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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
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
Salts
Name/CAS Structure Properties
Mepivacaine Hydrochloride
1722-62-9
Thumb
  • InChI Key: RETIMRUQNCDCQB-UHFFFAOYNA-N
  • Monoisotopic Mass: 282.149891075
  • Average Mass: 282.809
DBSALT000478
Brand names
NameCompany
CarbocaineNot Available
IsocaineNot Available
PolocaineNot Available
ScandicaineNot Available
Scandonest PlainNot 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
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
Mass Specshow(7.1 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentAlpha Amino Acid Amides
Alternative parentsAnilides; Piperidinecarboxylic Acids; Toluenes; Secondary Carboxylic Acid Amides; Tertiary Amines; Enolates; Carboxylic Acids; Polyamines
Substituentsacetanilide; piperidinecarboxylic acid; toluene; piperidine; benzene; carboxamide group; secondary carboxylic acid amide; tertiary amine; polyamine; carboxylic acid; enolate; amine; organonitrogen compound
Classification descriptionThis compound belongs to the alpha amino acid amides. These are amide derivatives of alpha amino acids.
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
Property Value Probability
Human Intestinal Absorption + 0.9568
Blood Brain Barrier + 0.9749
Caco-2 permeable + 0.6836
P-glycoprotein substrate Substrate 0.7866
P-glycoprotein inhibitor I Inhibitor 0.6872
P-glycoprotein inhibitor II Non-inhibitor 0.8665
Renal organic cation transporter Non-inhibitor 0.5878
CYP450 2C9 substrate Non-substrate 0.7853
CYP450 2D6 substrate Substrate 0.7423
CYP450 3A4 substrate Substrate 0.7726
CYP450 1A2 substrate Non-inhibitor 0.7996
CYP450 2C9 substrate Non-inhibitor 0.933
CYP450 2D6 substrate Inhibitor 0.6146
CYP450 2C19 substrate Non-inhibitor 0.9387
CYP450 3A4 substrate Non-inhibitor 0.5395
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7497
Ames test Non AMES toxic 0.8252
Carcinogenicity Non-carcinogens 0.9333
Biodegradation Not ready biodegradable 0.939
Rat acute toxicity 1.7237 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.908
hERG inhibition (predictor II) Inhibitor 0.6936
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
LiquidInfiltration
SolutionInfiltration
SolutionSubcutaneous
Prices
Unit descriptionCostUnit
Mepivacaine hcl powder318.33USDg
Mepivacaine hcl 3% cartridge0.46USDml
Carbocaine 1% vial0.26USDml
Polocaine 1% vial0.25USDml
Polocaine 2% vial0.24USDml
Carbocaine 2% vial0.19USDml
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 solubility6.21e-01 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 area32.34ChemAxon
rotatable bond count2ChemAxon
refractivity76.32ChemAxon
polarizability28.61ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US2799679
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC07528
PubChem Compound4062
PubChem Substance46507857
ChemSpider3922
ChEBI6759
ChEMBLCHEMBL1087
Therapeutic Targets DatabaseDAP001232
PharmGKBPA164748741
Drug Product Database2271796
RxListhttp://www.rxlist.com/cgi/generic2/mepivacaine.htm
Drugs.comhttp://www.drugs.com/cdi/mepivacaine.html
WikipediaMepivacaine
ATC CodesN01BB03
AHFS Codes
  • 72:00.00
PDB EntriesNot Available
FDA labelshow(180 KB)
MSDSshow(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