Mepivacaine Hydrochloride

(BANM, rINNM)
Mepivacaine Hydrochloride Chemical formula
Synonyms: (BANM, rINNM) Hidrocloruro de mepivacaína; Mépivacaïne, chlorhydrate de; Mepivacaini Chloridum; Mepivacaini hydrochloridum; Mepivakaiinihydrokloridi; Mepivakain-hidroklori d; Mepivakain-hydrochlorid; Mepivakainhydroklorid; Mepivakaino hidrochloridas. (1-Methyl-2-piperidyl)formo-2′,6′-xylidide hydrochloride.
Cyrillic synonym: Мепивакаина Гидрохлорид.

💊 Chemical information

Chemical formula: C15H22N2O,HCl = 282.8.
CAS — 96-88-8 (mepivacaine); 22801-44-1 (( )-mepivacaine); 1722-62-9 (mepivacaine hydrochloride).
ATC — N01BB03.
ATC Vet — QN01BB03.

Pharmacopoeias.

In Eur., Jpn, and US.

Ph. Eur. 6.2

(Mepivacaine Hydrochloride). A white or almost white crystalline powder. Freely soluble in water and in alcohol; very slightly soluble in dichloromethane. A 2% solution in water has a pH of 4.0 to 5.0.

USP 31

(Mepivacaine Hydrochloride). A white, odourless, crystalline solid. Freely soluble in water and in methyl alcohol; very slightly soluble in chloroform; practically insoluble in ether. A 2% solution in water has a pH of about 4.5.

pH of solutions.

For a discussion of the effect that pH has on the stability of local anaesthetic solutions and the pain associated with their injection.

💊 Adverse Effects, Treatment, and Precautions

Porphyria.

Mepivacaine is considered to be unsafe in patients with porphyria because it has been shown to be porphyrinogenic in in-vitro systems.

💊 Interactions

For interactions associated with local anaesthetics.

Local anaesthetics.

Studies in vitro showed that bupivacaine dramatically reduced the binding of mepivacaine to α-1-acid glycoprotein.1
1. Hartrick CT, et al. Influence of bupivacaine on mepivacaine protein binding. Clin Pharmacol Ther 1984; 36: 546–50.

💊 Pharmacokinetics

Mepivacaine is about 78% bound to plasma proteins. The plasma half-life has been reported to be about 2 to 3 hours in adults and about 9 hours in neonates. It is rapidly metabolised in the liver and less than 10% of a dose is reported to be excreted unchanged in the urine. Over 50% of a dose is excreted as metabolites into the bile but these probably undergo enterohepatic circulation as only small amounts appear in the faeces. Several metabolites are also excreted via the kidneys and include glucuronide conjugates of hydroxy compounds and an N-demethylated compound, 2′,6′-pipecoloxylidide. Mepivacaine crosses the placenta. See also under Local Anaesthetics.

Pregnancy.

There is considerable transfer of mepivacaine across the placenta after maternal doses and the ratio of fetal to maternal concentrations1 is about 0.7. Although neonates have a very limited capacity to metabolise mepivacaine it appears they are able to eliminate the drug.2
1. Lurie AO, Weiss JB. Blood concentration of mepivacaine and lidocaine in mother and baby after epidural anesthesia. Am J Obstet Gynecol 1970; 106: 850–6
2. Meffin P, et al. Clearance and metabolism of mepivacaine in the human neonate. Clin Pharmacol Ther 1973; 14: 218–25.

