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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 240
실험 및 물리화학적 성질
Human Drugs
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
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)
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 10.79 · 10.79±0.60(Predicted)
- 색상
- 무색 오일에서 회백색 왁스로
- BCS Class
- 1 · 1
- InChI
- InChI=1S/C12H21N/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10/h9H,3-8,13H2,1-2H3
- InChIKey
- BUGYDGFZZOZRHP-UHFFFAOYSA-N
- SMILES
- C12(N)CC3(C)CC(CC(C)(C3)C1)C2
안전 및 규제
GHS 분류
GHS Classification
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
독성 정보
Toxicity Summary
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
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.
Drug Induced Liver Injury
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
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
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
Agents used in the treatment of Parkinson'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
응용 분야
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
상류 원료
공급사101 곳
추가 설명
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.
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