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Mepivacaine

HCID 4062
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
96-88-8
Standard SMILES
Cc1cccc(C)c1NC(=O)C1CCCCN1C
InChIKey
INWLQCZOYSRPNW-UHFFFAOYSA-N
Molecular formula
C15H22N2O
Average molar mass
246.35 g/mol
Monoisotopic mass
246.17321332

Overview

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.

Names & identifiers

Preferred name
Mepivacaine
IUPAC
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
English name
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
Molecular formula
C15H22N2O
Molecular weight
246.35

Names & synonyms

mepivacaine96-88-8N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamideDL-MepivacaineScandicaineMepivacainaMepivacainumtevacaine2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl-Carboplyin Dental2',6'-Pipecoloxylidide, 1-methyl-Mepisv
Show more names
CarbocaineC07528CarbocainPolocaineMepicaineScandicainMepivacaine, 10 mM in DMSO
N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide(+-)-1-Methyl-2',6'-pipecoloxylidide1-METHYL-2',6'-PIPECOLOXYLIDIDEB6E06QE59JCHEBI:6759APF-135DTXSID90232595-22-01-00223 (Beilstein Handbook Reference)

Database identifiers

CAS
96-88-8
PubChem CID
4062
DTXSID
DTXSID9023259
ChEMBL
CHEMBL1087
ChEBI

Properties

Computed structural properties

XLogP
1.9
Topological polar surface area
32.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
18
Formal charge
0
Complexity
282

Experimental & physicochemical properties

DrugsPharmaceuticals
LogP · 2 items

2.2

2.11

Solubility6.21e-01 g/L
Human Drugs · 2 items

Breast Feeding; Lactation; Anesthetics, Local

Pharmaceuticals

Melting Point150.5 °C
Physical DescriptionSolid
Dissociation Constants7.7
Collision Cross Section · 2 items

156.66 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

159.1 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Physicochemical properties

Melting point
150 · 150-151°

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxicology

Treatment · 1 item

Treatment of a patient with toxic manifestations consists of assuring and maintaining a patient airway and supporting ventilation (respiration) as required. This usually will be sufficient in the management of most reactions. Should a convulsion persist despite ventilatory therapy, small increments of anticonvulsive agents may be given intravenously, such as benzodiazephine (e.g., diazepam) or ultrashort-acting barbiturates (e.g., thiopental or thiamylal) or short-acting barbiturates (e.g., pentobarbital or secobarbital). Cardiovascular depression may require circulatory assistance with intravenous fluids and/or vasopressor (e.g., Ephedrine) as dictated by the clinical situation. (L1712)

Exposure Routes · 1 item

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. Subcutaneous, injection ; Infiltration

Toxicity Summary · 1 item

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.

Chemistry & industry

Pharmacology

ATC Code · 3 items

N01BB03

N - Nervous system

QN - Nervous system

Protein BindingMepivacaine is approximately 75% bound to plasma proteins. Generally, the lower the plasma concentration of drug, the higher the percentage of drug bound to plasma.
Pharmacodynamics · 1 item

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.

Mechanism of Action · 1 item

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.

Biological Half-LifeThe half-life of mepivacaine in adults is 1.9 to 3.2 hours and in neonates 8.7 to 9 hours.
Metabolism/Metabolites · 2 items

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.

Related reactions

2 records
New reaction record
HRID 2273578 reaction equation
HRID 2273578As productuspto-grants-2015_09
HRID 2273579 reaction equation
HRID 2273579As productuspto-grants-2015_09

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CHEBI:6759
UNII
B6E06QE59J
EC Number
202-543-0
Nikkaji
J4.726K
Boiling point
389.35 °C · 389.35°C (rough estimate)
Density
0.9978 · 0.9978 (rough estimate)
refractive index
1.628 · 1.6280 (estimate)
storage temp.
-20 °C · Store at -20°C
solubility
30 mg/ml; · DMF: 30 mg/ml; DMSO: 25 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
form
A crystalline solid
pka
14.85 · 14.85±0.70(Predicted)
color
White to off-white
Water Solubility
2.217 g/L · 2.217g/L(25 ºC)
FDA UNII
6 E06QE59J · B6E06QE59J
NCI Drug Dictionary
Carbocaine
EPA Substance Registry System
2 · 2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl- (96-88-8)
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301
Precautionary statements
264 · P264-P270-P301+P310-P321-P330-P405-P501
TSCA
TSCA listed
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

mepivacaine

DILI Negative

Subcutaneous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataThe 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)

Safety data

tsca
TSCA listed
Signal word
Danger
Symbol(GHS)
GHS06
Hazard statements
H301
Precautionary statements
P264-P270-P301+P310-P321-P330-P405-P501
FDA Pharmacological Classification · 6 items

B6E06QE59J

MEPIVACAINE

Established Pharmacologic Class [EPC] - Amide Local Anesthetic

Chemical Structure [CS] - Amides

Physiologic Effects [PE] - Local Anesthesia

Mepivacaine is an Amide Local Anesthetic. The physiologic effect of mepivacaine is by means of Local Anesthesia.

MeSH Pharmacological Classification · 1 item

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.

Absorption, Distribution and Excretion · 2 items

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.

Cellular LocationsExtracellular
Metabolite PathwaysMepivacaine Action Pathway

Uses & manufacturing

Uses · 2 items

Use (kg; approx.) in Germany (2009): >1000

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.

Use ClassificationPharmaceuticals
General Manufacturing Information2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl-: ACTIVE

Applications

UsesMepivacaine can be used in biological study of 2-adamantanamine produces prolonged spinal block in rats.

UsesAnesthetic (local).

Upstream & downstream products

Upstream raw materials

Magnesium4-Bromo-2,6-dimethylaniline2,6-DimethylanilineBromoethane

Suppliers43 total

盐城通铭生物科技有限公司15195160625 · [email protected]
江苏艾康生物医药研发有限公司025-58851090 19370895928 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
Suzhou ARTK Medchem Co., Ltd.+86-18168183658 · [email protected]
江苏南创化学与生命健康研究院有限公司15720605021 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
United Life Science020-82099279 18988968278 · [email protected]
上海相辉医药科技有限公司13761987713 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
南京药石科技股份有限公司4000255188 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
上海毕楷科技有限公司18516304666 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海寰川实业有限公司021-61478794 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +86-15355479329 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
南京博米尔生物科技有限公司025-83453382-8005 · [email protected]
上海书亚医药科技有限公司400-685-9117 · [email protected]
爱必信(上海)生物科技有限公司13761418683 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
上海宏叶生物科技有限公司400-9205774 400-920-5774 · [email protected]
广州糖姆氏生命科学有限公司020-31155029 18902330969 · [email protected]
Aladdin Scientific[email protected]
上海博湖生物科技有限公司021-57763112 13585886131 · [email protected]
郑州汇聚化工有限公司037155153829 18003835034 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
上海迈瑞尔生化科技有限公司18621169109 · [email protected]
南京康满林化工实业有限公司025-83697070 13770331960 · [email protected]
上海捷世凯生物科技有限公司021-57520305 13795461237 · [email protected]
南京鼎石生物技术有限公司13501719342 13501719342 · [email protected]
上海安毕达生物科技有限公司021-61629020 18201956406 · [email protected]
上海弘渠生物医药科技有限公司88888888888 · [email protected]
Honest Joy Holdings Limited755-36694831 +8613798234863 · [email protected]

Additional notes

DefinitionChEBI: 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.