💊 Uses and Administration

It is mainly used for infiltration anaesthesia, peripheral nerve block, and epidural block. Mepivacaine has a rapid onset and an intermediate duration of action. The speed of onset and duration of action are increased by the addition of a vasoconstrictor and absorption into the circulation from the site of injection is reduced. The dosage of mepivacaine hydrochloride varies with the site of injection and the type of local anaesthetic procedure. In adults, the maximum single dose of mepivacaine hydrochloride should not generally exceed 400 mg and the total dose in 24 hours should not exceed 1 g. Doses should be reduced in the elderly, in debilitated patients, and in those with cardiac or hepatic impairment. Concentrations of less than 2% should be used in children under 3 years or weighing less than about 14 kg (30 pounds); the dose in children should not exceed 5 to 6 mg/kg.
For infiltration anaesthesia up to 400 mg as a 1% (40 mL) or 0.5% (80 mL) solution is used. For dental infiltration and nerve block a 2% solution with a vasoconstrictor or a 3% plain solution is used. For anaesthesia at a single site in the jaw a dose of 36 mg (1.8 mL) as a 2% solution or 54 mg (1.8 mL) as a 3% solution is used. For anaesthesia of the entire oral cavity 180 mg (9 mL) as a 2% solution or 270 mg (9 mL) as a 3% solution is used. Some recommend that no more than 400 mg should be given at a single dental sitting.
For peripheral nerve blocks, namely cervical, brachial plexus, intercostal, and pudendal blocks, 1 or 2% solutions may be used in doses of 50 to 400 mg (5 to 40 mL) as a 1% solution, or 100 to 400 mg (5 to 20 mL) as a 2% solution. For pudendal block half of the dose is injected on each side. For paracervical block a dose of up to 100 mg (10 mL) as a 1% solution on each side has been suggested allowing an interval of 5 minutes between sides. This may be repeated at an interval of not less than 90 minutes, and for a combined paracervical and pudendal block up to 150 mg (15 mL) as a 1% solution is injected on each side. For therapeutic nerve block in the management of pain 10 to 50 mg (1 to 5 mL) as a 1% solution or 20 to 100 mg (1 to 5 mL) as a 2% solution may be given.
For epidural block usual doses are: 150 to 300 mg (15 to 30 mL) as a 1% solution, 150 to 375 mg (10 to 25 mL) as a 1.5% solution, or 200 to 400 mg (10 to 20 mL) as a 2% solution. Hyperbaric solutions of mepivacaine hydrochloride without adrenaline have also been used for spinal block. Mepivacaine has been included in the intramuscular injections of other drugs to minimise the pain produced at the injection site. Mepivacaine has also been used as a surface anaesthetic but other local anaesthetics such as lidocaine are more effective.

Action.

For a comparison of the vasoactivity of mepivacaine and some other local anaesthetics.

💊 Preparations

USP 31: Mepivacaine Hydrochloride and Levonordefrin Injection; Mepivacaine Hydrochloride Injection.

Proprietary Preparations

Arg.: Mepigobbi; Austral.: Carbocaine; Scandonest†; Austria: Mepinaest; Scandicain; Scandonest; Belg.: Scandicaine; Canad.: Carbocaine; Polocaine†; Cz.: Mepivastesin; Scandonest; Denm.: Carbocain; Carboplyin; Scandonest; Fr.: Carbocaine; Ger.: Meaverin; Mecain; Mepihexal; Mepivastesin; Scandicain; Hong Kong: Mepivastesin; Ital.: Carbocaina; Carbosen; Mepi-Mynol; Mepibil; Mepicain; Mepident; Mepiforan; Mepisolver; Mepivamol; Mepivirgi; Molcain†; Optocain; Pericaina; Scandonest; Neth.: Scandicaine; Scandonest; Norw.: Carbocain; Scandonest; Port.: Isogaine; Mepivastesin; Scandinibsa; Scandonest; S.Afr.: Carbocaine; Scandonest†; Spain: Isogaine; Scandinibsa; Swed.: Carbocain; Switz.: Scandicain; Scandonest; Thai.: Mepicaton; USA: Carbocaine; Carbocaine with Neo-Cobefrin; Isocaine; Polocaine. Multi-ingredient: Ger.: Meaverin†; Thesit†. Used as an adjunct in: Austria: Estradurin; Belg.: Estradurine; Denm.: Estradurin; Fin.: Estradurin; Ger.: Estradurin†; Jpn: Amasulin; Bestcall; Lilacillin†; Pansporin; Takesulin; Malaysia: Nevramin†; Neth.: Estradurin; Norw.: Estradurin; Port.: Linamin Plus†; Singapore: Nevramin; Swed.: Estradurin; Switz.: Estradurin; Thai.: Nevramin.
Published November 17, 2018.