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N-(2,6-디메틸페닐)-1-메틸피페리딘-2-카르복스아미드

Mepivacaine

HCID 4062
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
96-88-8
표준 SMILES
Cc1cccc(C)c1NC(=O)C1CCCCN1C
InChIKey
INWLQCZOYSRPNW-UHFFFAOYSA-N
분자식
C15H22N2O
평균 분자량
246.35 g/mol
단동위원소 질량
246.17321332

개요

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.

이름 및 식별자

우선 이름
Mepivacaine
IUPAC
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
현지명
N-(2,6-디메틸페닐)-1-메틸피페리딘-2-카르복스아미드
영어명
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide
분자식
C15H22N2O
분자량
246.35

이름 및 동의어

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
이름 더 보기
N-(2,6-디메틸페닐)-1-메틸피페리딘-2-카르복스아미드CarbocaineC07528CarbocainPolocaineMepicaineScandicainMepivacaine, 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)

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
1.9
극성 표면적
32.3 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
2
무거운 원자 수
18
형식 전하
0
복잡도
282

실험 및 물리화학적 성질

DrugsPharmaceuticals
LogP · 2건

2.2

2.11

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

Breast Feeding; Lactation; Anesthetics, Local

Pharmaceuticals

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

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)]

물리화학적 성질

녹는점
150 · 150-151°
끓는 점
389.35 °C · 389.35°C (rough estimate)
밀도
0.9978 · 0.9978 (rough estimate)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 3 (100%)

독성 정보

Treatment · 1건

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 · 1건

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 · 1건

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.

화학 및 산업

약리 정보

ATC Code · 3건

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 · 1건

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 · 1건

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 · 2건

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.

관련 반응

2건
반응 기록 만들기
HRID 2273578 반응식
HRID 2273578생성물로uspto-grants-2015_09
HRID 2273579 반응식
HRID 2273579생성물로uspto-grants-2015_09

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
CHEMBL1087
ChEBI
CHEBI:6759
UNII
B6E06QE59J
EC Number
202-543-0
Nikkaji
J4.726K
굴절률
1.628 · 1.6280 (estimate)
저장 조건
-20 °C · Store at -20°C
용해도
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
물리적 상태
결정성 고체
산도 계수 (pKa)
14.85 · 14.85±0.70(Predicted)
색상
White to off-white
수용성
2.217 g/L · 2.217g/L(25℃)
EPA
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 · 5건

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)

안전 데이터

tsca
TSCA listed
FDA Pharmacological Classification · 6건

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 · 1건

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 · 2건

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

용도 및 제조

Uses · 2건

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

응용 분야

용도Anesthetic (local).

상·하류 제품 정보

상류 원료

마그네슘4-Bromo-2,6-dimethylaniline2,6-다이메틸아닐린에틸브로마이드

공급사43 곳

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United Life Science020-82099279 18988968278 · [email protected]
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Aladdin Scientific[email protected]
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추가 설명

정의ChEBI: 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.