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N-(2,6-Dimethylphenyl)-1-methylpiperidin-2-carboxamid

Mepivacaine

HCID 4062
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
96-88-8
Standard-SMILES
Cc1cccc(C)c1NC(=O)C1CCCCN1C
InChIKey
INWLQCZOYSRPNW-UHFFFAOYSA-N
Summenformel
C15H22N2O
Durchschnittliche Molmasse
246,35 g/mol
Monoisotopische Masse
246,17321332

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Mepivacaine
IUPAC
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
Lokaler Name
N-(2,6-Dimethylphenyl)-1-methylpiperidin-2-carboxamid
Englischer Name
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
Summenformel
C15H22N2O
Molmasse
246.35

Namen und Synonyme

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
Weitere Namen anzeigen
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)

Datenbank-Bezeichner

CAS
96-88-8
PubChem CID
4062
DTXSID
DTXSID9023259

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,9
Polarare Oberfläche (TPSA)
32,3 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
2
Schwere Atome
18
Formalladung
0
Komplexität
282

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals
LogP · 2 Einträge

2.2

2.11

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

Breast Feeding; Lactation; Anesthetics, Local

Pharmaceuticals

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

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)]

Physikochemische Eigenschaften

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxikologische Informationen

Treatment · 1 Eintrag

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 Eintrag

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 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

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 Eintrag

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 Eintrag

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 Einträge

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.

Zugehörige Reaktionen

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Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
ChEMBL
CHEMBL1087
ChEBI
CHEBI:6759
UNII
B6E06QE59J
EC Number
202-543-0
Nikkaji
J4.726K
Schmelzpunkt
150 · 150-151°
Siedepunkt
389.35 °C · 389.35°C (rough estimate)
Dichte
0.9978 · 0.9978 (rough estimate)
Brechungsindex
1.628 · 1.6280 (estimate)
storage temp.
-20 °C · Store at -20°C
Löslichkeit
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
Aggregatzustand
A crystalline solid
pka
14.85 · 14.85±0.70(Predicted)
Farbe
White to off-white
Wasserlöslichkeit
2.217 g/L · 2.217g/L(25 ºC)
EPA chemische Informationen
2 · 2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl- (96-88-8)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 Einträge

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)

Sicherheitsdaten

tsca
TSCA listed
FDA Pharmacological Classification · 6 Einträge

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 Eintrag

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 Einträge

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

Verwendung und Herstellung

Uses · 2 Einträge

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

Anwendungen

VerwendenAnesthetic (local).

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Magnesium4-Brom-2,6-xylidin2,6-XylidinBromethan

Anbieter43 Anbieter

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Ergänzende Hinweise

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.