Mepivacaine

Mepivacaine
Clinical data

AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a603026
Pregnancy category	C, use w/ caution, may cause fetal bradycardia
ATC code	N01BB03 (WHO)
Identifiers
IUPAC name (RS)-N-(2,6-dimethylphenyl)- 1-methyl-piperidine-2-carboxamide
CAS Number	96-88-8^Y
PubChem CID	4062
IUPHAR/BPS	7224
DrugBank	DB00961^Y
ChemSpider	3922^Y
UNII	B6E06QE59J
KEGG	D08181^Y
ChEBI	CHEBI:6759^Y
ChEMBL	CHEMBL1087^Y
ECHA InfoCard	100.002.313
Chemical and physical data
Formula	C₁₅H₂₂N₂O
Molar mass	246.348 g/mol
3D model (JSmol)	Interactive image
SMILES O=C(Nc1c(cccc1C)C)C2N(C)CCCC2
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)^Y Key:INWLQCZOYSRPNW-UHFFFAOYSA-N^Y
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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] which consists of R(-)-mepivacaine and S(+)-mepivacaine in equal proportions. These two enantiomers have markedly different pharmacokinetic properties. ^[3]

References

↑ Porto GG, Vasconcelos BC, Gomes AC, Albert D (January 2007). "Evaluation of lidocaine and mepivacaine for inferior third molar surgery" (PDF). Med Oral Patol Oral Cir Bucal. 12 (1): E60–4. PMID 17195831.
↑ 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. PMID 8989005. doi:10.1097/00000539-199701000-00016.
↑ http://journals.lww.com/anesthesia-analgesia/Fulltext/1997/01000/Pharmacokinetics_of_the_Enantiomers_of_Mepivacaine.16.aspx

External links

Mepivacaine at RxList

Local anesthetics (primarily sodium channel blockers) (N01B)

Esters by acid

Aminobenzoic	Benzocaine Butacaine Butamben Chloroprocaine Dimethocaine Lucaine Meprylcaine Metabutethamine Metabutoxycaine Nitracaine Orthocaine Propoxycaine Procaine (Novocaine) Proxymetacaine Risocaine Tetracaine
Benzoic	Amylocaine Cocaine Cyclomethycaine α-Eucaine β-Eucaine Hexylcaine Isobucaine Piperocaine
ArCO2- (not para-amino or Ph)	Amoproxan (3,4,5-Trimethoxybenzoyl) 3-(p-Fluorobenzoyloxy)tropane

Amides

Articaine
Bupivacaine^# / Levobupivacaine / Ropivacaine
Butanilicaine
Carticaine
Dibucaine
Etidocaine
Lidocaine^#
Mepivacaine
Prilocaine
Trimecaine

Combinations

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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