N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide

• ChemBase ID: 837
• Molecular Formular: C15H22N2O
• Molecular Mass: 246.34798
• Monoisotopic Mass: 246.17321333
• SMILES: O=C(Nc1c(cccc1C)C)C1N(CCCC1)C
• Canonical SMILES: CN1CCCCC1C(=O)Nc1c(C)cccc1C
• 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)
• InChIKey: INWLQCZOYSRPNW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
• IUPAC Traditional name: mepivacaine
• Brand Name: Arestocaine HCL; Carbocain; Carbocaine; Isocaine HCL; Polocaine; Polocaine-MPF; Scandicain; Scandicaine; Scandicane; Scandonest Plain
• Synonyms: Mepivacaina [INN-Spanish]; DL-Mepivacaine; Mepivacaine HCL; mepivacaine hydrochloride; Mepivacainum [INN-Latin]; Mepivicaine; S-Ropivacaine Mesylate; Mepivacaine; N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamide

Database IDs

• CAS Number: 96-88-8
• MDL Number: MFCD00243006
• PubChem SID: 46507857; 160964300
• PubChem CID: 4062

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.623901
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.4378594
• LogD (pH = 7.4): 2.9576306
• Log P: 3.1916199
• Molar Refractivity: 76.3197 cm^3
• Polarizability: 28.751305 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.16
• LOG S: -2.6
• Solubility (Water): 6.21e-01 g/l

PROPERTIES

Physical Property

• Solubility: Soluble (7000 mg/L)
• Hydrophobicity(logP): 2.2

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB00961

• Drug 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)
• 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: 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.
• 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
• Biotransformation: 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.
• 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.
• Half Life: The half-life of mepivacaine in adults is 1.9 to 3.2 hours and in neonates 8.7 to 9 hours.
• 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.
• 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.
• External Links: Wikipedia; RxList; Drugs.com