<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2984</id>
  <title>T3D2942</title>
  <common-name>Mepivacaine</common-name>
  <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)</description>
  <cas>96-88-8</cas>
  <pubchem-id>4062</pubchem-id>
  <chemical-formula>C15H22N2O</chemical-formula>
  <weight>246.173210</weight>
  <appearance>White powder.</appearance>
  <melting-point>150.5°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>7000 mg/L (at 23°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>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. Subcutaneous, injection ; Infiltration</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>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.</mechanism-of-toxicity>
  <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.</metabolism>
  <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 &amp;micro;g/mL.LD50: 23-35 mg/kg (Intravenous, Mouse) (A308) LD50: 280 mg/kg (Subcutaneous, Mouse (A308)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>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.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms></symptoms>
  <treatment>Treatment of a patient with toxic manifestations consists of assuring and maintaining a patient airway and supporting ventilation (respiration) as required. This usually will be sufficient in the management of most reactions. Should a convulsion persist despite ventilatory therapy, small increments of anticonvulsive agents may be given intravenously, such as benzodiazephine (e.g., diazepam) or ultrashort-acting barbiturates (e.g., thiopental or thiamylal) or short-acting barbiturates (e.g., pentobarbital or secobarbital). Cardiovascular depression may require circulatory assistance with intravenous fluids and/or vasopressor (e.g., Ephedrine) as dictated by the clinical situation. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:28:03Z</created-at>
  <updated-at type="dateTime">2026-03-26T18:34:59Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Mepivacaine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07528</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>6759</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Mepivacaine</stitch-id>
  <drugbank-id>DB00961</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C</moldb-smiles>
  <moldb-formula>C15H22N2O</moldb-formula>
  <moldb-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)</moldb-inchi>
  <moldb-inchikey>INWLQCZOYSRPNW-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">246.348</moldb-average-mass>
  <moldb-mono-mass type="decimal">246.173213336</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.95</logp>
  <hmdb-id>HMDB15096</hmdb-id>
  <chembl-id>CHEMBL1087</chembl-id>
  <chemspider-id>3922</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;&lt;a href="http://www.drugsyn.org/Mepivacaine.htm"&gt;DrugSyn.org&lt;/a&gt;&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002313</chemdb-id>
  <dsstox-id>DTXSID9023259</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00000534</susdat-id>
  <iupac>N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide</iupac>
</compound>
