injection, solutionSubcutaneousCaresteam Health, Inc.2011-01-01Not applicableUs
Carbocaine with Neo-CobefrinMepivacaine Hydrochloride (30 mg/1mL) + Levonordefrin (0.05 mg/1mL)Injection, solutionSubcutaneousSeptodont, Inc.2018-11-19Not applicableUs
Isocaine HCl Inj 2%Mepivacaine Hydrochloride (20 mg) + Levonordefrin (0.05 mg)SolutionInfiltrationNovocol Inc.1977-12-31Not applicableCanada
Isocaine with LevonordefrinMepivacaine Hydrochloride (20 mg/1mL) + Levonordefrin (0.05 mg/1mL)Injection, solutionSubcutaneousNovocol Pharmaceutical of Canada Inc.2006-04-14Not applicableUs
Mepivacaine Hydrochloride and LevonordefrinMepivacaine Hydrochloride (20 mg/1mL) + Levonordefrin (0.05 mg/1mL)Injection, solutionSubcutaneousDarby Dental Supply Llc2011-01-14Not applicableUs
Mepivacaine Hydrochloride with LevonordefrinMepivacaine Hydrochloride (20 mg/1mL) + Levonordefrin (0.05 mg/1mL)Injection, solutionSubcutaneousHenry Schein2011-01-01Not applicableUs
International/Other Brands
Carbocaine / Scandicaine
Categories
UNII
B6E06QE59J
CAS number
96-88-8
Weight
Average: 246.348
Monoisotopic: 246.173213336
Chemical Formula
C15H22N2O
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

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.

Associated Therapies
Pharmacodynamics

Mepivicaine 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 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
Human
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
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.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Mepivacaine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbacavirMepivacaine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Mepivacaine 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.
AcetaminophenAcetaminophen may decrease the excretion rate of Mepivacaine which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Mepivacaine which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Mepivacaine which could result in a higher serum level.
AclidiniumMepivacaine may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineMepivacaine may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Food Interactions
Not Available

References

Synthesis Reference
US2799679
General References
Not Available
External Links
Human Metabolome Database
HMDB0015096
KEGG Compound
C07528
PubChem Compound
4062
PubChem Substance
46507857
ChemSpider
3922
BindingDB
50417964
ChEBI
6759
ChEMBL
CHEMBL1087
Therapeutic Targets Database
DAP001232
PharmGKB
PA164748741
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Mepivacaine
ATC Codes
N01BB53 — Mepivacaine, combinationsN01BB03 — Mepivacaine
AHFS Codes
  • 72:00.00 — Local Anesthetics
FDA label
Download (180 KB)
MSDS
Download (73.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedHealth Services ResearchLocal Anesthetic Effectiveness1
1, 2CompletedTreatmentBack Pain Lower Back / Intervertebral Disc Degeneration / Intervertebral Disc Disease1
2RecruitingTreatmentKnee Arthroscopy1
3CompletedTreatmentAnesthetics, Local1
3CompletedTreatmentInsertion of Intrauterine Contraception1
3Unknown StatusTreatmentEmergency / Pain NOS / Traumatic Injuries1
4CompletedSupportive CareAnkle Fusion / Intraoperative Hypertension / Total Ankle Arthroplasty / Tourniquet Hypertension1
4CompletedTreatmentAmbulatory Surgical Procedures / Arthroplasty, Replacement, Knee / Early Ambulation / Pain Management / Spinal Anaesthesia1
4CompletedTreatmentArthroplasties, Hip Replacement1
4CompletedTreatmentKnee Arthritis1
4CompletedTreatmentOrthopedic Surgical Procedures / Postoperative pain1
4CompletedTreatmentSymptomatic Irreversible Pulpitis1
Not AvailableActive Not RecruitingPreventionArterial Hypotension1
Not AvailableCompletedNot AvailableImpact of Anesthetic Choice on Costs1
Not AvailableCompletedTreatmentAnaesthesia therapy / Caudal epidural block therapy / Neuromuscular Blockade1
Not AvailableCompletedTreatmentInterscalene Block / Shoulder Arthroscopy1
Not AvailableEnrolling by InvitationBasic ScienceCancer of Bladder1
Not AvailableNot Yet RecruitingTreatmentPostoperative pain1
Not AvailableRecruitingTreatmentRupture of Anterior Cruciate Ligament / Tear of Anterior Cruciate Ligament1

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
SolutionEpidural; Intracaudal1 %
SolutionInfiltration1 %
SolutionEpidural; Intracaudal20 mg
LiquidEpidural; Intracaudal10 mg
LiquidIntraspinal20 mg
LiquidEpidural; Intracaudal1 %
LiquidInfiltration1 %
LiquidEpidural; Intracaudal20 mg
SolutionSubcutaneous30 mg
Injection, solutionDental; Infiltration30 mg/1mL
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
LiquidInfiltration
SolutionInfiltration
LiquidInfiltration30 mg
Injection, solutionSubcutaneous
Injection, solutionSubcutaneous30 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

Taxonomy

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 / Piperidinecarboxamide / M-xylene / Xylene / Monocyclic benzene moiety / Benzenoid / Tertiary aliphatic amine / Tertiary amine / Carboximidic acid / Carboximidic acid derivative
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidinecarboxamide (CHEBI:6759)

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 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. [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]

Drug created on June 13, 2005 07:24 / Updated on December 18, 2018 05:46