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Identification
Name Mepivacaine
Accession Number DB00961 (APRD01094)
Type small molecule
Groups 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
DL-Mepivacaine
Mepivacaina [INN-Spanish]
Mepivacaine HCL
mepivacaine hydrochloride
Mepivacainum [INN-Latin]
Mepivicaine
S-Ropivacaine Mesylate
Salts Not Available
Brand names
Name Company
Arestocaine HCL
Carbocain
Carbocaine
Isocaine HCL
Polocaine
Polocaine-MPF
Scandicain
Scandicaine
Scandicane
Scandonest Plain
Brand mixtures
Brand Name Ingredients
2% Polocaine Dental with Levonordefrin 1:20,000 Corbadrine + Mepivacaine Hydrochloride
Arestocaine Hcl 2% W Levonordefrin 1:20000 Levonordefrin Hydrochloride + Mepivacaine Hydrochloride
Carbocaine 2% Neo-Cobefrin 1:20,000 Liq Levonordefrin Hydrochloride + Mepivacaine Hydrochloride
Carbocaine 2% with Neo-Cobefrin Corbadrine + Mepivacaine Hydrochloride
Isocaine Hcl Inj 2% Levonordefrin Hydrochloride (Levonordefrin Hydrochloride) + Mepivacaine Hydrochloride
Mepivacaine Hcl 2% W Levonordefrin Inj Levonordefrin Hydrochloride + Mepivacaine Hydrochloride
Scandonest 2% Special Inj Epinephrine + Mepivacaine Hydrochloride
Categories
  • Anesthetics, Local
CAS number 96-88-8
Weight Average: 246.348
Monoisotopic: 246.173213336
Chemical Formula C15H22N2O
InChI Key InChIKey=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)
Plain Text
IUPAC Name
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
SMILES
CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C
Plain Text
Mass Spec show (7.1 KB)
Taxonomy
Kingdom Organic
Classes
  • Acetanilides
Substructures
  • Amino Ketones
  • Benzene and Derivatives
  • Acetanilides
  • Carboxylic Acids and Derivatives
  • Aliphatic and Aryl Amines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Anilines
  • Piperidines
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.
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.
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
Pathway Name SMPDB ID
Smp00399 Mepivacaine Pathway SMP00399
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
Form Route Strength
Liquid Infiltration
Solution Infiltration
Solution Subcutaneous
Prices
Unit description Cost Unit
Mepivacaine hcl powder 318.33 USD g
Mepivacaine hcl 3% cartridge 0.46 USD ml
Carbocaine 1% vial 0.26 USD ml
Polocaine 1% vial 0.25 USD ml
Polocaine 2% vial 0.24 USD ml
Carbocaine 2% vial 0.19 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 150.5 °C PhysProp
water solubility 7000 mg/L (at 23 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 1.95 HANSCH,C ET AL. (1995)
logS -1.55 ADME Research, USCD
pKa 7.7 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 6.21e-01 g/l ALOGPS
logP 2.16 ALOGPS
logP 3.19 ChemAxon
logS -2.6 ALOGPS
pKa (strongest acidic) 13.62 ChemAxon
pKa (strongest basic) 7.25 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 32.34 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 76.32 ChemAxon
polarizability 28.61 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07528 Link_out
PubChem Compound 4062 Link_out
PubChem Substance 46507857 Link_out
ChemSpider 3922 Link_out
ChEBI 6759 Link_out
ChEMBL 6759 Link_out
Therapeutic Targets Database DAP001232 Link_out
PharmGKB PA164748741 Link_out
Drug Product Database 2271796 Link_out
RxList http://www.rxlist.com/cgi/generic2/mepivacaine.htm Link_out
Drugs.com http://www.drugs.com/cdi/mepivacaine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Mepivacaine Link_out
ATC Codes
  • N01BB03
AHFS Codes
  • 72:00.00
PDB Entries Not Available
FDA label show (180 KB)
MSDS show (73.2 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Sodium channel protein type 10 subunit alpha

Pharmacological action: yes
Actions: inhibitor

This protein 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. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms

Organism class: human
UniProt ID: Q9Y5Y9 Link_out
Gene: SCN10A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19