Mepivacaine inhibits sodium influx and membrane depolarization by binding to particular voltage-gated sodium ion channels in the membranes of neuronal cells. This causes a barrier in the initiation and conduction of nerve impulses, which causes a temporary loss of feeling. This drug acts more quickly and for a moderate amount of time when compared to other local anesthetics[2]. Mepivacaine acts for a medium amount of time, which is shorter than procaine's, and with a fairly quick start (faster than procaine's)[3]. S(-)-bupivacaine shows a selectivity for TTXs Na(+) channels while mepivacaine exhibits a preferential use-dependent block of Na(v)1.8[4].

Absorption, Distribution and Excretion
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.
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.

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Metabolism / Metabolites
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.
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.

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Biological Half-Life
The half-life of mepivacaine in adults is 1.9 to 3.2 hours and in neonates 8.7 to 9 hours.

Toxicity Summary
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.

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Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
No information is available on the use of mepivacaine during breastfeeding. Based on the low excretion of other local anesthetics into breastmilk, a single dose of mepivacaine during breastfeeding is unlikely to adversely affect the breastfed infant. However, an alternate drug may be preferred, especially while nursing a newborn or preterm infant.
Mepivacaine given during labor as a local anesthetic to the mother has been reported to interfere with initial nursing behavior of some infants, but not weight gain during the first 5 days postpartum. Although not well studied specifically with mepivacaine, it appears that with good breastfeeding support, epidural local anesthetics with or without fentanyl or one of its derivatives has little or no adverse effect on breastfeeding success. Labor pain medication may delay the onset of lactation. More study is required to clarify the effect of mepivacaine during labor on breastfeeding outcome.
◉ Effects in Breastfed Infants
Relevant published information was not found as of the revision date.
◉ Effects on Lactation and Breastmilk
In a study that compared extradural administration of mepivacaine, bupivacaine and lidocaine for analgesia during normal childbirth, no differences were found in weight changes over the first 5 days after delivery among the breastfed infants of the 3 groups. Overall weight gain was within normal limits for all groups.
Of 6 infants whose mothers received a pudendal block with mepivacaine within the hour before delivery, 4 took longer to begin nursing behavior and nursed less initially than 10 infants whose mothers received no anesthesia during labor. The long-term consequences of these differences were not reported.
A national survey of women and their infants from late pregnancy through 12 months postpartum compared the time of lactogenesis II in mothers who did and did not receive pain medication during labor. Categories of medication were spinal or epidural only, spinal or epidural plus another medication, and other pain medication only. Women who received medications from any of the categories had about twice the risk of having delayed lactogenesis II (>72 hours) compared to women who received no labor pain medication.

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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.

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Toxicity Data
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.
LD50: 23-35 mg/kg (Intravenous, Mouse) (A308)
LD50: 280 mg/kg (Subcutaneous, Mouse (A308)

[1]. ECMO for Cardiac Rescue after Accidental Intravenous Mepivacaine Application. Case Rep Pediatr. 2012;2012:491692.

[2]. mepivacaine hydrochloride.

[3]. Pharmacokinetics of the enantiomers of mepivacaine after intravenous administration of the racemate in volunteers. Anesth Analg, 1997. 84(1): p. 85-9.

[4]. Leffler, A., J. Reckzeh, and C. Nau, Block of sensory neuronal Na+ channels by the secreolytic ambroxol is associated with an interaction with local anesthetic binding sites. Eur J Pharmacol, 2010. 630(1-3): p. 19-28.

Mepivacaine is a piperidinecarboxamide in which N-methylpipecolic acid and 2,6-dimethylaniline have combined to form the amide bond. It is used as a local amide-type anaesthetic. It has a role as a local anaesthetic and a drug allergen.
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)
Mepivacaine is an Amide Local Anesthetic. The physiologic effect of mepivacaine is by means of Local Anesthesia.
Mepivacaine is an amide-type local anesthetic agent. At the injection site, mepivacaine binds to specific voltage-gated sodium ion channels in neuronal cell membranes, which inhibits both sodium influx and membrane depolarization. This leads to a blockage of nerve impulse initiation and conduction and results in a reversible loss of sensation. Compared to other local anesthetics, this agent has a more rapid onset and moderate duration of action.
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)
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)
See also: Mepivacaine Hydrochloride (has salt form).

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Drug 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.
FDA Label

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Mechanism of Action
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.

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Pharmacodynamics
Mepivicaine is an amide local anesthetic. 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.

C15H22N2O

246.35

246.173

96-88-8

(+)-Mepivacaine;24358-84-7;Mepivacaine hydrochloride;1722-62-9;Mepivacaine-d3;1346597-90-7

4062

White to off-white solid powder

1.077 g/cm3

383.062ºC at 760 mmHg

150.5ºC

185.47ºC

2.737

1

2

2

18

282

0

INWLQCZOYSRPNW-UHFFFAOYSA-N

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)

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

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO: 33.33 mg/mL (135.30 mM)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)