Memantine Hydrochloride

HCID 181458

기본 정보

CAS
19982-08-2
표준 SMILES
CC12CC3CC(C)(C1)CC(N)(C3)C2.Cl
InChIKey
LDDHMLJTFXJGPI-UHFFFAOYSA-N
분자식
C12H22ClN
평균 분자량
215.76 g/mol
단동위원소 질량
215.14407738

개요

Memantine hydrochloride is a hydrochloride obtained by reaction of memantine with one equivalent of hydrochloric acid. A low to moderate affinity uncompetitive (open-channel); NMDA receptor antagonist which binds preferentially to the NMDA receptor-operated cation channels. It has a role as an antidepressant, an antiparkinson drug, a dopaminergic agent, a NMDA receptor antagonist and a neuroprotective agent. It contains a memantinium(1+).

이름 및 식별자

우선 이름
Memantine Hydrochloride
IUPAC
3,5-dimethyladamantan-1-amine;hydrochloride
영어명
Memantine
분자식
C12H21N
분자량
179.3

이름 및 동의어

MEMANTINE HYDROCHLORIDE41100-52-1Memantine HCL3,5-dimethyladamantan-1-amine hydrochloride3,5-Dimethyl-1-adamantanamine hydrochlorideAkatinolNamenda XRMemaryMemantine MylanMemantine MerzMemantine AccordMemantine LEK
이름 더 보기
C137361-Amino-3,5-dimethyladamantane(1r,3R,5S,7r)-3,5-dimethyladamantan-1-amineMEMANTINEMemartineAKOS BB-9600AURORA KA-7643Memantine(Base)7-DIMETHYLXANTHINETIMTEC-BB SBB002574
1-Amino-3,5-dimethyladamantane HydrochlorideAcrescentBalaxurAuxuraMemantine ratiopharmJY0WD0UA60SUN-Y7017NSC-102290

데이터베이스 식별자

CAS
19982-08-2、41100-52-1
PubChem CID
181458
DTXSID
DTXSID90961439
ChEMBL
CHEMBL1699
ChEBI
CHEBI:64323
UNII
JY0WD0UA60
EC Number
255-219-6

물성

구조 계산 물성

극성 표면적
26 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
1
회전 가능 결합 수
0
무거운 원자 수
14

실험 및 물리화학적 성질

Solubility29.4 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs · 6건

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

Collision Cross Section145.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점
258 °C · 258 °C
끓는 점
239.8 · 239.8±8.0 °C(Predicted)
밀도
1.046 · 1.046
굴절률
25 · nD25 1.4941
저장 조건
2 · Keep in dark place,Inert atmosphere,2-8°C
용해도
클로로포름 (약간 용해됨), DMSO (약간 용해됨)

안전 및 규제

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 5% (1 of 20) of reports.

Warning

H302 (80%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 20 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (80%)

독성 정보

TreatmentAs in any cases of overdose, general supportive measures should be utilized, and treatment should be symptomatic. Elimination of memantine can be enhanced by acidification of urine. (L1712)
Exposure RoutesWell absorbed orally with a bioavailability of approximately 100%. Peak plasma concentrations are reached in 3-7 hours. Food has no effect on absorption.
Toxicity Summary · 1건

Memantine exerts its action through uncompetitive NMDA receptor antagonism, binding preferentially to the NMDA receptor-operated cation channels. Prolonged increased levels of glutamate in the brain of demented patients are sufficient to counter the voltage-dependent block of NMDA receptors by Mg<sup>2+</sup> ions and allow continuous influx of Ca<sup>2+</sup> ions into cells, ultimately resulting in neuronal degeneration. Studies suggest that memantine binds more effectively than Mg<sup>2+</sup> ions at the NMDA receptor, and thereby effectively blocks this prolonged influx of Ca<sup>2+</sup> ions through the NMDA channel whilst preserving the transient physiological activation of the channels by higher concentrations of synaptically released glutamate. Thus memantine protects against chronically elevated concentrations of glutamate. Memantine also has antagonistic activity at the type 3 serotonergic (5-HT<sub>3</sub>) receptor with a potency that is similar to that at the NMDA receptor, and lower antagonistic activity at the nicotinic acetylcholine receptor. This drug has no affinity for gamma-aminobutyric acid (GABA), benzodiazepine, dopamine, adrenergic, histamine, or glycine receptors or for voltage-dependent calcium, sodium, or potassium channels.

