Mepivacaine
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Mepivacaine
Brand names: Cambridge™ Mepivacaine, Carbocaine®, Isocaine®, Polocaine®, Scandonest™
Chemical formula:
Last updated: 7/1/2002
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Mepivacaine
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Mepivacaine
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| Systematic (IUPAC) name | |
| (RS)-N-(2,6-dimethylphenyl)- 1-methyl-piperidine-2-carboxamide | |
| Clinical data | |
| AHFS/Drugs.com | Consumer Drug Information |
| MedlinePlus | a603026 |
| Pregnancy cat. | C, use w/ caution, may cause fetal bradycardia |
| Legal status | ? |
| Identifiers | |
| CAS number | 96-88-8  |
| ATC code | N01BB03 |
| PubChem | CID 4062 |
| DrugBank | DB00961 |
| ChemSpider | 3922 |
| UNII | B6E06QE59J |
| KEGG | D08181 |
| ChEBI | CHEBI:6759 |
| ChEMBL | CHEMBL1087 |
| Chemical data | |
| Formula | C15H22N2O |
| Mol. mass | 246.348 g/mol |
| SMILES | eMolecules & PubChem |
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Mepivacaine (
/mɛˈpɪvəkeɪn/) is a local anesthetic[1] of the amide type. Mepivacaine has a reasonably rapid onset (more rapid than that of procaine) and medium duration of action (shorter than that of procaine) and is marketed under various trade names including Carbocaine and Polocaine.
Mepivacaine became available in the United States in the 1960s.
Mepivacaine is used in any infiltration and regional anesthesia.
It is supplied as the hydrochloride salt of the racemate.[2]
Chemistry
Two primary methods of synthesis have been suggested. According to the first, mepivacaine is synthesized by reacting the ethyl ester of 1-methylpiperindine-2-carboxylic acid with 2,6-dimethylanilinomagnesium bromide, which is synthesized from 2,6-dimethylaniline and ethylmagnesium bromide.
- E. Thuresson, H. Egner, U.S. Patent 2,799,679 (1957).
- B.T. Ekenstam, B. von Egner, G. Petterson, Acta Chem. Scand., 11, 1183 (1957).
- Rinderknecht, H. (1959). "Neue Lokalan�sthetika". Helvetica Chimica Acta 42 (4): 1324–1327. doi:10.1002/hlca.19590420430.
According to the second method, reacting 2,6-dimethylaniline with the acid chloride of pyridine- carboxylic acid first gives the 2,6-xylidide of α-picolinic acid. Then the aromatic pyridine ring is reduced to piperidine by hydrogen in the presence of a platinum on carbon catalyst. The resulting 2,6-xylidide α-pipecolic acid is methylated to mepivacaine using formaldehyde with simultaneous reduction by hydrogen in the presence of platinum on carbon catalyst.
- B.G. Petterson, U.S. Patent 4,110,331 (1977).
References
- ^ Porto GG, Vasconcelos BC, Gomes AC, Albert D (January 2007). "Evaluation of lidocaine and mepivacaine for inferior third molar surgery". Med Oral Patol Oral Cir Bucal 12 (1): E60–4. PMID 17195831. http://www.medicinaoral.com/medoralfree01/v12i1/medoralv12i1p60.pdf.
- ^ Burm AG, Cohen IM, van Kleef JW, Vletter AA, Olieman W, Groen K (January 1997). "Pharmacokinetics of the enantiomers of mepivacaine after intravenous administration of the racemate in volunteers". Anesth. Analg. 84 (1): 85–9. doi:10.1097/00000539-199701000-00016. PMID 8989005. http://www.anesthesia-analgesia.org/cgi/pmidlookup?view=long&pmid=8989005.
External links
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