Signs and Symptoms · 1건

Side effects include pain, abnormal crying, leg pain, fever, increased apetite. Adverse drug reactions include: dizziness, confusion, headache, hallucinations, tiredness. Less common side effects include: vomiting, anxiety, hypertonia, cystitis, and increased libido. Doses of up to 400 mg have been tolerated.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Memantine hydrochloride

vLess-DILI-concern

7

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

안전 데이터

hazard_code
Xi
safety_code
24/25
유해 물질 데이터
19982-08-2(Hazardous Substances Data)

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

Excreted largely unchanged. About 20% is metabolized to 1-amino-3-hydroxymethyl-5-methyl-adamantane and 3-amino-1-hydroxy-5,7-dimethyl-adamantane. Route of Elimination: Memantine undergoes partial hepatic metabolism. About 48% of administered drug is excreted unchanged in urine; the remainder is converted primarily to three polar metabolites which possess minimal NMDA receptor antagonistic activity: the N-glucuronide conjugate, 6-hydroxy memantine, and 1-nitroso-deaminated memantine. It is excreted predominantly in the urine, unchanged. Half Life: 60-100 hours

FDA Pharmacological Classification · 6건

MEMANTINE HYDROCHLORIDE

NMDA Receptor Antagonists [MoA]; N-methyl-D-aspartate Receptor Antagonist [EPC]

MEMANTINE HYDROCHLORIDE ORAL

NMDA Receptor Antagonists [MoA]; N-methyl-D-aspartate Receptor Antagonist [EPC]

MEMANTINE HCL

NMDA Receptor Antagonists [MoA]; N-methyl-D-aspartate Receptor Antagonist [EPC]

MeSH Pharmacological Classification · 3건

Agents used in the treatment of Parkinson&apos;s disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists.

Any drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.

Drugs that bind to but do not activate excitatory amino acid receptors, thereby blocking the actions of agonists.

용도 및 제조

UsesFor the treatment of moderate to severe dementia of the Alzheimer's type.
응용 분야 · 2건

역사Memantine was first synthesized, patented, and described by Eli Lilly and Company in 1963 as an anti-diabetic agent, but it was ineffective at lowering blood sugar. By 1972, it was discovered to have central nervous system (CNS) activity, and was developed by Merz for treatment of neurological diseases, such as Parkinson's disease. Memantine was first studied in the treatment of Alzheimer's disease in 1986. The drug was first marketed for dementia in 1989 in Germany under the name Axura. Memantine was approved in the European Union in 2002 and in the United States in 2003.

용도Recent phase 3 clinical trials have shown that Memantine is an effective way of treatment of both mild and moderate-to-severe Alzheimer''s disease and possibly vascular dementia (multi-infarct dementia). Memantine’s method of action involves an uncompetitive, low-affinity, open-channel blocker; it enters the receptor-associated ion channel preferentially when it is excessively open, and, most importantly, its off-rate is relatively fast so that it does not substantially accumulate in the channel to interfere with normal synaptic transmission.

상·하류 제품 정보

공급사101 곳

北京华美互利生物化工010-56205725 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
추가 설명 · 1건

정의ChEBI: A primary aliphatic amine that is the 3,5-dimethyl derivative of 1-aminoadamantane. A low to moderate affinity uncompetitive (open-channel); NMDA receptor antagonist which binds preferentially to the NMDA receptor-operated cation channels.

관련 반응

4건

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